What I Got Wrong About Success | Andrew Alpaugh
When I was younger, I had a very clear picture of what success looked like.
It had a job title in it. A certain kind of car in the driveway. A house in the right neighborhood. It looked like confidence from the outside — moving fast, making decisions, knowing exactly where you were headed.
I spent a lot of years chasing that picture. Some of it I caught. Most of what I caught didn't feel the way I thought it would. And eventually I had to sit down with the question I'd been avoiding: whose version of success was I actually running toward?
The answer was uncomfortable. It was assembled from pieces I'd picked up along the way — from how my parents measured things, from what got respect in the environments I worked in, from the cultural shorthand of what "making it" was supposed to look like. Very little of it was actually mine.
I don't think this is unusual. I think most people operate on a borrowed definition of success for a long time before they realize it's borrowed.
The Recalibration
The thing that starts to crack the borrowed definition is usually something going wrong.
Not always dramatically wrong — sometimes it's just a slow accumulation of winning things you thought you wanted and noticing the feeling isn't what you anticipated. Sometimes it's an actual loss — a job, a relationship, a status marker you'd built your identity around.
Either way, the cracks are useful. They let you start asking real questions.
What do I actually want to be doing with my time? What kind of person do I want to be in the rooms I'm in? What am I building, and who is it for?
Those questions are harder than they sound. The borrowed definition gives you clear metrics — salary, title, square footage. Your own definition requires actually knowing yourself, which is a longer project.
What I've Replaced It With
I'm not done figuring this out. But here's what's replaced the old picture, at least for now:
Useful over impressive. I care more about whether the work I'm doing actually matters to the specific people it's supposed to serve than whether it looks significant from the outside. These sometimes overlap. They often don't.
Depth over breadth. A few relationships I've genuinely invested in are worth more to me than a wide network of shallow professional contacts. This is not a popular position in the LinkedIn era. I hold it anyway.
Optionality over optimization. For a long time I optimized aggressively — trying to be in the right place, positioned for the right opportunity, always calculating. Somewhere along the way I started valuing having choices more than having a perfect plan. The ability to pivot, to try something different, to say no to a path that doesn't fit — that turned out to matter more than I expected.
The quality of the days. This one sounds obvious and took me the longest. The destination isn't the thing. The quality of the actual days on the way is the thing. How are you spending your time? What are you thinking about? Are the people around you ones you'd choose again?
None of this means I don't care about outcomes. I care about outcomes. I work hard. I want things to succeed.
But I've stopped believing that success is a fixed address you're trying to reach and started thinking of it more as a direction you're trying to stay pointed in — one that's genuinely yours, adjusted as you learn more about who you actually are.
The version I was chasing at 25 would have made me miserable by 45. I know that now. I didn't know it then.
The knowing is what matters. And the willingness to act on it.
Andrew Alpaugh — Scott Andrew Alpaugh — writes about personal development, life lessons, and the slow work of figuring out what you actually want. Based in Greenville, South Carolina. More at andrewalpaugh.com and scottandrewalpaugh.com.
Written by Scott Andrew Alpaugh — technology professional and entrepreneur based in Greenville, South Carolina. Also at andrewalpaugh.com and scottalpaugh.com.
Comments