Managing your psychology as a founder

Bad news for startup founders: your job sucks. Here’s how to manage that fact.

1138  words • 6 min read

Attention founders: this job sometimes sucks. A lot. Even when it’s going well. No one says it out loud, but everyone feels this way.

Here are two (lightly edited) questions from founders in my network, both of whom express a sentiment that is incredibly common:

The company is doing well and growing a ton. I love the product, and customers love it too. But I spend all day in front of a computer, because we’re remote-first. I eat dinner and then go back to doing more email. My cofounder is starting to have health problems because he works so much. I don’t see family as much because they live far away.

I’m starting to wonder about the sacrifice and my quality of life. Is this how I want to spend my life? Am I doing this just for the chance at an eventual payout?

Then again, this is the best job I’ve ever had. What’s the alternative, though? Does anyone else have these moments? How do you fix them? 

and

My startup is doing well, but honestly, the growth is stressful. I look at the path ahead and I’m not sure I even want to be on it. I don’t envy Mark Zuckerberg, Aaron Levie, or other CEOs who have been at it for 20+ years.

How do I motivate myself in the near-term if I’m not even sure I want to end up in their position?

Here’s how I recommend you grapple with these feelings:

Avoid burnout

Long-term, existential questions can absolutely drive unhappiness. But I’ve also found that if short-term/tactical concerns are not addressed, they can sometimes present as anxiety about longer-term issues.

Said another way: on days that I’ve actually exercised and slept eight hours a night, I find that I feel better about how the business is going—and the opposite is true as well.

In the short term, what can you do to avoid founder burnout? The short version of what works for me is:

1. Be actively productive, or actively recharging—the worst is when you’re middle zone of trying to work when you should be resting, and being totally unsuccessful at it

2. Spend time with friends and family

3. Sleep eight hours a night and exercise regularly

The point here is not “don’t work hard”—of course you should work hard. What I’m really saying is: give yourself permission to be at your desk for slightly less time in a given day, to maximize the total effort you’re able to put in on the startup.

Again,  this is what works for me—what works for you might be different, though I do recommend you give this list a shot.

Understand that the promise of being super-rich will not solve all of your problems

Refresh your memory on reasons not to start a startup. If you’re doing this entirely for the money, you’re going to have a tough time:

1. Your liquid compensation will be dramatically below-market-rate for a long time. If you’re looking to make a lot of cash in the near term, you’ve picked the wrong job. Your equity is the vast vast majority of your compensation, and hopefully it’ll have meaningful value. But most startups fail. There are much safer/lower-variance ways to accumulate material wealth, so it’s not a rational strategy if that’s your only goal.

2. The hedonic treadmill is extremely real. You will never feel like you have enough money (even if you very clearly do by any objective standard).

Anyone who tells you that money is not at all a factor is probably lying to you. But there’s a big difference between “I’m doing this for the love of the game and for the chance to win the lottery” and “My only motivation is finding the fastest path to becoming super-rich.”

Know why you’re actually doing this

Avoiding “reasons not to” isn’t enough—it’s important to have a handle on why your startup will make you happy.

For me, the reasons I enjoy doing startups are:

1. I like the craft and intellectual challenge of it—there’s a puzzle that we’re solving. In our specific case, it’s the puzzle of “How can we run the back office for lots of companies out there, so they can, in turn, be more successful.” But the existence of the puzzle is more important than the exact, specific nature of the puzzle. (This is surprising to most people, but I’ve found it to be consistently true for me.)

2. I want to be surrounded by smart, talented people who challenge me to do my best work every day—and my cofounders and our team do exactly that.

3. I derive a lot of satisfaction from making our customers happy—hearing about how much they like the service is always a highlight.

Remember that you can quit at any time

On days when it’s really frustrating, remember that if it were truly terrible, you could just walk away. It would be a punishingly hard decision. It would let down the team, your cofounders, your customers, and your investors… and you’d feel a ton of disappointment and guilt about it. But nothing structurally prevents you from being able to walk away if you want to.

I’m the one choosing to show up every day, so therefore I must like it. There must be things I find genuinely rewarding and fun—or I wouldn’t continue to make that choice.

Most of the time that people say “I can’t,” what they really mean is “I am choosing not to.” This is a really powerful thing to internalize. (Aside: telling this to your spouse is also an easy way to annoy them if what they actually wanted was sympathy for a difficult situation.)

You are in control. You are choosing to do this job every day. And if you ever want to choose not to do it, that’s OK and you will be OK. The world will not end. This is not a decision to be made lightly. But I find it helpful to reflect on when things are especially tough.

Parting thoughts

Not to be too dark, but: ultimately, you are going to die, and therefore this whole endeavor is kind of pointless anyway. (I did warn you that this was going to be dark.)

So if you’re not enjoying the journey, why bother? If you actually hate this job on more days than you don’t, you should leave.

I doubt that’s the case, though. My guess is that you’re generally really engaged and enjoy the job, but that you need to find structures that allow you to recharge and that cause you not to neglect the other important things in your life.

Finally: it can be hard to talk to non-founders about this stuff, so if there’s anything I can do to help or you just want to talk it through, please get in touch.