The question we stopped asking

Many successful solopreneurs stop asking themselves what they actually want. Daily life crowds out the question, and the feeling that we should be satisfied takes care of the rest.


Close-up of a plate with gravel and small stone cubes on a concrete surface, next to an open book. Title: The question we no longer ask ourselves.

And yet something doesn't feel right.

It usually starts with that nagging feeling of dissatisfaction. Many brush it off. My standard line was "Stop being so dramatic." I should be satisfied with what I have.

This quiet voice is one we're all too happy to ignore. But that's a mistake.

The short version

Sometimes we feel dissatisfied even though we have a successful, well-running business. Something doesn't fit anymore and we can't quite put our finger on what it is.

The reason is that we've stopped asking ourselves the most important question: What do I actually want?

This article covers why that question is so hard to ask, what happens when we avoid it, and what changes when we ask it again.

We forget the most important question

Every decision starts with the same question: "What do I want?"

At first glance, the answer seems obvious. We want more money, more freedom, more happiness, more time, more love, and some wild combination of all of the above.

This question has much more to offer than it seems. But we rarely dig deeper.

The daily grind is too strong.

Most of us have packed calendars. There's always plenty to do.

We follow the advice of time management and productivity experts. We plan and structure our work. We even make sure to work not just in but on our business. We want to be well prepared.

And with some luck and goodwill, we carve out time for the personal things too.

We've built a solid routine. It could probably be better, but it fits and offers us stability.

That's fine until we turn the routine into a corset.

One day follows the next. Before we know it, we're on the hamster wheel. In a groove that keeps everything running smoothly, structured and reliable.

And when things are working, we just keep going without thinking.
There's no reason to change anything. Nothing feels urgent.
Other things need our attention first.

I should be satisfied now.

There's something else underneath all this. It's often more of a feeling than a conscious thought.

We've worked hard to get where we are today. We've invested time and money in education, courses, strategies. We threw ourselves into building the business and in the process gave up things others take for granted.

We had a goal and we reached it.
We're proud of that. And rightly so.
We shouldn’t be dissatisfied now. We should be happy and grateful. We’re where many others are still striving to be.

As if the question were a sign of being ungrateful.

Many feel the question simply isn't allowed. Wrong. We can be satisfied, happy, and grateful and still want more or something different. That's a sign of growth.

Thoughts like 'I should' or 'I have to' are a signal. We're caught between what's expected and what we actually want.

Whatever is holding us back from asking what we want, in the long run we're creating unexpected problems for ourselves. Especially when it comes to decisions.

Without this question, we lose our bearings

For years, the goal was simple: build a successful business. Everything went into that. We knew what we were working toward. And the numbers told us where we stood.

Now we've arrived. And we're still not satisfied. That's unsettling. Something doesn't fit, even if we can't quite name it.

If we don't stop and take stock, there will be consequences.

Then we work against ourselves.

We need goals if we want to grow. Reaching a goal brings a sense of fulfillment, pride, and satisfaction. At least when it's a goal we actually want and that feels right.

There are serious consequences when we're quietly dissatisfied. As solopreneurs, we're both the boss and the employee. We just sometimes forget the boss.

Without that leadership, we drown in our work. We keep going. We're dissatisfied and do nothing about it. Because we never stop to ask what we actually want.

Dissatisfaction almost always leads to disengagement.

Even when it's our own business.

Sometimes we start sabotaging ourselves without noticing. We get sloppy. We daydream about walking away.
None of that helps. Neither changes anything.

And it's not the work that's the problem. It's that we've lost the thread. Because we stopped asking what we want.

Or we can't find an off switch.

Sometimes the reaction is to push forward.
We try to fill the emptiness with work. To get back the satisfaction the business used to give us.

We bury ourselves in work and give everything we have. Maybe more than we have.
That makes sense. This part of our lives has fed us, not just financially, but emotionally. Success feels good. So does being recognized.

Work matters.

But when that's all there is, everything else starts to feel flat. It's just not all of life.

We may start neglecting friends, family, our health, our long-term wellbeing.

Throwing more work at dissatisfaction gets results.
It just costs more than it should.

Asking the question isn't weakness

For me, as for many others, this question carried weight for a long time.

I grew up in a generation where children weren't really consulted. We were rarely asked what we thought or brought into decisions that mattered.

