How to be successful and miserable
When you’re good at the wrong thing [Existential Explorer: Part 7]
Update: I been quiet lately because I’ve been working on a SUPER SECRET PROJECT. It came out of nowhere and has claimed most of my attention. I’ll be posting less for a bit… but if you’re curious, stick around. I’ll share more soon.1
The Way of Work explores stories of where we fit in the world of work. This is part of the Existential Explorer series. A few suggestions to start:
Part 1: From Businessman to ‘Existential Explorer’
Part 2: The Open Frontier of Meaning
Part 3: What You Need is a Midlife Crisis
Part 5: just kidding… work actually is the meaning of life!
Check out my other series, such as The Other Side of Enough (when you have enough).
Mastery without meaning, is still meaningless.
Tell me if you’ve heard this one before:
“You should pursue mastery, because in mastery, you’ll find: satisfaction/purpose/money/etc.”
Another variant of it is:
“Find something to get good at first and that will turn into something you love over time.”
Except, well… sometimes, it doesn’t.
The world values mastery. People who go above and beyond to excel at something specific. We like to do things we're good at, are valued, and challenge our skills forward. And it sort of helps when we make a boatload of money from it.
But what if the thing that makes you successful, also makes you miserable?
The Making of the Mask
I carried the pain in my face and my gut.
Before I get to that, allow me to brag for a second…
I built my career as an operator and builder, especially at the early stage of things. I was better than most at turning a new, ambiguous idea into reality. Some come up with ideas. Some take an existing process and improve it. I was damn good in between, building when an idea is just an idea.
And (sorry, some more bragging), the systems I built, helped a company grow from almost zero to a multi-billion-dollar public company.
Have I mentioned that I’m a very important and distinguished businessman who should be taken seriously?!
No, it wasn’t all me, nor do I believe I was the most important piece. Repeat, I got lucky. But (and I promise, here’s my last and ultimate brag) I’m convinced the company wouldn’t have been a success without me. Sorry, ain’t nobody gonna persuade me otherwise!
On top of all that, this was in healthcare! It’s not like we fixed the system (spoiler: still fucked up), but we nudged it in the right direction. It always feels good to make an impact on an obvious problem.
Doesn’t this all sound like the perfect setup for a rich and fulfilling career?
But man… doing the work was draining.
First, if you didn't know, startup operations doesn’t deal with “fun problems.” Instead, it’s continual firefighting. It has a way of putting you in a permanent state of high-alert – constantly scanning for the next failure, inspecting every little problem that could metastasize into a bigger catastrophe. It’s a job of anticipating what could go wrong next, which means living in constant future-based fear.
I also grew into a senior executive in charge of things, so people looked to me for answers (sorry, still bragging). People problems, bad metrics, products failing, unhappy customers, you name it… it had to be handled.
And I was pretty good at it.
But I was wearing a mask, and my face knew it. I would end each day with tension under my eyes and across my forehead. Like I had been flexing my face into an acceptable expression: keeping calm during stress, performing optimism, reassurance, authority, competence. All. Day. Long. Torn up on the inside, but unable to express it on the outside.
Where did all this tension go? I swallowed it. From The Value of Disappearing:
“I was an expert in plowing through unease and overcoming obstacles. I could always outwork my problems. Suppressing distracting questions, and shoving discomfort back down where it came from.
‘Shut the fuck up and get back to work!’”
I didn’t let go of the stress, I ingested it. And it sat like a ball in my gut. I didn’t even realize it was there (or that it wasn’t normal), until I finally released it a few months after leaving work, almost 2 years ago.
Sounds horrible? Well, this persona also got me money, validation, relevance, power, security, status. The success was so good, I never stopped to ask if it was good for me.
And why would I question it? I was getting promoted. I was getting paid. People admired me. I was praised for my competence, leadership, and ability to fix things. Caught in the momentum, “liking something” wasn’t even allowed to be a question.
What? Like you would have turned down the rewards? The pain, in retrospect, even to me, seems like a fair trade. I mean, isn’t that just the nature of work? Suffering is required.
It wasn’t until I left that I could even ask the question: “do I like what I’m good at?”
The Trap of Competence
I don’t believe I'm entitled to perfect work (see Fulfillment FOMO). Nor do I have illusions about what the market requires of me. But, and it’s taken me a while to understand this, what started as a skill, turned into a track, and then into a trap.
It sounds so obvious looking back, but during the doing, I had no idea. I needed the distance myself to see the truth:
I didn’t choose my skill set, I fell into it.
I got good at something early, which was reinforced by others.
I leaned further into what I was good at.
And so on in a cycle.
I never fell in love with the work, I just adapted to it.
