I’m thrilled to announce that my friend, Faith Harron, and I are co-authoring a book together.

The book dovetails nicely with many of the themes that my Substack covers, as well as with Faith’s professional work.

The basic idea is that we’re going to write about “What College Didn’t Teach You About the Corporate World.”

Because I’m sp…

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Do you ever feel like your boss is micro-managing you by checking too frequently on your progress?

If so, it might behoove you to consider two things. (I’m not opining on whether your boss is or isn’t micromanaging you. I’m just saying that thinking about these two things might help.)

Your boss may be checking because:

1. Your work matters to them.

2. Work requirements may have changed.

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Perhaps you’ve had the following experience:

You’re working on a PowerPoint presentation, report, or other deliverable for your boss. It’ll ultimately go to the client.

Your boss emails, texts, or calls, to find out how far along you are.

You sigh, annoyed. You’re working on it, and having to answer emails or communicate about your progress is just distracting or slowing you down. You’re frustrated at your micro-managing boss.

Your boss may be asking because: Your work matters to someone other than you.

Your work matters to your boss – in a way it didn’t matter to professors

In college, your work mattered mostly to you. In the corporate world, your work is often part of a bigger picture.

In college, when you did your assignments badly, it didn’t matter to anyone except you. You suffered because of a low grade or because you didn’t learn. Your professor may have suffered through reading a dreadful essay, but was otherwise not affected.

Therefore, the professor had little incentive to ensure that you were on track to complete your assignments, or to otherwise excel.

But in the corporate world, if you do a poor job on work product, it does affect your boss. If you do a bad job on a work product, such as a slide deck, your boss (or someone else) will need to redo it before he can present it to a client.

So if you’re working on something that’s important to your boss, it makes sense for your boss to check with you about progress on the task.

Work requirements have changed

In the corporate world, people are trying to find solutions to problems that don’t have existing solutions, where information is limited. Therefore, the solution itself may change depending on what information is learned to about the problem, or depending on what the client specifically wants.

Your boss often has more direct communication to the client than you do. So if the client’s desires change, your boss will almost certainly hear before you do. When your boss enquires about your progress, sometimes your boss may need to update you that the project will change course.

What if it is micromanagement?

Sometimes (actually, far too often!) bosses do micromanage. I don’t know your situation, and I’m not saying that a micromanaging boss isn’t micromanaging. Rather, I’m suggesting that when you feel micromanaged, it could make sense to ask whether your boss may just be trying to receive more information.

Of course, there are better and worse ways for bosses to communicate.

Vague emails like, “How’s the report going?” might leave you unsure why your boss is asking. “How’s the report going? Just checking in to make sure we’re on track to finish by next Friday,” is much clearer. So is, “How’s the report going? The client called me with an update so we’ll need to change Section 3 – call me when you can.”

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Summary

When you feel micro-managed, consider your boss’s reason for checking in. Maybe your boss isn’t actually micro-managing.

It’s often preferable to have a clear line of communication between you and your boss. Bosses can help their employees by clearly stating why they’re asking. In turn, employees can be prepared to give reports on their progress and not feel micromanaged (if possible) because they know that the end outcome is important to the boss, too.

In her book The Twenty-Something Treatment, psychologist Meg Jay, Ph.D. characterizes ages 18 to 35 as, “the most uncertain years they [people] will ever know.”1

If you believe the myth that your twenties are automatically the “best” years of your life, you may be quite disappointed. It’s actually normal to feel anxious, uncertain, lonely, or depressed at various points.

When you expect uncertainty, you can be better prepared. Sometimes, expecting a challenge can make experiencing the challenge easier.2

Many people in their twenties experience more uncertainty than they have before in life, and they may feel alone. Uncertainty about careers, about dating, about where they’ll live, about friends. But none of us needs to feel alone, because we’re not the only ones experiencing uncertainty.

Why Your Twenties Can Feel Off-Track

Your twenties include uncertainties of all kinds, many of which you probably didn’t have before (depending what kind of family you grew up in).

Uncertainties about where you’ll live – maybe you’re trying to sign a new lease within the next few months. Uncertainties about work: many of my Stanford classmates were laid off from high-paying tech jobs soon after graduating, due to a difficult market. Uncertainties about dating or marriage: whether we want it, or whether it’ll happen.

The uncertainty can lead to feeling off-track in life. Partly, this is because many twenty-somethings feel that they no longer know what track they’re supposed to be on.

People can feel off-track for many reasons, including:

1. There’s no societally-defined track for ages 22-35

2. Many life-changing factors are outside your control

3. You receive less feedback than before

No defined track: there’s a clear path before graduation...

In the way our society is currently set up, from elementary school until college, you’re clearly ‘on track’ to be accepted and then graduate from college – or you’re not.

Pre-college, you probably went to elementary school. Then middle school. Then high school. You knew what your GPA was. You probably knew how you ranked compared to the rest of the class.

In college, your world probably got bigger. Maybe school become less (or more) important. Likely, your idea of priorities shifted.

Accomplishing those priorities may also have become more difficult. Maybe your college didn’t give you your GPA in real-time, only at the end of the semester. Maybe it was harder to figure out how to do well at your extracurriculars, because there was more competition in college. But at least you had some idea of whether or not you were ‘doing well’.

… but suddenly the map disappears

But there’s no defined track after you graduate. (Unless you choose to stick with law school, or med school, or a few other exceptions. Even then, the rest of your life may be much less scripted than it was.)

There’s not a defined track to figure out your career, or making lasting friends, or dating/marriage/having kids, or many other things that people care about.

Friends may be confident about their career while you’re not. Family may be pressuring you to date. Maybe you’re struggling to make friends.

These things are all hard. But when you anticipate that – at some point – you’ll feel lost and off track, you can be prepared for the feeling. Countless twenty-something year-olds feel this way. When you feel off-track, you’re not alone.

Life-changing factors are outside your control

You might feel less agency over your life than you did in college, because your individual actions have less influence on an outcome than they did before. In some regards, that’s because the sphere of things that can potentially affect you is just so much greater than it was before.

For example, if you joined the work force, you’re now playing in a huge economy, as opposed to a small high school or medium-sized college. So there are countless factors beyond your influence as you begin your career.

Career plans can shift due to a variety of factors, many of which aren’t your fault. Even if you’re working your hardest at a job, you might get fired due to a terrible economy.

So even if it’s not your fault, your plans might have to change in a big way.

On top of that, you might not even know if you’re doing well at a job.

You receive less feedback than before

Your boss probably won’t give you feedback as regularly as your professor did. How much feedback depends on the company and depends on the boss, but you may often lack a clear idea of how well you’re actually doing, or how well your boss thinks you’re doing.

This problem won’t necessarily go away as you become more experienced, but you may get more used to it. However, when you’re straight out of college and enter your first job, the lack of feedback can be jarring.

Similarly, priorities at work that shift quickly can be unnerving. Unlike your class syllabus, your company’s plan for next quarter is not etched in stone. Assuming your company has a plan, that plan can – and probably will – change.

Similarly, your personal life can change in a big way. Maybe you thought your long-term dating relationship was going well, but your partner realized that they wanted to travel the world, “find themselves” and break up with you. Again, a massive, painful change that’s not the result of you doing anything ‘wrong’.

What can you do? Three mental reframes

Cheesy as it sounds, even an awareness of the uncertainty can help you combat it, perhaps by mentally reframing the uncertainty.

Here are three reframes that I’ve found helpful. If there are others you think of, please leave a comment!

• “It’s normal to feel uncertain.”

• “There’s no track anymore, but I get to create the track.”

• “The best things in life can’t be quantified.”

It’s normal to feel uncertain, so when you feel uncertain, know that you’re not alone. In fact, next time someone asks you how you’re doing, you might even tell them you’re struggling with uncertainty (if you are). I had a great conversation the other day with a friend who told me he’d been in “a bit of a slump” because he was unsure where his life was going.

Because there’s no track anymore, you get to create the track! Other posts on this blog include suggestions of habits, mindsets, and attitudes that can help you as you create your track.

The best things in life can’t be quantified3 – so there’s no way to be ‘on track’ or compare ourselves to others in some of the best areas in life, such as relationship, purpose, or meaning. There are certainly things that you can do to create more meaning in your life, or improve relationships, but comparing yourself to others whom you perceive to be having ‘more’ success in relationships isn’t helpful.

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Summary

Your twenties (or really, the years 22 to 35, give or take) can be an uncertain time, even if you’re doing what you think you ‘should’ be doing.

When you feel uncertain, realize that you’re not alone. If the above mindsets help you at all, please let me know in the comments! And please feel free to add any that have helped you cope with uncertainty.

Early in your career, a career switch can feel like a permanent decision.

But it’s usually not.

This post will discuss a reframe of the career switch, and examine two questions to help test this hypothesis.

Reframe: You’re testing a hypothesis

In some cases, you can think of a career switch (or even an internship) as testing a hypothesis.

You’re figuring out, “What aspects of this job, industry, company, or work do I like and not like? What am I good at or not good at? What skills do I want to grow?”

The answers to those questions will begin to appear once you actually begin at the new position.

Two questions to ask about long-term fit

Two questions can help you decide if you want to be in the career longer term, or whether it’s just a stepping stone.

The questions are:

1. What skills do I need to get to the top, and do I want to develop them?

2. Would I actually WANT to get to the top?

1. What skills do I need to get to the top, and do I want to develop them?

Based the skills success in a particular career requires, you may decide that a particular career is – or is not – for you.

The skills needed to get to the “top” of a career path can, surprisingly, be quite different from those required when you’re first starting out.

For example, in consulting, many entry-level analysts need to be detail-oriented and become quick at making slides. Being a good salesperson isn’t a priority.

But to be a top-level partner at a consulting firm, you must have an extensive network and be good at sales. You spend much more time than an entry-level analyst on relationships and much less making slides. You’ve also got to be a good manager.

