Rebel Take-Aways From Reinvention Strategist Karen Koepp

Karen Koepp splits her time between LA and Utah, describes herself as a "strategist and mountain wanderer," and recently showed up to our conversation with a black eye from a roller skiing wipeout in the Bay Area. She's my kind of person. Here's what she said that I haven't been able to stop thinking about.

Look Backwards to Figure Out What's Next

When I asked Karen Koepp what her go-to move is for unlocking someone's next chapter, I was expecting something complicated. A framework, a matrix, a personality quiz. Instead she said the answer is already in your history. Specifically in the stories of when you've felt fully alive, when you were in flow, when you made a difference that actually mattered to you. It sounds deceptively simple, which is usually how the best ideas present themselves.

Stop Treating Direction Like It's the Finish Line

Here's where Karen Koepp politely blew up one of the most popular myths in the reinvention space. Knowing what you want to do is not the same as being able to do it. She referenced a theorist named Peter Block whose book essentially argues that deciding is enough. Karen's 20-plus years of working with real humans says otherwise. (I appreciated her gentleness in disagreeing with a published academic. That takes its own kind of nerve.)

Expect the Overwhelm. It's Not a Warning Sign, It's a Milestone

Karen Koepp calls overwhelm "a natural second stage of a mission," and the first time she said it I actually wrote it down on a sticky note. We tend to treat that frozen, panicked, I-can't-do-this feeling as evidence that we've made a mistake. Karen reframes it as proof you're heading somewhere real. Knowing it's coming doesn't make it comfortable, but it does make it survivable.

Build Prosthetic Systems Around Your Weak Spots

This was one of those moments where a single phrase does more work than a whole chapter of a business book. Karen Koepp's "readiness retrofit" is about diagnosing where the stall is happening and then designing around it, not muscling through it. Want to write a book but hate writing? There are ways to extract your ideas that don't require fingers on a keyboard. The goal is to honour your genius while being honest about your gaps.

Rehabilitate Procrastination

Karen wrote her master's thesis on procrastination, and she will not let you use it as a reason to beat yourself up. She says it's a feedback mechanism, a signal that something is out of alignment. The move isn't to shame yourself into action. It's to get curious about the resistance and figure out what it's telling you. As someone who does some of his best work in the final 45 minutes before a deadline, I found this deeply comforting.

Find Your Stories in the Small Moments, Not Just the Big Wins

Karen Koepp told me she can trace her passion for writing all the way back to age four, when she was writing stories about her stuffed animals in Wisconsin. She wasn't waiting for a career milestone or a performance review to confirm that writing was her thing. It was just always there. When she works with clients, she's not only looking at their professional résumé. She's looking at all of it, the whole life, because the clues show up everywhere.

Run Low-Stakes Experiments Before You Bet Everything

Karen's third piece of advice for rebels was the one that landed quietest and stuck longest. She talks about "low-stakes reps," little experiments you plan, execute, and then actually debrief. You try something small in the direction of your new vision. You see what happens. You adjust. Over time, those small experiments build a body of evidence that starts to support new beliefs and new behaviours. It's not a dramatic leap. It's a series of very intentional small steps that add up to something you couldn't have imagined at the start.

Catch the full conversation with Karen Koepp on The RebelRebel Podcast and hear how a face-plant on roller skis, a 400-page unfinished manuscript, and a bolivian mud puddle all connect into one remarkably coherent philosophy about finding your next chapter.