I Am The Man: The Retirement Shift from Working for the Man to Becoming the Man

By Dave Smith, The Ultimate Retirement Coach

For most of your adult life, you worked for the man.

A boss.
A company.
A system that defined success, set expectations, and told you where to be and when to be there.

And now, retirement is here—or right around the corner.

This is the moment many people underestimate. Because retirement isn’t just a financial transition. It’s a mental and identity shift.

The real work of retirement begins when you can confidently say:

“I am the man.”


The Idea: Working for the Man Prepared You—Now It’s Time to Become Him

Let’s start with the truth.

Working for the man wasn’t a mistake. It wasn’t wasted time. It was the training ground.

Your career gave you:

  • Financial security

  • Discipline

  • Skills and experience

  • A nest egg that makes retirement possible

You followed rules, met expectations, and built something real.

But here’s the shift few people talk about:

The structure that helped you succeed in your career can quietly limit you in retirement.

There’s no boss now.
No performance review.
No defined path.

And that’s exactly why retirement feels unsettling for some.

Becoming the man means you take full ownership:

  • Of your time

  • Of your priorities

  • Of what “success” looks like now

Retirement isn’t about doing nothing.
It’s about doing what matters—by your definition.


The Question: When You Say “I Am The Man,” What Does That Mean to You?

Say it slowly:

“I am the man.”

Now ask yourself:

What does that actually mean in your life?

Does it mean:

  • Freedom over your schedule?

  • Strong health and physical capability?

  • Being present with family without distraction?

  • Creating, building, or learning something new?

  • Giving back through mentoring or service?

  • Living with peace instead of pressure?

Most people spend decades living inside someone else’s definition of success. Then they retire—without ever defining their own.

Becoming the man isn’t about power or ego.
It’s about intentional living.

If you don’t define what “I am the man” means, your retirement will default to habits, distractions, and drift.

Clarity is not optional. It’s leadership.


The Action: One Step You Can Take This Week to Claim “I Am The Man”

Here’s one simple, powerful action you can take this week:

Create Your “I Am The Man” Definition

Set aside 15 quiet minutes.

No phone.
No interruptions.

Write this sentence at the top of a page:

“I am the man because I choose to…”

Then finish it—honestly.

You might write:

  • “…protect my health and energy.”

  • “…spend my time intentionally.”

  • “…live by my values, not my calendar.”

  • “…invest in relationships that matter.”

  • “…create a legacy, not just memories.”

This isn’t for anyone else.
You don’t need to perfect it.

Just write it.

Then read it each morning for the next seven days.
Let your decisions start aligning with your definition.

Clarity follows action—not the other way around.


Final Thoughts from Dave Smith

You already proved you could work for the man.

You showed up.
You provided.
You built security.

Now comes the most important role of your life:

Becoming the man—on your terms.

Retirement isn’t an ending.
It’s a leadership promotion.

And the first step is being able to say—with confidence and clarity:

“I am the man.”

If you’d like help defining that next chapter with purpose, confidence, and direction, that’s exactly what I do as The Ultimate Retirement Coach.  Visit www.leapretirement.com and use the free tools to build your plan.

Your career is complete.
Your ownership of life is just beginning.