Maybe you have the skills it takes to be an analyst, but not a partner. Maybe you enjoy researching and making slides, but don’t love interacting with people. That’s something you should know as you wonder whether to be a top-level consultant.

Once you better understand what skills are required to be at the top of the field, you’ll be better able to decide whether you want to develop those skills or not.

2. Would I actually WANT to be at the top?

You may also have a gut feeling or intuition that a particular career just isn’t what you really want to do.

For example, after nearly four years in private equity, Alice thought that she might want to work in venture capital. So, she methodically tested her hypothesis: she interned at a venture capital firm.

“It was clear to me,” said Alice, “that as I worked in VC and spoke to the startup founders, that I wanted to be the founders.”

Then one of her mentors asked her a powerful question:

“It’s Friday night at 7pm, and you’re a venture capitalist. You’re about to sit down to dinner with your family, when you get a call from one of your founders. You speak on the phone for two hours about his funding troubles.

“Who would you rather be – the founder or the venture capitalist?”

“The founder!” Alice thought almost immediately.

That made it pretty clear to Alice that she didn’t actually want to be a venture capitalist.

So Alice is founding her own company!

Check out more about what Alice is doing on Substack or LinkedIn.

Summary

Two questions can help you better understand whether a chosen career path is actually something you might want to stick with long term.

These questions are:

1. “What skills do I need to get to the top, and can I develop those skills?”

2. “Would I actually WANT to be at the top?”

Have you ever asked yourself these questions? If so, what happened?

When considering where to spend a bulk of your time — whether that’s finding your next career role, or starting a new hobby — there’s an important parameter many people overlook.

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Commonly considered parameters

Many discussions around choosing a career (or even a hobby, though many of the below are more applicable to a job) include factors such as:

• Tangible benefits

  • Salary / opportunity to make money

  • Benefits

• Growth opportunities

  • Opportunities for career growth (growing skills, obtaining promotions, etc)

  • “Career capital”

• Lifestyle

  • Flexibility or autonomy

  • Location and commute time

• Values-related judgements

  • Passion or enjoyment

  • Status or prestige

An overlooked parameter

I rarely hear people ask, “What kind of people will this job put me around?”

A variation on this question is, “What mindsets or attitudes will this job reward?” or, “What kind of person will this job/industry encourage me to become?”

It’s important to ask these questions because you’ll almost certainly adopt some of these attitudes.

And if you don’t want to be like the people who succeed in the industry or job function, maybe that’s a good indicator that you shouldn’t join the industry.

Environments can shape your behavior

It’s no secret that people become like the others around them.

If you consistently spend time in a particular environment, chances are that you’ll become like the people you’re with.

Some careers tend to attract people with specific qualities. To take an extreme example, an Olympic athlete is almost certainly much more driven than someone working at the DMV is.

If you don’t want to be like the people at a particular company or in a specific industry, then maybe you shouldn’t join that company or industry.1

The same point is perhaps more obvious when it comes to hobbies, because hobbies are more of a voluntary time expenditure than are careers.

Industry as a proxy for important values

The industry you choose can be a proxy for finding others who share some of your core values. For example, if you work in clean energy — whether you’re an engineer, a marketer, or a journalist who writes about CleanTech — you probably care more about the environment than the average person.

Of course, this isn’t always true. For example, many teachers don’t like kids; they just teach because they don’t have a better alternative. On the flip side, there are excellent teachers.)

However, many industries and job positions tend to attract people who are similar to each other in some important way.

What might you look for in colleages, peers, or bosses?

Qualities you may consider in colleagues include:

• Drive / ambition

• Care for a bigger cause (such as the environment, a religious cause, etc)

• Ability to get things done

• Respect for colleagues (teamwork versus constant competition inside the firm)

• Stress level (you might want a low stress level, for example)

• …and many more

Note: you may not prioritize all the above criteria

Maybe you want some of these and not others.

For example, maybe you don’t care if your colleagues care about a bigger cause, because you don’t derive your life’s meaning from work.

Or, maybe you don’t care whether your colleagues are driven or ambitious, because you’re primarily interested in collecting a paycheck from your employer and using that money to fund the things you really care about, separate from your job.

Does the job form people, or does the job pre-select for those people?

In some sense, it doesn’t matter.

Here’s why: either you’ll make it to the top and probably develop that quality, or you’ll be weeded out.

For example, let’s say you’ve chosen to participate in an industry where there’s lots of backstabbing. To get to the top, you basically must backstab your colleagues. If you find this to be objectionable, either: 1. you’ll fail at the job or 2. you’ll betray your principles.

To me, the above proposition seems to be a lose-lose proposition. (Do you disagree? If so, please let me know in the comments!)

What next?

Personality and character are intangible, but they’re still very important. The people whom you spend your time around influence how you view the world, yourself, and others. They can change you.

So next time you’re considering where to spend a bunch of your time, consider paying attention to what kind of people you’ll be around.

Ask yourself these questions, and see what your answers tell you:

• “What kind of people will this job put me around?”

• “What mindsets or attitudes will this job reward?”

• “What kind of person will this job/industry encourage me to become?”

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Starting an internship or your first job right out of college is often exciting — but the corporate world can be quite different from school.

I’ve written on a similar topic before, but I haven’t covered all the below points yet – things which I wished I’d known during my summer internships and jobs.

These things include:

1. Your team might not have a clear plan

2. Managers often remember your attitude, not your “expertise”

3. Don’t broadcast your inexperience

4. Ask to do more things you’re interested in

5. “Bringing the coffee” (digitally) may be part of the actual job

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Your team might not have a clear plan

Your team might seem like they don’t know what they’re doing. And maybe they don’t. Maybe they’re still figuring out their goals and how to best achieve them.

During my junior year internship, I was on a small team. At first I thought it was my fault that I didn’t understand my role.

I gradually learned that the team didn’t have a clear vision for my role, because it was a new team. My bosses’ view of their goals kept changing, and that meant my goals changed, too.

I realized that there was no clear vision for my role. This realization helped me feel more ready to craft my own role.

Managers may lack experience

Maybe your direct manager doesn’t know what he or she is doing.

Maybe your manager hasn’t been taught how to manage an intern. If you’re at a small company, this is almost certainly the case. Consciously or not, your manager may expect you to figure many things out on your own. (I hope this blog can help both interns and managers figure out how to be more effective on their teams.)

To better understand – or craft – your role, you can ask questions and try to understand the bigger picture.

You may be able to help yourself and your manager by considering:

1. What are your manager’s goals (as they relate to the business)?

2. How can you help your manager reach their goals?

Putting in the extra thought might seem like a hassle, but it’s actually great experience for later internships and roles in business. A large part of business is actually about planning and making sure you execute on your team’s goals. (Unlike school, where the most important goals are often simply set for you, and those goals don’t change.)

Managers remember attitude, not expertise

Managers don’t rely on summer interns to be “experts” in any field. Instead, managers often care about your attitude as an intern. This often includes:

• your work ethic,

• your ability to figure things out, and

• your demonstrated dedication to adding value.

Work ethic

No one wants a lazy employee.

Almost everyone wants an employee who works hard – and finishes the work that needs to be done. I wish I could quantify what “working hard” means, but “working hard” differs a great deal by industry and firm. For example, some companies are more focused on employees producing results, whereas other companies are more focused on their employees demonstrating that they work hard.

Some firms appear to have a culture of hard work for the sake of hard work. Based on what I’ve heard from friends, this culture appears to be especially prevalent in fields like investment banking or private equity, as opposed to tech companies are large corporations like Google.[1] However, exactly what “hard work” means varies across firms.

For positions that don’t measure your success based on ‘hard work’ alone, it’s important to work hard on work that’s likely to yield results. I wrote a post about that here.

Ability to figure things out

Your boss or manager simply doesn’t have time to show you how to do everything that needs to be done.

Instead, you’ll have to figure some things out for yourself.

Nevertheless, you’ll need to ask your boss some questions. To make it easier for your manager to teach you, consider suggesting potential solutions to your boss when you ask questions. I wrote an article on that here.

Adding value to your firm

Your manager probably wants to see someone who’s committed to adding value to your company. Ask yourself, and your boss, “What’s valuable for me to do?”

Another question to ask yourself is: “Do I understand why my boss thinks this matters?” If not, you might ask questions to your boss to get a better sense of their motivation.

Refer a friend

Don’t broadcast your inexperience

I’ve met interns who introduced themselves to clients with the equivalent of, “I’m just an intern.”

Well, if that’s the way you see it, that’s how it’s going to be. BUT, if you behave with slightly more confidence, you can usually make a better impression.

Don’t over-exaggerate your experience, but there’s no reason to under-sell yourself. Your manager may suggest that you say something like, “I joined the team recently” or “My role is [insert your role here]”.

When I was an intern at Silicon Valley Bank, I began introducing myself as, “I’m on the Strategic Partnerships Team,” rather than “I’m an intern.” The more confident introduction – while just as factually accurate – made clients and prospects respond with more trust than they otherwise would. Because they trusted me more, I was able to learn more about them and how we could potentially help them. Because I knew more about them, I could better connect them to the right people at SVB.

My confidence created a win-win situation.

If you’d like to be on an interesting initiative, just ask

You can become involved in work even if you’re not directly asked to be.

If your boss or a co-worker is working on something which seems interesting, you can usually just ask how you get can involved, or what you can do to help.

Sometimes, you don’t even need to help – you can just show up to the event. (Although you should check with your boss first.)

I tried this when I was at Silicon Valley Bank. I really wanted to go a virtual startup night during which we’d network with potential startup clients. I wanted to meet new startup founders (albeit online), so I simply asked my managers if I could come. As I recall they said yes, with no hesitation. Sometimes, you can participate in interesting initiatives that your bosses wouldn’t have invited you to if you didn’t ask.

Talk to others in the company

People will often take time to speak to you as an intern, when they wouldn’t normally do so for others not in the company.

Take advantage of this opportunity! Talk to other people at the company. Ask them how they got into the business, what they like about it, what they don’t like, etcetera.

