How to survive when your startup turns to an Emotional Nightmare


Most people view your emotional makeup as something you either have or you don’t.

Unconfident about what you’re doing? Too bad, I guess you weren’t cut out to be an entrepreneur.

Depressed? People look at you like you’re diseased.

Lost your Motivation? No one can tell you how to get it back. They just think you’re lazy.

I say Screw these Emotions.

Our society is crazy.

Our focus on science and repeatability causes us to forget the internal experience of the individual.

But our emotions are extremely important, and a startup is a brutal environment. You work a lot, but that isn’t even the challenging part. Tons of professions require a lot of work, just ask lawyers, doctors, and people in finance.

What separates entrepreneurs from the other fields is the amount of emotional crap they experience.

Crises of confidence, depression, unshaking self-belief, self-doubt, self-discipline, perseverance with no positive feedback.

You get a glimpse of the emotional turmoil when you read post-mortem posts like Nikki Durkin’s, from 99dresses, but I’ve never seen solutions.

Maybe you have something I can’t help you with, but I’m going to try. Below is a guide to all the feelings I experienced, and how I eventually overcame them.


1. Social Isolation

When I was working on my company, I made the mistake of spending 6 months socially isolated. I worked every day from my house, with only my remote founder and my dog to talk to.

I had recently broken up with my girlfriend. We had moved from another part of the country together, and as often happens when couples live together in a new place, we never extended our social circles beyond each other.

When we broke up, I didn’t have a single friend in the area. Couple that with no steady job, and I had no social life whatsoever. My family all lived elsewhere. Plus, when you do talk to people, most people can’t relate to starting a business.

This is why entrepreneurial groups and MeetUps are so important.

In my case, I felt too guilty to branch out. I was starting a company after all, and I needed to spend every waking moment working on it and thinking about it. If I didn’t do that, I was going to fail. And I desperately didn’t want to fail.

But not branching out was going to cause me to fail anyway – bad, bad idea.

Prisoners in solitary confinement lose brain cells for a reason. We are social creatures.

After 6 months of this, I went crazy. I was in such a dark, lonely place emotionally, that I knew I had to make a change. So I finally made the right call, said to hell with the startup, and decided I was going to spend my days in coffee shops. My productivity went down because of the time I spent talking to random strangers, but holy crap did my happiness improve.

I went to startup MeetUps, I experimented with co-working spaces, and I joined a running group.

Because I finally had contact with women again, my dating life immediately improved, which lead to even more happiness.

Honestly, this is what I should have done in the beginning. For many of you, this will be obvious. You have to have balance. But it’s amazing how much what you think you “should” be doing can affect your actions.

I’ve realized how important it is to listen closely to what your emotions tell you. They’re like alarm bells that go off when you have unmet needs.

I still believe that you have to put in your hours to get good at anything and hard work is NOT over-rated. But if you go insane, that’s obviously not a good thing. When you’ve fallen far out of balance, your productivity drops to zero anyway, so you might as well spend a bunch of your time making yourself happier.


2. Fear Of Failure

Like a climber fighting for breath above 20,000 feet, this emotion makes every step as an entrepreneur arduous and painful.

If you’ve been successful in your life until that point, fear of failure can be devastating.

Personally, I had worked for Google as an engineer, and gone to a top 10 school, and my co-founder had graduated from MIT and experienced a successful career in finance.

So as I mentioned earlier, I desperately did not want to fail. Screw Fail Fast. Failure didn’t mesh with who I was.

Getting smacked in the face by reality isn’t easy.

But the reality is that starting a business is an independent skillset from your previous successes. Of course there are exceptions, but most founders I know find themselves in situations they never could have predicted. Nothing in their lives could have prepared them for those challenges.

My solution to this problem is “outcome independence.” You train yourself to only worry about what you can control. So if you took “right action” today, you allow yourself to forget about your worries. Hakuna Matata.

When the thoughts come up, and they always do, you tell yourself it’s okay to let them go because you did what you could today to get to your goal. You “release” the outcome completely, and recognize that it’s largely out of your control.

Okay, I know this is easier said than done, so let me explain.

This isn’t giving up, nor is it relinquishing responsibility. It’s just acknowledging how small you are in the scheme of things.

You’ll do what you can, and the rest is up to the universe.

Plus we’re terrible at prediction. It’s hard. Some examples:

  • “I think there is a world market for maybe five computers.” — Thomas Watson, chairman of IBM, 1943.
  • “There is no reason anyone would want a computer in their home.” — Ken Olson, president, chairman and founder of Digital Equipment Corp., 1977.

Nice predictions.

