Michael J.A. Davis spent seventeen years building a design career before he left it to found Tinycup Coffee, and he's now building a second act as a brand strategist for other food and beverage founders. This post pulls from our conversation about what actually changes between a first pivot and a second one, what rest looks like when it's not a reward you've earned, and how to stay inside an unclear season without rushing yourself out of it. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾

The Second Pivot Doesn't Come With a Villain

You already know the signs of a first career pivot. The Sunday dread. The meetings you can't sit through anymore. The moment your body starts keeping score before your mind agrees to look at the evidence. What almost nobody talks about is the second one, the pivot that comes after you've already done the brave, terrifying thing once. You built something real and it still doesn't feel finished. That version of a career pivot gets skipped in most advice, because it's harder to sell and harder to turn into a checklist.

Michael's First Pivot Started in His Blood Work, Not His Calendar

Michael spent the back half of his design career running equity-centered programs inside a Fortune 100 company. After the wave of corporate DEI commitments that followed George Floyd's murder in 2020, he watched the funding and the follow-through fade year over year, while he kept making the case, quarter after quarter, for the value of Black and brown life in rooms that had already stopped listening. His body answered before his calendar did. Routine bloodwork came back with a list of deficiencies that explained the depression, the mood swings, the sense that he could no longer show up for his family the way he'd promised.

That's when the decision stopped being theoretical. He talked it through with his family, left the role, and founded Tinycup Coffee, built around rest as a direct answer to the grind culture that had made him sick. What I love about this part of his story is that it refuses the tidy version we tell about pivots, the one where a person wakes up one morning with sudden clarity. His clarity showed up on a lab report.

The Real Signs of a Career Pivot Show Up in the Body First

A pivot doesn't announce itself in a strategy meeting. It shows up in the body, months before it ever reaches your calendar, and most of us have gotten very good at overriding that signal on purpose. We've built the skill of pushing past "this isn't working" because somewhere along the way, someone taught us that endurance is the price of getting ahead. So we override, and we tell ourselves the fatigue is normal, and we wait for a external permission slip that was never going to arrive.

Most lists of pivot signs read like a symptom checklist: burnout, misalignment, boredom. Those are real, but they're the surface. The deeper tell is the gap between what your body is doing and what your calendar still expects of you. Michael's blood work is one version of that gap. A body that's been asked to override itself for long enough will eventually stop cooperating quietly.

Why the Second Pivot Doesn't Come With a Villain

A client of mine put language to this that I haven't stopped thinking about. She told me her second pivot felt harder than her first, and when I asked why, she said the first time she had somewhere to point. The org. The manager. Whatever the system had done to her. This time, the only thing standing between her and the change was a version of herself she'd believed was doing fine, or fine enough.

That's the part nobody prepares you for. I wound down HmntyCntrd at the end of 2025, after five years of coaching executives through building healthier workplaces, and I realized most of that work was helping people stay somewhere, when what I actually wanted was to help people be free. Leaning fully into Choose Courage was, on paper, an easier decision than the first one. I'd already survived a pivot before. I understood myself better this time, what I need, what I won't compromise on. But the hard part was never the logistics. It was confronting my own fear, watching old doubt resurface wearing a new outfit and insisting it was breaking news. A month or so before this conversation, I had what my partner correctly diagnosed as a crash out, and the fix wasn't a strategy session. It was eating something, taking a nap, and coming back to it with an open mind instead of a panicked one.

Rest Is Not the Reward for a Pivot. It Is How You Find the Next One.

Rest as a reward means you have to earn it with output first, and the moment you frame it that way, it stops being rest and becomes payment. That's why so many people take a sabbatical, or their two weeks off, and come back feeling just as empty. They spent the whole time performing recovery well enough to justify having taken it. Clarity doesn't arrive on a deadline you set for it.

Michael put this more plainly than I could. Discernment needs stillness, and clarity rarely shows up when we're constantly pushing and constantly grinding. It shows up when there's room to sit long enough and listen carefully enough to actually reach it. He asks himself a version of the same question every Monday: what does he want to feel like by Friday? Not what does he want to finish, what does he want to feel. That single question has done more for his direction than any five year plan.

I build rest and resist weeks directly into my business calendar for the same reason, one in spring, one in fall, two consecutive weeks in summer, and I've learned I have to self-sabotage my way into actually taking them. I'll book a non-refundable Airbnb months out so my past self forces my future self to show up. It sounds small. It's the whole mechanism.

How to Tell If You're Actually Ready to Pivot Again

Michael's sister gave him a filter he still uses: pay attention to which thoughts make your chest expand, and which ones make it contract. Fear about the right decision usually still expands your chest, underneath the nerves. Dread contracts it. That distinction is more reliable than trying to reason your way to certainty, because certainty isn't actually what a pivot requires.

I call the space between "this isn't working anymore" and "I know what's next" the in the meantime, and I try to treat it like a hallway instead of a dead end. Something is connecting me to the next thing, even when I can't see what that thing is yet. In those seasons I lean on tools that keep me curious rather than guarded, a well-worn copy of Rick Rubin's The Creative Act, small experiments I don't over-commit to. I spent a year and a half building a CBD coffee and tea brand I eventually shelved, trademarks and all, and I don't regret a single month of it, because it taught me how branding actually works and gave me the clarity that I didn't want to build that particular thing right now. That's not failure. That's information.

If you're in that hallway right now, the work isn't to force an answer. It's to keep experimenting small enough that you can actually feel which direction makes your chest open.

If you recognize yourself in the diagnosing part of this, sensing that something's off before you've named what needs to change, How to Audit Your Life Before It Falls Apart is built for exactly that stretch. It's a set of exercises for spotting misalignment and the golden handcuffs that keep it invisible, before you're forced into the decision instead of choosing it.

Originally aired as Episode 64 on the Choose Courage Inc. podcast.