How I Got Ahead by Being in Over My Head

Jump in, then learn to swim

Jan 30, 2025

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"If someone offers you an amazing opportunity but you are not sure you can do it, say yes – then learn how to do it later" - Richard Branson

My career looks nothing like what I once imagined. If you had told me five years ago that I’d be working in taxes?

I would have called you a lunatic.

I used to think success came from mastering what I already knew. That the key was to get really good at something and stick with it.

What I quickly learned is that the real breakthroughs happen when you’re in over your head—and choose to swim anyway.

Looking back, three lessons stand out as to why this approach works:

1️⃣ Pressure Forces Growth

2️⃣ Action Attracts Opportunity

3️⃣ Fail to Do, Fail to Learn

At first, it’s overwhelming. But that’s exactly why its effective.

If I’m ever lucky enough to be a father—a life goal of mine—these are the lessons I’ll pass down to my kids one day.

💎 Pressure Forces Growth

My career started with me being thrown into a fast-growing startup as a customer service rep, managing relationships with customers as they wrapped up their engagement with the company.

Sounds easy enough, right?

Except… I was the first person on this brand-new team. No roadmap. No processes. Nothing to follow. On top of my day-to-day responsibilities, I was tasked with building out the department’s workflow from scratch—something scalable, something repeatable.

The most “process building” I’d done up to that point? Figuring out which frozen meals to buy at Target every week.

But I did it anyway.

Three months in, my work caught the attention of the company’s COO. He asked me to join a new team he was building—one focused on defining the processes that would shape the company’s ability to scale.

The only problem? I had a degree in Marketing… and this was pure operations.

But I did it anyway.

Saying yes to things I wasn’t ready for forced me to learn—fast. And because I was willing to take on more than I thought I could handle, I didn’t just survive in these roles… I leveled up.

🎯 Action Attracts Opportunity

Most people assume opportunities come when you’ve earned them—when you’ve checked all the right boxes, built up enough experience, and finally qualify for the next level.

But in my experience, that’s not how it works.

Opportunities come to the people who are already moving. The ones who step up, take action, and figure things out as they go. The ones who don’t sit around waiting for permission.

Early on, I realized that saying yes to things I wasn’t ready for put me in rooms I had no business being in. It got me noticed by people who could open doors. It built a reputation that I was someone who could be trusted to figure things out.

No one is looking for someone who might be ready someday. They’re looking for someone who will step up right now.

If you’re waiting until you feel 100% prepared, you’re going to be waiting a long time.

🔥 Fail to Do, Fail to Learn

Here’s the truth: You will screw up.

I definitely have.

But here’s the second truth: If you never take on something beyond your comfort zone, you won’t even get the chance to screw up in the first place.

Every mistake I’ve made taught me something. Every time I’ve stumbled, I’ve walked away with a new skill, a better understanding, and a clearer sense of what I need to improve.

The people who grow the fastest in their careers aren’t the ones who never fail.

They’re the ones who fail forward—who learn, adjust, and keep moving.

So take the risk. Say yes before you’re ready. Get in over your head.

Because that’s where the real growth happens.

🔑 My Takeaway

If I’ve learned anything from these experiences, it’s this: You don’t grow by waiting until you feel ready.

In business, as in life, my biggest jumps didn’t come from sticking to what I knew—they came from stepping into the unknown and figuring things out as I went. Every time I took on more than I thought I could handle, I walked away with more confidence, more skills, and a bigger sense of what was possible.

Yeah, it was uncomfortable.
It was overwhelming.
There were countless moments when I second-guessed myself, wondering if I had taken on too much.

Turns out, that’s where the real growth happens—not in the moments of certainty, but in the moments of doubt when you choose to push forward anyway.

The people who build, who lead, who grow—are always the ones who say yes anyway.

So, when the next opportunity comes knocking—when you’re faced with something that feels just a little too big, a little too far outside your comfort zone—take it.

Then figure it out as you go.

This is the first entry in a week focused around Lessons as a Young Professional. My experiences in business have intrinsically shaped who I am. I’m excited to share more with you all throughout the week.

With love and appreciation,

Brady