Accept that you can’t predict the future anyway, so you might as well not worry about it.

You have no idea if your actions are going to pay off. Sometimes the simplest action can have an exponential payoff, a payoff that’s totally unmatched by the action you put in. But you have to keep taking actions to find the one with the large pay off. If you stop, it’ll never happen.

Have the courage to have faith that everything is going to be okay.

If you took as much action as you wanted today, then relax, you did everything you could. Pat yourself on the back, congratulate yourself. Then get up and do it again tomorrow.

If you didn’t take action, then it’s okay to get on your own ass.


3. Crises of Confidence

There are entire books written about the deep “fake it until you make it” culture in Silicon Valley.

But what if you’re not at all confident in what you’re doing? Should you lie to people? Isn’t that incongruent to who you are?

Ideally, you’ll be getting positive feedback so this won’t happen. But what if it doesn’t? What if all you seem to get is negative feedback? In fact, you couldn’t find positive feedback if your life depended on it. 

Either way, you’re undoubtedly going to have plenty of WTF moments, where all you can say is “WTF am I doing here?”

When I’ve had a WTF moment, I’ve usually compared myself to my idols.

I’d think “man Steve Jobs always seemed so confident in what he was doing”, and then I’d think “I’m not confident like that. I must not have what it takes to make it in this game.”

And then you lose faith in yourself, and it shows to everyone you interact with. Your co-founder notices it. Investors notice it.

But try to remember that your heroes weren’t nearly as confident as you thought they were. When Steve Jobs raised money for Apple he thought there was a good chance the investor would never see his money again.

Confidence my ass.

Mark Zuckerberg spent an entire summer building a file sharing service as a hedge against Facebook failing. Kind of a silly maneuver in retrospect, even if it wasn’t at the time. But would a person confident in Facebook’s future have done that?

Oh and let’s not forget Larry and Sergei spent ~a year longer in graduate school and tried to sell their invention to everyone before finally taking the leap of faith and starting Google. Oh and they made sure not to really leave their graduate programs. They took a leave of absence so they could always come back. If they were 100% confident would they have done any of these things?

Anyway, I have no idea the true stories of these famous startups. I don’t think anyone does. You weren’t there. You didn’t interact with them, so you never got to experience them in person, and even if you did, you’d have no idea what they were feeling or thinking.

Every story about these companies was written many years later and probably went through 2-3 layers of filtering.

But I think it’s safe to say that they weren’t nearly as confident as we think they were. Of course they act confident after the fact. It’s easy to be confident when you have huge successes under your belt.


3. Lack of Motivation

About halfway through my startup I started having serious problems with motivation.

I stopped getting joy out of what I was doing, and I spent a great deal of energy endlessly questioning everything.

I had left my engineering job at Google to find greater meaning, but that’s not what I found by running a company. Actually it was just really hard, and I found myself stressed out all the time.

What about extrinsic rewards like money? I was a well paid software developer, right out of school. In many ways, working for a big company makes more sense financially than working for a startup, either founding one or being an employee.

Plus the following thought experiment always failed for me:
How does my life change if I have a net worth of 10 million dollars?

My answer was that it didn’t; I already had most material things I wanted.

First world problems.

I realized I had originally started a company because I needed to be somebody. I needed to be someone like Steve jobs or Mark Zuckerberg to feel complete as a person.

I felt incomplete inside, and I was looking for success in the startup world to feel like I was “enough”. But I don’t believe this is how success works. You have to believe you’re enough first, and then success comes after. At least that’s how it’s always happened for me, whether it be in athletics, dating, school, or jobs.

And if you don’t trust yourself, or you don’t feel good enough to get what you want, you’ll struggle with motivation and you’ll have trouble getting yourself to take action.

Many ambitious people suffer from this affliction. It’s part of what drives us onwards.

So if we you feel incomplete, how do you deal with it?

1) Diversify your identity.

An easy way to boost your self esteem is to take the pressure off. If your entire identity revolves around what you do, then everything is on the line when you start a company.

I realized that whenever I introduced myself to other people, I would first ask what they did, and I was guilty of judging them for it. Likewise, I derived my own personal value from what I did for work.

I had to realize that I’m many, many things besides just a tech entrepreneur. I’m an athlete, a decent friend, a decent boyfriend, social, well-read, grateful, intelligent, hard working, a good son, a good brother, and a generally happy guy.

My startup caused an identity crisis because I went from being “the Google engineer” to “the guy smoking crack.” In many ways, it became unpleasant to talk about what I did for work, so I had to make this adjustment.

A happy side-effect was that I began taking a more complete look at other people as well as myself.

From Fight Club: You are Not Your Job.

