THE BRAVERY IN FEAR-SETTING

THE BRAVERY IN FEAR-SETTING 💪 

February 25, 2026 • Issue No. 31

After 3 consecutive nights of sleeping on a dorm-quality twin-sized mattress, I was beginning to regret my decision to attend a 2-week educational leadership program hosted by Columbia University on the campus of a grassy New Jersey boarding school. I missed my full-sized bed, a private shower, and all of the other comforts of home. Those first few days, I wondered if anything I’d learn in the program would be worth back pain and under-eye bags — but as it turned out, I would learn something that shifted my path.

In one of the workshops, the 30 of us were scattered around a classroom ready with pens and notepads. The facilitator asked us to write down what we were afraid of.

Then to write down what would happen as a result.

And then what would happen as a result of that.

We were to continue writing until we couldn’t go any further. I believe my paper looked something like this:

When we’d all come to a stop, the facilitator explained the purpose of the exercise. Often, we think we’re scared of that first thing that’s written down when really, we’re afraid of that thing because of the chain reaction we predict it will set off. And the end of that chain is our real fear.

I stared at my starting point, getting fired, and at my end point, moving in with my parents. Even though the line of thinking made perfect sense, I was shocked to know this was inside me. I’d had no idea how worried I was about the possibility of having to leave New York or how closely I associated asking for help with lack of freedom.

This helped me to make sense of why the idea of getting fired ever even crossed my mind. I hadn’t been reprimanded at work, I wasn’t on a PIP, and my organization wasn’t undergoing layoffs, but here I was walking around wasting precious brain power to tell myself, “I can’t lose this job!” This was not an efficient use of my energy nor a compelling motto for self-talk.

Fear-setting is about naming your fears so that you can face them — like peeking under the bed to see if the monsters are real (and fighting them, or politely asking them to leave, if need be!) Now fear-setting is not my invention or that workshop facilitator’s. It actually comes from Tim Ferriss’s 2017 Ted Talk called “Why You Should Define Your Fears Instead of Your Goals”. (Note: Tim’s talk makes mention of self-harm.)

Tim starts by describing stoicism and how a philosophy of being unmoved helped him reach inner peace. If nothing matters, nothing can bother you. I have not (and do not) wish to adopt stoicism, but Tim sold me on his stoicism-inspired strategy for focusing on what’s within my control.

To hone this focus, he indulged his imagination. He let his mind paint the worst possible picture and then took a step back to admire his work. After that, he wrote down how he could prevent the fear from coming true and how he could repair the damage if the worst case came true anyway.

Tim has even more steps for his process, and you can watch his video to learn more. But just this first step of writing down your fear, unpeeling it, and taking it apart like a tangerine can be powerful. The notes I wrote down on what I was afraid of made it clear that I was afraid of losing my independence and that I’d anchored my independence in my job. Seeing this on paper helped me focus on the real solution; it wasn’t about trying not to get fired (especially because this wasn’t even a logical threat!), it was about building self-reliance so that I would be okay, or at least feel okay, no matter what happened at or outside of my job.

That journey of building self-reliance is part of how I ended up starting my own coaching practice. In my work with clients I see how talking about fears can reveal deep insight about our own motivations, significantly more so than our goals. It’s human nature to set goals and abandon them; that same nature keeps fear top of mind. I encourage you to take the brave step of “looking under the bed” to find out what fears might be influencing you without you realizing.

If I took away nothing else from 2 weeks of sleeping on a mattress made of gravel, it’s that I’m strong, I’m brave, and I’m better at facing my fears when I know what they are. 💎

P.S. On 3/11, Michaela and I are hosting a virtual discussion event called THE BUZZ. Consider this an official invitation! Learn more and RSVP here: https://wrkwell.co/ (just scroll down to Events!)

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