The guidance out there for those of us in the solopreneur / teaching / speaking / writing space is to frame topics provocatively, in ways that run counter to popular wisdom. With that in mind, I’ve delivered talks on embracing your inner imposter, befriending your fear, and the new workout of doing nothing. It’s fun to shake up a popular topic—like imposter syndrome—by questioning it from an unexpected perspective, allowing the classic truth of the original to appear, freshened with a new look. It’s like giving your beautiful friend or mom a style makeover: same essence, but revitalized.

The challenge is to keep it real versus merely clever. Clever clickbait headlines and titles abound, but if you want to be trusted, you have to deliver substance. Or at least sincerely intend to, even if it doesn’t resonate with everyone. This leads me to a bigger theme I’ve been mulling over—one that might evolve into a book or course—about the power of losing.

This idea emerged from “Quitters Win,” a reflection on how I quit smoking (twice) and drinking alcohol (a much longer relationship). Quitting harmful habits does bring significant benefits, but framing it as “winning” felt a little off. Maybe it’s the “winning” mindset that drives us into those habits in the first place and could just as easily drive us toward new ones.

So I began to consider the idea of losing. It’s not a popular perspective; no one aspires to be a “loser.” Yet in Twelve Step programs and many spiritual traditions, the power of surrender—of letting go—is foundational. Recognizing that you can’t negotiate or “win” your way out of certain kinds of thinking is liberating. It’s about letting go of battles, often with our own minds, which drain our life force.

For me, I lost my battle to keep alcohol as a friend. I kept negotiating our relationship, until alcohol itself told me it was over. She was meant to be occasional, ceremonial, celebratory (and optional), and I was demanding more. She couldn’t give that to me and so I let go.

But there’s more to losing than laying down your sword. Losing also means not finding something again. Letting it stay lost. How do you truly lose the mindset that led to a Big H harmful habit (alcohol, tobacco, drugs, gambling, food, sex) so it doesn’t sneakily lead you into a small h harmful habit? For me, that’s now binging content to the exclusion of other activities because it’s so interesting it seems essential (even though it isn’t). The mindset of “The solution is outside of me” persists.

Therein may lie the power of losing: letting the underlying mindset stay lost.

So here’s to letting what no longer serves you stay lost! And to finding greater joy, peace, and connection, especially over this holiday week!