Last Tuesday, I sat in our weekly L10 (a structured, weekly leadership meeting format from the Entrepreneurial Operating System (EOS)) and did something that felt physically painful: I kept my mouth shut.
Someone asked a question about resource allocation. It was the kind of thing I have answered on instinct for 20 years. My brain instantly queued up an explanation, complete with my usual out-loud processing and circle-back thinking.
But I did not say a word.
I sat there, forcing myself to let the team lead the discussion. They asked clarifying questions, weighed options, and mapped out next steps. The solution they landed on was far better informed and ultimately smarter than anything I would have thrown out in the moment.
It was a solution I would not have thought of, because I was reaching for the one that worked three years ago.
That is when a line from Steve Jobs surfaced in my mind:
“It does not make sense to hire smart people and then tell them what to do.
We hire smart people so they can tell us what to do.”
The Swiss Army Knife Problem
For two decades, Chris and I have been the Swiss Army knives of Sanctuary. Visionary roles, integrator roles, operations, sales support, client work, relationships, finance, and decision-making. We did all of it.
But the truth is, we have not been the ones “keeping Sanctuary running” for a long time.
We built a great team. They picked up what we started, strengthened it, and pushed it further than we ever could alone. Yet I stayed in the middle of everything because that is what founders tend to do.
Here is what “being good at a lot of things” really bought me:
- A team that checked with me before making decisions I should not even know about.
- Great leaders asking for more responsibility, then waiting while I waited for the “right time” to hand it over.
- Client relationships that should have lived with the account team but came through me.
- A one-year plan I helped build but did not have time to think about because I was too busy fixing last month’s problems.
And the kicker was this: I kept telling myself I was being helpful.
I was not. I was building dependency.
And dependencies do not scale. They crack under their own weight.
The Training Wheels Are for Me
We are officially transitioning the Integrator role to Cortney in January. Right now, we are in what I’ll call “training wheels mode.”
The wheels are not for Cortney or the team. They are for me.
Here is what I have learned about myself. I am a people pleaser who cannot stand watching someone search for an answer if I have one.
It is not about control.
It is not even about ego (well, maybe a little).
It is simply that someone asks a question, my brain fires, and my instinct is to help.
But every time I reflexively answer, I take the ball back. I crowd out the better thinking, insights, and ideas that emerge when the person who is actually accountable for that area is given room to lead.
That forty-five-second pause in last week’s L10, the one where I almost jumped in, ended up proving the point.
Cortney did not just answer. She reframed the issue. She spotted something I missed because I was too busy being efficient. Because she framed it better, the team contributed more effectively and found a stronger solution, faster.
The surprising part was the feeling that followed.
I felt relieved. Not validated. Relieved.
It was like I had been carrying something I did not need to carry anymore.
She is going to be a better Integrator than I ever was.
What Letting Go Really Costs (And Nobody Talks About It)
People talk about “letting go of the vine” like it is a heroic milestone.
Nobody talks about what it feels like in week three when your Wednesday afternoon has four hours of white space and you do not know what to do with yourself.
Nobody mentions the guilt, or the loneliness, or the identity freefall. Nobody mentions how uncomfortable “strategic thinking” feels at first, or how tempting it is to jump back into tasks just to feel useful.
When you have spent twenty years being the person who solves the crisis, stepping back does not feel like freedom at first.
It feels like failure.
It feels like you are letting the team down by not sweating as hard as you used to.
And that is exactly when you are most likely to sabotage your own progress by jumping back in.
The Realization That Shifted Everything
There was no dramatic moment that forced a change. It was a slow, steady realization that came from months of planning, reflection, and honest conversations with the team.
We have been preparing for this evolution for years.
But here is the truth. I had been carrying around this old, self-created pressure that I had to “keep it all running.” It came from years of operating in a mindset of scarcity, where if I did not stay vigilant, something important might fall through the cracks.
But that was not reality. It was a story I kept telling myself.
The real story is this. We have built a great team over many years. They have been leading the company, solving problems, and making smart decisions long before this transition even started. They did not suddenly become capable. They have been capable for a long time.
I was the one who had to catch up.
Shifting from a scarcity mindset (“If I let go, something might break”) to an abundance mindset (“Look at how strong this team already is”) has required rewiring habits that have been with me for decades.
Once I finally saw that the pressure to “keep it all running” was self-imposed, everything looked different.
This transition is not about making the team ready. They have been ready for a long time.
It is about making me ready.
What Is Happening Now
The team is stepping up in quiet, consistent ways that show real leadership.
- Lauren brought a six-month marketing plan that was better than anything I would have created
- Tom closed deals with clarity and momentum I would have unintentionally complicated
- Cortney is running L10s with steadiness and structure that I never reached while juggling too many roles
They are solving problems faster than I ever did.
They are removing things from my worry list.
They are strengthening the business in very real ways.
I am not sure if I feel more proud or more irrelevant. Probably both.
But mostly, I feel lighter.
It feels like I have finally exhaled after holding my breath for twenty years.
What I Am Learning, Still In Motion
I am not writing this from the other side. I am still in the messy middle, figuring it out as I go.
Here is what I am learning.
If the business only works when I am grinding, it is not a business.
It is a dependency with an expiration date.
I do not want Sanctuary’s best days to be behind us. I want our best days to be ahead. I want the team that helped build this place to be the ones leading it.
That means my role has to evolve.
It means spending time in the community.
It means building partnerships.
It means contributing thought leadership.
It means exploring new technologies.
It means developing future leaders.
It means thinking in years instead of weeks.
It means finally doing the work a Visionary is supposed to do.
It is uncomfortable.
It is unfamiliar.
And it is necessary.
Because every time I let go of something I thought only I could do, someone else does it better.
Where I Am Now
I will not end this with advice. I am still learning.
Here is the truth:
- I have more white space on my calendar than feels natural
- The team is thriving without my constant input
- I am realizing I confused being “busy” with “doing my job” for far too long
- And for the first time in years, I have space to think about what the next version of my job should be
Letting go of the vine is not about becoming irrelevant.
It is about finally being free to do the work I am actually meant to be doing.
I am still learning what that looks like.
But for the first time in a long time, I have room to learn it.