If you’ve ever looked around and thought, “Is this really it?
Is this what the rest of my life is going to look like?”—you’re not alone.
I’ve been there. And so has Heather Stewart.
Recently on the podcast, I had the chance to sit down with Heather, a former corporate finance exec turned coach, wellness entrepreneur, and creator of “Coach in Your Pocket.” What unfolded wasn’t just a conversation about building a coaching business—it was a deeply human journey through burnout, reinvention, and learning to serve people in a way that truly matters.
Here’s what stood out.
From Corporate Success to Soulful Pivot
Heather didn’t just “start coaching.” She left a high-ranking position in corporate finance 20 years ago—a job everyone else would have called successful. On paper, she had it all. But inside, she was asking the same question many of us wrestle with: “Is this what I want to do every day for the rest of my life?”
Her first leap? Yoga.
She opened a yoga studio, became a personal trainer, a massage therapist, and, unknowingly, started coaching before she even had the title. Her clients came for the physical healing—but they stayed for the perspective and support. That’s when she realized: there’s something deeper going on here. And she leaned into it.
Reinvention Is a Process, Not a Jump
What I appreciated most about Heather’s story was her honesty: change wasn’t instant.
It took months—maybe even a year—to make the move. She didn’t have a coach. She didn’t have a roadmap. What she had was the awareness that staying was costing her more than leaving.
To give herself space and clarity, she traveled to India for three months. And from that experience, she didn’t just come back rested—she came back aligned. Ready to serve. Ready to start again on her own terms.
The Realities of Starting a Coaching Business
Here’s where things get real.
Even with her business background, Heather found herself surprised by how hard it was to market a business—not just run one.
She joked about thinking she’d hang one sign and clients would roll in. (Spoiler: they didn’t.) She realized that knowing business doesn’t automatically mean you know how to get clients.
This is something I see all the time with new coaches—they spend hours choosing brand colors, tweaking websites, and waiting for confidence to magically appear. Heather calls this “procrast-branding.”
And she’s right: you’re not a coach until you have clients.
Start Before You’re Ready (But Get Smart About It)
Heather’s advice? Start by coaching people in your circle. Offer sessions in exchange for honest testimonials. Practice. Get feedback. And don’t just collect “Heather is great!” fluff—ask for structured testimonials that show transformation.
And when it comes to pricing? Stop undercharging. If you don’t see your own value, neither will anyone else.
Yes, it’s vulnerable to ask for money. But if you’re pouring your energy into helping people change their lives, it’s worth more than a $20 coffee date.
The Power of Niching Down
One of the most powerful moments in our chat was when Heather explained how she found her niche: she coaches the former version of herself.
Overwhelmed, high-achieving women who are quietly falling apart under the weight of too many expectations. That used to be her. She gets it. And her clients feel that. They trust it.
She’s not excluding people—she still works with men, business owners, artists but her message is clear, and clarity builds credibility. It’s not about who you leave out. It’s about who hears you.
A Fresh Approach: “Coach in Your Pocket”
One thing I loved was Heather’s creative approach to client support. She realized her audience—busy, ambitious people—didn’t always want to wait a week for a Zoom call. They needed immediate support, quick check-ins, and flexible communication.
Enter: Coach in Your Pocket.
It’s coaching via WhatsApp: text, voice notes, even short videos. A lightweight, accessible, low-friction way to stay on track and get unstuck. And it’s proof that coaching doesn’t have to look one way. You get to meet your clients where they are.
The Bottom Line
Heather’s story is a masterclass in intentional reinvention. She didn’t leap without a plan. She didn’t wait for perfect clarity. She made space, took small steps, and learned to let service lead.
Whether you’re just starting out or rebuilding something that no longer fits, her journey is a reminder that you don’t need to do everything. You just need to do what matters most.
Want to take the first step?
Head over to HeatherStewart.coach and check out her community or book a free curiosity call.
And if this conversation lit a fire in you—don’t let it fade. Pick one small action and take it today.