Where You Are Now

A company can only grow as tall as the vision of the person running it. If a founder cannot picture a place, the company will not arrive there, because nobody is steering toward it.

But there is a part of that sentence people skip. Vision is not only the destination; it includes an accurate view of the ground you are standing on, and that is where almost everyone is least honest.

Why is it hard to be honest about where you are?

It is hard because your current reality does not look like your vision, or simply, you have not practiced listening to yourself so there’s a lot of denial and resistance at first.

Ask a founder where they want to be in five years and you get detail. Revenue, headcount, markets, the shape of the thing. Ask where they are today and the answer goes soft. Sometimes it describes where they were two years ago. Sometimes where they hoped to be by now. Rarely the actual position, with its actual constraints, in the season the business is actually in.

It is not dishonesty; nobody enjoys looking straight at a hard position. But a roadmap drawn from an approximate location takes you somewhere approximate.

Is it okay to take a break?

Yes, it is. In fact it is an essential step to make a growth cycle sustainable. Go full throttle for extended periods of time and you risk burning out and dropping everything altogether.

I know this because I spent a stretch unable to answer it myself.

In May 2022 I took a break. It was not a planned sabbatical and it was not strategic. I had been running at a pace that eventually used me up, and stopping was less a decision than a consequence. For a while I could not have told you where I was going, because I could not have told you where I was.

What I did instead was smaller. I read. I went to cities I had not seen. I paid attention to my own signals in a way I never had, mostly because I had never needed to.

By 2023 I was working again, but differently. The work was strategy rather than execution, so it did not take out of me what the previous years had. I would not say I was restored; I was recalibrating, and the difference matters. Restored implies you went back; recalibrating means the instrument is reset against a new reality.

When someone asked me to take on a project that July, I could say yes. Not because I had returned to who I was, but because I had become accurate about who I was now.

A lot of what I think about strategy came out of that stretch, which is uncomfortable to admit, because from the outside it looked like nothing was happening.

Is it bad to feel lost?

Not always, but only under one condition.

When you drift it feels like being lost. Maybe you are overwhelmed. Maybe you do not know where you want to go. Maybe right now you do not intend to go anywhere at all. That sounds like the opposite of what I do for a living, and I still believe you should set your goals.

But setting a goal does not mean you know the road. Sometimes the alignment you need arrives in a season where you are not moving forward in any way anyone could measure.

Here is the distinction I hold onto. Drifting is useful when you know you are drifting. If you are aware you have let go of the wheel, and you are watching where the current takes you, that is information. If you do not know, you are not drifting; you are lost, with better vocabulary for it.

Does a business always have to grow?

When I draw a road, it is never a straight line and it does not always climb. There are maneuvers in it. Places where the route doubles back. Stretches where it circles before it moves. That is not a flourish; it is what the road actually looks like.

Most of us were taught that progress means forward and upward, and that anything else is failure. So when a season calls for a different movement, we override it. We push harder in a direction that is already blocked, because pushing feels like progress and everything else feels like quitting.

Sometimes the strategically correct movement is less. In practice that usually looks like one of three things:

1. Letting go of a client who takes more from the business than they bring, or who wants work you do not want your name on.
2. Running a smaller team rather than a larger one, because the structure you have cannot carry the headcount you want.
3. Moving an expansion to next year, not because you lost your nerve, but because this year does not have the structure to hold it.

Those decisions feel wrong because we are conditioned to read growth as more. More clients, more people, more markets, more revenue, more motion. But a business is not always in a season for more. Sometimes the correct move is sideways. Sometimes backward. Sometimes it is dropping something. Sometimes it is standing still long enough to understand what the next move should be.

You cannot choose any of those well without knowing your position. The same move that is brilliant in one season is reckless in another. A loan that saves one company kills another; a hire that unlocks one team buries another.

So before you decide where you are going, find out where you are standing. Not roughly. Exactly.

Answer that one honestly and the rest gets easier.