At the edge of the map

This month is the 6-year anniversary of my coaching practice, and my 10th year of self-employment. In “normal” times, I might draw up a tidy list of personal and client wins, maybe throw in a business lesson learned. This year, what I have instead is a post that is equal parts triumph, gratitude and grief. It’s an articulation of all the complicated thoughts about myself and my business, that I've been uncomfortably sitting with over the past couple years.

But this isn't just my story. It's a pattern I've watched play out across my clients, my peers, and the tech world since 2023. Many of us are still inside it and trying to find our way through or out.

Since early 2023, the tech industry has been through a prolonged and painful contraction of mass layoffs, a brutal job market, eroding working conditions, and socioeconomic and technological enshittification.

As a business owner whose livelihood depended on tech workers having jobs, I watched the market collapse, and my business went down with it. This wasn’t simply a rough patch I could hustle through or pivot my way out of. It truly broke something in me.

As a single income household, the financial pressure made it nearly impossible to think about anything beyond survival. Underneath the material conditions, my sense of self was eroding, and I lost the plot of my own story. I have always shown up for myself no matter what, so it felt like I had lost everything.

The worse part was how hard I was being on myself for struggling. I was frozen for what felt like eternity. But what I couldn't see in the fog of anxiety, anger, and isolation was that I was doing my best to hold it together with what I had left.

For too long, I’ve watched people I respect—my clients, peers, friends, even internet strangers—go through their own versions of this unravelling, blaming themselves for their situations. The silence and shame around not being ok is part of what makes it so isolating and psychologically corrosive. We don't talk about our shared struggles, so we assume everyone else is managing better than we are.

These days, I believe the majority of people in our orbit are not. We’re barely keeping our heads above water at work. We’re going into year two of a job search with no end in sight. We’re walking away from careers we spent years building. And the entire world is on fire.

These situations are unfair and unsustainable. They can do real damage to your sense of self, especially if we’re accustomed to being rewarded for our talents and hard work. It's easy to internalize the struggle as a personal failure, that you’re not good enough or you don’t belong.

If any of this sounds familiar, you are not alone, and you are not behind.

The narrative that success is purely a matter of effort and ambition is bullshit. It doesn’t account for the unrelenting conditions of the system we’re operating in. When we can't see that clearly, we end up trying to solve a systems problem with personal optimization, which doesn’t address the underlying problem.

For a long time I was caught in the same loop—optimizing myself while the conditions stayed the same. There was no single moment when things turned around. I didn't wake up one day with a new mindset or revelation or plan. I slowly started finding just enough footing to push through, one decision at a time. I rested. I journaled. I opened up to peers. I went to therapy. I birdwatched. I sold my personal belongings. I cashed out my IRA. I did odd jobs. Eventually I found some consulting work, which for a while I thought of as a backslide, proof that I'd failed at what I built.

I tried really hard not to talk shit to myself for "being bad at running a business" or taking so long to figure things out.

Piece by piece, I started to recognize myself again. The reframe didn't come easy, but it's the most useful thing I've learned: it's not that I wasn't good enough—I was operating in conditions that were genuinely untenable.

Today I'm showing up for myself in a familiar way. I’m designing the next chapter of my coaching practice from a place of hard-won resolve. The challenges are lingering, but my work feels alive again because I'm making real, gradual, sustainable progress.

I still have moments of doubt and fear, but I'm also excited and hopeful about what I’m building. We're traversing unknown terrain while the map is unfolding in front of us. I want to bring as much ease, autonomy, and stability to my life as possible, so I can support those who are trying to do the same. It’s less of a struggle when we're not going it alone.

If you're in the thick of it right now, barely holding on at work, or wondering if the job search will ever turn around, I want you to know that what you're dealing with is genuinely, systemically, relentlessly hard. It's not a reflection of your capabilities or your worth. Humans aren't meant to absorb this much stress and uncertainty for this long.

The most useful thing I can offer isn't a to-do list or silver lining platitudes, just an idea to consider: you don’t need to be so hard on yourself for struggling in conditions that aren’t designed to help you thrive. And a nudge to take one small action, even if right now it feels pointless, followed by another one for the next few days, to see if they give you a flicker of momentum.

It doesn’t get better overnight, but the small, unglamorous actions, the ones that don't look like progress from the outside, are the things that can restore our capacity just enough to take the next step, and then the one after that.

Autotune dog 🐕