Intro / aside:

My posts have been so sparse that the space between them looms larger and larger in my mind every day. I start to raise the expectations on myself to write something really great, since it’s been so long since I last published. As time goes on, the topics I feel I need (and want) to cover in order to catch readers up grow so numerous, it all becomes sort of paralyzing.

Enough. I just want to blog. I’m lowering the stakes and adjusting my format.

Here’s how I now intend to deal with this, instead of Rare-Posting like before:

• From now on, I’ll tag posts as [field notes] or [essays].

• Field notes, like this one, will be more casual and frequent. I probably won’t always notify readers via email about these posts. I want them to feel more like blog posts of yore, without all the pomp and circumstance and effort of an “essay.”

• Essays, by contrast, will be more intentionally-formed writing pieces that I put more effort into. I want to produce more of these, but I don’t want them to get lost amongst more frequent, low-stakes Field Notes.

Today’s notes

This summer I took time off. I lightened my workload for a while to start to tackle my burnout. Without getting into all the details, a few things really served to burn me out in recent years, chief among them (1) a surprise cancer diagnosis, and subsequent extremely intensive, life-altering treatment in 2022; (2) ending a relationship and moving back to my hometown after a decade away; and (3) being laid off and immediately starting my own business, which quickly became much busier and more demanding than I anticipated.

Prior to that, I’d been grinding in leadership roles at high-growth startups for a solid decade, so taken together it was really all a bit much. Aside from two- or three-week vacations here and there, I hadn’t taken a proper break in my entire adult life, so this was the first time I actually allowed myself to slow down for any meaningful length of time.

(I don’t count time off for cancer treatment as a break, since it’s more like a surprise journey into 24/7 hell).

In this post I don’t want to dwell on cancer too much, except to point out that even that couldn’t really slow me down. I’ve always worked hard, and always wondered why I worked so hard. Most surface-level self help nonsense will tell you that in order to cure your burnout, you just need to meditate, consider a job change, set good boundaries, and do a bunch of other obvious things. For some reason, that advice never works. Usually it’s given by people who can’t really relate to the problem in the first place.

As a lifelong workaholic (a word I am not using derogatorily), I now realize that the thing that drives me to work goes much deeper than any structural element of my employment, and it’s far harder to tackle than any of that generic advice would suggest.

You’re wired a certain way

I used to think that I could out-work anyone, and the only limit to my potential was whatever the limit of my cognition implied. Once, when I was feeling particularly worn out as a tech VP running a 25-person team, working long hours, and travelling internationally two or three times a month for business, I complained to my therapist. It must have been 2016 because I remember saying, “Hilary Clinton seems to be on stage thirty times a day in different places, and we know she answers emails too. How come she can do it without burning out, but I can’t?”

I expected her to give me a pep talk, but her response really offended me at the time. “We aren’t all wired like Hilary Clinton,” she said.

I had never in my life considered the possibility that, intellect aside, we might have different tolerances and proclivities for the amount and nature of work we were capable of doing. I continued to reject this notion for a long while, but I now take it to be an inviolable law of nature.

Case in point: when I adopted my cats a couple years ago, I noticed the way the rescue organizations described the animals in their care. “I’m shy and anxious and will do best in a quiet home without kids, where my personality will shine,” some of their bios said. Others would read things like: “I’m active and high energy! I’ll be happiest with other pets around, and family members who are active and like to play a lot.”

If you’ve ever had a dog or a cat, you know this is real. Pets possess obviously innate characteristics, and different environments will cause them to suffer or thrive. I have a particularly shy cat who, over time, has come to be confident, happy, snuggly and playful. But around strangers, small children, or dogs, he runs and hides. This is just who he is.

Why don’t we grant ourselves the same grace?

It took me years of trial and error in environments that were wrong for me. Can I run a big team? Yes. But the constant conversations, people management, and meetings really wear me down. I start to get bummed out when I can’t do long, uninterrupted periods of deep work. Can I work in a big corporate business? Sure. But office politics make me crazy, and interfere with my long, happy, silent periods of deep work. Can you drop me on the ground in a foreign country and task me with getting 150 targeted leads to attend an event? No problem, but I’ll really start to miss my long, quiet, blissful, uninterrupted periods of deep work.

You see what I’m getting at? I can’t help it.

Some people love being on calls, in meetings, going to the office, wheeling and dealing, saying “hey Jimbo,” etc etc. Their worst nightmare might be a week of total silence with an empty calendar, a blinking cursor, and a bunch of material to work through. Others, like me, are the complete opposite.

As a result, certain types of work and certain employment structures are far more enjoyable and sustainable for me than others. Anytime I begin to deny this reality, I risk tripping into burnout.

What’s more, I suspect that the load on your nervous system over time has a huge effect here. The word ‘trauma’ is way overused in our culture, and I hesitate to call even something as life-and-death as my experience with cancer “trauma,” because I hate the idea of taking on labels or making myself a victim. Still, I can’t deny the fact that my nervous system sustained extremely high levels of stress for a prolonged period of time, and it has had a very real and lasting effect on me.

This has been hard to come to terms with, because I’ve always been so passionate about my work, and rather ambitious in nature. My ambitions are more meaning-based than financial. I want to do great work that I’m proud of, and I want to take on big challenges. I’ve had a very hard time over the past couple years reconciling this with the reality that, nowadays, I clearly need to put my health above all else, and I need a very specific cadence and style of work. My tripwire is more sensitive than it used to be. I just can’t tolerate working out of alignment for long.