These conversations can help you understand more about whether the business – or the company itself – could be a good fit for you.

Pay active attention to what you enjoy and don’t enjoy about your role

The more you pay attention to what you like, to what engages you, and to what you want to continue doing, the easier it will be obtain opportunities doing things you like.

That’s because you’ll know how to ask for them.

Personal example

During a meeting with my mentor/manager early in my SVB internship, he asked me, “What do you hope to get out of this internship?”

I had NO idea.

I wish I had replied by saying something like, “Here’s what I have enjoyed doing in school. Here’s what I’ve enjoyed doing in extracurriculars. Here’s what I suspect I might be good at or enjoy doing at work. I’m looking to figure out what I’m good at, what I like and don’t like, and if this company could be a good long-term fit for me. I’m also just looking to learn new things.”

That would have made me seem more confident and thoughtful than I did.

Having said that, it’s certainly not the end of the world if you don’t know exactly what you want to do. Most managers realize that a lot of interns really don’t have much idea what they’re doing!

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“Bringing the coffee” (digitally) may be part of the job

During my first internship – and even my first job – I resented the digital equivalent of bringing the coffee.

For those who aren’t familiar with the expression, “bringing the coffee” to the team refers to the time before DoorDash and UberEats when interns would actually go across the street to pick up the Starbucks order.

(I’d be many digital tasks will soon be run by AI assistants rather than actual people. I recently spoke with a startup founder who said that before the advent of AI, his team would have had 20 people. It now only has 14. That’s because he has trained AI to do the work of six people who would otherwise be sending LinkedIn messages or doing other outreach!)

You might not have to literally bring someone coffee, but you probably will need to do a fair amount of work that doesn’t actually require particular skill. If you expect anything different, you may well be disappointed.

For example, in business-type roles, you’ll probably have to send out emails. Or comb through online databases for potential prospects. Or fill out spreadsheets with tedious numbers or information. Or write Excel code that doesn’t require a high level of skill. (Although now, you can probably get ChatGPT to write most of it for you!) Or formatting PowerPoints. (Can ChatGPT please learn how to do this well?!)

Although interns do much more of this work than CEOs, depending on the size of your team, the CEO is probably doing this kind of work too.

Your CEO isn’t necessarily pawning all the tedious work off on you. Instead, your CEO is probably getting you to do some of it. But they probably did (and might still do) much tedious work.

Conclusion

Starting an internship or summer job can feel overwhelming. But if you approach your role as an opportunity to shape your experience — rather than just following orders — you’ll add more value to your team and gain more from the experience yourself.

Buy me a cofee

[1] For example, one of my friends, who did a Masters of Finance degree at the MIT Sloan School, told me that when she worked for a private equity firm in Chicago, her bosses and peers wanted to see her working – or appearing to work – all the time. Even if there was no “real work” to be done. Even if she’d already put in many hours and was past her ability to be productive. On the other hand, one of my friends who’s a software engineer at Amazon says that he frequently works only 5 hours per day. I note these differences to say that no one can give generalized, hard-and-fast rules about what ‘working hard’ means because it differs so much across industries and firms.

If fear is preventing you from making a decision, try asking yourself:

“Will I regret NOT doing or trying this?”

When there’s no strong logical reason to say no, and fear is the main thing holding you back, this question can help bring you clarity.

Two personal examples

I’ve used this question at least twice in my life to make non-trivial decisions.

One was deciding where to live after college; the other was about taking my first solo vacation.

Deciding where to live

Regarding where to live after college, as I considered my options, I knew I’d be comfortable living in California, where I grew up. Although I felt curious about the East Coast, the unknown admittedly invoked some apprehension.

Did I really want to pick up and move to a city where I’d have no friends or family?

I asked myself, “If I live in California my whole life, will I regret it?”

The answer was clearly “yes.” Realizing that made it easier to decide to search for an East-Coast-based job.

I don’t regret it.

Deciding to travel

Another time I used this question was last summer, when I considered taking my first solo trip.1 Halfway through the summer, I realized that I wanted to travel, but I currently had no plans. I figured out pretty quickly that I wanted to walk a large chunk of the Camino de Santiago, through Portugal and Spain.

There were many reasons to hesitate. But the biggest reason was: I didn’t want to go alone.

Unsurprisingly, it was hard to convince friends to spend their vacation walking for two weeks carrying their belongings on their backs. I felt stuck, because I wanted to take the trip but couldn’t find anyone to go with.

Then I asked myself the question. “Would I regret NOT trying this?”

And I realized: “I’d regret NOT going more than I’d regret going – even if I travel alone.” In the worst case, I had a boring or lonely time alone. Even that wouldn’t be so bad: I’d know that solo travel isn’t for me.

Once I realized my main hesitation was fear of being bored or lonely, I saw that I could tolerate that worst-case scenario. I didn’t want it to happen, but if it did, I’d still be okay.

The “Will I regret NOT doing this?” question can’t always give you the answer to whether or not you should do something, but it can help you gain intuition about what you want. It can also help you take the next step to answering the two following questions. When you think carefully about the next two questions, you can help make sure you’re not just making a rash or impulsive decision.

Understanding downside risk

Two further questions can help you consider the flip side of regret.

• What is the downside if your decision goes badly?

• Can you handle the bad outcome?

These questions are paraphrased from billionaire Sam Zell, who noted that these are questions he asks himself when making an investment.2 In an interview on the Capital Allocators podcast, Zell described that he calculated a risk of losing $50 million in a certain deal. Of course, Zell didn’t want to lose the $50 million – and wouldn’t have invested had he thought the outcome was likely. He asked himself if he could deal with the outcome – and he could. The bad outcome did end up happening.

Zell wrote, “…from my perspective that was a very successful deal because I had identified the risk,” and “turned out … I could handle [the downside].”

Acknowledging the downside risk might help you articulate, and thus begin to overcome, your fear.

If the bad outcome would not be devastating, or if you could find a way to deal with it, you can make an informed decision that you’re willing to tolerate the downside risk.

Creating emotional distance

The question “Will my future self regret NOT doing this?” helps you put emotional distance between your present self, which has to make the decision, and a future version of yourself that will deal with consequences of that decision. The emotional distance can help you realize that the present version of yourself may be hesitating for no good reason.

Asking, ‘Will I regret this?’ gives your future self a voice in the decision—creating helpful emotional distance from present-day apprehension.

Conclusion

You don’t need to let hesitation or fear have more influence than they should.

To avoid this, ask what your future self would want. Sense-check by thinking about downside risk. You might be surprised by the clarity you get.

Have you ever used this question to help you make a decision? If so, leave a comment below about whether (or how) it helped you.

Buy me a coffee

If so, this post might be for you.

This post is intended for people who will be starting a summer internship or first corporate position. It’s a compilation of five posts which I think could be helpful to new employees – things I wish I’d read when I was just starting as an employee.

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Could this skill make you a more valuable employee?

This post explains how employees who plan ahead (instead of merely following orders) can add value for their employers, their company, and themselves.

Link to post: https://trailblazingtwenties.substack.com/p/could-this-skill-make-you-a-more

Why Managers Might Ignore Your Work: The Hidden Game Theory Behind Feedback (or Lack Thereof)

This post explains to employees that if they don’t get feedback on their work, it’s probably not personal. Through the lens of real-life examples and an explanation of the prisoner’s dilemma from game theory, I explain why manager’s incentives can differ from employee’s incentives, and what to do about it.

Link to post: https://trailblazingtwenties.substack.com/p/why-managers-might-ignore-your-work

New Roles May Require New Rules for Success

This post explores how different roles (such as school versus work) may require different rules or best-practices to become successful. For example, perfectionism may be useful at school, but can waste endless hours at work. When you’re aware that there might be new rules, you can begin to figure out what those new rules might be, instead of being stuck in your old rules.

Link to post: https://trailblazingtwenties.substack.com/p/new-roles-may-require-new-rules-for

Don't Just Blindly Follow Your Manager's Orders

Instead, learn to ask questions instead of assuming that your manager is always right. This post explains why asking for clarification can be good for employees – and their employer.

Link to post: https://trailblazingtwenties.substack.com/p/dont-just-blindly-follow-your-managers

Why isn't my hard work getting me anywhere? Hard work in school vs ‘real life’

In the real world, it’s important to figure out what to work hard on – not just plug away and assume that results will follow. Because the conditions in “real world” environments can differ greatly from conditions in school, figuring out what to work on can be more difficult. Hard work yields results in less linear fashions than in the real world.

Link to post: https://trailblazingtwenties.substack.com/p/why-isnt-my-hard-work-getting-me

Next steps

If you found any of the above posts helpful, please subscribe! Or share this post with anyone whom you think might benefit.

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People seem to think that not making a decision is “safer” than making an active decision.

Often, people fail to make an affirmative decision. They end up making a decision by not-deciding. But they didn’t really mean to.

This post aims to help us understand two reasons behind the tendency, and suggests two ways to avoid it.

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Why do we default to a decision instead of deciding?

Behavioral economics suggests two reasons:

1. Loss aversion, and

2. Status quo bias

Let’s look at each of these.

Loss aversion

The term loss aversion, in behavioral economics, means being more afraid of a loss than excited to gain the equivalent. Here’s an example: “It’s better not to lose $100 than to win $100.”

Behavioral economics studies suggest that “losing something makes you [approximately] twice as miserable as gaining the same thing makes you happy.”[1]

That conclusion comes from a study performed on college students who were given mugs emblazoned with their college insignia. The students with the mugs were invited to sell their mugs to students without the mugs. Students with the mugs demanded twice as much, on average, as students without mugs were willing to pay.[2]

Some people might call the behavior irrational, but I think it makes a lot of sense.

Here’s why: If you already have something, you’re used to having it. Psychologically, you probably feel (whether consciously or not) that you ‘deserve’ it. Practically, you may not know how to live without it.

