High Performing Leaders Know How to Protect the Downside

I didn’t go after the job of a lifetime.

After nearly 19 years at Martha Stewart, my boss of six years resigned to join a competitor. I assumed I’d step into her role—the job I had been working towards for years. I was ready, more than qualified.

BUT, I didn’t go for it.

I didn’t raise my hand. I didn’t tell them there was no better person for the job.

I convinced myself to avoid the risk.

I let self-doubt sabotage the possibility...questioning my capabilities and thoughts of getting fired if I was hired.

I let hope become my default. I hope they pick me! Hope requires no action, no plan. Hope was protection from risk.

I wish I'd considered my options...for the best and worst-case scenario.

While listening to the Earned Happy podcast, I learned that Richard Branson, one of the world’s notable entrepreneurs, bought his first airplane from Boeing for Virgin Airlines; he didn’t just dream big—he protected his downside.

Branson negotiated a buyback clause.

If his airline failed, he could sell the plane back to Boeing.

That’s the brilliance behind his risk-taking. It wasn’t blind optimism; it was calculated with a safety net.

What is your buyback plan?

Most of us shy away from risk.

In my work with leaders, I hear they wish they had a higher tolerance for risk. The stakes are high, and the fear of failure looms large. But a buyback plan offers a way to manage that fear.

It’s not about eliminating risk but being smart with it.

A buyback plan is a risk mitigation. And, a solution for moving forward.

What are you holding back on because “it would be very bad” if things didn’t work out?

What decision, opportunity, or leap have you been avoiding?

Maybe it’s a career move, a new investment, an ask to your boss or a choice you’ve been resisting.

Now, ask yourself: What’s the real likelihood of the worst case? Be honest.

What’s the percentage chance that the worst will actually happen? [Likely that % you settle on is less than 50%]

And even if it did—what’s the best outcome that could emerge from the worst case?

The BEST case from the WORST case.

This is how you protect the downside.

This is how you build your buyback plan.

Our lizard brain spin stories, gather evidence, and do everything possible to keep you right where you are. But you don’t have to believe it.

Don’t let the fear of the worst-case scenario hold you back. Evaluate the actual likelihood—chances are, it’s smaller than you think. And once you’re aware of it, build a plan to cushion the impact if it happens.