Yesterday evening I finally had words for something that had been bothering me since around January.
Not a crisis. Nothing dramatic enough to name at the time. Just a low, persistent sense that something in how I was relating to my own business wasn’t right, sitting underneath emails, planning documents, replies to people asking how it was going. I’d feel it, fail to catch it, and move on.
I want to tell you about the six months before yesterday evening, not just the moment itself, because the moment wasn’t the interesting part. The not-knowing was.
Here’s where I first noticed it, though I didn’t know that’s what I was noticing. I’d sit down to write about the business, and something in my own sentences would feel slightly false. Not wrong, exactly. Off by a few degrees, the way a photo looks fine until you notice the horizon isn’t level. I’d read a note back to myself, or a reply I’d sent a subscriber, and think, that’s not quite it, without being able to say what “it” was.
Then I noticed it again in a different place. Whenever I sat down to plan where the business would be in six months, a year, three years, five, I could produce the plan easily. Thirty years of doing exactly that for other people’s businesses meant I could build the projections in my sleep. But something in the exercise felt like I was doing it to the wrong subject, the way you’d feel odd running someone else’s five-year plan through your own name.
I didn’t connect these. Each one just registered as a small, private discomfort I filed away and got on with the day.
The honest reason it took me six months to understand what was wrong is that I had exactly the wrong toolkit for finding it quickly.
Thirty years of executive strategic thinking gave me excellent instincts for almost everything except this. I kept reaching for the categories that had always worked. Structure, reporting lines, ownership, roles, the language you use to describe a division inside a company, a business you run but do not personally constitute. I’d spent a career being extremely good at seeing organisations clearly, and I aimed that exact same lens at my own business.
It kept coming back slightly blurred.
And I assumed the fault was mine for not looking hard enough.
It wasn’t a lack of effort. It was the wrong instrument for what I was trying to measure.
You cannot use an organisational chart to identify the thing an organisation should eventually be built around.
That was the part I had missed.
I was trying to build the business before I had fully identified what the business was actually being built around.
What became clear yesterday, after all that quiet static, is that I had spent thirty years starting with the structure. The company already existed. The purpose was understood. The customers were there. My job was to look at the whole thing, see what wasn’t working, decide what needed to change and build the strategy to get it there.
This time, there was no existing structure to examine.
There was me.
Thirty years of experience. Judgement. Pattern recognition. Things I know how to see because I have seen them hundreds of times before. Questions I ask without thinking. Connections I make quickly. The kind of problems people have been bringing to me for years, long before I ever considered that any of it might become the foundation of something of my own.
And instead of starting there, I had been standing a few steps ahead, trying to design the company that might one day be built around it.
I had the order wrong.
The business had to begin with me before it could become bigger than me.
That’s an uncomfortable sentence to write plainly, because there is a part of me that immediately wants to make it sound less personal and more professional. To put some distance around it. Give it a structure, a title and perhaps a very respectable five-year plan.
But I think that instinct is exactly what kept the horizon a few degrees off for six months.
Starting with myself does not mean building a business that can never exist without me. Quite the opposite. If I want The Strategic Second Act to become the methodology, the programme, the community and everything else I can already see somewhere in the distance, I first have to be precise about the thing at the centre of it.
You cannot build something bigger around an asset you haven’t identified yet.
And perhaps that is one of the stranger parts of building something after a long career. Your experience is an enormous advantage. I believe that more strongly than ever. But experience also comes with frameworks, and we don’t always notice when we have carried the wrong one into a new room.
I don’t think this is something you can find by looking harder or on a schedule. I looked, on and off, for six months, with considerable strategic training behind the looking, and none of it arrived faster for the effort. It arrived in small, unconnected pieces until enough of them were sitting on the desk at once to finally read as one sentence.
So if you’re building something of your own after a long career, and the plan looks perfectly sensible but something about it still feels quietly off, I wouldn’t immediately assume you need a better plan.
You may simply be starting a few steps too far ahead.
Keep writing. Keep noticing the small moments where a sentence feels a few degrees off. Look at what you are trying to build, yes, but look just as carefully at what you are building it around.
The clarity tends to arrive in its own time, usually later than you’d like and earlier than you expect, and rarely on the day you go looking for it hardest.
If you’re sitting with years of experience and an idea that looks sensible on paper but still doesn’t feel quite right, that’s exactly the kind of knot we work through in a Strategy Session.
Warmly,
Pia
I like this because it doesn’t pretend the wrong order was a minor detail, it treats it like something structural, which is usually where the real problem lives. So many people try to force their way through life in the sequence that feels familiar instead of the one that actually works, then act surprised when everything feels off. There’s a quiet kind of relief in realizing the issue wasn’t lack of effort, it was misplacement, timing, or the way you were arranging the pieces. That’s a useful kind of honesty, because it gives you something concrete to change.