There is a specific kind of oblivious I was, for quite a few months, that I want to describe accurately in case others are being that same kind of oblivious right now and nobody has told them.

I had ten years in high tech behind me that spanned countries, companies, technologies, and teams. All of them had a routine that structured my whole day whether I liked it or not, a team that needed things from me by 9 AM, and a long list of tasks and exciting challenges on a daily basis (including weekends). Then, through a fascinating series of synchronicities, coaching crossed my radar and I decided on a radical change of my professional life. I finished my coaching certification with the same energy I had finished every project before it: head down, engaged focus, energy and will (true to my Enneagram Type 8 approach to anything and everything in life then), checklist cleared, done. Now build this new coaching business. I made a plan. I had a spreadsheet, obviously – column for outreach, column for offerings, column for “things to figure out” that I updated with the grim satisfaction of a man checking off a packing list. Give me a broken system and enough hours and I will hand it back to you fixed, improved, and buzzing. That was more than a skill I built. It was closer to a religion, or whatever it can be called for an atheist.

What the spreadsheet couldn’t hold – what no spreadsheet can hold – showed up on an ordinary Tuesday some weeks in, when I realized I had made coffee, sat down at my desk, and had genuinely nothing that needed me. No urgent tasks. No one waiting on a decision. No commute to mark the start of anything. Just a day, wide open, with my name on it and nothing else. I remember the specific horror of an empty calendar – the way a room is empty when the furniture has been moved out and you can suddenly hear yourself breathe in it. I sat there for a while doing the thing I now recognize as a tell: I made a to-do list for a life that didn’t have any tasks in it yet. Reorganize the office. Research fonts for a logo nobody was asking for. Anything with a checkbox. Anything to give me a sense of a tangible something.

I spent a genuinely embarrassing number of weeks (likely months, actually) treating the aimlessness like a scheduling problem, as if the discomfort was really about not having enough on my calendar, and if I just filled it with the right busywork the hollow feeling would go away. It didn’t. It doesn’t work that way, because the hollow feeling wasn’t about the calendar. It was that the man who knew exactly who he was – the one with the title, the team, the standing meeting, the juicy challenges he knew how to solve, the commute that told his nervous system you belong somewhere at 8:47 every morning – that man had nowhere left to stand. As I understand it now, it was because coaching hadn’t built its own floor yet, and the old one had already been taken away out from under me the day I walked away from that contract, company, career, and that way of life.

Here is the part I really want to land, because I think it really is the whole thing. It took me leaving tech to actually understand it: this isn’t a one-time toll you pay at the start of a transition and then you are through. I keep waiting for the day I graduate past this question, and it keeps not arriving. It showed up again a year or so later, when the business finally had traction and I noticed I missed being managed – missed having someone else decide what mattered today – and had to sit with the uncomfortable fact that some part of me still wanted the structure I had been so relieved to escape. It showed up again after a good year, when success itself asked me to drop the identity of “the guy still proving this was the right call.” Every real shift – a new contract, a puppy entering my life, a marriage, a move to a different house or city, a cancer diagnosis, a death of a dog, a divorce – asks the same thing, over and over, in a slightly different costume each time. It is not a door you walk through once. It is a door that keeps reappearing in different rooms of your life, and every time you are a little surprised it is there, and every time you reach for the same wrong toolkit and mindset first.

Nobody warns you about this part because it doesn’t photograph well. “Started my own coaching practice” photographs well. “Sat in an empty apartment on a Tuesday making a to-do list out of nothing because the silence was unbearable” does not make it onto anyone’s feed. So you go looking for the discomfort in the visible stuff – the outreach plan, the logo, the pricing page – because that is the discomfort I had tools for. You will organize the hell out of the wrong problem for as long as it takes you to admit the real one isn’t organizable, and then you will do it again next time, because apparently that is how I was built, and I suspect I might not be alone.

I want to be careful here, because I know what this can sound like from a stage – some tidy little insight, wrapped up with a bow, the real challenge of transition is identity dissolution, everyone nods, claps, goes back to their spreadsheets. That is not what I am pondering here. I was given an empty calendar and a to-do list about fonts nobody asked for. The insight doesn’t fix anything. It simply tells you where to stop digging for the fix, both this time, and, if you are anything like me, the next several times after that.

So here is the question I have stopped expecting to answer once and be done with: what version of you is this transition asking to end? Not evolve. End. And, what have you been keeping busy with instead of grieving it? I have learned to expect this question back, uninvited, at every real threshold from here forward. I would like to tell you it gets easier to recognize. Mostly what gets easier is recognizing it faster, and hating it slightly less each time.

If you are in the middle of one right now, whatever that transition might be, that question is probably standing right behind whatever you have convinced yourself the actual problem is. Mine was an empty calendar. Yours has a different name. It is not the last time it will ask.