Beaches and Boss Moves: Leadership Lessons on Letting Go

This month, I spent 2 weeks in Thailand with a friend in celebration of our 50th birthdays.

No kids to drive around. No meetings to run. No clients to email. No social media. 

Just space.

Halfway through it hit me: why had it taken me eight years to allow this? How had I never been offline from Reimagine Work? 

Sure, I have gone away but never was away from the operations side of the business. 

Even on my “off” time, I believed I had to hold everything together. That being self-employed meant hustling. Carrying the weight. Saying “yes” to things I didn’t have time for. Sacrificing myself (and time with my family) for the work.

But sitting across the world from it all, I had to ask—was that really how leadership had to look for a founder? Or was it a legacy left over from entrepreneurial survival mode?

The 5 Biggest Shifts in My Leadership 

I’ve spent the last eight years learning (sometimes the hard way) what it really takes to lead well—not just in business, but in life. Thailand gave me the space to look at how far I’ve come and the shifts I’m still making.

Here’s what I’ve learned.

1. Shifting from Overcommitment to Strategic Focus

Then: In the first few years, I was drowning in work. Waking up at 3:30 AM, squeezing in client calls at all hours, and feeling guilty whenever I tried to step back. I was saying yes to everything—clients who drained me, and tasks that kept me stuck in the weeds.

Now: I’ve let go of the idea that more equals better. I’ve set clear “CEO” boundaries, focused my business on projects and retainers and not hourly work, and built systems that allow things to run without me. 

I’m choosing depth over hustle—investing my energy in the work that actually moves things forward in the businesses we work with.

2. Letting Go of Guilt

Then: I carried guilt for everything. If a leadership team I was working with was struggling, I felt responsible for fixing it. If a client was unhappy, I absorbed the stress. If I took time off, I worried I was letting people down.

Now: I’ve learned that not everything is mine to carry. I can let go of bad clients, decline work that drains me, and step away without everything falling apart. My well-being matters more than business success.

3. Moving from Execution to Leadership

Then: I was running every meeting, handling every hiring decision, managing teams, overseeing directors—if something needed to happen, I was doing it. My business was growing, but I was still operating like a one-person show.

Now: I’ve stepped into actual leadership. I’ve trained excellent people to take on operations. I’ve built structured processes, so things don’t live in my head. 

4. Unplugging from Outdated Work Models

Then: I felt stuck between two worlds—financial security and exhaustion. I was saying yes to work I didn’t even want because I didn’t trust that I could let it go.

Now: I’ve let go of my old success stories. The ones that say to succeed I need to grind harder, work more, be everything to everyone. I’m choosing business modes and models that energize me, not deplete me. I’m building based on values that align with where I want to go—not where I’ve been.

5. Trust Over Hustle

Then: I was over-reliant on myself. If something broke, I fixed it. If a team member struggled, I stepped in. I was running a business, but I was also running myself into the ground.

Now: I’ve built systems that support my leadership instead of demanding my energy. I’ve created repeatable processes. I trust my team and show it.  I’ve shifted from being the lifeguard (rescuing everything) to the swim instructor (teaching others to lead themselves).

What’s Next

Thailand wasn’t just a trip—it was a reset. A chance to step back and see how much had changed, and where I still have work to do.

I don’t have everything figured out, but I know this: I want to share what I’ve learned with other leaders.

Over the next few months, I’ll be exploring ways to help other people step out of the weeds and into leadership—whether that’s through workshops, coaching, or something else entirely.

For now, I’m sitting with it. Maybe even celebrating it. 

But if any of this resonates, I’d love to know—where are you in your own leadership journey? What are you ready to let go of? Tell us on social media or at connect@reimaginework.ca.