Success is a great servant, but a terrible master. It builds expectations, income, status – a weight that you need to keep pulling. Like, okay man, you’ve built your house. Now go live in it forever.
And didn’t I have a duty to others? To use my skills and experience in a problem area (like healthcare) for the good of others? So what if “I didn’t like it?” Boo hoo, poor, selfish, Rick!
You see, this is a kind of success that’s hard to walk away from because no one else thinks it’s a problem. Like what if Superman didn’t like superman-ing and instead, wanted to be a musician? I doubt everyone else would think that’s normal, let alone be okay with it. As one mentor explained to me:
“What do you mean you don't want to use your superpower?”
And boy, I was so close to going back to using it. But a nagging feeling stuck with me that something was not right.
Did I truly like what I do? Or was it more about the ego, social status, and approval that convinced me that's what I “like?”
Did I want to become a master at my old skills? Or try something new?
Did I have a duty to that old world, one of obvious problems and impact? Or did I have a different duty to the world? A higher calling that I hadn’t understood yet?
I’m reminded of my interview with Marlo (from Rich, Powerful, and Ready to Quit):
“It goes to the core of, who do I want to be?
Do I want to be this turbo executive, stressed out, pressed for time, but achieving and accomplishing in a business sense? Or do I want to be a more thoughtful, engaged person?”
Glimpses of Alignment
If I was better at paying attention, I would have noticed that, deep down, I actually loved certain types of work. The times where I broke through the day-to-day noise, and entered into moments of depth, truly in the zone.
In that space, my work could create something transcendent.
One simple example… I worked with a colleague on a slide that would depict the customer’s journey, including some future-oriented stuff no one had seen before. It was a few days of heads down work, closing my office door, shutting out the world, and thinking.
What we created ended up connecting the dots on everything we had built to date. It shaped our company strategy going forward. It was a primary way we pitched ourselves to customers and partners. And it was featured in our company’s IPO as a core explanation of our strategy.
Calling one slide “transcendent” may seem like hyperbole. But that’s what it felt like.
On the surface, I was a startup operator, adept at fighting fires and inching the business forward. But my real power, or more precisely what fueled me, was as a creative thinker in solitude. Someone who could create clarity out of chaos.
And isn’t that what I’m trying to do here, at The Way of Work? Maybe on another wavelength or at another altitude. What is writing if not sitting alone, wrestling with a messy problem, and turning it into something (hopefully) elegant and useful?
The work was hard and draining. But burnout, for me, had a lot more to do with chronic suppression of the work I really wanted to do.
Some might say: “what about giving back? What about all that high-impact stuff you left behind?” Sure. But is my suffering required to give back? Is there not some other purpose that I can pursue? A higher duty that doesn’t require sacrificing my soul?
No doubt, I’d rather have success over no-success. I’m no saint. And I’m so grateful for the part of the story where I got the reward. If I hadn’t received that pot of gold at the end of the rainbow… man, I’d be in a different mental state now.
And I’m not sure bypassing the rewards would have been the answer either. Success can be an enabler, if you do it right. Maybe I had to be miserable, so I could be not miserable now. Maybe I needed to go through all of it to figure myself out. So no, I don’t regret any of it.
But for me at least, the greatest trap isn’t in doing something I hate. Because if I hate it, I’ll do something about it. The trap is when I do something that I’m good at and rewarded for it. Because that situation locks me in: comfortable, successful, miserable.
Mastery without meaning is still meaningless.
I’ll end with Sara Pendergast, the consultant-turned-artist, who is pursuing mastery at a depth that’s rare (from Waiting Decades to Finally Follow Your Dreams):
“Unlike the hollow expertise I developed during my corporate career, the mastery I pursue now feels very rich and rewarding. It helps me explore why I exist at all and allows me to connect to others in ways that feel very natural.
What is it in life that means something to me? What catches my eye? Why do I think about what I think about? All of these things I can't describe, but I might be able to create a visual language for showing what they are and what they mean to me.”
📚 Further Exploration: Open: An Autobiography, by Andre Agassi
⍰ Question: do you like what you’re good at?
🙏 My Ask: If this essay meant something to you, pass it along, ❤️ or 🔄.
Also, I dropped a hint in my last essay.
Great article, Rick! Sara's "hollow expertise" and your perspective on burnout rising from not pursuing your passion and interests are the main takeaways from me.
Yeah, Rick, it’s surprising how being rewarded for serving a greater “good” can trap you in misery. I’m glad you have a chance to explore what’s next. Luck definitely plays a part in having that chance for me too. Without a certain financial security, I wouldn’t have the guts take the time to do what I’m doing.