But if you don’t already own the item, you’re not used to having it. You’re less likely to think you deserve it, and you know you can live without it.

So loss aversion suggests that people avoid making decisions because they fear losing benefits they already have.

Status quo bias

Status quo bias refers to the fact that when we have a choice to keep our current situation or do something different, we often keep our current situation.[3]

It’s often easier to keep your current situation. You don’t have to search for alternative options. You don’t have to make a change to actually reach those options.

For example,

• Staying at your current job means you don’t need to find a new one

• Staying at home for the summer means you don’t need to plan a trip

• Continuing to date someone who’s not great for you means you don’t have to break up

Change can feel risky. But avoiding change is also risky, albeit in a different way.

Is choosing the “default” really less risky?

Some people believe that sticking to the status quo is less risky than the alternative.

But sticking to the status quo ignores the risk of doing so.

It ignores the risk of boredom, stagnation, underperforming your potential, and regret.

Risks of sticking to the status quo

A risk of the status quo is that you never get to explore other alternatives.

Maybe you have a pleasant summer at home – but you miss out on the adventure of traveling with a friend.

Maybe you keep your safe, predictable job, but you miss out on other important opportunities. Maybe you don’t develop get to new skills, meet interesting people, or make more money.[4]

Potential solutions

Two potential solutions to help you make active decisions may be:

1. Surround yourself with proactive people

2. Keep track of your decisions

Surround yourself with proactive people

People tend to become like the people around them.[5] You’ve probably noticed that you start to care about things that the people around you care about, or that you start to adopt speech and behavior patterns similar to the people around you.

IF you want to become better at making active (not passive) decisions, it can be a good idea to spend time or mental energy around people who are also making active decisions.

It can be hard to find those people. I hope this article can help people find other proactive decision-makers, and we can at least correspond online even if we can’t spend time together in person. (I encourage you to leave a comment if you’re also interested in making active decisions.)

Track your decisions

Here’s one exercise to try:

1. Write a list of decisions you need (or would like) to make

2. Put the list in a visible location

3. When you make the decision, write down what you chose and why

The act of writing will force you to articulate WHAT you did and WHY.

You’ll get to be clearer with yourself that you are making a decision and what that decision is.

Conclusion

It’s so easy to make a decision without making one – so easy that we don’t always realize we’re doing it.

It’s an understandable, human response. Behavioral economics can help us explain why it occurs.

But if you want to make difficult, active decisions, you can try hanging out with other active decision-makers, and tracking your decisions.

Did anything in this post resonate with you? If so, please leave a comment!

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[1] “Nudge: Improving Decisions about Health, Wealth, and Happiness” by Richar Thaler and Cass Sunstein.

[2] Ibid.

[3] The term was coined in 1988 by behavioral economists Samuelson and Zeckhauser. https://www.researchgate.net/publication/5152072_Status_Quo_Bias_in_Decision-Making

[4] Of course, simply changing your job doesn’t mean that you will automatically develop new skills or meet interesting people or make more money. However, if these are goals you care about, it’s very likely that you can figure out how to make at least some of them happen in your next position.

[5] This can show up in surprising ways. For example, a 2007 study suggests that if your friends gain weight, you’re also likely to gain weight.

We all get advice. But what makes advice actually helpful?

Bad advice can come from people who mean well, but who:

• fail to recognize their own biases or

• fail to ask questions and understand your situation

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When you recognize features behind good advice-givers, that can help you figure out how to seek and receive good advice.

Seeking information is pivotal to good decision-making. Some people have the tendency to want advice from others along with those decisions they seek.

If you’re someone who asks frequently for advice, you might ask yourself, “How can I tell if this is good advice?”

I’ve found a couple things to be helpful when seeking advice:

1. Understand the other person’s biases as best you can

2. Make sure the other person understands relevant details about my situation

Conversely, if I’m asked for advice, I try to understand the other person’s situation and reveal my biases before offering an opinion.

The advice-giver should try to make their biases clear

Advice can become a lot more useful when the advice-giver makes his or her biases clear.

“You have to take everything I say with a grain of salt,” one of my friends, Z, told another. He was in the military, and he was giving advice about whether the person in question should consider joining the army. “I’m in a period right now where I’m second-guessing myself and feel like I haven’t gotten what I wanted out of the army. Like, my experience let me down.”

He paused. “So, just keep that in mind as we’re talking. I’m trying not to seem too bitter, but honestly, I am.”

Z’s awareness of his emotional state mirrors an idea from Laura Huang’s work. In this article, Huang talks about how important it is to give ourselves time before we make a difficult decision, so that we don’t end up making an overly emotional decision.

My friend Z was essentially trying to do something similar. He couldn’t put time between his emotions and the situation – because he was in the midst of it – so instead, he explictely warned his friend that he couldn’t fully overcome the emotional barrier.

Advice to their previous selves

Sometimes, people might seem like they’re giving advice to you, but they are really giving advice to their previous selves.

They’re thinking about their preferences, their desires, and their goals – and then assuming you share those. Their advice seems to be about you, but it’s really not.

Here’s an example.

“You should go to Venice to study abroad,” one of my Stanford alumni friends told me, when I was in my sophomore year of college.

“But I don’t want to learn Italian,” I said. “And I’m not really interested in Italian culture right now. I was thinking of going to England, if I study abroad at all.”

My friend launched into an explanation of why my experience in Italy would be more exciting than in England.

She didn’t realize (perhaps because she didn’t ask) that I wasn’t looking for an exciting experience. Instead, I was looking for a place where I could continue my studies while getting to become friends with foreign students. There would be a huge language barrier in Italy, and I had no interest in investing time learning Italian. There would be little language barrier in England.1

Understanding your personal circumstances

When you’re trying to get advice or give advice, it’s important to realize that both your current circumstances and your future goals may differ from those of the person in the situation you’re in.

In such cases, it can be helpful for you to explicitly ask the other person what their goals were in the specific situation.

Asking for disconfirming evidence

When you get advice like, “I had a great time – that means you will too,” you may ask dis-confirming questions such as, “What did you dislike about your experience, and what might I dislike?”

For example, when I was a senior in college trying to decide whether or not to accept a job offer, I spoke to some of the people doing the job I was considering. “What don’t you like about your job” I asked them. Their answers helped me see some of the negatives of joining the company, which helped me make an informed decision.

Conclusion

Whether we’re giving or receiving advice, perhaps advice works best when we treat it as a conversation—not a conclusion.

And good advice isn’t perfect. Instead, it’s honest, self-aware, and shaped around the person who needs it -- not the person who gives it.

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Startups are glamorous. Cool. The dream career.

At least, that’s what many people seem to think.

But that caricature of owning a startup can ignore the reality. In this article, you’ll hear from five startup founders about four important skills in startup life.

We’ll discuss these skills, and then suggest a resource at the end to help you if you’re considering starting a startup.

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Essential skills for founders

You probably know that founding a startup will be hard work. But you might not know that you’ll also have to become good at:

• Making decisions under uncertainty

• Becoming a generalist

• Managing unstructured work

• Maintaining mental and emotional flexibility

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Making decisions under uncertainty

Decision-making is hard – partly because sometimes, it’s impossible to know if you made a good decision. Founders must find a way to become “okay” with the uncertainty.

“You should only run a startup if you LOVE ambiguity,” founder Katie Kirsch said. “You’re constantly making decisions, and you often don’t know if you made the right or wrong decision.” The world might give you feedback on your decision. Or it might not.

Katie’s coaching startup, lume, helps ambitious people solve the problem of uncertainty, by empowering clients (including founders) through coaching services.

Katie described the myriad decisions that she makes each day. Decisions about sales, operations, team building, pricing the product, and scaling the company. And because the company has never been run before, there’s no “roadmap” Katie can follow.

Decision-making without clear evidence

Even data-driven insights can be ambiguous, forcing founders to trust their instincts.

Shanee Benjamin reiterated how difficult it can be to make decisions without clear evidence. Her product is a dry shampoo for the African American community – a product that she created because she couldn’t find anything that suited her well.

But even when she solicits feedback from her active Instagram community, it’s hard to get clear answers. “I posted a poll to see what [the community] liked the most. But Instagram users didn’t give me a clear answer.” She’s tested multiple iterations of the shampoo – “but I’m not the only customer.”

She’ll have to make a decision, and she’ll have to sit with the ambiguity of never quite knowing whether it was right.

Becoming a generalist

Many founders are specialists—engineers, marketers, product designers. But to succeed, they often need to deal with many more aspects of the business, such as HR, taxes, and sales.

In short, if it needs to be done, you have to do it – and you have to figure out how.

Ryan Hughes, who was trained as a software engineer at Northeastern University, has had to learn a whole host of new skills. with a degree in software engineering. He runs a software consulting startup, Fan Pier Labs, and had to learn to negotiate contracts, and do taxes for a small business -- among other things.

“You’ve gotta learn as you go,” Ryan said. He had to learn to network and to delegate, including networking with potential clients and pulling in other dev shops.

Managing unstructured work

There’s always more work to do – and there’s no clear end goal. Prioritization and managing unstructured work is key. You must always be working on multiple things.

“There are always fires to put out,” said Jaime Paris Meseguer, founder of pet care startup Pronova. “You go to bed on a fire and you wake up on a fire.”

"Your plate has to be pretty big. You need to take on a lot of tasks at once, and focus on a subset of them at a time,” Jaime told us.

But identifying the right guiding questions to help you figure out an effective use of your time is KEY.

At this stage of his company, Jaime has identified the right questions to ask to help him prioritize his activities and effort. He asks two questions:

1. Does the activity prove the tech works?

2. Does this activity prove people will buy the product?

Of course, the two questions will differ for every founder, but learning to ask the right questions is key. Jaime identified an over-arching question to help him prioritize his work: “Does it make the boat go faster?”

Every founder must develop their own questions to guide them toward their goal.

Managing mental and emotional flexibility

Running a startup is hard.

You always feel “on”. You’re torn down by customers, and users, and other people.

