Last week was set aside to write my résumé. My first one in 7 years. For my first real job in 4 years. But my mind has been wandering willfully. Once I begin typing a work history I’ll have given up at last. This résumé has become the final comma in the run-on sentence that was my four years of self-employment.

A few weeks ago I shut down a product I solely programmed, designed, and operated for 3 years. Over the past year I rebuilt it and relaunched it as a new concept. It didn’t work. That’s not saying it couldn’t have worked. It just didn’t work. Let’s save that for another day.

When I first started, I partnered with a mentor who gave me a tiny bit of money to build the prototype. Last year I received an equally tiny, no strings attached grant from Y Combinator to build the updated concept. Otherwise, the development and daily operations of my projects have been totally self-funded.

So here I am today, carrying a non-trivial amount of credit card debt. I still owe an equally large amount on last year’s taxes because a filing error meant I got hit twice as bad. And I owe some to family too, who graciously saved my ass when I screwed up. Fortunately my soul is less worn down than my bank account.

We’re tricksters, you know. We’re our own worst dupes. My gut says our emotions point to some internal truth worth exploring. So in times like this I try to record how I feel. To be able to point back months and years in the future and say “Remember what you did last time, you fool!” The truth may not exist on the surface. But if we sit and unpack these feelings maybe we can learn something.

You won’t find any lessons here. Just a letter to future myself which may resonate with you. Or maybe you’ll think I should fuck off. I don’t particularly care. That said, hopefully you’ll forgive it for being a little self-involved.

Hole People

I dug myself a hole. A fairly deep hole, I’m embarrassed to admit. I’m alone here, shouting so you can hear me up there where things are fine.

I retired a lot of old projects this year. Even more in the years before. Four years ago I left a high-flying startup job in San Francisco and moved back to Chicago to work for myself. I did freelance design and programming work every few months to pay bills. I charged a lot of money. Then I used what was left to build my own things. As you’ve likely noticed, they were such good things that few of them are around anymore.

Including the aforementioned debt, I spent at least $75,000 of my own money building things over the years. Forgoing paychecks, stability, and clients, most of it was spent on living costs, food, my dog, and far too much alcohol. A lot was spent on web servers and tools. All for building products I dreamed only to convert into a steady and humble income. Instead, I’m buried in a hole of my own design. [Author’s note: I’ve designed better things.]

This hole idea isn’t just about money, though you’d hardly find someone in a hole like mine not fraught with money problems. Rather, it’s the place we find ourselves when we set out to do something new. It’s the place we go when we start. It’s how we find ourselves isolated, confused, wondering if anybody will ever care about the work we’re doing.

Unsurprisingly, there’s no trophy for working hard and driving yourself to madness. No magnificent “welcome back!” parade on your return to normal life, failures stacked up behind you. For many of us, it’s hard to recover from being stuck in our hole.

Living With It, Alone

Life spent in the hole is unsustainable. You’re in over your head. But something feels noble about it. You’re breaking new ground and paving way for something coming. Making the future happen sooner. The work is honest. You don’t just collect checks and toast champagne to your loved ones in the evenings. [Author’s note: I don’t know what real life is like.]

Many of my friends with tiny businesses are struggling. These are bold people trying to make something of quality. They struggle with self-doubt, affording bills and taxes, health insurance for themselves and their children, getting to the next step, fulfilling orders, marketing their wares, just getting anybody to give a single flying fuck. It’s a lonely, questionable existence.

Nobody cares if you self-fund your business. But it defines so much while you’re doing it. Early on you can’t afford to hire, so it’s lonely and hard. You have to do everything yourself, so it’s difficult to get the word out while also making your products. When customers have problems, it can feel like a personal attack (even when you know it’s absolutely not). Loans are difficult to get and risky to have. Each day is exhausting.

Being alone in your hole means you’re unable to see all the other wonderful people around you who are also stuck in theirs. Some of these folks are your allies, and you need them. Don’t keep yourself shut off. Nobody can dig their hole alone, physically or psychologically. It’s OK to call for help.

