When Success Stops Feeling Like Success: Redefining What It Means to Make It

It looked like getting into the rooms I once dreamed about entering. It looked like seeing companies I admired on my résumé, watching projects I'd worked on reach millions of people, earning recognition for work I was proud of and building a career in television and media that a younger version of me would have been amazed to know was waiting for him.

And the truth is, I loved it.

I loved the creativity, the energy and being surrounded by people who could take an idea scribbled on a page and somehow turn it into something the world could see. I loved knowing that my work mattered, that my perspective had value and that I had earned my place in an industry I had spent years working toward.

Success gave me something else, too: freedom. It expanded my world. It allowed me to travel, support people I loved, experience new places and enjoy the kind of independence that comes from years of building a career and a life for yourself.

For a long time, that was exactly what I wanted.

Until one day, it wasn't.

Not because the career stopped mattering. Not because I suddenly became ungrateful for everything it had given me. And not because I stopped being ambitious.

Something much simpler happened.

I changed.

And eventually I had to ask myself a question I hadn't anticipated:

What happens when the definition of success that got you here is no longer the definition capable of taking you where you want to go?

The Question Behind "What's Next?"

Media teaches you to think about what's next.

In many ways, that's one of the things I love most about it. Our industry is driven by curiosity: the next idea, the next project, the next platform, the next opportunity, the next way audiences will experience stories.

That same instinct inevitably follows us into our careers.

For years, I understood the formula. Work hard. Learn. Become better. Take the opportunity. Earn trust. Get into the room. Once you're there, figure out how to get into the next one.

There is nothing wrong with that formula. It took me places I once couldn't imagine going.

But eventually, "What's next?" stopped being enough.

I found myself asking something slightly different:

What do I actually want next?

That one word changes everything.

"What's next?" asks us to identify the next logical step. "What do I want next?" asks whether the logical step is still the right one.

And that requires something ambition alone cannot provide.

It requires self-knowledge.

Because at some point, we have to ask ourselves: How much of our ambition is actually intention, and how much of it is simply momentum?

We Define Success Before We Really Know Ourselves

Most of us begin constructing our definitions of success remarkably early.

We decide what kind of career we want, what we'd like to accomplish and what kind of person we hope to become long before we've accumulated enough life experience to understand what will ultimately make that life meaningful.

At 22, success might simply mean getting the opportunity. Later, it might mean leadership, creative ownership, greater influence or finally being recognized for work you've spent years perfecting.

But life keeps happening while we're building our careers.

We fall in love. We lose people. We move. We fail. We succeed. We become responsible for others. We discover parts of ourselves we didn't know existed. We learn what gives us energy and what quietly takes it away.

Eventually, if we're paying attention, the person pursuing the dream may no longer be exactly the same person who created it.

But perhaps the danger isn't changing the dream. Perhaps it's never stopping long enough to notice that we've changed.

That doesn't make the dream wrong.

It means the dream did its job.

It got us somewhere.

And from that new vantage point, we're allowed to decide where we'd like to go next.

Gratitude Doesn't Require Permanence

This may be one of the hardest ideas for ambitious people to accept.

Sometimes we confuse gratitude with obligation.

If an industry gave us extraordinary opportunities, questioning our relationship with it can feel as though we're diminishing everything it gave us. If a job once represented a dream, changing our minds can feel suspiciously like failure.

We can become so determined to prove that our sacrifices were worth it that we keep sacrificing long after we've received what we came for.

I've had to rethink that.

I can be profoundly grateful for my career and still allow myself to evolve beyond the version of success I once associated with it.

Those ideas are not contradictory.

My years in media taught me how to communicate, collaborate, create, lead, improvise, solve problems and trust my instincts. They showed me what happens when talented people rally around an idea and decide to make it real.

Most importantly, they showed me what I was capable of.

I don't want to erase any of that.

I want to build from it.

Perhaps that's the difference between running away from a chapter and allowing that chapter to become part of a larger story.

The Industry Has Changed. Maybe Our Definition of Success Should Too.

Media itself increasingly reflects this kind of reinvention.

The traditional career ladder still exists, and for many professionals it remains an extraordinary path. But it now sits alongside possibilities that previous generations of media professionals could not have imagined in quite the same way.

Executives become entrepreneurs. Journalists become podcasters. Producers become consultants. Creators build companies. Industry veterans become educators, advisors, authors and speakers. People move between organizations, industries, platforms and even countries while carrying their expertise with them.

