What If the Safest Bet… Is on Me?

I was catching up with a friend recently when we got on the topic of taking risks.
Not cliff-diving or quitting-your-job-to-move-to-Bali kind of risks—but the quieter, sneakier kind. The kind that sounds like:
What if I actually bet on myself?

And that’s when I had to admit something I don’t say out loud very often:
I don’t really do that.

I am a planner by nature (and profession). I play things safe. I make decisions based on data, gut checks, and at least three backup plans. I manage risks like it’s my job because it is my job. And while that’s made me dependable and steady (hi, fellow control freaks 👋), it’s also kept me from stretching in ways that matter personally.

And yet working in agile has always encouraged a different way of thinking.
Agility invites experimentation. Learning through action. Trying, failing, iterating, improving. We apply it to products and teams and processes all the time.

But what about ourselves?

When something is uncomfortable, when it’s not perfectly clear or guaranteed… my instinct is to step back. Wait. Polish. Perfect. But lately, I’ve been wondering:
What might happen if I just… went for it?

What if I applied the same mindset I bring to my work—testing ideas, embracing change, responding with curiosity—instead of clinging to certainty?

What if I stopped needing to feel 100% ready before I moved?

I have learned from Agile that there’s value in uncertainty. That showing up and trying is better than waiting for perfection. And that it’s okay to not have it all figured out as long as you’re learning, adjusting, and moving forward.

It’s not easy to unlearn the muscle memory of safety. But I’m realizing that sometimes, the safest choice isn’t the one with the least risk it’s the one that moves you toward the person you actually want to be.

So here’s to the gentle risks. The personal leaps. The decisions that don’t come with guarantees but might come with growth.

Because if I’m willing to take risks for the things I plan, the teams I support, and the goals I drive…

Maybe it’s time I take one for myself, too. And hey, if it doesn't work out right away? That’s what retros are for.