3 Pivotal Times to Invest in Your Coaching Business (And Why They Matter)
How do you know when it’s time to invest in your coaching business—and when it’s smarter to hold off?
In this week’s episode of The Coaching Edge, I’m breaking down three pivotal turning points in every coach’s business where the right kind of support can make all the difference.
Here’s what you’ll learn:
- Why investing before your official launch can help you avoid wasted time and money.
- How to recognize the “crisis of confidence” stage—and why outside support can stop you from quitting too soon.
- What to do when you’re 3–5 years in, working hard, but still feeling capped and hustling for every client.
- My own stories of investing at each of these points (from pricey 1:1 coaching to masterminds to skill-specific programs).
- How to think about investment without pressure, and why the timing matters just as much as the investment itself.
This is part one of a two-part mini-series. Next week, I’ll dive into how to actually evaluate if a coaching investment is worth it—so you can ...
Author & Host
Wendy McCallum
Business Coach for Coaches, Burnout & Alcohol Coach for High Achievers
I’m Wendy McCallum — a coach, mentor, and former lawyer who’s spent the last 15 years helping people build lives and businesses they actually want to wake up to. When I first left law, I had no guidebook for how to do this coaching thing. I floundered — hard. I undercharged, overthought, and overinvested in shiny solutions that didn’t really move the needle. But every mistake taught me something, and eventually, I built the kind of coaching practice I once only dreamed about — one that’s profitable, sustainable, and full of work I truly love. Today, I coach two kinds of people: ✨ Busy professionals who are ready to make big, meaningful changes — whether that's finding balance, recovering from burnout, or rethinking their relationship with alcohol. ✨ And newer coaches who are building their businesses from the ground up and want a clear, sustainable path forward without all the gimmicks and noise. Whether I’m helping someone simplify their business or reclaim their personal life, the heart of my work is the same: giving smart, capable people the clarity, encouragement, and real-world tools they need to move forward — in a way that feels good, not overwhelming. If you’re ready for something better — in your work, your life, or your business — you’re in the right place. And I’m so glad you’re here. IMPORTANT: Blog content including Wendy's podcasts are for information purposes only and not intended in any way to be health advice. Please see full Terms of Use, by clicking on the link in the footer of this page, for details.
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