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.
I’m sitting in my garden typing this to you this morning. It’s a beautiful day in the Pacific Northwest and I’m enjoying some peaceful moments before another busy week of works kicks off on Monday.
I hope you’ll grab a cup of coffee or tea and find a moment of peace and quiet in your own world to enjoy this week’s newsletter with me.
And of course, I always love hearing from you. Please do hit reply and tell me if this one resonates with you (and why) or share something that you’re challenged by in your business right now.
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
In a recent group coaching session, one client—a creator in the food and lifestyle space—shared something that hit a nerve.
They said their business didn’t feel like it was doing “enough.” Something about it just didn’t feel quite meaningful enough. what she was building doesn’t really matter because… because why?
It came out in phrases like: “It’s just content.” … “It’s just recipes.” …“It’s not really important.” … “It’s not making a real difference in anyone’s life.”
They were laced with judgment that felt foreign to what I know of this entrepreneur. Like there was an external voice weighing in on their worth.
When I asked her to define what “enough” would look like, she paused. She didn’t know.
There was a vague sense of misalignment—like something was off—but she couldn’t name it. That’s when I knew there was more to be discovered.
The Emotional Blocker
As we explored, I asked: “Is there anyone whose business or career you admire? Someone who represents a future you might want for yourself?”
She hesitated. Then said, “Well… hmm no, I don’t think it’s relevant.”
That sounded like another external judgment to me, so I decided to dig in. “Let’s just assume that it doesn’t matter whether anyone else thinks the person is relevant. It only matters that it makes sense with you. Who might it be?”
“I don’t know… I guess someone like Joanna Gaines?”
That name stopped me. As soon as I heard it, everything made so much sense in my mind. And Joanna Gaines was one of the most relevant names I could think of. But why didn’t my client see it that way too?
She explained: Joanna has built a wildly successful business empire out of design, home cooking, and lifestyle content. Things some people dismiss as “soft” or unimportant.
But Joanna has treated them seriously, to the tune of an estimated net worth of $50M. She’s brought intention, style, and serious business sense to categories many people might dismiss.
That’s what my client admired: Someone who took beauty, creativity, and warmth, and scaled it without apology.
And so the real issue came into view… this entrepreneur doesn’t think her work is meaningless. She just hadn’t yet given herself permission to dream even bigger.
The Breakthrough
The truth was this: She didn’t feel like her business was “enough” because she wanted more. We dug in on what “more” might look like.
- Working in person
- With a talented and growing team
- In a beautiful physical space
- On an expanding product line
- Including digital and physical products
- And growing it into her own empire
When she said it out loud, she smiled and let out a big breath. (A large sigh or release of breath is a telling sign that a client has had a big emotional release).
“How does it feel to say it out loud?” I asked.
She sat quietly for a moment and then replied, “I guess I never realized I can just say what I want. Like… wait, I can just build that?”
Yes. You can.
That’s the gift of entrepreneurship. You get to name the business you want. And then you get to build it. No permission needed. No external judgments factor in. What matters is that you see what you want and you build a profitable business around it.
Once we put our finger on it, we knew the discomfort didn’t come from outside judgment. That was just a remnant of something in the past that was ready to be let go.
No, the discomfort came from a gap between her current reality and the future she hadn’t yet named. Once she named it, the shame and judgment fell away.
What replaced it was excitement, clarity, and momentum.
Coaching Questions to Apply This to Your Business
- Where are you telling yourself your work “isn’t enough”—and why?
- What kind of business would feel right-sized for your joy, creativity, and growth? Write down every element.
- What would you build if you weren’t trying to meet anyone else’s expectations? Would you play bigger or smaller if you let go of the perceived judgment of others?
Some people fear maintaining the beautiful business they’ve built because being content will be judged as “not enough.” And some people have a belief that if they grow too much, they’ll be judged just as harshly for “getting too big for their britches.”
If you’re going to be judged no matter what you do, you might as well build the business you really want. That business will be most sustainable in the long run. And joyful. And fun. Because joy and fun do matter.
Much love and respect,
