Idea to Startup: Stop Beating Yourself Up

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This Episode

If you’re like most of our founders, one of your favorite pastimes is beating the everloving crap out of yourself.

This is a problem for a whole bunch of reasons, but the biggest is that it kills your startup’s potential. When you’re stressed, you think small. You think safe. You’ve got smooth edges and lowercase letters.

Today, we help you first identify the parts of entrepreneurship that are causing you to beat yourself up, then teach you how to navigate each.

Here they are, for easy reference:

The 8 Eccentricities You Beat Yourself Up Over (But Shouldn't):

1. Everything you're doing is new, but you expect to do it fast and perfect

2. You don't know what "good" looks like yet

3. You refuse to believe you're a goldfish (no extra time without creating it)

4. You think discomfort is a negative signal

5. You forget that bad things happen fast, good things happen slow

6. You're comparing your beginning to someone else's middle or end

7. You misunderstand how startups work (90% of things won't work)

8. You think progress should look like a ski lift, not a staircase

The 3 Practices to Break the Cycle:

1. Lower Your Identity Exponent - Text your friends and ask what they'd think if your startup failed (spoiler: they'll still love you)

2. Calibrate Your Expectations - When you start spiraling, ask which of the 8 eccentricities this is

3. Build Your System - Weekly expectation audits and daily affirmations that counter the 8 patterns

Stop beating yourself up so you can take the creative, strategic risks your startup actually needs.

Pod References

• Tacklebox - start your company before you quit your job

• Stop Beating Yourself Up Post

00:30 Stop Beating Yourself Up
02:53 The Beating Yourself Up Equation
06:49 Smooth Jazz
07:04 The Reality of Baseball
09:18 The Eight Eccentricities of Startup Progress
17:16 Three Practices to Break the Beat Yourself Up Cycle

Transcript - feel free to read like a long-form article

Today, we’re going to help you stop beating yourself up.

Because when you beat yourself up, you make safe choices. And when you make safe choices, your startup ends up undifferentiated and boring. A bunch of smooth edges. A grilled chicken sandwich.

And we don’t want that, because your customers don’t want that.

I wrote a No Whisper Ideas post on this a few Sundays ago and it got a ton of responses, so I figured I’d expand it into a full pod, since way more people listen here than read the posts I send out on Sundays.

But if you did read that post, you’re not off the hook. You still gotta listen. Don’t you dare flip over to that charlatan guy raz. Because I thought a lot more about this and came up with a framework that’ll help you. Which is more than Raz has ever done for you.

I’m kidding, I actually like guy raz. As far as you know.

Anyway, I think the post hit a nerve because nearly every founder I meet spends an enormous percentage of their waking hours beating the ever-loving crap out of themselves. And, worst of all, I think they think that’s a good thing. That Steve Jobs probably did it, too, or whatever.

But it still feels awful, so when someone like me calls it out and gives you permission to… stop, you send an email saying the post helped. And hopefully, you change.

I’m taking a lighthearted tone here, but your startup really does depend on you not beating yourself up when things don’t go to plan. It’s a terrible use of time because it results in you thinking small.

When you’re stressed, your world of possibilities shrinks by a few standard deviations. You ditch anything you perceive as risky and stick to things with predictable outcomes. In most other parts of your life - paying bills, showing up to work, maintaining relationships - this is a good strategy. In the startup world, it is not.

Because the things you revert to when you’re stressed are the same things everyone else will revert to when they’re stressed. Which means you’ll all be doing the same 5 things as everyone else and need those five things to lead to a meaningfully different outcome, somehow. Which is unlikely. You’ll just end up in the middle of the bell curve.

Startups reward spikiness and uncertainty.

So, the path to the edges of the bell curve require you to understand why you beat yourself up, and then to stop.

The Beating Yourself Up Equation

The beating yourself up equation is an offshoot of our old friend, the happiness equation. There are two variables - expectations and reality.

You might remember our happiness equation. It’s simple. Happiness equals reality minus expectations. If your expectations are lower than reality, you’ll be happy. If not, you won’t. Your happiness is entirely controlled by your expectations.

The Beating Yourself Up equation has most of the same components of the happiness equation - it, too, hinges on reality and expectations. But it’s got a kicker. An exponent that dramatically amplifies the two other variables: Identity.

So, it’s reality minus expectations, all in parenthesis, raised to the Identity power. I know podcasts aren’t the best medium for equations with exponents, so here’s what I mean. If reality is a 7 expectations are a 10, and your identity is 10, that -3 is getting raised to the 10th power and you’re going to be pretty upset.