2). Find the joy in what you do again.

If you’re suffering from an identity crisis, many times you lose sight of what you enjoy working on. You’re like a leaf in the wind, drifting around doing things that you think will make you successful, instead of things you enjoy.

When you do too many things you hate, for too long, you completely lose motivation.

This isn’t some feel-good advice about “only doing things you love.” That isn’t practical. You have to get out of your comfort zone to grow as a person and to achieve your goals. Some of the time, you’re going to feel uncomfortable, or bored, or both. And that’s okay. That’s life.

But when you don’t know who you are, you spend a lot of time trying to live someone else’s life.

Personally, I spent a lot of time completely emulating other people, and I lost myself entirely. If I had to ignore my own wants and desires to be successful, then so be it.

In fact I was so lost, that I didn’t even believe I was a passionate person. I didn’t believe that anything I actually liked would lead me to success, so I ignored those things. And I needed success so badly.

It turns out I have plenty of things that bring me immense joy.

I love programming. I love reading about tech and technical problems. I love solving problems. I also love writing and reading.

You need to have faith that what you enjoy doing will eventually lead you to success.

This doesn’t mean you won’t have to grow as a person, put yourself in uncomfortable situations, or acquire new skills. You don’t have to enjoy what you do ALL of the time. But if you absolutely hate a particular line of business, then you probably shouldn’t be in that line of business.

To hell with the possible rewards or the status it gives you as a person. At least you’re being honest to who you are.

In the case of being an entrepreneur, this means starting the type of business that you want to start without feeling pressure to start something in a sector you hate, or in a way that you hate.

3) Realize you are just as good as your idols.

Many times we compare ourselves to our idols, and we think there’s no way we can measure up to them. We can’t accomplish anything that they’ve accomplished because they must have something special that we don’t. They were born with it. We weren’t. That’s just life.

Remember that your idols are just like you. For me, this happened by:

  1. Realizing my idols were human. They still have to use the bathroom multiple times per day, every day. Bill Gates hasn’t discovered some magical way not to poop.
  2. Realizing we all die in the end. Kind of depressing. But death has been called “the great equalizer.” Regardless of how much you accomplish or how little, you still die, which makes us all the same. That is, unless Ray Kurzweil has his way.

Because my idols are the same as me, I realized I’m not defective as a person. There is no reason I’m not inherently “good enough” to go after my goals and dreams.


4. Depression

I’m no doctor, so if you’re clinically depressed, please don’t listen to me.

But I have experienced a fair amount of depression during my life.

Everyone seems afraid to admit that. But I believe depression is a normal, and even a healthy part of your emotional experience.

Fortunately, if you lead a balanced life with good relationships, you’re much less likely to deal with it.

So tip #1 would be to follow the other tips I listed above.

Much of my depression was caused by a psychological disconnection from parts of myself. As mentioned above, much of my journey was figuring out who I was, what motivated me, and what I like to do. So when I stopped fighting those parts of my personality and embraced them, my general mood improved instantly.

I’ve also found various hacks and tricks to overcome depression during the short term:

1) Workout.

Working out daily is one of the most powerful anti-depressants available. The runner’s high got it’s name for a reason.

2) Meditation.

Thousands of peer reviewed studies back up the benefits of meditation. I practice every day.

3) Working daily on goals that matter to you.

Having the discipline to go after long term goals every day can be a powerful source of self-esteem and happiness.

4) Get out of the Victim Mentality.

The victim mentality is one of the most toxic emotional states a human being can be in. You give away all of your personal power and control. Many studies show we are happy to the extent that we feel in control over our lives.

Personally, my social life was totally out of whack. I had to take responsibility for it and take action to make friends and re-build my dating life.

What problem is affecting you?

5) Change how you relate to bad things that happened to you.

Train yourself to see your disadvantages as advantages.

There are 2 sides to everything in life. So if you didn’t get that job you were hoping for, see the disappointment as enabling a new and better opportunity in the future.

I’ve found this to be extremely difficult in practice, but usually it’s true. Things that pissed me off and depressed me in my teens turned out to be enormous advantages in my 20s.

History is bookmarked by famous people who used apparent disadvantages to accomplish everything.

But you have to have faith that the universe is not screwing you over and that each setback is an opportunity. 

6) Practice Gratitude

Each morning, I make a list of everything I’m grateful for. Gratitude works. Try it. Numerous studies have proved the link between feeling grateful and physical and emotional well being.

Even if you don’t feel like being grateful, try forcing yourself to think of 5 things you’re thankful for and write them down.

Questions or Comments?  Drop me a line below.

Photo Credit: SparkyLeigh