Why risk is a skill you can’t ignore
I’m traveling this week for my Miami Pivot Point Retreat, which means I’ve had a lot more “think time” than I normally do in my day-to-day from being on the plane, in Ubers, and even just walking between places.
And in that think time, I kept coming back to one theme: risk.
Not just the big, dramatic risks (like leaving a secure corporate job to build a business, aka one of the biggest risks I've ever personally taken), but also the quieter, everyday ones that shape our careers and leadership in just as powerful of ways.
Risks like...
✨ Speaking up with a contrarian idea.
✨ Asking for more responsibility.
✨ Admitting you want something different & taking the first step toward it.
Those are the bets on yourself that can change everything. Because when you risk on you, you can't lose.
You grow. You learn. And you lead differently.
So let's talk about how you can take more of those risks in your own career & leadership ⤵️
What is risk in leadership?
Risk in leadership often shows up in the moments where you go against the grain in pursuit of real growth & real results.
It can feel really scary, because it’s always easier to go with the flow, nod along, or do things the way they’ve always been done.
But that’s exactly what makes it a risk: you’re choosing the harder path, the one that stretches you, instead of the safe one that keeps you stuck.
Let’s look at some real examples of those who have taken these kinds of risks & what happened when they did.
Leadership Lessons on taking risks
1. Whitney Wolfe Herd, Founder of Bumble Leaving Tinder wasn’t just a career change for Whitney Wolfe Herd, it was a massive risk. She was dealing with harassment, a lawsuit, and the fear that stepping away could mean starting over in an industry she already helped build.
But instead of retreating, she doubled down on her vision and launched Bumble, an app designed to put women in control. The bet paid off: Bumble grew into a publicly traded company with millions of users. Even recently, when the company struggled, she took another risk by stepping back into the CEO role.
Leading again in a moment of uncertainty could have backfired, but it signaled belief in her vision and gave the company renewed momentum.
2. Barnes & Noble, Holding the line on DE&I In a moment when many companies are quietly rolling back Diversity, Equity & Inclusion commitments, Barnes & Noble chose a different path. The risk? Alienating customers or investors who see DE&I as “too political.”
It would have been easier to quietly step back like others. Instead, they doubled down on their DE&I efforts, knowing that real leadership sometimes means standing firm when it’s easier to blend in.
Their choice reinforces trust with employees and readers who are paying attention to which companies stay true to their values.
3. Taylor Swift on New Heights Taylor Swift is one of the most strategic artists in the world. Her moves are carefully controlled. Which is why sitting down for a two-hour, unedited podcast was a risk.
In a world that says audiences have short attention spans, it could have flopped. She could have been criticized for being “too long,” “too casual,” or revealing too much.
Instead? The New Heights episode drew over 15 million views (& counting!), became a cultural moment, and reminded everyone that connection, especially when it’s authentic, will always cut through.
Each of these individuals and organizations could have chosen a different path that "played it safe" but they didn’t and that’s exactly why their impact grew.
Easy Ways to be more risky
Here are a few simple, practical ways you can take more risks in your own career + leadership right now:
Say the thing you’ve been holding back. In your next meeting, share the perspective others are avoiding.
Volunteer for stretch work. Put your name in for the project that intimidates you a little.
Ask for more clarity. Risk “looking uninformed” by asking the questions no one else will, I promise your team will thank you.
Own your ambition. Tell your manager the next step you want, instead of waiting to be tapped for it.
Practice the power of no. Decline a task or project that doesn’t align with your priorities, and explain why.