You can spend a very long time thinking about what comes next without getting much closer to an answer.
That can be particularly frustrating when you are someone who is usually good at figuring things out. You are used to taking something complicated, looking at it from different angles and eventually finding your way through. So you approach this in much the same way. You think. You research. You make lists. You explore possibilities. Perhaps you talk to people you trust. You give yourself more time because surely, eventually, something will become clear.
I’ve been doing some version of that for the past few years.
And until recently, I assumed the difficulty was finding the right answers. I’m no longer sure it was.
Because there is something rather strange about asking yourself what you want to do differently while standing in the middle of everything you’ve already built.
Your life is already in the room
We talk about questions such as What do I want next? as though we approach them with a blank sheet of paper.
We don’t.
By the time you have spent twenty or thirty years building a career, raising a family, earning an income, developing expertise and becoming someone other people rely on, there is very little about that sheet of paper that is blank.
Your experience tells you what you’re good at. Your reputation tells you what other people value in you. Your income tells you what the market has been willing to pay for. Your responsibilities tell you what cannot simply be abandoned. Your calendar tells you what requires attention now. And behind all of it sits years of evidence that certain choices have worked.
None of this is a problem. Much of it is the result of a life you have deliberately built and may still value enormously.
But it isn’t neutral either.
It means that when you start imagining what could come next, some possibilities arrive carrying considerably more weight than others. They are familiar. They make sense. You can explain them. You have evidence for them. Other people can see why you would do them.
And then there are the possibilities that don’t have any of that yet.
I wonder how often we mistake that imbalance for knowing what we want.
Last week, I wrote about how easily competence can recruit us back into work we no longer want to build our lives around. I’ve been thinking since then that the same thing may happen one step earlier.
What we already know doesn’t only influence the answers we find.
It can influence which questions we think to ask.
Some questions come with the answer already inside them
Suppose you’ve spent years in senior leadership and you’re beginning to think seriously about doing something of your own.
You might ask:
How could I turn my leadership experience into a business?
It sounds like a wonderfully open question. But you’ve already made one important decision before you reach the question mark: your leadership experience will sit at the centre of whatever you build.
Or perhaps you ask:
How could I build something of my own alongside my current work?
Again, entirely sensible. But the current work has already been given permanent status. The new thing is what must learn to fit around it.
What could I do that would eventually replace my salary?
A real consideration for many people. But now the economics of one kind of working life have become the benchmark by which another must prove itself.
There is nothing wrong with any of these questions. The answer may ultimately be exactly where you began.
That’s what makes this difficult to notice.
The questions that narrow our thinking are rarely ridiculous ones. They’re usually the sensible ones. The responsible ones. The questions built from everything we know about how the world works.
I caught myself doing exactly this.
For months, I had been thinking about my business, my writing and the work I want to do with experienced women. I wasn’t short of ideas. If anything, I had too many. And because I have thirty years of experience behind me, I could see plenty of commercially viable ways to turn that experience into something people would pay for.
I thought I was considering my options quite broadly.
Then I stepped away from my normal life for two weeks and realised how many of my questions already contained assumptions about the answers.
Distance didn’t make me stop thinking
I went to Spain thinking I needed time.
What I hadn’t anticipated was how much difference it would make to change what was around my thinking.
My normal inputs changed. I read things I wasn’t reading because I needed an answer to something. I studied businesses that had been built in ways quite different from the ones I knew. I followed people because their thinking interested me. I had conversations. I noticed what I kept returning to and what suddenly seemed much less important when I wasn’t looking at it from inside my usual working day.
I didn’t stop thinking. Quite the opposite.
But some of the questions I had been carrying with me began to loosen.
Instead of asking only what I could build from my experience, I became much more interested in which parts of that experience I actually wanted to build around.
Instead of asking how to reach more people, I started asking whether I could recognise the right people more precisely.
Instead of looking only at the offers I had already created, I started looking at the journey between them and asking what problem was still unresolved.
These may sound like small changes in language. They weren’t.
The first version of each question was trying to improve something I had already decided.
The second allowed me to question the decision itself.
That was the part I hadn’t been able to see from so close.
Experience gives us options. It also gives them a ranking.
There is a paradox in becoming more experienced.
You have more to work with than you did twenty years ago. More knowledge, more judgement, more relationships, more evidence, more understanding of yourself and, usually, considerably more ability to create value.
Objectively, your options have expanded.
But experience also makes some options much easier to recognise than others.
You know what is viable in the world you already understand. You can assess opportunities quickly because you’ve seen versions of them before. You know what people will pay for, where your credibility transfers and which doors your experience is likely to open.
That judgement is valuable. I have no interest in throwing mine away.
But there is a difference between using experience to evaluate an option and allowing experience to determine which options make it onto the table.
I think that distinction matters enormously when you’re trying to build something different after a long and successful career.
Because the obvious next move may be obvious for a reason.
It sits closest to the evidence you already have.
That doesn’t make it wrong.
But perhaps it shouldn’t make it inevitable either.
You don’t need to pretend your existing life doesn’t matter
There is a tempting conclusion to all of this that I don’t believe.
Ignore the sensible questions. Forget the salary. Stop worrying what anyone thinks. Walk away from everything familiar and dream without limits.
No.
Real lives have consequences.
Income matters. Responsibilities matter. People matter. The life you have spent decades building matters. And if you genuinely love much of it, as I do, the point isn’t to treat it as something you need to escape before you can imagine anything else.
The challenge is almost the opposite.
How do you allow everything you’ve built to inform the decision without allowing it to define the boundaries of the decision?
I don’t have a neat answer to that yet.
Two weeks away happened to give me enough distance to catch some of my own assumptions in the act. Now I’m back inside ordinary life, I’m much more interested in whether that distance can be created deliberately.
Not simply more empty hours in the calendar. Not another morning with a notebook trying harder to answer the same question.
Enough distance to examine the question itself.
Because perhaps when you’ve been thinking about what comes next for months, the useful thing isn’t another answer.
It might be taking the question you’ve been trying so hard to solve and asking:
What have I already decided by asking it this way?
You may decide not to change a thing.
But at least this time, you’ll know you chose it.
Thanks for reading!
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Great post, thank you for sharing your reflective process. The way that we frame questions really does often lead us to a particular answer. I find it helpful to think about framing a question at a more strategic level, and a more tactical level, and using that process to work out the long list of options.