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Why I write memoir
Also: I have my own 'Phoenix rising from the ashes' narrative—I just don't like telling those kinds of stories
One of my favorite sayings ever comes from Tracy McMillan:
Everything works out in the end. If it hasn't worked out yet, then it's not the end.
Nothing else so crystallizes how utterly intent we humans are at making sense of our existence by telling a story about it.
Looked at one way, the quote speaks to our willingness to self-delude. We’ll stop at nothing to construct a personal narrative that makes us the hero of our own story. We’ll even delude ourselves about the nature of time and space.
Looked at another way, nothing is more natural. We tell ourselves stories and always have. It’s part of what makes us human. Our capacity for making up grand narratives is in some sense part of our superpower as a species—we make sense of things, we are meaning-making machines. It’s what we do, and it’s gotten us this far.
I’ve written before about how life is not a path, there are no forks in the road—in actuality, life is a wilderness. We choose direction based on imperfect information. There are no campsites, no trails, no way to even know which way is forward.
And yet, these metaphors about paths and journeys are kind of the water we swim in. It’s hard to even have a conversation about a significant life decision without using the language.
Even this newsletter can’t escape it. I have nothing to offer but stories—
And in that spirit:
I. Why I write memoir
Substack has this great chart that they published as part of a series on how to find and engage your audience, which they in turn borrowed from People & Company’s Get Together resources.
It shows eight reasons people might decide to subscribe to or follow your stuff:
I’ve often looked at this chart and wondered which one I am—it’s important to me, after all, that people actually read my writing, but it can be a struggle to understand one’s own positioning. Why do you people subscribe? (Feel free to write me and let me know!)
It’s difficult to know ahead of time which pieces will resonate and which won’t. Sometimes my favorites wallow in obscurity, while casual, off-hand passages end up having a deep impact.
Occasionally, the two overlap—what I personally think is good writing is also what resonates. But it’s never a sure thing. I usually have to wait and see. I have to wait for people to email me, or send me a voice memo, or tell me in person the next time we get together.
For a while, I looked at that chart and thought I was “Guidance.” I thought maybe I was helping people navigate complex topics or challenges. Specifically, I was helping location-independent digital nomads (or those who aspired to location independence) navigate the complex decision-making around where to live, what to invest in, and how to create meaning and legacy in their lives.
Except, when I told this to a close reader of this newsletter, she said no, you’re not Guidance—you’re Inspiration.
The thought had honestly not occurred to me, especially since I tend to be highly suspicious of inspirational content.
And yet, I could see what she meant. I have very deliberately crafted the life I want, according to values that are important to me. I spend a huge amount of my time doing the things I love and that are important to me: climbing, kitesurfing, traveling, and spending time with friends and family. I have been location independent for a decade now, having built my own consulting business that I can run from anywhere. In February, I purchased an old fixer-upper in a climbing town in Spain. This Summer, I will move with my son to Barcelona.
All these things can serve as inspiration to others who might share similar aspirations.
But one thing I don’t do (or, do very rarely), is give advice. I don’t give advice because I don’t think my own life is necessarily instructive of anything.
I am a data point of one.
It would be the height of hubris to suggest that because I did something some way, therefore now you should do something the same way. I am but a single example of how to do something, and probably a not particularly applicable one. That is why I write memoir.
It comes down to this: I can only speak for myself. Anything else feels dishonest.
But it’s a constant pull to try to make myself into some kind of guru. To suppose that I have some profound wisdom or method to impart to the masses. To essentially say to the world: look what I’ve done with my life, AND THEREFORE here’s what you should do with yours.
I say this, despite the fact that I have derived a huge amount of personal and professional inspiration from others who do give advice, who have written books, published YouTube videos, and inspired me to dig deeper and live better. I owe a lot to those people, and I think they should keep doing it.
It’s just not for me. I have to stick to what I know, and the only thing I know for sure is my own experience. So, that is what I write about. Memoir.
