When Success Is No Longer Enough: Finding Meaning in Your...

There is a particular kind of career problem that tends to emerge after you've achieved at least some of the things you once wanted.

You're not necessarily failing.

Quite the opposite.

Perhaps you've built a successful business, climbed reasonably high in your profession, developed a valuable skillset, made decent money, or accumulated enough experience that you're no longer worried about whether you're capable of succeeding.

And yet, somewhere along the way, a different question starts appearing:

Is this really what I want to spend the next twenty years of my life doing?

I think this question becomes particularly interesting for men somewhere between their thirties and mid-forties.

By this point, you've lived enough life to know yourself considerably better than you did at 22, but you're also young enough to have decades of productive life ahead of you. You may have accumulated skills, relationships, capital, credibility and experience. Perhaps you've also accumulated responsibilities, a family, a mortgage and a lifestyle that makes changing direction considerably more complicated than it once was.

So this isn't another article telling you to quit your job and follow your passion.

It's about something I've wrestled with personally for years:

What happens when success itself is no longer enough?

When You Get What You Wanted

I've had a rather non-linear career.

I've worked in factories and blue-collar jobs, worked in sales, product, built businesses, failed at businesses, advised startups, coached people and spent large parts of my career trying to figure out where exactly I fit.

For years, like many ambitious men, I was primarily interested in moving forward.

Build something.

Make money.

Become successful.

Create freedom.

Prove to myself that I could do it.

At one point I found myself leading a company, something an earlier version of me would have considered a dream outcome.

And I was unhappy.

That was confusing.

It's much easier to explain dissatisfaction when you're failing. If the business isn't working, you aren't making enough money or your career is going nowhere, there's an obvious problem to solve.

But what happens when the thing you wanted starts working and you're still not fulfilled?

That's a much more confronting question.

Because now you can't simply blame the circumstances.

You have to start questioning the goal itself.

The Things That Drive Us Toward Success Aren't Always What Give Us Meaning

I don't think there's anything wrong with wanting success.

I still do.

Ambition, competition, money, recognition, achievement and the desire to prove something can be extraordinarily powerful sources of motivation.

They can push a man to develop skills, take risks, build businesses, create wealth and become considerably more capable than he otherwise might have become.

But there can come a point where proving that you can achieve something stops being enough reason to continue achieving it.

You already have the evidence.

You know you can build.

You know you can earn.

You know you can survive difficult periods.

You know you can figure things out.

And a different question begins to emerge:

What do I actually want all of this capability to be used for?

This isn't necessarily a rejection of ambition.

It can be the maturation of it.

The goal isn't to become less ambitious. It's to become more conscious about what your ambition is now in service of.

When Your Career Becomes Your Identity

I think this transition can be particularly difficult for men because work often becomes intertwined with identity.

Ask a man who he is and one of the first things he'll usually tell you is what he does.

Founder.

Lawyer.

Investor.

Doctor.

Executive.

Entrepreneur..

Whatever it happens to be.

Spend ten or fifteen years becoming successful at something and eventually the distinction between what I do and who I am can become surprisingly blurry.

This makes career transitions psychologically expensive.

You're not simply asking:

What should I do next?

You're potentially asking:

Who am I if I'm no longer this?

If you've spent fifteen years building a company, leaving entrepreneurship might feel like abandoning part of yourself.

If you've spent your adult life climbing a professional hierarchy, stepping away from it can feel like moving backwards even if the new direction makes you considerably happier.

There can also be status involved.

Income.

The expectations of your family.

What other successful men your age are doing.

The uncomfortable feeling that you should be further ahead.

And perhaps the most confronting question of all:

If I'm no longer achieving at the level I've become accustomed to, what is my value?

That's why I don't think a meaningful career transition is purely a career decision.

It's often an identity transition.

Success According to Whom?

One of the most useful things I've done throughout various periods of reinvention is reassess my values.

Not the values that sound impressive.

Your actual values.

Because what you optimize your life around at 23 may not be what you want to optimize it around at 38.

Maybe money mattered enormously because you grew up without financial security.

Maybe status mattered because you spent your younger years feeling insignificant.

Maybe entrepreneurship represented freedom.

Maybe achievement gave you confidence.