The Identity variable depends on how strongly you’ve tied your identity to the outcome of your business, and how much you think your family and friends opinion of you depends on the outcome of your business.

Most founders - at least the ones that gravitate towards Tacklebox - seem to have their identities and the outcome of their startup weaved together tighter than a twizzler pull and peel. So that exponent is big. Call it a 10. Or 100.

The stakes are extraordinarily high, even during the absolute earliest days of your business.

We can take a step back and recognize how silly this is if we’d like - we don’t put this level of expectation on just about anything else we do - a new job, a new hobby, learning a language, even a spouse. But it won’t change it. High achievers usually tie their identity to their startup.

This creates trouble the second your expectations exceed reality.

Here’s an example.

Let’s say you get 10 customers to agree to interviews that you’re hoping will push your idea forward. But, 7 no show, and the other 3 don’t give much of an indication that the problem you’re focused on matters all that much.

Reality doesn’t match expectations, your identity kicker ratchets up the feeling, and you tighten up. You’ve set the cost of failure so damn high and you view this result, since it’s different from your expectations, as a failure.

Which means you’ll want your next strategic move to have a more reliable outcome. Something to get you back on track. Something like, say, hiring someone to build you a website, or paying a lawyer to establish your stock structure, or building a pitch deck so you can start fundraising. Predictable, reliable, visible progress.

Or, more accurately, the same things everyone else will do when they’re smacked in the face a bit.

Strategy is about being different. Beating yourself up will push you towards being the same.

Today’s episode exists to help give yourself the space to execute a real startup strategy. One that includes a bunch of actions that have a low likelihood of, quote, working, but if they do, they deliver enormous, differentiated value.

This approach isn’t hard because the actual tactics are hard - it’s hard because of the mental toll of doing 10 things and having 8 of them fall flat. We’ll dig in on that.

And one quick note before we do.

Our goal here isn’t to just have you lower your expectations and stop being ambitious. Totally the opposite. The way to actually be ambitious is to stop beating yourself up.

And we’ve got a framework that’ll help. After… a little smooth jazz.

Winter is Coming

As a kid, I was much better at baseball than basketball.

Unfortunately, I couldn’t handle the realities of the game.

When you play baseball, you get, maybe, 4 at bats each game. If you get a hit in one of those at bats, you’re doing fine. If you get a hit in two, you’re doing great. You’ll very rarely get hits in 3 or all 4 at bats. Which means that more often than not, you get out.

11 year old Brian got out fewer times than just about anyone else in our town, but even one time a game was too much. Every time I made an out, I was devastated. It felt gut wrenchingly personal and I couldn’t shake it off. My identity exponent - since I was young, my entire identity was built on being an exceptional athlete - was too high.

This built up until, during my sophomore year of high school, I quit, to the absolute bewilderment of my high school coach. It’s easily one of my biggest regrets, because I loved playing. I was just never emotionally equipped to handle a very basic part of the game. I couldn’t separate an out, a totally foundational and normal part of the game, from my identity.

The parallels to startups are clear.

There are foundational realities of startups that founders completely misunderstand or ignore and, subsequently, beat themselves up over.

I never built an internal system for handling strikeouts. If I had, who knows what would’ve happened.

We need you to build an internal system for handling things that are systemic to startups but might not be obvious. You need to handle these and not overreact to them.

I weirdly like a lot of Tony Robbins stuff.

One thing he’s said that has stuck with me is around recessions. Every 10-15 years, there’s a recession in the US economy. It happens like clockwork. But every time, people act like the sky is falling. He likens it to people freaking out every winter when the weather gets cold.

So, let’s jump into 10 things that are like getting out in baseball or a stock market crash - totally normal, but things founders constantly overreact to and beat themselves up over.

8 Eccentricities of Startup Progress

HEre are 8 things that founders beat themselves up over, but shouldn’t.

1. 98% of everything you’re doing is new, but you get mad when you can’t do it fast and perfect the first time.

A good example of this is drafting up a cold email to get customer interviews or to try to get your customer to do… something. It’s an email, so it should only take a few minutes, right? You’ve done emails before. You’ve maybe even done cold emails.

But, it takes you 2.5 hours to write and another 3 days to build up the courage to send. Sometimes it takes 3 weeks to send. And you get endlessly frustrated with yourself.

The challenge here is realizing that even if a task rhymes with something you’ve done before, the execution of it in the startup world is entirely new. It’s like swimming in the pool at the YMCA for 10 years and then being dropped in the middle of the ocean at midnight. They’re different things. You’ve never written a cold email for a business you’re starting before. The emotional tax on doing anything new is huge, so applying your old expectations to time and effort to it are useless.

