Bootstrapped startups and the shit I learn in therapy

I’m writing this from my new home office in Detroit, Michigan.

Last week I packed all of my things into a small Uhaul trailer, and left South Carolina after almost 28 years.

There are boxes everywhere. What didn’t seem like that much stuff when going into the Uhaul has exploded to take over my girlfriend’s apartment. I used a circular saw as a doorstop earlier this morning, the new window unit AC is laying by the window half installed, and our pictures are scattered about the house near the walls where they will someday hang (probably).

As a neat freak who needs order and clean spaces to calm my frantic head, it has my cortisol levels rising.

But slowly, surely, the place is coming together.

A pile of boxes turns into a cool vintage bar set with all of our combined glasses on proud display (enough to provide cocktails to half of Detroit). Another pile and a few hours of work, and I have the new standing desk I’m using to write this essay.

(What does it say about us that the first thing we set up was the bar?)

It’s coming together, but I also know it’ll never really be finished. We’ll get things the way we like them for a while, and then we’ll find a new table at a thrift store and break everything down to move it around. Or we’ll slowly replace the cheap IKEA furniture with slightly nicer pieces.

It all feels remarkably similar to building a business.

Cognitive distortions and finding good enough in your business

I regularly fall into the trap of telling myself that if we can just make this hire or figure out this process, everything will be easy.

But it doesn’t work that way in business either.

Sometimes it does get easier, for a time. Then someone leaves, or you get a new opportunity, or find a better tool, or a process stops working.

And you tear it down, rearrange, and build it back up again.

I try to remind myself that building a business isn’t about creating the perfect structure. It’s not about getting to done. Done will never exist, we will always be tweaking and updating and growing and changing.

What we’re really talking about here is perfectionism, or the cognitive distortion known as All-or-Nothing Thinking. Cognitive distortions are patterns of thinking that are false and have the potential to cause psychological harm.

All-or-Nothing Thinking means you see the world in terms of extremes, rather than with a realistic dose of nuance. In other words, you fail to see shades of grey.

When I try to eliminate the chaos in the business, I will inevitably come up short. It feels like I’m failing, and I start to spiral. Building a business is a long game, and while these feelings are natural, they decrease my motivation and make it harder to keep up positive momentum.

Here’s the process I’m developing (through lots and lots of therapy) to shift my thinking to be more positive and more productive.


The first step in changing your thought pattern is to acknowledge your current thoughts and approach them from a place of curious observation.

Label the thought for the cognitive distortion that it is. Don’t beat yourself up for thinking that way, it’s normal, but acknowledge it and focus on understanding where it’s coming from and what you can do about it.

Sort problems into what you can and can’t control

Whether it’s a stack of boxes in your apartment, or unhappy clients in your business, sort the problems you’re facing into what you can and can’t control. You can’t control how a client feels, but you can control your client communication process.

Focusing on problems you can’t control is another natural, but unnecessary drain on your energy.


Once you’ve clarified what is within your control, you’re likely to end up with a set of problems that is much longer than you can realistically tackle. You can pretend that you can tackle everything on your list, or get realistic and do the tough work to sort out what is really important.

The bar is clearly a priority, but painting the office can probably wait until you have more time and energy.

Define good enough

This last piece of advice is the piece I continue to struggle with the most. It’s easier to accept good enough in the apartment, than in the business. The stakes are admittedly quite different. The layout of the dining room only affects me and my girlfriend, not our entire team. No one’s livelihood is affected by our table not matching the rug. And we haven’t spent 7 years working on it.

I know good enough for Krit has more to do with the happiness of our team than with our profit margins. But I still panic when we aren’t hitting what I think we should be.

If we’re creating value for our clients, our team is healthy, and we’re paying the bills, that’s a pretty good start.

I do know this. No one’s apartment is perfect. And no one’s business is either.

This is a long game. Pace yourself and remember that you create the pressure. Turn the pile of boxes into a bar and then move on to the next pile.

This post originally appeared on the Krit blog.

You’ve successfully subscribed to Andrew Askins
Welcome back! You’ve successfully signed in.
Great! You’ve successfully signed up.
Your link has expired
Success! Check your email for magic link to sign-in.