Welcome back to Little Leadership Lessons, my newsletter highlighting short but powerful insights to help you lead with confidence and create lasting results. These lessons come directly from my research, interviews, and coaching work with six- and seven-figure creator-founders.
Hope you’ve had a wonderful week and are making the most of this last month of summer (or winter down there in the southern hemisphere).
My wife and I went to visit my parents this past week to support my Dad on his journey with Parkinson’s. It was a meaningful and important trip and now I’m happy to be home with my kids.
Around this time of year I do a little exercise to check in on my goals from the beginning of the year and to reset expectations for what’s most important before the holiday season.
That makes me curious: what’s your biggest goal before the end of the year in your business? I’d love to know! Hit reply and share what you want to make happen.
Let’s get to it!
A Beautiful Photo to Quiet Your Body and Mind
As a reminder, each edition of this newsletter is the direct learning from a $1,500 coaching session translated to you and your business in 10 minutes or less. Here’s this week’s…
The Situation
A client came into a session looking frayed. He’d recently stepped into his role as CEO, taking over for the founder who was ready for a new leadership challenge.
My client was leading through a season of rapid growth and change, but it wasn’t going well. His team was tense from all of the change, interpersonal conflict had surfaced, and he wasn’t proud of how he was showing up in meetings.
He felt like he wasn’t living up to the quality of work that the founder used to do. He felt unnatural when delivering webinars, under-resourced for the ambitious goals they had set, and like he was failing on every front.
On top of that, his family life was heavy with stress. He was stretched so thin that by the time we met, he said, “Something feels off. I can’t name it. But I’m not myself. I don’t even feel like I have time to check in with myself on how I’m doing day to day.”
He wasn’t asking for a tool or a new productivity system. He just wanted to find his footing so that he could settle into the role and start finding some wins.
The Emotional Blocker
As we unpacked what was happening, a simple truth came into view. He was comparing himself to the founder in everything he did. In hosting a team meeting, he’d wonder why the team reacted differently to him than the founder. In writing emails to his audience, he’d question why open rates were down or why webinar show-up rate had dropped.
“Is it something about me? Is there something fundamentally broken about my leadership? Am I not cut out for this job?” he wondered out loud as the spiral he was in came into focus in the middle of our session.
This was the core block for him: he was so busy comparing himself to the entrepreneur he replaced that he was putting an unreasonable amount of pressure on himself. In the process, he was chasing a leadership style that wasn’t his rather than leading authentically.
The Breakthrough
In the midst of all that self-imposed pressure, he had stopped doing everything that once kept him whole. He wasn’t working out. He wasn’t taking his normal hikes with his dogs. Sleep was poor. He ate quick meals at his desk.
The very practices that used to center him had quietly fallen away. And yet, he felt ashamed to admit it.
“I don’t have time for that anymore,” he said. I see this over and over with high-level clients. It’s the lie most high achievers believe. The more we have to do, the less we can afford the rituals that restore us. In reality, abandoning those practices accelerates our downward spiral.
I asked, “What did you used to do that helped you feel most like yourself?”
He paused. Then: “Long hikes. No phone. Just me and the dogs.”
That was the opening. Not another system. Not a hack. Just permission to return to what was already there.
We planned a hike to the top of a nearby mountain. No technology, no music or podcasts in his ears, just a peaceful but strenuous hike in nature.
I invited him to tune into what it might feel like to be grounded and centered in his body and to anchor it in a posture that reflects who he really is as a leader. He stood up across the Zoom screen, held his arms wide, and tilted his face to the sky.
We wrapped up there with a commitment that he’d take a hike before our next session.
At our next session, he told me, smiling, “I did the hike. At the top of the mountain I stood tall with my arms out and my head high. There was no one else there but my dogs and for the first time in months, I felt like myself again.”
One hike didn’t fix everything. But it gave him a practice to return to and a center to rebuild from. That was enough to shift his capacity and allow him to start leading with more authenticity and vulnerability.
Coaching Questions to Apply This to Your Business
- What practice once made you feel grounded, creative, or whole, but has quietly slipped away?
- What’s the story you tell yourself about why you don’t do it anymore
- What would change if you reclaimed that practice, even once this week?
When you’re in a downward spiral and questioning what you’re capable of, the tendency is to grind it out. Those are the exact times when it can be even more impactful to take time to return to what restores you
If you give it a try, I’d love for you to write to me and tell me how it goes.
Much love and respect,
