Buyer’s Remorse—it’s something we’ve all experienced at some point in our lives.
It happens when reality doesn’t meet our expectations—when the thing we thought we wanted doesn’t actually bring the satisfaction or happiness we thought it would.
But it doesn’t just happen over a pair of expensive shoes, a fancy car, or the latest high-tech gadget we thought would solve all our problems.
Buyer’s Remorse also happens when we achieve success.
Because it’s not just the price you pay to achieve success, it’s also the price you pay after achieving success.
Most of us never think about what the successful version of what we’re chasing actually looks like.
This is why so many people who achieve success feel empty or overwhelmed—because they didn’t actually want everything that came with success.
Sometimes becoming a bestselling author, world-renowned course creator, or beloved celebrity isn’t actually the kind of success we want.
Here’s what I mean…
When Success Becomes a Nightmare
One of the most powerful questions I use before committing to a new project or opportunity is:
Do I want the successful version of this?
I started using this question after realizing I didn’t want to “succeed” as a psychologist.
It took me 12+ years to become a psychologist. But “success” as a psychologist means eventually becoming the director of behavioral health for some big medical clinic. It would’ve meant drowning in administrative bullshit, endless staff meetings, eventually becoming president of my state psychological association and leading mind-numbingly boring presentations so other psychologists could check off a box to get enough continuing education credits to maintain their license, and hitting an income ceiling by age 40—regardless of how great I was at my job.
It would have been my living nightmare.
But one man’s nightmare is another man’s dream.
My internship supervisor was the director of behavioral health. One time, I caught him in the hallway dancing and smiling to himself.
Know what he was doing?
Making fucking copies of a therapy manual.
This dude legitimately loved all the administrative work. He’s now the CEO of a medical company and thriving. If I was in his situation, I’d be ready to jump out a fucking window (jk, unless it was like, a ground-level window that was already open).
For him, he wanted the successful version of being a psychologist. I didn’t, but I almost realized it too late (more on that in a bit).
But this question of “Do I want the successful version of this?” can help us think through whether the path we’re on is leading us to a destination we actually want.
Because it’s easy to focus on the prestige of “arriving,” but lose sight of what the day-to-day reality of success looks like.
Here’s what I mean…
Paying the Price of Success
We’ve talked before about how life is about sacrifice, but most of us only ever think about the price we have to pay to achieve success—not the price we have to pay after we achieve success.
Maybe you want to become a bestselling author…
Cool. After grinding it out and spending years crafting a stellar book, you achieve success.
Now comes the lack of privacy and constant requests to make an appearance that comes with celebrity, the army of trolls in your comments, and the nagging insecurity that your next book won’t be as good because people expect more out of you.
Do you really want the successful version of this?
You might, just be aware of the price of success.
Maybe you want to build a thriving membership community that generates 6-7 figures in revenue…
Awesome! Let’s say you do just that.
Have you thought about how much time it’ll take on a day-to-day basis to actually run a community like that?
Either you spend tons of time every day managing everything yourself, or you have to hire people to help you.
You’re no longer living the “carefree solopreneur” lifestyle you daydreamed about.
Instead, you’re mired in logistics, managing employees, and have effectively created a full-time job for yourself.
If this is your dream job, then go for it. If not, maybe reconsider how big you want to scale your current business.
Maybe you want to build a community with thousands of people, like David Perell has with Write of Passage.
Or maybe you’d rather build a mastermind capped at 35 people, like my friend Mel Varghese.
Both are viable, it’s just a matter of which success you actually want to achieve.
Maybe you want to become a successful actor…
Being a famous actor sounds awesome!
Until you have a family and realize you’ll have to spend 12 hours a day, 5 days a week on set and away from your family during filming, then travel for months on end promoting it.
Here’s a clip of a great conversation from the Armchair Expert Podcast between Dax Shepard and Jake Johnson (aka, Nick from New Girl) on this exact dilemma:
While Jake Johnson recalibrated what success meant to him, Dwayne Johnson takes a different approach and fully embraces all aspects of being a celebrity:
So what do you do if you realize you don’t want the successful version of what you’ve been pursuing?
When Quitting to Avoid Success is How You Ultimately Win
When I lost my therapy job in 2020, it felt awful. But it ended up being one of the best things that’s ever happened to me. Because shortly after getting fired, I realized I didn’t want to “succeed” on the path I’d spent the last 12+ years of my life pursuing. So I quit that path. I still use my training as a psychologist every day. But instead of dealing with psychopathology (mental illness), I use my skills to coach, build courses, and create content to help creators reach their potential. I’m way more fulfilled than I would have ever been on my old path.
But it’s not just me.
Paul Millerd quit a fancy, lucrative career at a big-name leadership consulting firm.
He embraced the digital nomad life, then self-published a book that’s sold over 20,000 copies within its first year. He’s way happier, way more fulfilled, and is legitimately improving peoples’ lives by showing them there’s another way to go about life—what he calls the “pathless path,” which is also the name of his book.
On his podcast, he’s also had amazing guests recently like Derek Sivers and Kevin Kelly—opportunities he attracted by “quitting” the path he was originally on.
Khe Hy quit a fancy job on Wall Street.
In his words:
“A big motivation to leave Wall Street was looking at peers who were 15 years older than me.
They had a great life – second homes, cars, fancy vacations – but it wasn’t for me.
Not only did many looked haggard, drank a lot and had dicey relationships with their spouses/kids. They were still prisoners to email, meetings and the need to be ‘always on.'”
Here’s a beautiful post by Khe where he talks about walking away from close to a million dollars at his old job:
Now, Khe spends his days being a kickass dad, suave surfer, and all-around rad dude. This is what he wants the successful version of, not being a Wall Street zombie.
All three of us, along with everyone else who’s chosen the path of a creator, will tell you the same thing:
Being a creator is full of uncertainty, doubt, and a constant struggle to get out of your own way. But it’s also full of freedom, creativity, and the ability to inspire others to build a fulfilling life on their terms.
Do we want the successful version of being a creator?
For me, at least, the answer is…fuck yes.
Success isn’t a static, isolated state.
Success is an ever-evolving, multifaceted, complex interconnectedness of deep existential identity issues, interpersonal dynamics, and constantly reconsidering and renegotiating the balance between “enough” and “more.”
Which is why each of us has to decide what success we actually want to achieve.
- It doesn’t matter how long you’ve dedicated to a specific life/career path. You’re under no obligation to stay on it.
- It doesn’t matter how big your paycheck is if it costs your soul.
- It doesn’t matter if everyone around you criticizes your decision, if none of them have a life you’d gladly trade places with.
You—and only you—get to decide what success means to you, what success you actually want to achieve, and what success you want to avoid.
Because success has two costs—the price we pay to achieve it, and the price we pay after achieving it.
So be sure you actually want the successful version of whatever it is you’re pursuing.
Because you just might get it—and you don’t want Buyer’s Remorse.