Mistakes: Lessons Learned in the Coaching Profession

Twenty years into full-time coaching, I’ve made more than my share of mistakes. None of them ended me — but some came close to burning me out, blurring my vision, or draining the meaning from the work I love.

If you’re early in your coaching journey — or looking to recalibrate after a few years in — I hope these lessons offer you insight, clarity, or even a little relief.

Here are five of my most valuable mistakes — and what I’d do differently now.

1. Neglecting the Business Side of Coaching

Serving clients with heart is essential — but it’s not enough. If you don’t build a business that supports your mission, your mission won’t last.

I learned this the hard way.

Early on, I said yes to every opportunity. Ran a gym. Taught workshops. Took every client that came my way. Added in blogging, YouTube, books, podcasts, even mentoring other coaches — all at once.

Result: constantly busy, barely sustainable. A full heart with an empty bank account.

Eventually I got selective. I started saying No. Not to service, but to chaos. I studied business, not just coaching technique. And I built a model that could support both my clients and my life.

Takeaway:

Don’t mistake passion for a business plan. Serve fully — but build wisely. You can’t coach well from a place of constant financial stress.

2. Pricing from the Bottom Up

Most early-stage coaches price based on time: hourly rates, per-session fees, short-term packages.

I did too. I also gave generous discounts, undercharged for keynotes, and often worked extra hours unpaid — just to “prove my value.”

That model eventually broke me. Not because I didn’t love the work — but because I couldn’t sustain it.

What changed? I stopped pricing based on time and started pricing based on value. Outcomes. Transformation. Impact. I offered longer-term engagements, stopped quoting hourly, and began charging what the work was worth.

And the kicker? My clients got better results — because we both had more skin in the game.

Takeaway:

Don’t price your coaching like a commodity. If your work creates deep value, your pricing should reflect that. Think top-down — not time-up.

3. Losing Myself in Someone Else’s Vision

It’s easy to get pulled into a mentor’s orbit — especially when you’re hungry to learn. I joined projects, volunteered, and got deeply involved with mentors I respected. Sometimes that was transformational. Other times, I overstayed.

I let loyalty override clarity. I put their mission above my own. I helped build someone else’s vision while mine gathered dust.

There are mentors who lift you up — and mentors who absorb you. I’ve learned to tell the difference.

Today, I seek out “king-makers” — mentors who want to see their people thrive independently, not just in service to their empire.

Takeaway:

Learn from great mentors — but don’t lose your own thread. The best mentors help you grow your own tree, not just water theirs.

4. Waiting Too Long to Invest in Coaching

For years, I poured money into certifications, courses, and tools — but I didn’t invest in business coaching or specialized mentoring. I figured I could figure it out on my own.

I couldn’t.

I spent thousands on ads with no strategy. I launched a podcast with no business model. I published a book with no plan to amplify it. All the passion was there — but no structure.

When I finally hired a coach, I got back everything I spent — and more. Not just in revenue, but in clarity, focus, and time.

While I waited too long to invest in strategic coaching, I did receive valuable free support over the years from an amazing group of friends and mentors. I recommend building both kinds of support into your ecosystem.

Takeaway:

If you’re building a business, don’t just buy tools — invest in people who’ve already solved what you’re struggling with.

5. Thinking I Was Too Late

This one’s sneaky.

I skipped a meeting on the “World Wide Web” in the 90s because I thought I’d already missed the moment. Later, I held back on YouTube. Podcasting. Course creation. Always telling myself it was too late.

I was wrong every time.

There’s always room for a voice that’s clear, useful, and real. And if you bring consistency and value, you’ll earn your place.

I now remind myself: The best time to start was probably five years ago. The second-best time? Today.

Takeaway:

You’re not too late. You’re just one clear step away from forward motion. Stop comparing. Start creating.

Mistakes Become Lessons — If You Let Them

I don’t regret these mistakes. I learned from each. They shaped how I coach, how I run my business, and how I support other coaches now.

If you’re in this profession, my hope is that these lessons help you shorten your learning curve — and extend your career.

And if you’re building something that matters, I hope you’ll keep going. Keep refining. Keep showing up.

Because we need more great coaches. And the world is better when they last.

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