From Leading 22 to Leading Myself
This post is part of "The Entrepreneur's Safari" – a series of candid reflections exploring the entrepreneurial journey of building Complete Safaris with my Kenyan partner, alongside lessons learned from leadership and business development.
Before Complete Safaris, there was a team of 22. At one point, six direct reports.
Twenty-two people to motivate, develop, challenge, encourage, and occasionally redirect. Twenty-two different learning styles, communication preferences, and definitions of what "done" looked like. The work of leading them was relentless and energizing in equal measure.
Then: a business built from scratch with a partner in Kenya. No team. No direct reports. No one to delegate to, develop, or redirect.
Just the work. And the person doing it.
What followed was one of the more humbling realizations of a long career: every leadership lesson confidently delivered to others would eventually need to be relearned in the first person.
What Carried Over
Years of leading people builds a vocabulary for growth, accountability, and forward momentum that doesn't disappear when the team does.
The curiosity stayed too - but it changed shape. Dr. Jes DeShields writes in 9 Leader Touchstones about the kind of curiosity that keeps leaders honest and growing. In a team environment, that curiosity pointed inward: what does this person need, what am I missing, what's the dynamic I'm not seeing? Now it points outward. The questions potential clients ask about Kenya, about safari planning, about what they're really looking for - those questions are the signal. Listening to them carefully reveals what needs to shift internally. Different direction.
Same muscle.
And the commitment to doing things right stayed. But doing things right is considerably easier when surrounded by people who will call you on your bullsh*t. Working solo means learning to call yourself on your own. Maintaining the same standards without external pressure turns out to be a different skill entirely.
What Didn't
Delegation. Every unfamiliar, tedious, confusing task lands on the same desk.
The energy of a team. There's something that happens in a room full of people working toward a shared goal that simply cannot be replicated alone. The momentum, the creativity, the way one person's enthusiasm lifts another's - that's gone.
Nobody's watching. That's the point. That's also the problem.
The Lessons That Came Back Around
Here's where it gets interesting.
Two pieces of advice given repeatedly to that team of 22 came back around hard.
Ask questions before giving answers.
A potential client asked how long a Kenya safari should be. Without hesitation: "Ten days." Confident. Certain.
She went quiet. Then said: "I only have my daughter every other week. Seven days is all I can manage."
The conversation recovered. But the lesson landed. This was advice given countless times - understand the context before offering the solution. Apparently it still needed learning.
Progress over perfect.
Told to team members who would refine endlessly rather than finish. Who kept adjusting, improving, perfecting until the moment passed.
Then came YouTube. Complete Safaris needed to be there. That much was clear.
What wasn't clear was anything else. Months of podcast episodes about YouTube strategy. Pages of notes. Hours watching other people's videos trying to reverse-engineer format, algorithm, what made something actually work. All of it overwhelming. All of it sitting in notebooks while the Complete Safaris YouTube channel stayed untouched.
The answer was already there. Progress.
The Instagram reels already being created could be uploaded to YouTube. Not perfect for the platform. But good enough to begin. Get comfortable with the process, learn the algorithm in real time, understand what
works before trying to perfect it. Build toward better rather than waiting for perfect to arrive.
Progress over perfection. Said it to a team more times than can be counted. Had to live it before it actually landed.
The Honest Reflection
Leading a team of 22 built something that solo entrepreneurship keeps drawing from. The frameworks, the language, the curiosity, the standards - none of it was wasted. It just changed form.
But the humbling part is real. The lessons most confidently delivered to others are often exactly the ones most urgently needed when the room empties out and the only person left to lead is yourself.
That's not a failure of leadership. It's just what leadership looks like when the mirror turns around.
What about you? What accountability structures have you had to rebuild intentionally now that they're no longer structural? What leadership language do you find yourself using on yourself that you used to use with a team?
Curious for more? (There's that word again: Curious) We have two leadership blog posts from the perspective of 2 of the Big Five in Kenya.
Every Complete Safaris safari starts the same way a good leader starts: with questions. Not assumptions. A conversation before a proposal, every time. Start yours here.
