A Joke That Isn’t Really a Joke
“When I grow up, I want to be middle management.”
It’s a funny line from a commercial. I’ve laughed at it. Repeated it.
But it reveals something deeper: we’ve been conditioned to see certain roles—and certain careers—as “less than.”
That belief is the problem.
Most of us were taught that success looks like this:
Entry-level → Manager → Senior Leader → Executive
A straight line. Always up.
So, when we see peers becoming Senior Directors, VPs, or CEOs—and we’re not—we start asking:
Am I behind?
Did I miss something?
Should I be further along by now?
That’s when comparison kicks in—and pressure follows.
Why This Thinking Fails You
Chasing only linear success creates three traps:
Comparison Trap: Measuring your life against someone else’s timeline
Catch-Up Trap: Making reactive career moves just to “keep pace”
Fulfillment Trap: Achieving titles that don’t actually make you happy
The result? Progress on paper… but dissatisfaction in reality.
A Better Way to Define Success
Success isn’t one path. It’s personal.
Not everyone wants to be a senior leader. Not everyone should be.
And choosing a different path isn’t failure—it’s alignment.
One framework that resonates with me is the idea of a portfolio career:
A mix of roles, industries, and experiences
Growth through variety, not just promotion
Success measured by impact, not title
My Perspective
I haven’t reached the C-suite.
But I’ve built a career across industries, taken on increasing responsibility, and contributed to meaningful outcomes.
I measure success by:
The impacts I’ve made
The skills I’ve developed
The growth I’ve sustained
That’s a successful career—just not a linear one.
A Simple Reset
Next time you feel the pull to compare, pause and ask:
What does success actually mean to me?
Not what it should mean. Not what it means for others.
For you.
Maybe it’s:
Fulfillment
Flexibility
Growth
Balance
Meaningful work
All of those are valid.
Final Thought
There’s nothing wrong with being in middle management if that’s where you thrive.
There’s nothing wrong with choosing a path that looks different.
The only mistake is letting someone else define success for you.
This is your story.
Define success in a way that aligns with your values—because your story isn’t behind.
It’s unfolding.
And as always, Your Story Matters.