Success is not a destination, it’s a debate

I’m successful, but still argue with myself about it [Not Obvious: Part 7]

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The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us. A few suggestions:

• Burnout, Balance, and the Bullshit in Between (on “hard work”)

• You Will Never Feel Done (on “productivity”)

• Fulfillment FOMO (on “passion”)

"90% of success is showing up."
The rest is pretending you know why you're there.

I used to think success was a static conclusion you arrived at. Something that could be decided once and for all, the case closed:

“The final verdict is… you are successful!!!

(the imaginary crowd cheers)

Okay, you can go home. You’re done now.”

Sure, I’ve been pretty successful. By most objective measures, I’ve done quite well.

Financially, I’m on solid ground and even fortunate enough to examine the question of “enough.” Let me be clear: I would not be writing to you now in this non-money-making passion project without financial stability. I’ve joked that the best way to be a rich writer is to become rich, then become a writer.

Professionally, I’ve “checked all the boxes” far earlier than expected (before the age of 40), concluding I don’t need another level up the ladder. I’ve done some big/important things, too, like helping build an innovative company (in healthcare no less), that successfully IPOed and is still going strong today.

Admitting this out loud sounds like a confession, like it’s not something I’m supposed to say. But it would be dishonest to say it any other way:

“Yes, I am successful.”¹

But that was the old me. I’m someone new now. And being successful is not the same as being done. Even the wildly successful must wake up and figure out what to do with their day.

I remember the moment I thought I had “made it,” but I felt… weirdly empty. Like success had arrived, but I hadn’t. Achievement is unending in this way – a loop where one triumph begets the need for another, and so on.

And every major milestone invites an inevitable appeal:

• Is my success my own, or was I lucky?

• Am I chasing the right type of success?

• Am I still successful if I can’t recreate new success?

• Who am I if I become unsuccessful?

I know I’ll never fully resolve these questions. And I wonder if maybe I’m not chasing success as much as just trying to win the argument in my head.

So what if success wasn’t a destination, but a debate? No resolution, only negotiation. A tension you live with inside yourself.

“You just have to want it bad enough.”
Yeah, because wanting has solved literally everything, always.

Alleged Answers

For a while, I thought I could skip the debate and go straight to the template.

I’d listen to the classic definitions of success and the templates of how to get there: the formulas, the blueprints, the 10-steps. I hoped success could be wrestled down and conquered, like hitting a bullseye on a career choice, working the perfect amount, or getting everything done.

Uncertainty bad! Certainty good! The more order put on the world → more success.

I wanted the success without the struggle. Struggle, not in terms of hard work, but as in, “I have no idea what I’m doing!” So in the absence of clarity, I turned to the ready-made answers. Each made a persuasive case. But together, they’d drown out my ability to decide what I really wanted. Loud voices in an ongoing argument I’m still trying to moderate.

“Success” seems so obvious on it’s face, that we forget it can be so malleable.

For example, success to you, could be failure to me. All the professional success in the world, without time to see my kids, is still a big net negative from my lens. That’s why certain types of broad generalized success-prescriptions make no sense. A healthy dose of cross-examination is needed.

Then there’s the inconvenient fact that we have no way of knowing what someone else’s inner life is really like, despite the arguments they make out loud. Striving for success, as we know, so often comes from a source of deep psychological pain – an unloving parent, childhood trauma, a void of meaning.

Or maybe what you’re doing looks unsuccessful today, but turns into success later on. Or what you want right now, will look different in the next decade. Or maybe… Do I need to keep going?

You will hear many definitions of success in your life (whether you want to or not). Feel free to swallow them whole without interrogation. Because, as I’ve found, they will assuage your anxiety. They will give you the comfort of certainty.

Until someday you can no longer defer the deeper questions, and the backlog builds up from a quiet hum to a rousing revolt. Take it from me: even armed with success, at some point, you will need to finally face the questions.

“Think outside the box.”
What box? I never got a box. Did you get a box?

The Final Verdict

Others turn to me for my template: “how to be successful?” But I feel uncomfortable answering with all the questions still rolling around.

I’ve given enough advice in my life to know I don’t share all the evidence. Not that I’m lying, the bumps just get smoothed out to create a cleaner picture. Successful people post-rationalize their journey to make it sound linear, presenting the closing argument without all the evidence ahead of time. It’s a rewrite, not a reality. You can read my linear story here.

Advice givers rarely face the risks of advice takers; they have no real downside other than being ignored.

So the most unsatisfying advice you’ll ever hear would probably be the most accurate:

“This is what worked for me. I think. Based on what I can remember.

But I’m probably leaving stuff out. Maybe even lying a bit. Not to deceive you, more to deceive myself.

It’s what I think mattered. But I could be wrong. And circumstances mattered too, as well as many other factors outside my control (like luck).

And on my road to success in this one particular lane, I became unsuccessful in many others. Maybe it wasn’t all worth it.”

It’s not exactly the kind of thing that goes viral on LinkedIn. But it’s more honest.

The real skill, as I’m learning, is not finishing the perfect path, but learning to live with the paradox. Less of a judge, more of a witness.

I’ve found there is no destination called “success.” It’s not something you ever arrive at. It’s something you constantly question, redefine, and argue with yourself about. And the ones who stop debating often end up stuck in an old definition (or someone else’s idea of success).

My advice? Question it all. What your parents think. What your idols think. Definitely question that random guy online (myself included). And even question yourself. But don’t expect a verdict where you find your final answer, once and for all.

Maybe someday I’ll clean it all up. Turn the questions into a tidy, 10-part lessons learned. Or someone can do it for me (you know, at the eulogy).

Until then, I guess. I choose. I argue with myself. And the debate goes on.

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Next up, will be a new series: Existential Explorer - Ideas from the Edge of the Map. Subscribe to stay tuned.

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1. Some will say, “yeah, but you’re not that successful.” Which is true… but sorta underlines my point that this is all debatable.