The Truth About Success Nobody Talks About

For a long time, I thought successful people probably felt more certain than everybody else.

I thought there was a like a moment where people finally became confident in their decisions and successful people just stopped second-guessing themselves. When they stopped feeling behind or feeling like an imposter in their own story.

Then I talked to Lee Goldberg.

Goldberg has spent decades building the kind of creative career most people dream about. He’s a bestselling author. A television writer and producer. Someone who has worked across Hollywood and publishing long enough to see multiple versions of success come and go.

And yet, at one point in our conversation, he laughed and admitted something that felt like I feel a lot of the time.

“Someday, they’re gonna come to me and say, ‘Lee, you are an awful writer. What the hell?’”

I laughed because it's funny and also feels so far removed from where the apex that he's reached in his career. But the truth is, it's It’s honest. Because underneath most ambitious people is usually some version of that fear, that eventually everyone else will realize you’re improvising your way through things too. And maybe that never really goes away.

It reminded me of something I wrote previously on Guyset in “The Strange Uncertainty of Your 20s”: and the understanding that maybe no one really has it all figured out. Some people are just better at hiding the uncertainty than others.

That’s probably the biggest misconception people have about success in general.

We imagine successful careers as clean stories when we’re looking at them from the outside. We see the finished version. The polished resume. The bestselling books. The dream jobs. The confidence that comes from it all.

We don’t see the days where there was nothing to write. The weeks where it felt impossible to move forward. The years where everything felt unclear while it was actually happening.

And Goldberg’s career is a perfect example of that.

Long before he was producing television shows and publishing bestselling novels, he was just a kid in California writing detective stories and selling them around his neighborhood for a dime. He interviewed celebrities while he was still a teenager. He took freelance writing jobs wherever he could get them. He wrote, in his words, "terrible" action novels under a fake name because he thought “Lee Goldberg” wasn’t interesting enough.

None of it sounds glamorous when he tells the story now.

It sounds messy.

But that’s usually what ambition actually looks like in real time.

Not certainty or success. Just simply forward motion.

One of the most interesting things Goldberg said during our conversation was that he never built his career around comfort.

“The way I keep myself fresh is by challenging myself,” he told me.

That line stayed with me because so many people spend their 20s believing success is supposed to eventually remove uncertainty from your life. Like eventually you’ll arrive at some stable version of yourself where everything finally clicks into place.

But most ambitious people don’t really experience life that way.

They just continue evolving, they just keep going.

A police procedural becomes a heist novel. A heist novel becomes another series. Television turns back into books. One project becomes the next version of yourself.

And honestly, that feels true far beyond creative careers.

You see it in relationships. Friendships. Careers. Confidence. Identity.

Most people aren’t discovering one final version of themselves.

They’re building themselves in real time. Again, and again.

That’s part of why your 20s can feel so disorienting sometimes. Everyone around you looks more certain than you feel internally. Everybody seems like they have a clearer timeline, a better plan, a more defined future.

But usually, they’re just experiencing uncertainty in their own heads.

I wrote about that feeling before in “The Inner Monologue of Your 20s”, especially the pressure people feel to turn uncertainty into proof they’re failing instead of recognizing that it's just a normal part of growth.

Goldberg’s perspective also cuts directly against the modern obsession with shortcuts.

There’s no moment in his story where somebody simply handed him a perfect opportunity. Most of his career came from consistently putting himself in rooms where opportunities could eventually happen. He went to television tapings, met other aspiring writers, interviewed people he admired, and continued to put himself out there.

“You have to put yourself in a position for the luck to happen,” he said.

That might honestly be one of the most realistic definition of success I’ve heard in a long time.

Not manifestation.

Not pretending to be fearless.

Not waking up one day suddenly feeling fully confident in yourself.

Just staying close enough to your interests, your work, your people, and your curiosity long enough for your life to slowly start taking shape around them.

It may be a less cinematic version of ambition but it's probably the realest one I've learned to be true.

Goldberg also spoke openly about rejection in a way that felt refreshing compared to the overly career advice people usually hear online.

“I think that’s the biggest problem with today’s generation of writers,” he said. “They don’t know how to handle rejection.”

Again, he wasn’t saying it cruelly.

If anything, he was describing rejection as something unavoidable, as a part of it. Not evidence that you should stop.

And honestly, that applies to way more than writing. It applies to dating. Friendships. Job applications. Creative work. Almost every meaningful part of life eventually requires the ability to keep going while things still feel uncertain.

Goldberg has decades of success behind him and still jokes about being exposed as a fraud someday. That alone should probably make younger people feel less alone in their own uncertainty.

And maybe that’s the bigger takeaway from all of this.

Success rarely feels as complete internally as it looks externally.

People don’t suddenly transform into fearless, perfectly certain versions of themselves after they “make it.” They just become more experienced at continuing anyway. They just keep going.

That’s a much more comforting idea than perfection.

And honestly, probably a much more realistic one too.