The Loyalty Trap
Loyalty is one of the most praised virtues.
Stick it out. Stay the course. Be the dependable one.
For years, that was my identity.
I was loyal—to my old boss, my business partner, the company we built.
To income streams that weren’t aligned anymore.
To an old version of success that stopped fitting, but I kept squeezing into it anyway.
I told myself I was being responsible.
What I was really being… was afraid.
The Problem with Loyalty? It’s Rewarded.
The environment I came from praised it.
Loyalty got you recognition. Status. Security.
So I doubled down.
More systems. More effort. More optimization—squeezing every last drop from a life I wasn’t sure I wanted anymore.
Looking back now, it was all one big tangled knot of fear, obligation, and pride.
And here’s the hardest part to admit:
I stayed too long not because it was working… but because I didn’t want to disappoint anyone.
My clients.
My coworkers.
My boss.
Even my wife—because I believed my exit would shake everything.
I told myself I had made commitments.
But these weren’t wedding vows.
They weren’t till death do us part promises.
Still, I treated them like they were.
Misplaced Loyalty Will Crush You
Let me be clear:
Loyalty is a beautiful thing—to a point.
But past that point?
It’s a trap.
Because the longer you stay loyal to something that’s expired…
The more you start to resent it.
And worse—you start to lose yourself in it.
Loyalty should be to your future.
Not just your past.
Where I See It Now (Everywhere)
It’s easy to spot now.
Husbands stuck in dynamics that worked for 25 years but no longer serve the next 25.
Adult kids still trying to meet childhood expectations.
Friends tiptoeing around each other because it’s “been too long” to be honest now.
Even my relationship with my mom had to evolve.
I used to do things for her without question.
Eventually, those things no longer fit the life I was building.
But I still did them—out of guilt. And guess what?
It made me want to avoid being around her.
That’s not loyalty. That’s resentment with a nice label.
So I stopped.
Not out of rebellion. But out of respect—for both of us.
Now we have a better relationship.
Not based on guilt, but on choice.
What If You Let Go?
I’ve had to let go of people. Roles. Revenue. Expectations.
Some ended in clean breaks.
Others didn’t have to. The relationship just evolved.
And every time I thought it would lead to collapse…
It led to something else entirely:
Freedom. Joy. Space.
A kind of quiet happiness I didn’t know was possible.
It’s hard to describe.
Like walking through fog for years and suddenly realizing—oh… there was a mountain view this whole time.
You can’t make others see it.
But you can go first.
You can show that it exists.
You can prove that it’s real.
This Week’s Challenge: Audit Your Loyalty
Ask yourself:
What am I still doing out of obligation, not inspiration?
Who am I loyal to that I’ve outgrown—but feel guilty leaving?
What roles or routines feel “expected of me” but aren’t aligned with who I’m becoming?
Then try this:
Don’t abandon them. Re-negotiate them.
Speak the truth. Let the next version of the relationship emerge.
You don’t have to burn everything down.
But you can stop pretending that what once worked is still working.
Be loyal to the future you.
Not the outdated script of you.
Next week: We explore the hardest self-leadership lesson of all—real delegation. Why letting go isn’t about productivity—it’s about who you’re becoming.