II. When I quit a job I hated, started my own business, and rose like a Phoenix from the ashes
You know the entrepreneurial hero’s journey? It goes like this:
I was laid off; I didn’t know what to do; I felt like my life was in crisis; then I searched within myself, I found the answers I had been looking for, and now I’m a successful online consultant with a growing roster of clients that I’m passionate about and a glorious life working from a beach in Thailand. Or Bali. Or take your pick.
I have my own entrepreneurial hero’s journey, but it’s a story I’ve always resisted telling for precisely the reasons stated above.
It is a classic, click-bait tale of when I reached a low point, quit a job I hated, started my own business, and rose from the ashes like a Phoenix, now location-independent and able to pursue my dreams—and it is instructive of next to nothing.
But maybe, just maybe, it is a little inspiring.
Anyway, it’s time I got it off my chest.
It was September 2020, six months into the pandemic, and I’d been unemployed for more than a year.
After I was first laid off in 2019, my partner and I went to Mexico to work on our Spanish. When covid hit, we came back to my house in New Hampshire. I spent the time renovating the garage, rock climbing, and writing. I’d started two Substacks, this one and another built around everything I knew about the business of healthcare.
But eventually, the severance package, savings, and unemployment insurance were all running out, and I still had no clear idea of which “path” I wanted to take next.
This is the context for why, in September 2020, I decided to take a job.
It was a normal, traditional, full-time job at a marketing agency. They were headquartered in Northern Virginia and at one point expected me to come into the office—but the pandemic was still on, and allowances were still being made. For now, I could continue to work from New Hampshire.
It felt good to have a team again, some structure to the days. It especially felt good to have money just flow into my bank account each month.
The agency had a bunch of healthcare clients, and I’d been in healthcare for more than a decade, at times managing my own clients. It all seemed well suited to me, a good fit as they say, and more importantly, the job fixed all my financial anxiety.
I jumped in head first—ready to be a team player, ready to manage whatever clients they threw at me, and ready to help grow the business however I could.
This all lasted about a month.
By November, I felt overworked and was glad to have a few days off for Thanksgiving. By Christmas, I’d begun to sense that everything about the place was pretty toxic. I won’t dwell on the gory details, but I was having trouble understanding how anyone could run a business this way. In December, school was back in-person and we’d come back to the DC area. I’d never had a particularly stressful work environment—but by January, after the holiday break, just over two months into the job, my stress levels were through the roof.
I took walks each day during lunch just to cool my head. By 5 pm or 6 pm, when the work day was over, I would be so frustrated that I’d walk out of my office, march straight to the kitchen, and pour a large glass of wine so I could chug it.
My stress overflowed into the entire household, to my partner, to the kids. I couldn’t hide it, and they’d never seen me this way.
I won’t belabor the entire saga—it gets into the nature of work and time itself. Suffice it to say that in 20 years of healthy participation in the market economy, neither I nor my labor had ever been treated with such disregard. Never in two decades had I experienced such a disconnect between the quality of the work I was doing and how that work was being judged. Never before had I clashed this seriously with an employer.
By February, I knew there were irreconcilable, fundamental philosophical differences.
After a particularly fraught call with the CEO, I hung up, walked into the other room, and told my partner, who had been half-listening in on my side of the conversation, “I think I need to quit.”
It was not a good time to quit a well-paying job. We’d just signed a lease on the house in Bethesda. Inflation was starting to rear its head. I had already exhausted much of my savings during the previous year.
Without this job, my income would plummet. I had a side client at the time that was paying me $775/month to do content marketing. Another, larger client I had brought to the agency, but wasn’t sure I’d be able to leave with now due to a non-compete.
I had bills to pay, a family to support, and absolutely no guarantees of anything.
This was the low point.
Still, I knew I had to leave. The job was taking an extreme toll on my mental health, which impacted my physical health, and it was overflowing into everything else.
The next day I submitted my resignation.
And what happened next was… kind of incredible.