Maybe being extremely busy prevented you from having to think too deeply about other areas of your life.

There doesn't need to be anything pathological about these motivations. They may have served you extremely well.

But eventually it's worth asking whether you're still running an old operating system.

What matters to you now?

Freedom?

Family?

Money?

Creativity?

Contribution?

Adventure?

Faith?

Health?

Mastery?

Relationships?

Peace?

Service?

Building something that outlives you?

There is no universally correct hierarchy.

The important thing is that it's actually yours.

Because career fulfilment becomes almost impossible when your working life continually violates the things you claim matter most.

Don't Confuse Meaning With Passion

One piece of career advice I've become increasingly suspicious of is:

Follow your passion.

It's not entirely useless, but it's incomplete.

Passions change.

Some passions are terrible businesses.

Some things we find deeply meaningful aren't particularly enjoyable every day.

And sometimes we're passionate about something precisely because nobody is paying us to do it.

I think the better question is broader:

What kind of work allows me to use what I'm good at, in service of something I care about, while supporting the kind of life I actually want?

That's considerably less sexy than follow your passion, but much more useful.

Your career has to exist inside your life.

Not the other way around.

Know Yourself Before Choosing What's Next

This sounds obvious, but I think it's where most career advice goes wrong.

People immediately ask:

What should I do next?

Before properly answering:

Who am I now?

There are plenty of assessments that can help. Myers-Briggs, Enneagram, DISC, Big Five and various strengths assessments can all provide useful language for understanding aspects of yourself.

I've taken many of them over the years.

I wouldn't treat any single assessment as gospel. Humans are considerably more complicated than four letters or a personality type.

But patterns matter.

What kinds of problems do you naturally enjoy solving?

What work gives you energy rather than merely consuming it?

Do you enjoy building, leading, creating, teaching, selling, analyzing, organizing, advising or connecting?

Do you want to work alone or with people?

Do you want predictability or novelty?

Do you want to manage hundreds of people or never manage another human being again?

Do you enjoy competition?

Do you need creativity?

How important is autonomy?

What environments consistently bring out the best in you?

After enough years of working, you have something your 22-year-old self didn't have:

evidence.

Your career history is data.

Use it.

Look at the Skills You've Already Built

One of the advantages of changing direction later in your career is that you aren't actually starting from scratch.

It might feel that way.

But you're starting with ten, fifteen or twenty years of accumulated skills.

Entrepreneurs in particular tend to underestimate how transferable their abilities are because they've spent years doing a little bit of everything.

Sales.

Negotiation.

Hiring.

Leadership.

Marketing.

Problem solving.

Communication.

Decision making.

Managing uncertainty.

Raising capital.

Building relationships.

Recovering from things going horribly wrong.

These aren't simply skills for building companies.

They're assets.

The question becomes where else those assets can create value.

I think people often approach career transitions by looking at job titles when they should be looking at capabilities.

Don't ask only:

What jobs could I do?

Ask:

Where would the combination of things I've learned become unusually valuable?

That's a much more interesting search.

Meaning Still Has to Meet Reality

This is where I depart from a lot of career-fulfilment advice.

Meaning matters.

So does money.

You might discover that your deepest calling is writing experimental poetry beside the Mediterranean.

Wonderful.

If you have three children, substantial financial commitments and no desire to dramatically change your lifestyle, we may need a slightly more sophisticated plan.

A meaningful career transition doesn't require pretending economics don't exist.

You need to understand your resources.

How much money do you actually need?

How much runway do you have?

What assets have you accumulated?

What relationships can you leverage?

What skills can generate income while you experiment?

Can you transition gradually?

Can you consult while building something new?

Can you reduce your expenses temporarily?

Can you test the new direction before burning down the old one?

The younger version of me was much more comfortable making enormous leaps based on conviction.

I've learned to respect intelligent transition considerably more.

Courage and recklessness are not the same thing.

The Golden Handcuffs Are Real

One of the ironies of success is that it can make changing direction harder.

The more you earn, the more expensive your life can become.

The more status you accumulate, the more psychologically costly it becomes to start again somewhere you're a beginner.

The more successful the business becomes, the more people depend on you.

The more expertise you develop, the harder it becomes to walk away from the identity of being the expert.

Failure gives you an obvious reason to change.