That’s what Lucas Arfinengo – CEO of Daby – told us. He describes his company as, “Coursera meets Unidays.”

Lucas is passionate about what he’s building, and that passion is necessary to help him combat the mental toll. He thinks founders should consider what sacrifices they’re willing to make.

“Are you ready to make drastic sacrifices?” he asked, “I’ve lost a lot of friendships, sacrificed a lot of personal net worth—95% of my net worth as of now to bootstrap.”

Prepare before you plunge in

“DO YOUR RESEARCH,” Shanee Benjamin told us. “Before you go out there and create a product, interact with your community and target customers and how to make it better for them.”

Lucas told us: don’t assume that just because you build a product, your target market will care about it. “You have to be wary: you can’t take your assumptions without validating them.”

In other words, make sure there’s demand before you build.

One suggestion and one resource

Suggestion on decision-making

All of the founders we spoke with mentioned that one key factor in making good decisions is: getting advice from people you trust. (Katie’s company is built around this idea, among others!)

A supportive community of advisors and peers can be crucial to help you make good decisions. Often, your community will see possibilities you did not think were possible. Foster a community of peers, advisors, friends who you can go to when you need to bounce off ideas.

You can ask questions like:

1. “What is your process for making decisions in your day-to-day?”

2. “Walk me through a difficult decision you’ve made recently. What went well? What would you have done differently?”

This can help you recognize the range of decisions that are possible.

Resource to learn more about the startup journey

Realist Lab is a startup accelerator to help potential founders learn more about the startup journey.

Realist often accepts founders who are at the idea stage. Over a course of two months, Realist helps you think about customer discovery, idea validation, and the needs of your product.

As Shanee and Lucas noted, building a product is HARD. Realist aims to help you de-risk the earliest parts of the founder journey. You could even do it while you’re still employed full-time.

Disclosure: Christian does work for Realist and is shameless about encouraging potential founders to apply. Realist offers a variety of programming for idea-stage founders but does not guarantee any funding, venture or non-dilutive grants.

The program could help you crystallize how to build a product with market demand and you go after it firing on all cylinders. Or, after talking with potential users and investors, you determine that this might not be the right time.

You may benefit from knowing that you gathered more information -- and did so without spending 25K on an app with zero traction. If you’re not sure what or how to build, I would highly encourage looking into Realist Lab and other idea-stage accelerators.

Are you ready to embrace ambiguity, master a bunch of different skills, and make decisions on the fly? If you’re still feeling energized after reading this, reach out to a founder, join a startup event, or explore programs like Realist Lab to take your first step.

Was anything in this article helpful? If so, please let us know in the comments. Or, email trailblazingtwenties.substack.com.

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A friend and I recently met a high school senior visiting MIT who was trying to decide between two colleges: Stanford and MIT. (I’ll call him Nathan, although that’s not his real name.)

Nathan asked us both about our undergrad experiences at Stanford. He asked MIT students who were present about their experiences at MIT.

“There’s no wrong decision,” my friend told Nathan.

I remembered how stressful the college decision can be. And I knew that Nathan was going to do his best to make a good decision, but he was going to do so with largely incomplete information.

Although he’d never have complete information to make his decision, I think he’ll be much better off continuing to ask questions, because he’ll obtain more information which may help him.

Furthermore, the process of asking and deciding may help guide future decisions.

Incomplete information when making important decisions

Once I realized why it would be so challenging for Nathan to make an informed decision, I better understood why it’s nearly impossible to make highly informed decisions in other areas of life.

It’s usually impossible to make fully informed decisions because we have:

• Incomplete (or conflicting) data

  • For example, when Nathan visited MIT, he only had a snapshot in time

• Incorrect data

  • For example, when Nathan asked others about their experience, they may have told him an untruth

• Important outcomes are largely unpredictable

  • Even if Nathan knows his priorities, he can’t know how specifics will play out

Let’s look at each of these.

Incomplete (or conflicting) data

Even if Nathan knew exactly what he wanted from a college experience, it would have been nearly impossible for him to obtain reliable data on all the parameters.

Parameters important to Nathan seemed to be: engineering program, social life, and Jewish community. And he was trying to gain more data about these.

Nathan was visiting MIT on a weekend in April to obtain more information about all these things. And I’m sure he gained more insight than if he hadn’t gone. But on the other hand, he was only gaining data about a small snapshot in time, rather than on the whole undergrad experience.

He did his best to speak to multiple people about their experiences. But unfortunately, he had no way to know how accurate those responses were.

Furthermore, not only did Nathan receive incomplete data, he received conflicting data. He asked my friend, who is part Israeli, about the Israeli community at MIT. (Note: Israeli and Jewish are not synonyms. They’re correlated, but not the same thing.) Nathan’s dad is Israeli, and Nathan speaks fluent Hebrew.

My friend told Nathan that there wasn’t much of an Israeli community at MIT. But about 40% of the people at the event Nathan attended was Israeli. In this case, Nathan would have to do some digging to figure out whom to believe: my friend, or his own eyes.

Incorrect data: people may not tell you the whole truth

When you ask strangers about their experience or their advice, they may give you advice that is either highly biased or irrelevant to your situation. Even worse, they may tell you things that are misleading or false.

I witnessed plenty of misleading information during college. For example, I once emerged from an Economics final, entered the bathroom right outside the classroom, and saw a girl sobbing in front of me in line. “I failed the final,” she wept (although obviously she couldn’t know that since the finals hadn’t yet been graded).

A few days later, as I recall, a younger student asked the girl about the class and how the finals had been. “Oh, it wasn’t bad,” she said.

This girl’s response was, presumably, not helpful to the younger student, who’d now been given incorrect information about the girl’s experience of the final. (Imagine how bad the younger student might feel if she believes that the class will be “not that bad” and then emerges from the final crying.)

So, is it pointless to ask questions? Not necessarily. There’s not a more reliable way (that I know of) to get the needed information. Just be aware that you may not receive correct information all the time.

To combat the potential for incorrect information, you may ask a wide variety of people to get a wide variety of experiences. You’d hope that similar to the Law of Large Numbers, if you ask enough people, you increase your chances of getting true and relevant results.

Important outcomes are often unpredictable

Important outcomes of your college experience may include: the friends you make, the job opportunities you source, homesickness, and opportunities for independence.

Friends

Some of the best parts of my college experience included the friends I made. Many of my friends say the same thing.

And it is almost impossible to predict, in advance, who these people will be. Some of my friends clicked with their best college friends within the first few weeks. For others, it took closer to two years. It’s not necessarily something you can predict in advance.

Nevertheless, visiting your prospective college can help you get some feeling for the type of people who are there. (Of course, it can be hard to get an apples-to-apples comparison. For example, MIT and Stanford often do not have midterms the same week as each other. So Nathan may find that the school which is currently having midterms has students who are more stressed. This may not be true in general.)

Job opportunities

For other friends, the job opportunities they got from college were really important. However, these cases tended to be when people networked with specific professors. Again, unless you already know what you want to study or have a personal connection to a specific professor, networking opportunities can be difficult to predict in advance.

Homesickness and independence

Some of my friends found their college experience difficult because they struggled to be away from home. Although “distance from home” is extremely quantifiable, “how homesick I’ll be” is not. Unless Nathan has been away from home for an extended period of time before, this will be hard for him to predict. Location may be hard from him to factor into his decision, because his family lives in Miami, not Boston or Palo Alto.

Some of my other friends found that the independence they gained during college was one of the most valuable parts of their experience. If that’s the case for Nathan, he’ll likely gain that at both MIT and Stanford.

Summary

Ultimately, Nathan—and all of us—can never make a fully informed decision, but we can make the best decision possible with the data at hand. Embracing uncertainty doesn’t mean avoiding decisions; it means making decisions with the understanding that they are always somewhat imperfect.

So, whatever decision faces you, proceed with confidence in your decision-making!

Do you know a high school senior who may benefit from this article? If so, please send it to them!

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You probably agree that making decisions can be stressful.

Major decisions can be stressful (like: ‘Should I move here? Or take this job? Or date/marry this person?”). Minor decisions can be stressful (“How many people should I invite for dinner? Who? When?”).

Unfortunately, that stress means that sometimes people are too paralyzed to make a decision. So they simply fail to act.

I’ve found three ways helpful to reframe decision-making so that it can be less stressful.

Reframe #1: I’m lucky to get this decision-making practice

When you’re feeling stressed about making a difficult decision, instead of focusing simply on how stressed you are, you might consider thinking: “I’m lucky to have this time to practice making a difficult decision.”

One way to get better and more comfortable at making decisions is to practice making decisions, and take note of the process you used.

A year ago, I had to make a difficult decision about whether or not to take a job. I could either: 1) take the job as it was offered, 2) decline the offer, or 3) negotiate the offer. I was working with limited information and under time pressure. I didn’t know what to do.

I spoke to several acquaintances about the struggle the day I had to make the decision. “No matter what happens,” I said, “at least I’m getting practice making the decision.”

I realized that the process itself – regardless of the outcome – was valuable. That helped me recognize that there was a purpose to some of the struggle I was going through.

Reframe #2: There’s no “best” choice

Many of the decisions we make have no “optimal” outcome.

For example, what is the “best” city to live in? Or the “best” job to have? Or the “best” table at the restaurant?

Clearly, there’s no right answer to the above questions, in most cases. There are pros and cons to each.

When I recognized the fact that there’s often no “best” decision, I felt freedom to stop second-guessing my decisions.

Above, I mentioned that one way to get better at making decisions is to make decisions, and then make note of the process you used. But in cases of small decisions, I don’t think this is necessary. Instead, what’s helped me more is to realize that it’s not a make-it-or-break-it decision, and then try to be comfortable with the outcome.

Reframe #3: Considering options isn’t a waste of time, even if you don’t change course

Is it a waste of time to consider other options, if you then don’t choose them?

For example, is it a waste of time to consider a new job if you end up staying in your old job, or to consider moving even if you don’t end up moving?

