A Millennial’s Journey in Designing Life

I grew up in a world where achievements weren’t meant to be spoken out loud. Hard work was something you did quietly, behind closed doors, because talking about it risked drawing the wrong kind of attention. If you celebrated too much, people might say you were arrogant. If you admitted to working hard, they might think you were showing off.

So instead, we stayed quiet. We smiled modestly when praised. We brushed away our efforts as luck, timing, or “not a big deal.” What grew inside us wasn’t humility. It was doubt. It was the quiet whisper of imposter syndrome: Do I really deserve this? Am I good enough, or have I just fooled everyone around me?

That mindset didn’t just hold me back from dreaming big. It made even Option A, the life I was already living, feel shaky. How could I imagine other possibilities when I couldn’t even stand confidently in my own present?

Bravery in Its Simplest Form

That’s when I began to see bravery differently. It wasn’t about erasing fear or doubt. It was about dulling the imposter voice long enough to act. The whispers will always be there, questioning whether you belong, whether you’re enough. But bravery is refusing to let that voice drive the decision.

I like to think of it like the buy and hold strategy in investing. You put your money in, and then you walk away. You don’t refresh the stock price every five minutes. You don’t obsess over the daily ups and downs. You trust the process.

Life works the same way:

You decide.
You take the step.
You execute.
And then; you let it go.

The imposter voice may bark in the background, but you don’t feed it. You move on. And in doing so, you begin to win. First Option A, then Option B, and even Option C. Not by silencing fear completely, but by choosing to act bravely in spite of it.

Designing Your Life: Options A, B, and C

In their book Designing Your Life, Bill Burnett and Dave Evans talk about creating three Odyssey Plans for your future:

  • Option A: The life you’re already living, the predictable, planned path.

  • Option B: The pivot, the version of your life if A disappeared tomorrow.

  • Option C: The dream, the one that feels impossible, too bold, too unrealistic to say out loud.

The first time I encountered this exercise, I felt both inspired and uncomfortable. Writing down Option C felt almost rebellious. After all, I grew up in a culture where even sharing Option A too proudly was frowned upon. And here I was, being asked to imagine the most outrageous version of my life.

But maybe that’s exactly the point. Bravery isn’t always about tearing down what exists. It’s about allowing yourself to even imagine something different. It’s giving yourself permission to say: This is what I want, even if it scares me. Even if others won’t understand.

The Cultural Weight We Carry

That’s the thing about bravery. For many millennials, especially those raised in cultures of silence, courage doesn’t start with action. It starts with permission. Permission to want more. Permission to write down the dream life. Permission to say, yes, I worked hard for this, without flinching.

The weight of cultural expectation makes bravery heavier, but it also makes it more meaningful. Because when we take even the smallest brave step, we’re not just defying our own doubts. We’re breaking patterns handed down to us.

When I chose to embrace this mindset, I realized bravery didn’t always mean chasing something dramatic. Sometimes it meant experimenting. Testing a new skill. Taking on a challenge outside of my comfort zone. Admitting to myself and maybe even to someone else that I wanted to grow in a different direction.

That small permission is its own kind of revolution.

Bravery as a Practice, Not a Trait

The more I leaned into this idea, the more I saw bravery not as something you’re born with, but as a muscle you can build. You don’t wake up one morning with perfect courage. You grow it, one small act at a time.

It could look like:

  • Telling a colleague about an idea you’ve been holding back.

  • Putting yourself forward for a project you’re not sure you’re “ready” for.

  • Saying no when your instinct is to always say yes.

  • Taking a tiny step toward a pivot without worrying about whether it’s the “right” one.

Each act strengthens the muscle. And like investing, the compounding effect is powerful. Over time, bravery doesn’t erase fear, but it makes fear easier to carry.

Bravery, I’ve come to realize, isn’t about waiting until we feel ready. It’s about giving ourselves permission to dream, taking the step, and trusting that the action itself is enough. For those of us raised in silence, that’s no small thing. It’s the beginning of designing a life that’s truly ours.

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