Overcorrecting and cultural scripts

When I lightened my workload and started to take a bit of a break, I did what anyone in my situation would do, and enrolled in a coaching program. I figured it was obviously time to get out of tech, since startups are so demanding. Plus, I’m not afraid to talk about anything at all anymore, and given my deep interests in spirituality and philosophy, I could probably transition into coaching. People often come to me for deep personal advice, so I figured I may as well make the leap.

I got a couple months into my program of choice, though, and realized I had to pull the chute.

Don’t get me wrong, I was really interested in the content of the coaching program. I was learning a lot, and all the people I dealt with were lovely. But I could feel that it wasn’t for me. I was coming at the problem entirely the wrong way.

Since I had burnt out in startups as well as while running my own business, I had basically drawn the conclusion, “tech work bad, other work good.”

But ultimately, I didn’t feel any passion for coaching work. I like other people easily, but I don’t feel particularly called to help them reach their highest potential as my own life’s work. I followed a weird cultural script where you burn out, go through major “trauma” (whatever), then become a coach. But it was all wrong for me. I wasn’t like these people, I could tell. I needed more chaos and creativity and rebellion in my work, I needed less structure, I needed less “curriculum” and pedagogy, and I needed a lot more zeitgeist, timeline, art, chaos – I needed to be back in the belly of the beast thinking about technology. Dammit.

Getting the diagnosis right

So I had the problem all wrong. It’s easy to see why I’d figured tech was the culprit. It’s relentlessly fast-paced, it’s notoriously demanding, everyone is super smart so you always want to be shooting three pointers and not lobbing in obvious, mid work that anyone could delegate to GPT 4o.

But there was something in my relationship to work that wasn’t right. I had been dealing with the problem at the object level so far, but I realized I had to go deeper. Therapy approaches, “boundaries,” parts work – all of that was fine up to a point, but none of it really hit for me.

When I started reading some of Carl Jung’s work this summer, however, and then tripped into Marion Woodman’s books, I hit the jackpot.

There is so much more to write about this so I’ll tackle it briefly and ineffectively, just to try to touch on the ideas at hand. First of all, Carl Jung’s focus on mythology, archetypes and the subconscious – as well as his incorporation of deep spiritual themes – rings a million more bells for me than the pop-psych CBT that pervades Western self-help culture.

And once I dug into Marion Woodman’s work, I couldn’t believe how hard it was hitting. She was a Jungian, but with a particularly feminine lens. She focused specifically on women with tendencies to pursue perfection and overwork. She also went through (and survived) a terrifying bout with cancer, and wrote about it in her journals, later published into a simply incredible book called ‘Bone: A Journal of Wisdom, Strength and Healing.’ No one – no one, no one – has ever written anything that resonated so deeply with me.

I have no desire to wade into “gender discourse,” but I have to admit I’ve always suspected there was something vaguely gender-related that influenced my struggles with work and overwork. I’m very feminine in nature, but I have a bunch of these incredibly masculine coded interests (tech, cars, space, science, politics, whatever), and so I’ve spent my whole life feeling vaguely different from everyone around me, no matter my milieu. I’ve found it hard to identify role models who I can relate to. It’s not clear what template life for a person like me is supposed to follow.

Meanwhile, it’s been hard for me to tease apart my passion for work from my tendency to overwork. My passion for certain types of work feels sacred and important to protect. It’s obvious to me that doing a job I don’t like just to limit my hours and/or retire early ain’t it. (Not interested!) But there’s been something off in my relationship to work, and it’s the thing that tips me into burnout.

Marion Woodman identifies in certain types of women an imbalance, or lack of appropriate integration, of the feminine and masculine within. This can, for some particularly sensitive women with certain proclivities, lead to a sort of ‘Type A’ addiction to perfection. (She wrote a book of the same name, which I highly highly recommend.)

It’s not about frothy ‘divine feminine connection’ like you might hear about on Instagram or at your local yoga studio. What Woodman digs into is deep, messy, and archetypal. It’s the self-abnegation, the repression of aspects of femininity that our culture doesn’t know how to uphold or ingest, and the way this manifests in perfectionist behavior.

I can’t easily summarize her thesis in this blog post, but if any aspect of this resonates with you then I really do recommend seeking out her books. Upon discovering her work, I felt like I finally found an answer to the morass I was lost in before: all the meditating and resting and good boundaries and self help and zen minimalism were ultimately a pursuit of nothingness, of silence, of the quiet dissolution of desire and emotion. Not only did this not resonate with me, it repelled me. It felt like the wrong antidote to my problem. Trapped in a cycle of overwork, I didn’t need silence and space, I needed to reconnect with myself, I needed art and life and fullness.

Cancer, facing my mortality, and burning out on work laid the groundwork for me to rapidly and easily reject a lot of ideas and beliefs that I had held for a long time. But I wasn’t sure what to replace them with. What do I do now? Marion Woodman’s work helped me to contextualize this struggle, to identify as real my newly-remembered appreciation for dance and music and perfume and art and literature, to stop starving myself of the things I loved most. I understand now that to heal my burnout, I don’t need to ‘have better boundaries,’ I need to do work that’s right for me, and seek equilibrium between my anima and animus, my inner feminine and masculine. It’s not likely to look the same for me as it does for many of the men around me. Aha! Because we’re not all wired the same way. It’s not meant to.

The deeper and more effective reframe

So then my question became not, “what type of work should I do now, since I’ve burnt out on tech?” But rather, “since I love tech, and I have these other burning aspects of my personality that have gone unused, unfed and unappreciated for a long time, what do I need and want to do now?”

This is a much more empowering question, but it requires being willing to jump off the well-trodden pathways a little more.

I have a working answer to this that I’m experimenting with now. More to come in a future post, since this is already long and unwieldy.

If you’ve read this far, thank you for being here.