I don’t think it’s a waste of time. That’s because: even if you end up staying with your old course of action, you’ve now made an affirmative decision to do so.

If you’re considering changing course, there’s probably a reason you’re considering that.

Generating other options can you understand available opportunities. And, as you work through the process of figuring out whether to choose one or the other, you will probably realize that you hold values which you didn’t realize you held.

In other words, the process of considering options and making a decision can help you understand your values. Even if you choose to go with the original decision, you’ve probably now clarified a value that you didn’t know you held. And you’ve made an affirmative, active decision (instead of a passive decision) to stay in your current situation.

Summary

I’ve found these three re-frames helpful.

Seeing decision-making as practice – View decisions as opportunities to strengthen your decision-making skills. Each decision, regardless of outcome, can be valuable experience.

Realize there’s often no best choice -- Many decisions have no single optimal answer. Recognizing this can free you from overanalyzing and allow you to confidently move forward.

Be comfortable rejecting options you consider – Even if you ultimately stick with your original choice, exploring alternatives helps clarify your values and makes your decision intentional and active rather than passive.

Have you ever felt like you’re doing everything you can, but still failing?

If so, perhaps you’re subconsciously believing messages which are more harmful than helpful.

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While self-empowerment messages can be motivating, they can also be misleading when taken in the wrong context.

Were you raised on messages such as:

“Work hard enough for long enough, and you’ll succeed” ?

Or:

“You’ll get out of it what you put into it.”

While such sentiments are certainly true at a specific time and a specific place, they aren’t universally true – and pretending that they are doesn’t help anyone.

A problem with the mindset “try hard enough, and you’ll succeed”

The problem with this mindset is that it’s simply not true in many cases.

When you believe that you get out exactly what you put in, you might blame yourself for your failures when failure isn’t your fault. (I’ve known some people who become depressed or overly self-critical when they fail to get their preferred job, for example.)

In many situations, our effort is only one factor out of many

We probably learned the messages above in contexts where effort was a KEY factor to help us reach an outcome.

But now, you probably find yourself in situations where your effort is a much SMALLER factor in achieving the outcome.

This can be true when you apply for jobs. When you apply for a job, you could be a ‘perfect’ candidate. But maybe there are two candidates who are just a little more ‘perfect.’ Or maybe the candidate who’s chosen is the senior partner’s nephew.

This can be true when you’re dating. Maybe you have a romantic crush on someone. You’re impressive, well-spoken, and good-looking. You do your best to win over the person you like. But for whatever reason, they’re not won over. Maybe they’re already dating. Maybe they’re just not attracted to you – through no fault of your own. Maybe they learned some irrelevant information about you that you couldn’t control.

A more helpful solution: realistic view of the difference our effort makes

Instead of assuming that if you do your best, you’ll automatically succeed, a helpful reframe can be:

“I’ll do the best I can, but there are so many other factors that influence how things come out.

“Even if I don’t succeed, I owe it myself to give this endeavor significant effort.”

Obviously, outcome is important. But in MANY situations – such as applying for jobs, finding a spouse, finding roommates, making a sale – your effort is only part of the equation. You may never fully know how much your effort influences the outcome.

A caveat: don’t let yourself be a victim

“But,” you may be thinking, “I can’t just let myself be a victim of circumstance. I have to look for ways to improve.”

I completely agree.

It’s hard to draw the line between empowering ourselves, and between being a victim. To help yourself learn from your experiences, you can ask yourself simple questions such as:

• “What did I learn from this?”

• “What do I want to do next with this information?”

• “What did I do well?”

“What do I wish I’d done differently?”

What other questions have you asked yourself?

Summary

Your effort is important – but it’s not the ONLY important thing.

You can give something your ‘all’, but it might still not go the way you anticipated. And that might not be your fault.

So, definitely reflect on your performance and your process. But also, try to realize that you can do a near-perfect job, and still not achieve your desired outcome – due to no fault of your own. It’s just the way the world works.

It sounds counter-intuitive, but constraints can actually be freeing.

When we don’t have constraints, we may face:

1. choice paralysis, and

2. a tendency to second-guess

Anecdotal evidence

“I wish someone would give me some constraints!” exclaimed my 28-year-old friend C. She works at a publishing company, and is a creative writer who just self-published a novel.

She has strong church community and many friends in the Boston area, but also feels restless.

“People say I can do anything,” she remarked, “but part of me wishes I just had more constraints…”

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Choice Paralysis and the Jam Study

One flip side of “lack of constraints” is more options. More options can make it harder for people to make decisions, even about seemingly simple issues like what flavor of jam to choose. In the year 2000, researchers conducted a study in which they set up tables of jam for sale on two subsequent days. The first table had 24 flavors of jam, as compared to the table on the second day, which only had 6. The table with 24 flavors attracted more people – but the table with only 6 flavors sold TEN TIMES as much jam!²

If fewer constraints make it harder to choose something as unimportant as a flavor of jam, no wonder it’s difficult to choose something much more important!

Problem with no constraints: frequent second-guessing

Even when constraints can make us unhappy, they may prevent us from second-guessing ourselves.

After all, if you make a choice because of an external constraint, that makes it harder to blame yourself.

One example of this occurs in the classic film It’s a Wonderful Life. The main character, George Bailey, played by Jimmy Stewart, wants to travel the world. George is about to go on a European tour before college, but his dad has a fatal stroke. Then the bank he’s in charge of faces a financial crisis. Event after event in his life forces George and his wife to postpone their trip, which they never get to take.

It’s unfortunate that responsibilities keep getting in the way of George getting to travel, but responsibilities combined with his clear sense of priorities means that George doesn’t have much room to second-guess himself.

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Be clear to yourself why you’re making trade-offs

If you’re prone to second-guessing yourselves, what are some steps you can take to do this less often?

One suggestion is: be clear about why you’re making tradeoffs.

For example, last year, I did an exercise where I tried to create a grandiose vision of what my life could look like. One possibility was a life of travel.

But I realized a huge tradeoff of moving frequently is that it’s harder to build deep relationships. If I want deep relationships, I can’t move all the time. And I value deep, in-person relationships a lot. So, I probably will never end up moving around the world.

But if ten years down the line, I wonder why I didn’t spend a few years of my twenties traveling the world, I’ll have a clear answer for myself: I wanted to invest in my relationships and my career. Other people may make different choices, and that’s great. It can really help to know what tradeoffs you’re making.

Too much of a good thing: the connection between dompaine and constraints

Science has found that easy access to dopamine can actually be bad for us.

Similarly, perhaps too few constraints can be bad for us.

Easy access to dompaine can cause harm

Anna Lembke, Stanford psychologist and author of “Dopamine Nation,” is an expert in the science of addiction. She writes and speaks about how, in many ways, humans are not wired for a world of abundance.

Lembke observed, “The problem is, in today’s modern ecosystem, those things [food, clothing and shelter] are provided. … [O]ur brains are not really wired for that.”¹ Instead, humans are built to need to work harder to derive physiological pleasure, and now we can attain high doses of pleasure through almost everything we do. Our smartphones provide constant dumps of “digital dopamine.” We have easy access to foods full of fat, sugar, and salt. Unlike our ancestors, we don’t need to work hard to obtain physiological rewards – and this messes with our dopamine levels.

In fact, too much easy access to dopamine may, according to Lembke, be one of the causes of high depression and anxiety rates.

It’s easy for humans to become controlled by their desire for quick dopamine hits, rather than freed by the experience.

Just like “too much dopamine” is a problem for many people, “lack of constraints” is a problem for many people.

Just like many people are constantly seeking more dopamine (whether or not we’re aware of it), many people find that a wide range of possibilities doesn’t necessarily help us find what we want.

Summary

Lack of constraints can create inaction, because of choice paralysis, and the tendency to second-guess ourselves.

One way to mitigate second-guessing is to be clear with yourself about when you’re making tradeoffs, and why you’re making those tradeoffs.

But we didn’t solve the problem of: what do I do with too few constraints?

What thoughts, questions, or life experience do you have? Feel free to share in the comments below!

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1https://www.npr.org/transcripts/1030930259

2https://hbr.org/2006/06/more-isnt-always-better

“Does my hard work still matter, and how important is it?”

Even if working hard got you to your current position, asking this question may shed light on your new role.

In a previous post, we examined the fact that when you enter a new role, the ‘rules’ for success may change.

My understanding of hard work has required a similar re-evaluation.

Working to figure out WHAT to work on

In the corporate world, you often have to invest effort to make sure you’re workign on the right things.

In school, it was usually enough to put your nose to the grindstone and work at the assigned task. You must execute.

Not so in the corporate world.

Instead, you must often figure out what to work on. You must plan AND execute.

The fact that you have to both plan and execute means that if your plan is poor, exhausting yourself on execution may not ultimately serve your goals.

In other words, if you do a poor job planning what to work on, your hard work might not make any difference.

What about goals in school means that execution (not planning) is enough?

When you are in school, the formula, “If you work hard, you’ll succeed” is fairly accurate. There are several conditions which made it fairly certain that if students worked hard, they’d succeed.

These conditions include:

• Defined goals that do not change

• Metrics upon which to evaluate progress toward those goals

• One ultimate, authoritative evaluator of your work

• A clear, charted path regarding how to reach the goal

Defined goals are something like, “Get an A in this class,”; metrics include the grades themselves and the grades on tests leading up to the final grade; and the ultimate, authoritative evaluator of your work is often a teacher or professor.

The clear, charted path regarding how to reach the ultimate goal – “Get an A” is broken down into lots of mini-goals, which usually includes understanding material taught in each class.

Although working to understand material taught in school can certainly require an awful lot of work (I know it did for me), students more-or-less have the guarantee that as they work to master each concept, they will progress toward the ultimate goal1 (at least, the “ultimate goal” in this school context).2

Why doesn’t hard work in the corporate world guarantee success?

Simply put, maybe you’re working on the wrong things.