The one question that did come up was: "What do you want to be when you grow up?" It overwhelmed me for years. I simply didn't know. And the pressure to have the right answer didn't help.

Later, it was silently expected that you always know what you want. As if the answer were hardwired. That too was a missed opportunity. Nobody taught us how to sit with the question.

The focus was always on the answer. Never on the question.

My secret conclusion was that something was wrong with me for not having one.

It isn't a weakness not to know what we want.
It means we take ourselves seriously.

We're at a turning point.

This question needs its own dedicated time. Not as a luxury or a nice-to-have, but as a necessity. It brings us back to what actually matters to us.

Because dissatisfaction isn't a character flaw. It's a signal. It tells us something no longer works or no longer fits.

When we see that, the question opens something up. We can start making conscious decisions again.

The first step isn't about having an answer. It's about giving ourselves permission to look. At what is and what could be.

We make our choices

We often hold on too long because letting go of something good is hard.

I picture myself standing on one bank of a river, wanting to cross to the other. My side is lovely. Everything is here. But the other bank beckons with exciting new possibilities.
The problem is the crossing. I know it will be cold, difficult, and uncomfortable. Like any change.

So it's worth letting the question in.

What do I want?

Everything begins with the courage to ask it honestly.

We strengthen what works.

Impatient as many of us are, we want to get started right away. Everything has to change. Now.

When I ask this question in a coaching session, I get a list of everything that needs to go. I start one step earlier.

We've put a lot of work into being where we are now. So we start by getting clear on what we want to keep.

That's usually much more than our dissatisfaction is whispering to us. Not everything is broken. Not everything needs to change.

A lot is good and worth holding on to. We can appreciate that, and perhaps even build on it.

Some things can go.

Of course there are things that no longer fit. We've grown out of them.

I compare it to going through a wardrobe. Some shirts are out of style, we don't like the color anymore, the cut doesn't fit, or it no longer feels like us. Some we bought on impulse and never wore. Some were just stopgaps.

Anything that no longer fits can go. Without regret, frustration, or resentment. It served its purpose, it was useful, and now we don't need it anymore.

Often it's just small things we want to adjust.

Usually we realize at this point that there isn't actually that much we want to change. Frustration makes us dramatize and see everything in black and white.

Even if we do want some significant changes, things are clearer now.

Sometimes it really is just small things that deserve more space. A little more time for hobbies, an assistant for more freedom, regular date nights for more connection.

Whether it's changes in the business or in our personal lives doesn't matter. That's the particular thing about solopreneurs. We're one person, in every part of our life.

A small adjustment in one area can have a larger impact across all the others.

We don't have to change everything at once.

Usually there are still one or two things left that we genuinely want to change. But even here, we don't have to tackle everything at once.

We've untangled the knot of ideas and wishes, the things that fit or don't. We have clarity now on what can stay, what should go, what needs a small tweak, and what needs to change.

This clarity shows us the next goal.

We won't always be ready to start today.

Maybe now isn't the right moment, or we're still missing something.

The difference is that we finally know what we want. That makes it easier to accept what we can't change right now. Not because we're giving up, but because we're consciously saying: not yet.

That's a good decision too.

It starts with a single question

Living a self-determined life means making clear, conscious decisions every day. Even if it's so tempting to follow others' expectations instead and forget our own reference points.

The question "What do I want?" gives us stability and a sense of direction.

We know what's good again, what can go, what we want to change or accept.

We decide for ourselves.

More on this topic:

Astrid von Weittenhiller

I work with successful solopreneurs facing decisions no one can make for them. My work starts where no option is clearly right.

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Once a week, I write about what's on my mind. Usually it's about decisions, sometimes about things that are only loosely connected.

Once a week, I write about what's on my mind. Usually it's about decisions, sometimes about things that are only loosely connected.


I talk about personal observations and experiences from my work with solopreneurs, share new articles, and occasionally give you updates about my offers.


Once a week, I write about what's on my mind. Usually it's about decisions, sometimes about things that are only loosely connected.


I talk about personal observations and experiences from my work with solopreneurs, share new articles, and occasionally give you updates about my offers.

I talk about personal observations and experiences from my work with solopreneurs, share new articles, and occasionally give you updates about my offers.

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