Do I Really Want to Do this One More Time?

Before deciding what comes next, decide how you want to work- and live.

THE EXPERT SHIFT

Executive Reinvention for Experienced Leaders

Reading time: 3 minutes

The last few days I spoke again with an executive in his mid-50s.

Long international career. Senior responsibilities. Financially secure. Plenty of energy for many more years.

We talked about the obvious options.

Another senior corporate role.

Interim management.

Consulting.

Perhaps building something of his own.

But at some point, the real question became:

Do I really want to do this one more time?

Another company. Another leadership role. Another five or ten years inside a large organization.

Not because he couldn’t.

Because he was beginning to wonder whether this was still how he wanted to spend the next chapter of his professional life.

And I hear different versions of that question surprisingly often.

Now, let’s get started.

THIS WEEK

I know the question because I had to answer it myself.

When my corporate career ended, I was 53 after more than three decades in one corporate world.

Of course, I could have looked for another executive position.

But something had changed.

I remember sitting in São Paulo and looking at the map.

Not for another corporate headquarters.

For a place where I could imagine building something of my own.

The question had shifted from:

What job could I get next?

To:

What kind of professional life do I actually want to build in my late 50s — and especially live in my 60s?

Those are very different questions.

And I increasingly believe experienced executives should ask the second one before answering the first.

THE EXPERT BRIEF

For most of our careers, progress had a familiar shape.

More responsibility. Bigger teams. Larger P&Ls. Higher compensation.

And I look back on that chapter with enormous gratitude.

My corporate career gave me opportunities I could never have imagined when I started.

It allowed me to work internationally, live in different countries, lead businesses, meet extraordinary people, make mistakes, learn from them — and build the experience I still draw on every single day.

I wouldn’t want to erase any of it.

But being grateful for a chapter doesn’t mean it has to continue forever.

At some point, you may simply realize:

That was a great chapter. Now I want the next one to be different.

Not better.

Not easier.

Different.

And after 25 or 30 years, another question deserves equal attention:

How do you want your life to work now?

Perhaps another CEO position is exactly right.

Perhaps you want less travel and more control over your time.

Perhaps you want to advise several companies instead of managing one.

Perhaps you want to turn your expertise into a small business and work from wherever you choose.

There is no universally right answer.

And this isn’t about rejecting the career that brought you here.

It is about using everything that career gave you to deliberately build what comes next.

WHY THIS MATTERS

The world around experienced executives is changing quickly.

Companies are restructuring. Management layers are getting leaner. AI and automation are taking over more analytical and knowledge work.

But I don’t believe that makes decades of experience less valuable.

It changes where the value is.

AI can analyze data, conduct research and prepare answers faster than any of us could a few years ago. But it doesn’t (yet) have your 30 years inside an industry.

It hasn’t led through a crisis, negotiated with difficult customers, built a market, made hiring mistakes, managed a transformation or learned what actually works when the PowerPoint meets reality.

I believe there will be an important place for experienced experts in the coming years who combine AI with deep industry knowledge, judgment and real-world experience — helping business leaders who are looking for external guidance, specialist expertise or simply a trusted sparring partner.

And AI may make these experts far more powerful than independent consultants could ever be before.

An experienced expert like you who embraces AI — perhaps working as part of a flexible network of other specialists — will increasingly be able to take on consulting challenges that once required the resources of a much larger firm.

Think about what that could mean for you!

Thirty years of industry experience.
A strong network.
Access to specialized expertise when needed.
And AI providing analytical, research and execution capabilities that previously required entire teams.

I truly believe we are seeing the beginnings of a new market for experienced, AI-enabled independent experts.

And that may create professional options that simply didn’t exist when we started our careers or even few years ago. It's truly a unique opportunity.

You may have another 10, 15 or even 20 productive years ahead of you.
The question is how you want to use them.

ONE NEXT STEP

Take ten minutes this weekend and complete two sentences:

In my next professional chapter, I want more of…

And I definitely want less of…

Don’t start with a job title.

Start with the life and work you want.

Then ask whether the path you are currently considering actually gets you there.

And then tell me.

I’m curious how experienced leaders in The Expert Shift community are thinking about this.

Hit reply and send me just two lines:

MORE: What do you want more of?

LESS: What do you want less of?

I read the replies personally.

And I will use what we learn to shape one of the upcoming editions of The Expert Shift.

If you are already further along and want to explore how your industry knowledge and experience could become a consulting business of your own, simply add:

BUILD

I’ll come back to you personally.

ONE MORE THING

If this edition made you think of another experienced leader asking similar questions, forward it to them.

Or invite them to join The Expert Shift.

Sometimes one good question starts an entirely new chapter.

Experienced leaders deserve another great chapter.

Your best professional chapter may still be ahead of you.

Enjoy a great weekend,

Dieter