But you can’t always know that in advance.

In the work world, unlike school, you may face some of the following issues:

• Vague goals, or goals that do change

• Fewer or lack of metrics

• Multiple authorities

• No clear path to reach the goal

The above conditions occur not because anyone is trying to make your life difficult. In fact, the bosses to whom you directly report may not be thinking of you at all! If goals or metrics are unclear, that may be because they simply haven’t been developed – not because anyone is trying to hide them from you.

Goals may be vague, or they may change, because the nature of business is more vague than is school.

Similarly, business or corporate goals are more multidimensional than school goals, so there may be fewer metrics.

There may be more stakeholders making business decisions – not just one professor or teacher deciding your grade. In many firms you may work for multiple bosses before they meet to decide whether you’re promoted or not.

In many cases, there’s no clear path to reach the goal because perhaps the goal hasn’t been reached before. This is especially true if you’re at a startup or new arm of a business.

In fact, a great way to add value in the work place can be figuring out how to create a clear path to reach the goal. (How to help your company figure out a clear path to reaching its goals is a worthy topic, but deserves an entire discussion of its own.)

One solution: Work hard, but also re-assess frequently

However, in addition to working hard, you may need to continually re-assess things including:

• Am I working on the right things?

o What are some indicators that I am working on the right things?

 Results in the workplace, approval of the bosses who matter, etc

o If I’m working on what I think are the right things and not getting results, why might that be? Is there anything I need to change?

• If I’m not working on the right things, what could I work on instead?

o What do my bosses think is important?

o What does the organization need / think is important?

Caveat: hard work may have “lumpy” payoffs

The hard fact is that in many areas of business — including sales, marketing, research, and development, — a great deal of work will yield no visible payoff. Your hard work may have “lumpy” payoffs. In other words, some of your hard work may be initially wasted on things that don’t matter.

Here’s an analogy. Suppose you know you lost your keys in a grassy field, but you don’t know where. To find them, you have to search the field carefully. Unless you have the good luck to find them immediately, you will spend a lot of time and effort looking in places where the keys are not. In one sense, this is “wasted” effort. But you can’t know that it’s “wasted” until you look and see that they’re not there. Because there’s no way to find the keys without looking in places where they’re not, the effort isn’t really wasted. But the effort, until you find the keys, will seemingly produce no result. (Actually, it produces the result that you learn many places where the keys are not. Much of real-world work is like this.)

But if you’re trying to solve problems with no well-defined solutions, you are naturally going to go down wrong paths.

And this is just part of the journey. When you know to expect it, you may be less put-off when it occurs.

I suspect that hard work with no immediate payoff, or hard work that feels wasted, may be especially common for people in their 20s who are trying to figure out what they’re good at, what they like to do, and what work environments they thrive in.

Does “hard work with no immediate payoff” resonate with you? If so, please leave a comment! We’re in this together.

Summary

Hard work is important in the real world, but it’s also important to figure out what to work hard on. Because the conditions in “real world” environments can differ greatly from conditions in school, figuring out what to work on can be more difficult. Hard work yields results in less linear fashions than in the real world.

But, that doesn’t mean that hard work isn’t valuable. It just means that you must learn to plan and re-assess as well as execute.

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You spent hours tailoring your resume and cover-letter to fit this company. You had an initial phone screening. You thought you did well.

But then you receive a standardized, form rejection letter in your inbox.

You’re probably disappointed – which is entirely natural. I felt that way more times than I can count.

I used to think that companies should avoid sending form rejection letters– but now I see the benefit of them.

Would you rather receive zero communication, or would you rather receive a standardized rejection?

If you’d rather receive a standardized rejection, you probably see the value in rejection letters. Standardized rejection letters make it more likely that you get an answer at all.

It’s a matter of economics. Interviewing is costly for companies. Standardized rejection letters are a low cost way for companies to tell you no.

Without standardized rejection letters, potential employers might ghost you completely.

Employers may ghost you because they are overwhelmed

Standardized rejection letters help would-be employers make sure that you actually get a response.

If you try to be sensitive to other people’s feelings, and you’ve ever had to send an email to someone telling them that you’re not going to go ahead with their application – or even that you’re not going to buy from them – perhaps you know a little about how difficult it can be to tell this to someone.

It can be painful for the potential employer to say no

I recently felt the difficulty of telling two vendors that I wouldn’t be using their services.

Given my experience, I imagine it must be just as difficult for potential employers to tell candidates – after

I’d submitted a request for a proposal to three mail-houses to send direct mail letters to over 30,000 addresses. I’d had several back-and-forth emails with each vendor. I’d even asked each vendor to put me in touch with three happy clients – and each vendor did.

I spoke to some of those happy clients, all of whom had good things to say.

But in the end, I could only choose one mail-house.

I found myself delaying for days telling two of the mail-houses that we wouldn’t be using their services right now. I felt bad that they’d spent their time giving me information, but that I wasn’t going to use their services. I knew, intellectually, that I wasn’t letting them down, but I felt like I was. So I was pushing this unpleasant task to the end of my to-do list each day – and it wasn’t getting done.

But I thought: How would I feel if I were them? I’d rather get some feedback or communication than be ghosted. I realized that the kind think to do was to actually email them and communicate that I appreciated their effort, but the company I worked for wasn’t going to go forward with their services.

I wished I had a template email. So I asked ChatGPT to draft something, then almost entirely re-wrote the draft. I ran it by my boss to check the tone of the email, because it still didn’t feel right. He re-wrote it again, with suggested changes that made it much better.

I sent the email to the two mail-houses whose services we wouldn’t be using yet.

One of them emailed me back within hours, saying she appreciated the communication. So I saved the email for future use by anyone in the company who might need it.

Summary

Although it sucks to get a standardized rejection letter, it’s better than getting no response at all. The fact of a standardized rejection letter enables you to have actual closure, instead of gradually concluding that you’re never going to hear.

Standardized letters help would-be employers or vendors overcome some of the inertia that is natural in telling a good candidate “no” or “not yet.”

When you enter a new environment, you won’t automatically know the “rules” for success, and no one is going to tell you.

By rule, in this context, I mean the practices, habits, or even assumptions, which – if you follow them – generally lead to success.

No one’s keeping these rules a secret – but they might not know them. Or they might not think to tell you.

You may save yourself a lot of heartache by actively trying to figure out the new ‘rules’ of your new environment or role.

If you don’t do this, you may be stuck in paradigms that worked well in one context—but can actually hinder your success in the new context.

New rules in a new environment

One example of a ‘rule’ that changes is the rule regarding self-promotion. When you leave school and enter the corporate world, appropriate self-promotion goes from being a potential negative to a virtual requirement.

Many of my friends and I grew up learning that we should work hard, but stay humble about it. We were taught that if we did excellent work, that work would speak for itself.

We were each surprised to find that in the corporate world, the opposite was true.

Each of us, in fields ranging from investment management to screen-writing discovered that if we did good work but didn’t promote our good work, that good work might go entirely un-noticed. Someone who did less-good work, but promoted it, might be praised.

We discovered that it wasn’t enough to work hard and do good work—we also had to make sure that our respective managers knew we had done it.

New rules in a new role

New rules are need in many other transitions, too. For example, new rules might be needed when you become a manager. Managers are often people who succeeded at their previous role, such as that of a software engineer, and have been promoted to managing a team of, for example, software engineers.

But managers often haven’t been trained as managers.

So when a successful software engineer becomes a manager, he’ll almost certainly have to learn a lot of new skills. For example, suppose he became successful by being an excellent coder and technical problem-solver. These technical skills may have little to do with being a good manager. Instead, management may require the abilities to: plan, prioritize, coordinate between teammates, deliver feedback, set and meet objectives, and other things. Much has been written about the differences between making products and managing a team.

Even highly successful people face this issue

In his bestselling book “What Got You Here Won’t Get You There: How Successful People Become Even More Successful”, executive coach Marshall Goldsmith tells the story of an ex-McKinsey director who had the bad habit of “adding too much value.”

Adding value doesn’t sound like a bad habit. And, to be fair to the McKinsey director, adding value is what allowed him to climb the corporate ladder and succeed at his job. But when he left McKinsey and started his own boutique consulting firm with a partner, he felt the need to correct almost every suggestion that his partner made.

Goldsmith, the executive coach, suggested to the ex-McKinsey director: “Stop trying to add value to the discussion.” Goldsmith realized that instead of helping the situation, the director was destroying his business partner’s ability to feel that the partner’s own ideas had any value. As Goldsmith noted, perhaps the director’s contribution would improve the content of the idea by 5%, – but they’d cut the partner’s commitment by 50%.

What had worked for him at McKinsey as the sole head of a project did not work for him as the partner of his own business.

Tweaking your old rules

You might not need to completely discard the rules which have helped you succeed. You might just need to tweak some of them a little – and others you might need to tweak some of them a lot.

For example, a habit of letting your work speak for itself may need to be tweaked a little. You might find if helpful – to you and your company -- to promote your work without bragging

On the other hand, a habit of perfectionism – such as spending hours debugging code – may need to be tweaked a lot when you become a manager instead of an engineer.

How can you figure out the new rules?

I don’t think there’s a one-size-fits-all rule to figuring out new rules. Here are some things I’ve found helpful:

• Be aware of your implicit beliefs. It might take some introspection to identify them, because they might be ingrained habits that have worked for you. For example such as “I should work as hard as I possibly can,” or “I should let my work speak for itself instead of promoting it.”

• Ask people whom you view as successful in your current role or new environment, who are only a few years older than you, what they’ve done to succeed

o “What do you wish you knew when you started?” can be a good question to help elicit helpful rules from people

• Talk to your friends who come from similar backgrounds and who are in similar situations about the challenges they’re facing and the things they’re learning

Summary

Each new environment or role will have its own set of “rules” for success. You probably won’t be told those rules at the outset. They may not be particularly obvious. You can do yourself a favor by actively trying to figure out those rules instead of merely trying to copy-and-paste new rules to an old situation.

