Stop Beating Yourself Up

A little founder therapy today on a hot summer Sunday.

One of our founders favorite pastimes (apparently that’s how you spell it?) is beating the crap out of themselves.

During 1:1s with founders I take a whole bunch of notes. I’ve had a system for these notes for the past 10 years - one side of the paper is me thinking in real-time, the other is full of checkboxes - things I need to say to the founder before the end of the call or send to them after. By far, the sentence that’s showed up the most on the right side of the page is “stop being so hard on yourself.”

You might think being hard on yourself is a good thing. Years ago, someone responded by shouting “well I bet Steve Jobs was hard on himself, too!!” Ok, sure. But being hard on yourself makes running a startup miserable. And people are much better at things (and way more productive) when they’re fun. Also, when you’re stressed, the creative side of your brain gives way to the analytical side. For early stage founders, this is a disaster. We need strategies / approaches / customers other people haven’t thought of.

But the biggest reason beating yourself up is counterproductive is that the stuff you’re beating yourself up over is systemic to entrepreneurship. You’re just wasting your time. It’s like beating yourself up because you couldn’t stop the sun rising in the morning.

So, here are a bunch of things that hopefully help you spend less time beating yourself up and more time building stuff that matters.

1. 98% of everything you’re doing is new. Literally, everything. Yet, you expect you’ll be great at it to start. Or that you can do 10 new things at once. Founders get mad that a cold email took them 2.5 hours to write. Well, you’ve never written a cold email like this before. Of course it took 2.5 hours. Treat this stuff like you’re learning to play the clarinet. It isn’t an extension of stuff you’ve done before - it’s brand new. It’ll take time and practice.
   

2. You don’t know what good looks like. Since you’ve never done the startup thing before, you don’t know what “good” looks like. Which means you make up some version of “good” in your head and get mad at yourself if real life doesn’t match. But, your definition of “good” came from… nowhere. Living up to it was always unrealistic. Lower or remove all your expectations for a bit as you learn what a good day as an entrepreneur actually looks like. Importantly - don’t lower expectations on effort - just results, for a bit, until you learn what “results” look like.
   

3. You refuse to believe you’re a goldfish. A personal favorite. Here’s how the conversation goes:
   
   “I’m so frustrated - I was planning on working 10 hours last week but I only did 2.” ”What did you remove from your life that you normally spend 10 hours on each week to make room for your startup?” ”Uhh… sleep?”
   You’re a goldfish and you’re the size of your bowl. You don’t have room for 10 extra hours a week unless you remove something that takes 10 hours a week. And sleep isn’t an option. You’re beating yourself up for not magically making each day 26 hours long.
   

4. Bad things happen fast, good things happen slow. This is a life thing, but it’s amplified in a startup. When you send 100 cold emails, you’ll immediately realize that 95 people won’t respond. That’s a lot of rejection. And the five that do speak with you might not be helpful. It’ll take five reps of 100 emails, and then 5 weeks of conversations, to get an insight. It takes a day or two to realize no one is responding. Don’t beat yourself up over the bad things that happen fast.
   
   

5. You’re just hungry or sleepy or you need some water. This works wonders for the little guy. Will probably work for you, too.
   
   

6. You’re comparing your beginning to someone else’s middle or end. When founders look at competitors, they usually get discouraged and angry with their progress. Often, this is you comparing your 4 month old business or 2 month old idea to someone else’s year 3. It’s not fair. Zoom in on the specific thing you’ll do better than competitors for a customer they aren’t serving well. That’s how to compare.
   
   

7. You misunderstand how a startup works - it’s a 95% 5% thing. In the startup world, you only need to make a few great decisions and you only need a few things to work out. Which means most of the stuff you do won’t work out. You do 10 things, 6 definitely won’t work, 3 will be meh, and 1 has a huge amount of impact. You can’t predict which will be which before you do the ten. That’s how a business grows early on. So, getting upset when things don’t work makes no sense - the nature of startups are that most things don’t work. If they did, other people would’ve already been successful and your opportunity wouldn’t exist. Again, importantly, this isn’t permission to let yourself off the hook. Do LOTS of things that are uncomfortable. Just don’t beat yourself up over results - learn from them and move on.

So, work extremely hard and do lots of things but don’t waste time and effort and potential beating yourself up because the sun rose again.