Nor is it easy to realize the incredible number of now-empty holes representing the many failures of those who made it out. People prefer to skip this part of history. Nobody wants to talk about all the holes they had to dig to finally make it out in one piece. And since we don’t have an empty storefront equivalent for all our failed projects, a physical manifestation of all our failed projects, we’re unlikely to see more people discuss them openly.

Champions Of Their Hole

We champion the big wins. We ignore the losses. That seems great when you’re winning. But when so many people feel like they’re losing they block out everything but all the people shouting their successes, small and large.

It almost feels like a requirement to forget where you’ve been once you’ve climbed a decently sized hill. You pan around to assess your place. Who is on a taller hill? How does your mound stack up next to their mountain? Keep reaching, grabbing, fighting and maybe you can make it up there.

You spend so much time looking up anymore you hardly remember the people still in their holes behind you. Why would you bother looking down upon them from way up there? No need to remind yourself how many times you screwed up to get there.

But you were down in a hole once too. You dug it yourself. You worked hard. Maybe alone, but likely with the help of many, many others along the way. Some were there at the start, others joined along the way. You made a lot of mistakes, had a fair bit of luck, and built something people seem to care about. Don’t forget the path worn on the way up there, how many people chipped in, reached a hand out to help.

Never In A Hole

A lot of people never climb into a hole at all. [Author’s note: this metaphor majorly tired now. Definitely force it upon the reader even more.] They join a group who already climbed out of the hole and are now up on their hill together. Why climb down when you can just start out above ground? And they’re right.

These folks work hard. They do a good job. They look around and enjoy the view. They see the people down in holes. A few of them are even friends. And because they can see them, they think they know what it’s like down there. That hole doesn’t look too bad, they think. I can dig. And look, I made it up onto this hill already. I know the way up.

Now imagine if your biweekly direct deposit stopped showing up. Ever. You don’t automatically have rent money on the 1st and bill money on the 15th anymore. You get paid solely for the hours you work, not the hours you stared at Twitter/Instagram/Reddit, took long coffee breaks, hung out on Slack, or whatever else. Products only were sold when you did the work to sell them, shipped when you shipped them, and support emails returned when you had a break.

There are a lot of silent folks out there grinding hard and feeling like they’re getting passed up. (Many of them in Chicago, one of many reasons why I love this city.) Sometimes their work is amazing, and people barely recognize it. Sometimes their work is mediocre (like mine?), but they just need the time to make it good.

Once you take into account how many people get praised for mediocre work when they don’t also operate every facet of a business, you start to see things differently. It’s hard to teach yourself this viewpoint, you typically learn it when you grind for yourself. The frustrated energy isn’t worth it, nor is it useful, but it’s a difficult feeling to avoid.

When you work for yourself and paychecks don’t just show up, it’s risky to buy a couch when you don’t have one. What if you need that money for rent 3 months from now? (I did.) That’s how a lot of people feel when you tell them to work less, take the weekend off, come out tonight instead. They aren’t working because they want to. And even though they chose this path, they’re working to survive. Remember that you’re probably working with a team, or from the perch of a hill. They’re doing the role of 10 people from the bottom of a lonely hole.

Accidentally Purposefully Not Successful

My time in San Francisco taught me a lot. Not facts people share directly, but indirect things about myself just by being there and observing how the machine worked. Oddly, I know a lot of millionaires and billionaires from my time there. Many of them accidentally rich. Spend a little time in Silicon Valley and you’ll meet plenty too.

Most of them are smart, talented, and worked really hard. But many of them either didn’t expect something like that to happen, or “made it” after “failing” no different than many people have. With a few exceptions, these people aren’t smarter than you or me. They aren’t kinder, more capable, harder working, worthy, or willing.

They just happened to be on that path. A path which took a lot of luck, timing, privilege, and a few decisions at some point to continue along that path. But there’s always someone further up or down that path. You can never “win.” As if there were even a way to know what winning was.

Four years ago I walked away from a job which would’ve made me something close to a million dollars. Actually, that money would’ve been mine tomorrow (literally). At the time I’d also been considering a job at a company which would’ve likely made me a few multiples of that.