People who care about happiness know that religious people tend to be happier than non-religious people.1

The research cites many factors explaining why religious people are happier than the non-religious. (Most of this research focuses on Judaism and Christianity, and because those are the religions most familiar to many of you, and to me, those are the religions I mainly focus on here).

I want to highlight a key factor that’s probably not talked about enough:

Religions require adherents to prioritize some of the things that are most essential in life – and to provide community support for doing so.2 One key way they do this is to, in effect, institutionalize time-blocking.

Time-blocking work activities makes them more productive

Time-blocking refers to the practice of setting aside specific time to accomplish specific tasks or work on a specific project. In the corporate world, it’s a well-known fact that time-blocking helps people ensure that they work on important tasks, and once they’re working on that task, focus on the task at hand.3

I suspect that certain religious practices, such as attending church or synagogue, have the effect of causing people to time-block activity that helps them avoid burnout, engage in community, and focus on something bigger than themselves.

Time-blocking helps you work on important tasks

Do you have a better success rate at accomplishing important tasks when you set aside dedicated time on your calendar and plan in advance to do those tasks, or when you fit them in wherever you can?

Most people have a much higher success rate when they plan to do important tasks – especially when those tasks require significant time or effort. This finding is supported by lots of anecdotal evidence, and has been well established in the psychological literature.

Important practices in your life include taking breaks, engaging in community, and focusing on something transcendent. It’s no surprise that if you time-block these important activities, you’ll be more likely to do them than if you don’t time-block!

Avoiding burnout, engaging in community, and focusing on transcendence have been shown to correlate positively with happiness.4

Time-blocking your breaks can help you avoid burnout

Observing a Sabbath (a 3500 year-old practice among Jews, and a practice which was common among Christians in early America and is now regaining popularity among some5 ) can help people avoid burnout by taking breaks without feeling guilty about it.6

“I know I’m going to need a break,” a religious Jewish grad student told me during my freshman year of college. It was a Saturday afternoon (Shabbat, the Jewish Sabbath) and I was with a small group walking on campus – walking for pleasure, not to get from one place to another.

“So,” he continued, “I love taking a day off on Shabbat. I am planning to take my break then, and I don’t feel guilty for not working.”

I found this comment insightful. During my sophomore year of college, some of my friends would be studying hard on Friday night – when my Jewish friends were congregating to celebrate the beginning of Shabbat. You’d think my friends who were studying would have been more successful than the friends who were observing their religious holiday.

But in fact, that wasn’t the case at all. Actually, some of my Shabbat-observant Jewish friends were more organized than my friends who studied on Friday nights. The students who planned to attend Shabbat dinners (on Friday nights) often woke up early on Fridays, studied efficiently, and used their time well – because they knew they’d have to stop working once the sun set.

And my Christian roommate who attended church every Sunday was just as productive as any of my secular friends. She made sure to study well every Saturday night.

Engaging in community

Without community, people tend to get very lonely. And religion can help, by enabling people to build community.

When I moved to Boston, I met an enterprising junior who went to Babson, an international business school in the area. This junior was incredible at networking with older experienced professionals. He was always working. But he confided in me that he was very lonely.

He had no community of any sort.

It’s no secret that religions help people create community.

One key way they do this is by meeting weekly to worship and focus on something beyond themselves. Essentially, committing to attend a weekly (or more frequent – some Jews and some Catholics attend religious services daily, or even more often) religious service is the same as blocking time for something important to you.

This forces you to 1) Attend physically and 2) Be present mentally, or at least intend to be, and put yourself in a space conducive to mental presence.

When you’re at a religious service, you’re there physically. You’re giving yourself the possibility to be in contact with other people whom you might connect with.

And you’re there mentally – or at least you’re intending to be. I’ve been to many hundreds of religious services in my life, and I’ve almost never seen anyone playing on a smartphone instead of paying attention (or at least pretending to pay attention) to the service.

In our modern world, that is almost a miracle itself!

Focusing on something bigger than yourself

Religious services are a block of time which provide you with ample opportunity to focus on something bigger than yourself. And happiness psychologists (for example Harvard professor Arthur Brooks)7 have found that focusing on something transcendent leads people to happier lives.

If you’re reading the Bible or listening to a sermon about the Bible, you’re engaging with something bigger than yourself. You’re exposed to ideas from traditions that are sometimes thousands of years old, focused on big questions and big ideas.

Religions provide a relatively easy way to seek something bigger than yourself with other people.

In fact, they specifically help you block aside time to do so, while providing a degree of external accountability to enforce that time-block.

That makes it easier to do the things that are good for you.

No wonder religious people – who get to time-block important parts of their lives – tend to be happier.

When you think about reasons to negotiate a job offer, there’s one you probably don’t consider.

You probably DO think about possibility of negotiating to get a better deal. Maybe this includes a higher salary, greater bonus potential, better health benefits (which may be negotiable at some companies) guaranteed support (e.g. mentoring, opportunities, etc.) or more flexibility.

But the mere act of negotiating may generate benefits for you.

A hidden reason to negotiate a job offer is: the manner in which an employer responds to your negotiation offers insights into what kind of employer they likely are.

It can be difficult to get information from an employer about what kind of bosses they are, how they treat their employees, and so on. You can ask about company culture all you want – but that doesn’t guarantee that you’ll get an accurate or meaningful response.

You know the old saying that actions speak louder than words. When you negotiate with a prospective employer, you get to see what they do, not just what they say.

Negotiation provides you with an actual opportunity to see how your potential employer treats you. If they treat you badly when they’re trying to recruit you, there’s probably not a good reason to think they’ll treat you significantly better when you’re an actual employee.

The job negotiation is a bit like a date: the employer is (presumably) trying to woo you. You expect potential employers to be on their best behavior. If their best behavior doesn’t make you comfortable, it’s unlikely that you’ll feel better about that behavior – or that the behavior will improve substantially -- once you take the job.

Is getting a “yes” really the goal?

People tend to think that a successful negotiation means having the other party accept their offer.

But should that really be your goal? Probably not.

Your goal should be to make a good decision about whether to work for this company on the best terms you can obtain. Those terms might not be enough. If your offer is accepted, but it’s an offer at a company that’s not right for you, you may actually have lost. Harvard Business School professor Deepak Malhotra notes: “You can negotiate like a pro and still lose out if the negotiation you’re in is the wrong one. Ultimately, your satisfaction hinges less on getting the negotiation right and more on getting the job right.”

Employers who rescind an offer, or behave inflexibly when you try to negotiate, may signal they’re a company with significant issues.

No one congratulates you for avoiding a mistake

We don’t usually get praise for avoiding mistakes. But maybe we should.

When we lose an offer, it’s natural to feel that we’ve lost something.

But perhaps taking the offer would have been a mistake. In that case, by losing out on the offer, we’ve actually avoided a mistake. And maybe we should be congratulated for that.

An extreme example

In a previous post, I wrote about how I negotiated the terms of a job offer, and the employer responded by withdrawing the offer. Although it was disappointing to lose the offer – given that I was excited about the job – it might have been better in the long term that I not get the job.

The way in which the company negotiated conveyed significant information about the way the company is run.

First, I was sent different versions of the offer two times. The first two offer letters contained information about the compensation package which conflicted with what the recruiter had previously indicated over email. When I later clarified these with the recruiter, she sent a new offer letter, but it took her three tries to send an offer letter that corresponded to the information she sent in the email.

I still don’t know if the two “wrong” offer letters were sent out of incompetence, or if they were trying to be vague with the compensation structure.

Second, the senior executive who was supposedly recruiting me was “out of town” and unavailable to meet. I wanted to meet with him to clarify what exactly my roles and responsibilities would be. However, he was out of town, and the company was rushing me to make a decision, so I could only meet with the boss’s employee.

Third, the company did not clearly communicate to me that they would rescind the offer if I didn’t sign the letter by a certain date.

Instead, after I sent an email on a Sunday to my potential future boss to outline the career development opportunities I expected/hoped for at that company, the company’s recruiter emailed me on Monday saying my offer had expired over the weekend.

It’s impossible to know whether I would have been “better off” had I not negotiated and instead just accepted the job at the company.

However, I suspect that I would not have thrived at the company, based on how they treated me as their supposedly top candidate, and based on reviews that they get from others.

Though I do not recall reading the online reviews at the time (I should have), in writing this I looked them up. What I found supports the concerns that I inferred in my above outlined reasoning.

For example, the company has 18 reviews online which say that the management is “emotionally immature” and “aggressive.” Fifteen comments say that “leadership is awful.” Nine reviews complain about “chaotic communication” and “lack of respect” for employees.

That data doesn’t mean I’m certain I avoided a bad situation, but it does support the belief that my experience in negotiating with the employer did in fact reveal real, valuable information, and information that was at odds with their verbal claims about what kind of employer they are.

Caveats

Every negotiation situation is unique.

For example, many large firms with well-oiled recruiting processes have standard offers that they present as a package. Some firms have company policies about salary, which are set and are unable to change (or unable to change without a great deal of effort, which recruiters are vanishingly unlikely to expend). Still, in some cases, candidates can negotiate for other perks such as more flexibility in time off, or bonuses, or professional development.

Nevertheless, each situation is unique. I’m not trying to present a hard and fast rule here; I’m providing a perspective about something you may not have considered.

In addition, your level of ‘need’ for the position might make you more willing to put up with potentially bad employment situations. For example, if you really need a job, you might care less about whether it’s a well-managed job than if you don’t need a job urgently. However, even if you do need a job, bad treatment by employers in the negotiating phase may signal that they’re willing to fire easily.

Summary

It can be tempting to view negotiation as merely a tool to get what you want.

However, negotiation can also provide insight into how your potential employer responds to you. The way your potential employer treats you when you’re negotiating can provide a signal to how they might treat you later on.

Have you ever discovered something surprising about a company through negotiation? Share your experience in the comments!