Everyone Has Failed—Even Those Who Win

If you’ve ever stared at a rejected proposal, a dead-end project, or a blank screen that refuses to cooperate, you’re in good company, not just among your peers but alongside some of the most celebrated creatives, designers, and innovators in the world.

Failure is often framed as something to overcome. Something we experience before success. But here’s the uncomfortable truth:

Even those who win—especially those who win—fail. Repeatedly. Spectacularly. Quietly. Publicly.

It’s part of the creative process, and pretending otherwise only fuels the myth that successful people are somehow different from the rest of us.

Spoiler: They’re not.

Failure isn’t a flaw in the system. It is the system.

There’s this misconception that failure is a detour. As if the “real” path is the one where everything goes smoothly, clients are always happy, and every design gets immediate applause.

But if you talk to anyone who’s built a creative career, they’ll tell you—failure is the system.

It’s how we learn what doesn’t work. It’s how we refine, simplify, and evolve. It's how we build resilience. It’s how we get good.

You may see a stunning poster on Instagram or a glossy campaign in a magazine, but what you don’t see are the drafts that didn’t land. The versions scrapped at the last minute. The weeks of doubt, messy layers, failed pitch decks, and the internal voice saying, “Is this even any good?”

It’s not just you. It never was.

The winners just didn’t stop

Freelancers often live in this constant loop of feedback, deadlines, and personal doubt. There’s pressure to show only our highlight reels, to present ourselves as always on and always winning.

But behind every bold piece of work is a history of missteps and wrong turns.

Here’s the thing: the people you admire? The ones who seem to glide from one brilliant idea to the next?

They didn’t avoid failure. They just didn’t let it define them.

- They showed the work anyway.
- They sent the email.
- They launched the thing, knowing it might flop.
- They learned.
- They moved on.

That’s what separates those who keep growing from those who quietly step away.

Failure isn’t just tolerated—it’s required

Designers, especially early in their careers, sometimes ask, “How do I avoid making mistakes with clients?”

You don’t. You do your best. You communicate. You learn. But you’ll still get it wrong sometimes. You’ll misunderstand a brief. Misjudge a budget. Miss the mark entirely.

And all of that is part of becoming someone who eventually gets it right more often than not.

The same applies to passion projects and personal work. That weird idea you think no one will get? That unpolished style you’re experimenting with?

That risk is where your next creative leap is hiding. But it won’t show up unless you’re willing to risk getting it wrong.

The quiet kind of failure

Not all failures are loud and dramatic. Sometimes it’s the project that never gets off the ground. The client who ghosts. The pitch that went nowhere. The great idea that fizzled in the execution.

These quieter failures can feel heavier because they don’t come with a dramatic crash. They just… fade.

But they count. They’re part of the journey, too.

Even deciding not to show your work can be a kind of failure—one rooted in fear of judgement.

But the longer you wait for things to be “perfect,” the longer you delay the growth that only comes from doing, shipping, and sharing.

You’re not broken. You’re building.

If you’re stumbling right now, it doesn’t mean you’re not cut out for this. It means you’re deep in it. It means you’re trying. It means you’re pushing past what’s easy and known.

No one talks about their failures on their portfolio site. But they’re there. In the background. In the lessons baked into each new iteration. In the choices made with more wisdom and less ego.

So if you’re sitting with a pile of rejected work, a stalled idea, or just the quiet fear that you’re behind—know this:

Everyone has failed. Even those who win. Especially those who win.

It’s not a badge of shame. It’s part of your creative résumé.

Keep going.
Keep making.
And remember: you’re doing better than you think.

Until next time, 
—Gary