Even if you’re a marketing director at a startup, it ain’t the same as getting the messaging right for your first landing page.

2. You Don’t Know What Good Looks Like

You’ve never built a startup before, so when you set expectations for what “good” should look like, you’re kind of just guessing.

You might decide your landing page should convert 5% of customers and take you a week to build, or that you should get 25 customers interviews in a month, or that your linkedin posts should get 50 likes. But these numbers and expectations come from … nowhere.

Then, when your landing page doesn’t convert or you can only get 3 interviews or no one likes your LinkedIn post, you beat yourself up for underperforming. But underperforming against what?

You haven’t earned realistic expectations yet. You’ve gotta get some reps in first.

So, remove your expectations and just work hard and reflect. Focus on learning and improving, not measuring against imaginary standards.

3. You Refuse to Believe You’re a Goldfish

A personal favorite of mine.

I’d say that 10 founders a week tell me about how frustrated with themselves they are because they planned on working 10 hours a week but only were able to do 4.

Then, when I ask them what thing they normally do that takes 10 hours that they removed from their life to make room for 10 hours of work on a startup, they look at me like I’m crazy.

You’re a goldfish that’s already grown to the size of your bowl. You have no extra time unless you actively create it.

Don’t beat yourself up for not magically making the day 26 hours long. And, don’t swap startup time for sleep. You need that. Remove something else.

4. Discomfort is Not a Negative Signal

I’ll do a very quick old man rant here.

I see a whole lot of stuff talking about removing discomfort. If something makes you uncomfortable, don’t do it. Of course that’s good advice in the places where we both know it’s good advice.

But, it’s horrible advice in the startup world. If something makes you uncomfortable, lean into it. Be curious about it. Do not take it as a negative signal. Do not take it as a part of the business you aren’t meant to handle, or something you can outsource, or whatever else. Maybe eventually it’ll be that, but if something makes you uncomfortable it makes everyone else working on solving a similar problem uncomfortable, too. Their instinct will be to quit. IF yours is to not quit, if it’s to be excited when something is uncomfortable, you’ll end up on the fringes of the bell curve.

Don’t mistake discomfort as a wrong step.

5. Bad Things Happen Fast, Good Things Happen Slow

This is one of my favorite pieces of advice and I first heard it from my Uncle, who wrote it in the book we put out at our wedding. It was his marriage advice, but it works just as well for startups.

Bad things will happen fast, good things will happen slow. The order of the two will often give you false signals on what you’re doing.

Earlier this year, a founder in Tacklebox wrote a cold sales letter - like, a physical letter in the mail - to about 50 potential customers. He had segmented them aggressively and had a pitch for a service he thought would be extremely valuable to them.

Within an hour, two had emailed back, outraged. How had he gotten their address? Who did he think he was offering that service? As a note, the service was in no way egregious or insulting or offensive or, anything, and he got their address the same way j crew does. But, he was immediately hammered with all the bad feelings I’m sure you’re feeling now.

Bad things happen fast.

But, a few days later, a few other customers came out of the woodwork. They were interested. Could they hear more? A few months later, and a few people from that group became customers.

Good things happen slow.

Don’t overreact to bad before you give good a chance.

6. You’re Comparing Your Beginning to Someone Else’s Middle or End

When founders look at competitors, they get discouraged and frustrated with their progress.

But this is usually you comparing your beginning to someone else’s middle or end. Your 4 month old business you’ve been working on nights and weekends to a 3 year old business with 7 employees. What do you expect?

Zoom in on one specific thing you can do better than competitors for a customer they aren’t serving well. Learn that process better than them, serve that niche customer better than them. That’s the comp to go after.

7. You Misunderstand How Startups Work - 90% - 10%

In the startup world, you only need to make a few great decisions. You only need a few things to work out. Which means that most of the stuff you do won’t work out.

Let’s say you do 10 big things each month. A good mix is for 6 of those things to fall completely flat, 3 to be meh, and 1 to have a serious impact. You then lean into that 1.

There’s no way to predict which of the ten are going to work, so you can’t get upset at yourself for wasting your time on the ones that didn’t. You also can’t throw good time and money at bad - when something doesn’t work, stop doing it.

It is absolutely ridiculous to get mad at yourself because something you did that had a 10% chance of working didn’t work. But founders do. Constantly.

8. You Misunderstand What Progress Looks Like - Ski Lifts vs Staircases

On the heels of the 90/10 rule, most founders don’t know what progress for a startup looks like.

For most things you do, your progress will look like a ski lift. You’ll slowly move up and to the right. You’ll do things and you’ll get a bit better and you’ll do more things and get a bit better.

Startups don’t look like a ski lift. They look like a staircase. And the length of each step is not consistent or known.

