The Conversation That Changed How I Coach Leaders Through Identity Shifts
There are coaching sessions you remember because they went well. Then there are the ones you remember because something deeper happened, not just for the client, but for you.
I was coaching someone with a big vision and a quiet heaviness. That heaviness didn't show up at first or all at once. It crept in layer by layer, conversation by conversation, through years of expectation, responsibility and unspoken assumptions about who he was supposed to be.
From the moment we started talking, I could feel his tension.
On the surface, he was saying, "I'm fine."
On the inside, he was saying, "What am I doing?"
I knew this wasn't going to be a strategy conversation. This was going to be a conversation that many high performers and leaders avoid until the discomfort becomes unavoidable.
And it changed how I coach.
When the Words Don’t Match the Truth
As normal, my client started talking about his business--marketing, clients, challenges, ideas, etc.
But, there was a creeping hesitation.
He was saying what he thought he was supposed to say…what he thought I wanted to hear and know.
So, when I asked, "What's actually going on here?"
He froze.
"I don't know Shakeena. I feel like I'm just winging it. Business is good, but, I don't know, nothing seems to make sense anymore."
There it was.
The moment every owner hits when they realize what they're doing no longer fits who they're becoming. He had outgrown the version of himself that had gotten him to this moment.
It's the identity shift that leaders feel long before they give themselves permission to admit it.
The Identity You Build Is Not the Identity You Keep
Your evolution is constant.
And, it'll happen with or without your permission.
That's the part no one warns you about.
It's not always loud either.
It doesn't always happen after some big life event or major realization of some kind.
It can happen in the interactions and conversations you have, the experiences you curate, and the things you don't say.
The life you live is a reflection of the beliefs you carry. When you are changing internally, those values and beliefs shift, and if you don't design the environment that mirrors who you are, you will feel the misalignment.
For my client, he had built his life around being "the person everyone could rely on."
But, he was exhausted.
Disconnected.
Uncertain.
He didn't have any meaningful goals.
He didn't know what he was supposed to do next.
He didn't have a direction or purpose.
He felt unraveled.
He was barely above threshold.
The misalignment he was feeling was showing up as "strategy problems."
He thought he needed a better marketing plan.
A new offer.
A different audience.
He didn’t.
He thought he needed to change his website and services.
Not exactly.
He was second-guessing everything he did.
He was no longer pulled to serve the very people he was once excited to work with.
He procrastinated when he was once decisive.
He was unclear on his direction and motives.
He was burning out, swimming in confusion, and feeling like a failure even though his business was profitable.
What he really needed was clarity on who he was becoming so he could stop forcing himself into a past identity he had outgrown.
He was shedding his old identity.
The Question That Changed the Entire Session
At one point, I stopped him mid-sentence and asked:
"What if you stopped trying to be who you think you're supposed to be and gave yourself permission to be who you are?"
That's when he froze.
Most of us are not confused about what we want.
We're conflicted about whether it's allowed.
What came next wasn't dramatic.
It wasn't emotional.
It was quiet.
Steady.
Honest.
He started talking about what he actually wanted:
More intentional, deep work
More creativity
More time to think
Less people chasing and pleasing
Less performing
Less pretending that he didn't want what he wanted
He didn't have all of the answers, but he finally had permission to acknowledge the questions and say what he wanted.
And it was the relief he needed.
Identity Work Is Strategy Work
This session changed something for me.
It helped me reaffirm what I see and have seen in so many of my clients: When what you do and who you are aren't in alignment, you plateau.
It becomes harder to:
Choose a direction (in life or business)
Communicate clearly
Make strategic decisions
Enjoy your life to the fullest
…not until you understand who you are and who you're becoming as a leader.
Gary didn't need tactics and strategies.
He needed clarity.
He needed to connect the person he was becoming with the business he wanted to build.
He needed a perspective that he owned.
A vision he could lead with.
A voice he could uphold.
So, when at the end of the session, I asked:
"What's the smallest and most natural step you can take from here?"
He didn't say, rebuild my business or launch something new.
He said, "I think I need to stop hiding from myself."
That was the beginning of his leadership transition.
This Isn't About Gary.
This is our story too.
It’s about the moment when the version of you that built the business can no longer carry what the business is asking for next.
It’s about realizing that confusion isn’t always a sign that something is wrong—sometimes it’s a signal that something is changing.
Many leaders try to out-strategize this moment.
They reorganize.
They rebrand.
They push harder.
But identity shifts don’t respond to pressure.
They respond to honesty.
The work isn’t to become someone new.
It’s to stop abandoning who you already are becoming.
Over the next few letters, I’ll be sharing more of this journey—not because Gary’s story is unique, but because it’s familiar.
If something in this letter stirred recognition, sit with that.
You may not need a new plan.
You may need to give yourself permission.
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P.S. Whenever you're ready...here are a few ways I can help YOU build your business with more clarity, structure, and intention:
The Executive Desk
Private asynchronous executive and business coaching for founders and CEOs seeking clarity, strategy, and confident decisions
TFC3 – Private 1:1 Coaching
For high-capacity business owners who want deeper support with systems, leadership, and strategic direction. Two coaching sessions a month + in-between support to help you create real movement and momentum.
The Focused CEO Academy
A growing library of tools, templates, challenges, and workshops to help you simplify your business, elevate your operations, and work with more intention — at your own pace.
Not sure where to start? Send me a message here — I’ll help you figure out the best next step based on where you are in your business.