What do you want?

She looked at me quizzically.

She had that sort of head cocked to one side, I don't know what you're saying, kind of look on her face.

"What do you want?"

She walked away from me slowly, eyes never leaving mine.

"What do you want? Just tell me!"

More silence.

I was getting frustrated.

If she really knew what she wanted, then surely she'd just tell me?

You'd think, by now, we'd be better at communicating. We've been living together for nearly a decade now.

Coco is my chocolate labrador and, despite many painstaking hours of language tuition, communication is still beyond her. Annoyingly.

But you and I have no such excuse.

So when my 12 year old asked me the other day, "What do you want to do for the next 20 years, Daddy?", I have to admit to being a bit stumped.

I have a fair idea what I'd like to do this afternoon. Even this weekend, maybe. But after that?

My parents are more than 20 years older than me, and still going strong. So maybe I should have a plan for the next 20 years? I mean that's enough time to build a whole new career from scratch, right?

I could become an architect, a politician (lol), an Olympian or a world famous musician (working on it...).

Be honest—when was the last time you really asked yourself that question?

Not what should you want?

Not what do people expect you to want?

Not what you've spent decades working towards.

But, what do YOU actually want?

It’s a question that matters at every stage of life, but if you’re my age (50 ish) with maybe another 20, 30 or 40 years left on this planet, then it’s more relevant than ever.

You’ve already proven yourself.

You’ve already ticked most of the big 'life' boxes.

So now what?

The Mid-Life Crisis

Many people hit this phase of life and suddenly feel… restless. Not miserable. Not lost. Just aware that they’re in a different place than they were 20 years ago, with different priorities.

Maybe you’ve built a great career but are starting to question whether you want to keep pushing for that next big promotion.

Maybe you’ve achieved financial stability, but now time and freedom feel more valuable than money?

Or maybe you just have a nagging feeling that your next 20 years should look different from the last 20—but you’re not quite sure how.

This is usually the point where people either:

1. Keep going on autopilot—because it’s easier than figuring out what they really want.

2. Make a dramatic change—sometimes the right move, sometimes just a reaction to boredom.

3. Get divorced, buy a Ferrari—and start shagging 20 year olds.

4. Pause and get clear on what actually matters now—so they can design the next 20 years with intention.

Option 3 is the smartest, obviously.

Sorry! Option 4. Option 4 is the smartest. Ignore that last bit.

But it requires getting brutally honest with yourself.

Do You Even Know What You Want?

Here’s the challenge: a lot of people think they know what they want… until they stop and question it.

- Do you want to keep climbing the ladder? Or do you just feel like you should because that’s what ambitious people do?

- Do you want to retire early? Or do you just want work that feels more meaningful or enjoyable?

- Do you want to start your own thing? Or are you just sick of pointless meetings and corporate politics?

If you don’t take the time to separate real desires from conditioned responses, you risk spending the next 20 years chasing things that won’t actually make you happy.

How to Figure It Out

If you’re unsure what you want next, here are a few ways to dig deeper:

1. Pay Attention to Jealousy

Jealousy is uncomfortable, but it’s also useful.

Who makes you envious? Not in a “I wish I had their car” way, but in a “I wish I could live like that” way.

Maybe it’s the person who left corporate life to become a self -employed consultant. Maybe it’s the one who took a year off to travel.

Your envy points to desires you haven’t fully acknowledged yet.

2. If No One Judged Me, What Would I Do?

A lot of career decisions—especially at our age—are made with one eye on how they’ll be perceived.

But if you stripped away all external expectations, what would you really want?

Would you stay in your industry? Would you work less? Would you pivot completely?

3. When Did You Feel Most Alive?

Think back to moments when you’ve been truly engaged, excited, or fulfilled.

Were you leading a team? Building something from scratch? Teaching or mentoring?

Those moments hold clues to what you actually value—not just what looks good on a CV.

4. Get Comfortable with Having No Answer

The idea that you have to pick one perfect answer for what’s next is what keeps a lot of people stuck.

You don’t need a 20-year plan—you just need a clear next step.

Clarity comes through action, not overthinking.

I may not be clear on my plans for next week, but I DO know that my current answer involves trying to become a music artist. Or at least someone who is making a living from music, one way or another.

I'm not sure of the exact path or where it will lead but it drives my day to day actions and priorities.

It's early days on this path (about 6 months into it so far) and things are trending in the right direction (my Spotify streams shown below):

The Worst Thing You Can Do? Nothing.

A lot of successful people reach this stage and think, I’ll figure it out later.

But years slip by fast. If you don’t actively decide what you want your next chapter to look like, inertia will decide for you.

So—what do you actually want?

And if you don’t know yet, when are you going to figure it out?

Until next time.

Jon "the artist" Kaye