So, you’ll work on something for a long time and get, seemingly, nowhere. Then, there will be a breakthrough and you’ll leap up to the next step. This is a visualization of the 90/10 rule.

It’s easy to get discouraged during the flat parts of the staircase. But that’s like getting discouraged because a leopard has stripes. It’s just how they are.

Note, a quick google tells me leopards have spots.

Ok, so you’re beating yourself up over things that are just natural, normal parts of a startup.

How do you stop?

Three Practices to break the beat yourself up cycle

Now that we know what you’re beating yourself up over, let’s help you… stop. There are three practices that can help, and they hit on the variables in the beat yourself up equation.

Practice 1: Lower Your Identity Exponent

The best way to stop beating yourself up is to disentangle your identity and your startup. To lower your identity exponent.

My favorite prompt here is to think about your closest friends and family - the actual people who have the opinions you care about. The ones who you think would think worse of you if this startup failed. Pick one. Maybe it’s your old college roommate Arthur. If your business failed, what would he do? Would he actually think any less of you? Or would he just support you?

Now, text him. Write “Hey Arthur, if my startup failed, what would you think?”

Expand it a bit. I’d imagine you’re worried about what your parents or uncle or favorite professor would think. Give them a call.

The pressure you’re putting on yourself is fake. Most people you know are never thinking about you or your career. They’re thinking about themselves. The ones that are thinking about you are the ones that actually care about you, and they’ll just want you to be happy. The way they view you is already set. A startup failing won’t change it.

It’s easy to feel the weight of outside expectations, but it’s helpful to really dig in on those to understand that’s mostly just a mirage.

The other way to lower that exponent is to ask yourself those questions. If this startup - a thing with like a 30% chance of working - doesn’t work… then what? Do you just pack up your bags and call it a life? Or do you try the next thing and then the next after that?

We want this thing to work, but if it doesn’t - you’ll probably be fine and no one that matters will think less of you. Now try like hell, in creative ways, to make it work.

Practice 2: Calibrate Your Expectations

When you notice you’re starting to kick your own butt a bit, run through this simple diagnostic. Ask yourself - “which of the 8 eccentricities Brian talked about is this?”

If it’s #1 - everything is new - stop holding yourself to old standards.

If it’s 2 - you don’t know what good looks like - write down where your expectations came from. If you can’t point to direct, relevant experience - let go of those expectations.

If its 3 - the goldfish - instead of beating yourself up for being lazy, write down, exactly, what you stopped doing that made room for your startup

If it’s 4 - discomfort - ask, am I avoiding this because it’s uncomfortable or because it’s actually wrong?

If it’s 5 - bad things happen fast - set a timer for a week before making decisions on a bad result or feedback.

If its 6 - comparing to others - write down the resources and time the competitor you’re upset about has that you don’t. Then, write out where you still have an advantage.

If it’s 7 or 8 - 90/10 rule or staircase progress - remind yourself that 9 out of 10 things not working is the expected outcome, not failure.

And, Practice #3: The Expectation Audit + Daily Affirmations

On Sundays, do two things. First, ask yourself a simple question: What did I expect to happen this week vs what actually happened?

This is where you’ll dig in on what you’re actually beating yourself up over, because the expectations vs reality will always uncover it. You’ll write about what you wished you’d had time for or where you fell short.

Zoom in on these and look for patterns. See if you can dispel any with the 8 we just talked through.

The second thing to do on Sunday is an affirmation. Pick any of these, or make up your own, that might be helpful:

• "Most of what I'm doing today is new. Slow and imperfect is normal."

• "I don't know what good looks like yet, and that's fine."

• "I have exactly 24 hours today, just like everyone else."

• "Discomfort means I'm doing something worthwhile."

• "Bad news comes fast, good news takes time."

• "I'm comparing my beginning to their middle."

• "9 out of 10 things won't work, and that's the game."

• "Progress looks like a staircase, not a ski lift."

I don’t think 11 year old Brian ever really thought about why he got so upset when he made an out. But if I’d realized that I’d tied my entire identity to every at-bat, if I was able to decouple that identity a bit, maybe I would’ve kept playing, because I’d realize how silly all that pressure was. Or, maybe I was never all that good and I’m just misremembering. Who knows.

The main thing is to stop freakin beating yourself up.

Because

Startups only work when you’re different. You only become different by doing things other people don’t, can’t, or won’t do. Those things are new and unproven and unlikely to work right out of the box. They’ll take time.

And if you beat yourself up, you won’t do em.

And now I feel bad about the guy raz jokes. Go listen to how I built this. We all love it. It’s great.

Have a great week.