Success doesn't.

That's why some people remain in careers they've emotionally left years earlier.

Nothing is sufficiently wrong to justify leaving.

The money is good.

People respect them.

They're competent.

Perhaps they're even still succeeding.

They're simply no longer particularly alive inside it.

And I think that's worth taking seriously.

You don't need to destroy a perfectly good career because you're having an existential Tuesday.

But you also don't need to wait until you're completely miserable before you're allowed to question whether the next decade should look like the previous one.

What Value Can You Create?

Of all the frameworks I've encountered around career development, I've increasingly come back to one very simple question:

What value can I create that someone else genuinely needs and is willing to pay for?

That question sits at the intersection of meaning and reality.

Because ultimately the market doesn't pay you because you're passionate.

It pays you because you create value.

The interesting challenge is finding the overlap between:

What you're good at.

What you care about.

What kind of life you want.

And what other people genuinely value.

That's where things become interesting.

I've come to think of career development in four broad steps:

Learn yourself.

Understand your values, strengths, weaknesses, motivations, personality and the kind of life you actually want.

Appreciate your value.

Understand the skills, experience, relationships, knowledge and perspective you've accumulated.

Find where your value is needed.

Look for people, markets, problems and communities where your particular combination of abilities is useful.

Learn how to communicate and sell that value.

Because being valuable and being able to demonstrate your value are unfortunately not the same thing.

This framework applies whether you're starting a company, changing careers, consulting, coaching, joining another organization or building an entirely new professional identity.

You Don't Need to Know the Final Destination

This has been one of the harder lessons for me personally.

I like clarity.

If I'm changing direction, I'd ideally like God to send me a PDF containing the next ten years, expected revenue, potential obstacles and a clear indication that I've made the correct decision.

So far, this service has not been made available to me.

Career transitions rarely happen with perfect certainty.

Sometimes you discover the next chapter by moving toward it rather than thinking your way into it.

You have conversations.

You experiment.

You write.

You advise someone.

You build something small.

You study something.

You work with different kinds of people.

You notice what keeps pulling your attention back.

You collect information.

And gradually a direction begins to emerge.

This is particularly difficult for successful people because we're accustomed to competence.

Starting something new makes you a beginner again.

That's uncomfortable.

But perhaps that's part of the point.

What Is the Next Chapter Actually For?

I think this is ultimately the question underneath the career question.

Not:

What job should I do next?

But:

What do I want the next chapter of my life to be about?

Maybe it's building enormous wealth.

There is nothing inherently wrong with that.

Maybe it's finally having enough freedom to be present with your children.

Maybe it's building something that contributes to a problem you deeply care about.

Maybe it's teaching.

Maybe it's creating.

Maybe it's mentoring younger people.

Maybe it's returning to entrepreneurship after years inside a company.

Maybe it's leaving entrepreneurship because you're tired of every problem in the building eventually becoming yours.

Maybe it's integrating spirituality into a life that has been almost entirely oriented around material success.

Maybe it's simply doing excellent work without allowing your work to consume your entire identity.

There isn't one correct next chapter.

But I do believe that at some point, an ambitious man has to decide what his ambition is actually for.

Because there will always be another milestone.

Another revenue target.

Another title.

Another company.

Another zero.

Another person ahead of you.

If you don't develop your own definition of enough, the game will happily keep giving you reasons to continue playing forever.

Success Can Evolve

I don't regret being ambitious.

I don't regret building businesses, chasing opportunities, wanting money or trying to prove what I was capable of.

Those experiences built parts of me that I value enormously today.

But I no longer believe success has to mean the same thing throughout an entire life.

The younger man might need to prove himself.

The next version might need to understand himself.

And eventually, perhaps, he begins asking how everything he's accumulated can be placed in service of something larger than himself.

That doesn't require abandoning ambition.

It requires integrating it.

Your career can make money.

It can challenge you.

It can use your talents.

It can provide status.

It can create freedom.

And it can mean something to you.

The balance between those things will change throughout your life.

If you've reached a point where the version of success you've spent years pursuing no longer feels like enough, that doesn't necessarily mean you've chosen the wrong path.

Perhaps that path brought you exactly where it needed to.

Perhaps the question now is simply different.

Not:

How much more can I achieve?