But there is a larger shift underneath all of this that I find particularly interesting:

The way we build media careers has changed faster than the way we measure whether those careers are successful.

For generations, professional progress was relatively easy to visualize because the architecture of a career was easier to recognize. You entered an organization, developed expertise, assumed greater responsibility and, ideally, continued moving upward. Progress had a visible direction.

But if the architecture of a career has changed, why are we still using an old scoreboard to determine whether someone is winning?

Today's media professional may build something far less linear and no less consequential.

A producer might consult between projects while developing an independent series. An executive might advise emerging companies while teaching the next generation of talent. A journalist might move between reporting, podcasting, authorship and speaking without any one role becoming the definitive description of who they are professionally.

In that environment, perhaps the question is no longer simply how far someone has climbed.

Maybe we also need to ask how effectively they've learned to carry their expertise with them.

The most valuable thing we accumulate over the course of a career may not ultimately be a title.

It may be the combination of judgment, relationships, perspective, credibility and skill that remains ours regardless of the organization printed beneath our name.

A career no longer has to move in one direction to be meaningful.

Perhaps success doesn't either.

Ambition Was Never the Problem

This is the part I don't want to lose in conversations about redefining success.

I am still ambitious.

Very much so.

I still love the satisfaction of getting something done. I love taking charge when something needs to happen, connecting dots, solving problems and watching an idea become real.

I still want to create meaningful work, contribute to important conversations and enter rooms I haven't entered yet.

I haven't become less interested in success.

I've become more interested in what success makes possible.

Over time, I've become increasingly drawn to one measure in particular: agency.

The ability to choose work that excites me. To say no when something isn't aligned. To follow an unexpected curiosity. To create something simply because I believe it deserves to exist. To have meaningful time for the people and experiences that matter beyond work.

Maybe one of the greatest privileges success can eventually provide isn't status.

It's choice.

Professional credibility can create opportunities. Experience can create perspective. Creative freedom gives us room to tell stories that might otherwise remain untold. And the things we accomplish can give us the ability to create opportunities for people beyond ourselves.

None of that requires abandoning ambition.

It requires giving ambition a purpose.

What Is Your Career Making Possible?

We spend enormous amounts of time asking people what they want to become.

Maybe we should spend more time asking what they want their careers to make possible.

A career can create independence, creativity, generosity, leadership, impact and access to people, places and ideas that fundamentally change how we understand the world.

But a career is still one part of a life.

Perhaps one of the responsibilities that comes with experience is periodically asking whether the career we're building is still serving the life we're becoming.

Not the life we were expected to want.

Not the life that looks most impressive from the outside.

The one we actually want to wake up and live.

You Are Allowed to Become Someone Else

I think about younger versions of myself differently now.

I don't look back at the person who wanted those titles, opportunities and accomplishments and think he had the wrong idea.

Quite the opposite.

I'm grateful he wanted them badly enough to pursue them.

His ambition got me here. His willingness to work opened doors. His curiosity introduced me to worlds I hadn't yet experienced. His courage gave me evidence that I could figure things out.

But honoring that version of myself doesn't mean I have to remain him forever.

You are allowed to outgrow a goal without disrespecting the person who once wanted it.

Changing your mind doesn't erase what came before it. Neither does reinvention require abandoning everything you've learned.

Starting a new chapter doesn't require burning the pages that came before it.

Maybe Making It Was Never the Destination

I've spent much of my professional life in an industry obsessed with what's next.

I still love that about media.

I hope I always will.

But these days, I'm equally interested in another question:

What's worth pursuing?

Not simply what opportunity comes next, but what deserves my time, my energy and my ambition.

There cannot be a universal answer.

For one person, success may mean becoming CEO. For another, building a company. It might mean creating something nobody else believes in yet, teaching, telling stories or having enough control over your time to be home for dinner.

It might be some combination of all of those things.

The point isn't to want less.

It's to make sure the things we're working so hard to achieve still belong to us.

For years, I thought making it meant arriving somewhere.

Now I'm beginning to wonder whether making it is something else entirely.

Maybe success isn't a destination we finally reach.

Maybe "making it" is developing enough courage, self-knowledge and freedom to choose our lives more intentionally.

Because in the end, our accomplishments were never supposed to become our lives.

They were supposed to help us build one.

Posted at MediaVillage through the Thought Leadership self-publishing platform.

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The opinions expressed here are the author's views and do not necessarily represent the views of MediaVillage.org/MyersBizNet.