
200: Seasons of Entrepreneurship: Growth, Contraction, and the Truth About Business
For our 200th episode of Money Skills for Therapists, I invited my business besties, Tiffany McLain and Maegan Megginson, to join me for a conversation that was more honest than polished. Together, we unpacked the real seasons of entrepreneurship — the times when you feel energized, expanding, and deeply aligned… and the times when you feel tired, restless, like you’re questioning everything, or quietly pulling back. If you’ve ever wondered whether it’s normal to feel both love and resentment toward your business at different points, this conversation is for you.
Navigating the Seasons of Business
Running a therapy-focused business isn’t a constant upward climb. It has seasons of expansion, contraction, clarity, confusion. In this conversation, we let ourselves name that truth.
We talked about what it feels like when you’re all in — launching, creating, hiring, dreaming bigger. And we also opened up about the quieter seasons: reducing your client load, winding down programs, letting team members go, or wondering if you even want to keep doing this work in the same way.
There’s so much pressure in entrepreneurship to always be scaling. But sometimes wisdom looks like pulling back. Sometimes contraction isn’t failure — it’s integration.
At the same time, building work you genuinely enjoy doesn’t happen by accident. It requires noticing your energy, building systems that support you instead of draining you, and being honest about what you’re doing because you want to rather than because you think you “should.”
We also talked about money — because underneath many expansion or contraction decisions is a financial story. Cultural conditioning around money. Fear of losing relevance. Fantasies about quitting. Fantasies about scaling. And how helpful it is to have friends who understand the nuance of all of it.
Listening to Your Season Instead of Forcing Growth
Entrepreneurship isn’t just strategy — it’s discernment. It’s noticing whether you’re in a building season or a gathering season. Whether something needs to grow… or gently end.
00:04:02 Life and Business Have Seasons
00:12:52 Shifting Beliefs in Business
00:14:25 Creative Business as Living Practice
00:24:06 Embracing Healthy Contraction
00:25:14 Winding Down with Care
00:32:46 Embracing Flexibility and Growth
00:38:21 Slow Down, Take a Breath
00:39:15 Discernment Before Building Something New
00:44:36 Value of Business Besties
00:46:02 Mastering Money for Therapists
Letting Your Business Evolve with You
One thing we kept circling back to is this: your business is allowed to change as you change.
There are seasons where you build aggressively, seasons where you stabilize, seasons where you question everything, and seasons where you rediscover joy.
You don’t have to cling to an old identity just because it once worked. You don’t have to keep scaling just because you can. And you don’t have to quit just because you’re tired.
Sometimes the most mature move is slowing down long enough to ask, “What season am I actually in?”
Ready to Improve your Business Money Skills?
Are you a Solo Private Practice Owner?
I made this course just for you: Money Skills for Therapists. My signature course has been carefully designed to take therapists from money confusion, shame, and uncertainty – to calm and confidence. In this course I give you everything you need to create financial peace of mind as a therapist in solo private practice.
Want to learn more? Click here to register for my free masterclass, “The 4 Step Framework to Get Your Business Finances Totally in Order.”
This masterclass is your way to get a feel for my approach, learn exactly what I teach inside Money Skills for Therapists, and get your invite to join us in the course.
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About Tiffany McLain:
Tiffany McLain, LMFT is a clinical fee strategist for therapists in private practice. Her mantra is, “Full fees are the new black.” Via her program, The Lean In. MAKE BANK. Academy, she helps therapists ethically earn significantly more per month while seeing fewer clients and doing BETTER clinical work.
The Lean In. MAKE BANK. Academy is a program that addresses the underlying money mindset stories that keep therapists broke so they can become THAT therapist who charges premium fees, cash pay. With the LIMB 4-step framework to make BANK, regular coaching calls to help you go to the next level, a phenomenal community of funny and intelligent therapists, be ready to get real raw and real rich.
Connect with Tiffany McLain:
Website: https://leaninmakebank.com/
Email: [email protected]
Instagram: https://www.instagram.com/leaninmakebank/
Facebook: https://www.facebook.com/leaninmakebank/
LinkedIn: https://www.linkedin.com/in/tiffanymclain/
About Maegan Megginson:
Maegan Megginson is a spiritual advisor and sabbatical coach who supports leaders and small business owners at pivotal crossroads in life and work. As a former psychotherapist and founder of a seven-figure mental health agency, her approach blends therapeutic insight, grounded spiritual guidance, and practical business wisdom to help people recover from burnout, reconnect with their intuition, and clarify what’s next for their work. She believes tending to your inner world isn’t a detour from success—it’s the foundation for sustainable growth and meaningful impact.
Connect with Maegan Megginson:
Website: https://deeplyrested.com
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/maegan-megginson/
Mentioned in this episode:
Start Feeling Calm and Confident About Your Group Practice Finances
Feeling overworked and underpaid in your group practice? You’re not alone. Running a group practice can feel like carrying the weight of everyone’s paychecks — including your own — and wondering if it’s all really worth it. That’s why I created a free guide called “How to Stop Feeling Overworked and Underpaid in Your Group Practice.” Inside, I’ll walk you through the four keys to becoming the confident financial leader your practice needs — so you can start feeling calm and in control of your money again. This guide is the first step toward the same kind of financial clarity and confidence I teach inside my deeper program, Money Skills for Group Practice Owners. 🙌 Download your free copy today — and let’s start building a group practice that supports you, not just everyone else.
Get the Free Guide: How to Stop Feeling Overworked & Underpaid in Your Group Practice
Want to work with Linzy?
Check out the FREE masterclass, The 4 Step Framework to Getting Your Business Finances Totally in Order, where you'll learn the framework that has helped hundreds of therapists go from money confusion and shame to calm and confidence, as well as the three biggest financial mistakes that therapists make. At the end, you'll be invited to join Money Skills for Therapists and get Linzy's support in getting your finances finally working for you. Click on the link to find a masterclass time that works for you!
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