I was friends with the co-founders of the second company when I was interviewing there. We used to drink beers on my roof in San Francisco. A few weeks ago one of them was named the youngest self-made billionaire in the world. In 2016, I still like to drink beers; they are on magazine covers.

A Silicon Valley-dozen stories just like this have stacked up over the years. It’s confusing at times to remember them. Not because I want their lives or the ones I passed up. I absolutely do not and I know it. But because it’s a reminder that there’s far too many ways to question your past-self.

Instead of following those paths, I moved back to Chicago to be closer to friends, a city I truly loved, and to work for myself. I wanted to write my own story, not join someone else’s. Sure, that’s a tacky line. But don’t tell me you don’t know the feeling. It’s why we move away from our parents. It’s why we make things. It’s why we aim higher and take our shots, even when things felt safe.

You have to move on from questioning your past self. The story thus far has already been written. Your decisions were made. I’d never trade my life and friends now for that of anybody I worked with or knew in San Francisco. Remind yourself you don’t want what those other people have, or what you could’ve had if things had gone differently. What’s the point of comparing?

There’s no single path for everybody. There’s not one narrow finish line fit for only a handful of people. We aren’t all on the same trajectory, yet we compare ourselves and others as if we are. What accounts for moving forwards or backwards for any given person won’t look immediately obvious. Don’t trick yourself into “knowing” which way you’re going. Just keep going. Use the internal compass you have. Not the external lighthouses others have planted to confuse you.

Nice guys finish first. If you don’t know that, then you don’t know where the finish line is.

– Garry Shandling

The Leaderboard

Don’t listen to the people who devalue your mistakes and failures. Don’t believe them when they act like they have none or argue theirs didn’t matter. These people want you to believe they’re infallible. They’re spreading their own propaganda, propping themselves up to be more important than they are.

As a society we’ve constructed a leaderboard where there isn’t a competition. And when that’s the case, it doesn’t matter which direction you look. You’ll always see far more people ahead of you than behind you. But have you ever wondered why you’re running a race in the first place?

The goal is to screw up in smaller ways than the combined good work you accomplish. Sprinkle some luck in there and maybe the fuck-ups will matter a little less (just look around and you’ll see what I mean).

The leaderboard doesn’t reward the mistakes, so people prefer to only mention their successes. The reality is we all screw up almost everything. We’ve done it many times. We have big fuck-ups and small fuck-ups, but we’ve all fucked up. Remember your mistakes. Remember how they sting. Help others who are stuck in the hole. Reach back as often as you can. We move forward together. Zoom out a bit and realize we’re each only as strong as the ground all of us build on.


Tomorrow I get to ease the effects of my failures and climb out of the hole. 2017 gives me a chance to start anew. A startup I worked for IPO’d in June and tomorrow I’ll have access to the stock I received as an employee. My debts can be cleared. I’ll start a savings account, breathe a little lighter for a while, and finally buy a couch.

I’m hopeful for the future. In the new year I’ll likely have a job again. I expect it’ll be somewhere where I feel I can do some genuinely good work for good causes. Beyond that, I have some ideas for initiatives to help people who can’t afford to take the hit I did. How to keep that hole from getting so goddamn deep.

Most people don’t have this saving grace. I’m lucky. But for now, I’m still in the hole. It’s my hole. I dug it. And while I’m here it seems worth taking inventory of the situation, for myself and for the rest of my hole people trying to cope with what we’ve done.

Underneath this redemption, I worry a little about coming in from the cold. Life in the hole wasn’t easy. When you’re down there you have to do a lot of things on your own. You change. You find pain, but you don’t know how to give it up. You harden in ways that make it tough to reacclimate to any normal working situation. My heart and brain are feuding. Why not go back to the field and start digging a new hole? It’ll be better this time.

No matter what happens next, I know I’ll be OK. I’ll always find a way to be OK. People who dig holes generally know how to find a way out of them. Sometimes quickly, sometimes it takes a little while. I guess if there was any point to this post that would be it. Everything is going to be okay. You made the right choices, even when you made the wrong ones. I think. I’ll let you know.