The very next day I received an email out of the blue from an old colleague. He wanted to introduce me to a doctor friend of his who had started a new physicians group and needed “a content guy.” Within a few weeks, I’d pitched and won the business and had a sizeable new client.
Other things also fell into place. I retained my existing client, and meanwhile the agency and I mutually agreed I could leave with the one I’d brought in. That relationship was mine and it was clear they still wanted to work with just me. A few days later, that client in turn sent me a referral—business I pitched and won and which turned into my fourth client.
Within a month of quitting, I was actually billing more in client revenue than I had been making at the agency—and I still am to this day.
Those few weeks after leaving, when everything clicked, felt almost as if the fates were smiling down. It had taken some bravery, some guts, to do what I did. And it had taken faith. And it seemed I was being rewarded for it.
Fortune favors the bold, I thought. Everything works out in the end.
The clichés came hard and fast, and more than a few times I thought about how everything I’d done, the professional risk I’d taken, seemed to have all been validated. I was telling myself a story with me as the hero, and this one had a familiar arc—in the end, I’d won, if indeed this was the end.
Still, I knew that my success hadn’t come from luck, or from being brave, or from having faith. The answers were more mundane.
My referrals had come because I asked for them, and also because I’d been in the industry for ten years and had a large network of colleagues who knew and trusted my work. My first two clients had come through the newsletter, the one I’d been writing about the business of healthcare. Former colleagues were reading it and ultimately reached out when they needed help (the full tale is on my company’s About page).
That’s really all the secret sauce there is to impart, and it’s certainly not enough to get all presumptuous doling out advice. I’m not gonna write a book about it or anything.
Because the truth is all of this could collapse tomorrow. ChatGPT or some other fancy new platform could come along and destroy my business. The industry could change. My clients could get bought by other companies. A recession could finally come. Anything could happen.
And whatever does, I’m sure it’ll be tempting to tell myself some story about why it happened that way. To place everything within a narrative, with me at the center.
Just take it with a grain of salt. I’m a data point of one.
III. Work and life aren’t a balance—they’re a matrix
There is at least one thing that the owners of the marketing agency I agreed on: the concept of work-life balance is kind of bullshit.
There is no HR policy that will ever solve for a toxic work environment, no amount of rah, rah mission, vision, and values preaching that will make up for a genuine lack of purpose. No amount of vacation time will negate a culture of workism (workism being the idea that to work is to be virtuous, and that to work more, harder, or longer, begets yet more virtue.
But success in business is not the same as success in life, and by now it should be rather obvious to everyone that the number of hours one spends at one’s desk has little bearing on your value to an organization, even less bearing on your value to society, and virtually no bearing whatsoever on whether you are living a good and meaningful life.
Your work is part of your life. You should do what you can to make the work itself sustainable. Not set up some dichotomy where one must balance the other.wrote about this last year:
When we describe work and life as things to be balanced, we are suggesting that work and life are at odds with each other. More time or energy allocated to work means less time and energy allocated to life.
This is obviously absurd, though. Work is just another part of life like family, community, food, fitness, creativity, travel, fun, spirituality, etc.
The question isn’t how do you balance work and life, but how do you create a healthy relationship among work and the various other important areas of life?
Work, life, spirituality, travel, fitness, fun, and all the rest of it aren’t a balance—they’re a matrix.
Each has its own weight and importance. And everything is interconnected, intertwined, and mutually dependent.
We crave validation, or to serve. We want to be good partners, good parents. We seek novelty but also safety and comfort. We pursue wealth, status, freedom. Maybe we want to travel to all the places, do all the things, live multiple lives if we have to. We try to balance the expectations of society against what is innate to our being, if we can even figure out which is which.
Yet there is no one rule for how to sort through this matrix—it’s just too complicated—and whatever conventions once existed for solving, or at least navigating (surviving?) it are no longer up to the task.
This is why we fall back on aphorisms and proverbs. We share pithy quotations, and we tell stories. Maybe it’s the only thing we can do. I’ve done it myself. I’m doing it now.