My 5 messiest coaching mistakes | ep212
When I first started coaching almost 10 years ago, I had no idea what I was doing. I made so many mistakes, questioned myself constantly, and let fear dictate way too many of my decisions. But here's the thing: those mistakes became some of the greatest lessons in my career. They shaped who I am as a coach and as a person.
Today, I want to get honest and vulnerable with you about my journey—the messy, imperfect path I took to create Wholehearted Coaching. My hope is that by sharing my five biggest coaching mistakes, you can learn from them, avoid them (if possible), and maybe even feel inspired to embrace the beauty of making mistakes in your own journey.
Before we dive in, just a quick reminder that applications for the Wholehearted Life Coaching Certification close December 15th
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Mistake #1: Letting Fear Dictate My Decisions
When I first discovered coaching, I almost talked myself out of it. Multiple times. I delayed signing up for my certification, launching my business, and putting myself out there because I thought I wasn’t ready. I thought I had to be perfect from the start—fully polished, experienced, and prepared for every single challenge.
Lesson Reframe
You don’t have to be perfect to start. You don’t even have to feel ready. Growth happens when you take the leap and build as you go. The truth is, none of us are "ready" when we begin. We figure it out along the way. Start where you are, with what you have, and trust that you’ll learn what you need to as you go.
Mistake #2: Trying to Be Everything to Everyone
In the beginning, I thought I had to appeal to everyone. My social media posts were generic and "coachy," full of feel-good platitudes that didn’t really reflect my heart or values. At the same time, I was obsessed with finding my niche—who exactly I should be working with and how I could define myself in the most specific terms possible. It was exhausting and confusing.
Lesson Reframe
Clarity comes from being true to yourself. When I started sharing posts that aligned with my values and beliefs—even when they felt scary—I found my people. The clearer I became about who I was and what I stood for, the more aligned my community became. You don’t have to figure it all out right away. Just start with what feels true to you and let that guide the way.
Mistake #3: Undercharging and Overworking
I struggled with pricing when I started out. I charged way too little because I thought I wasn’t experienced enough, I worried about my worth, and I wanted my work to be accessible to everyone. The result? I ended up resenting my work and burning myself out.
Lesson Reframe
Your pricing reflects your worth, your experience, and the value you bring to the table. It’s not just about the hours you spent getting certified—it’s about your life experience, your unique perspective, and everything you’ve poured into your craft. Charging what you’re worth allows you to show up fully for your clients and create a sustainable business. Remember, accessibility doesn’t mean undervaluing yourself; it’s about finding balance in your offerings.
Mistake #4: Having Zero Boundaries
When I started coaching, I thought I had to be available 24/7 to succeed. I worked weekends, let sessions run over, and answered emails at all hours. I told myself I’d set boundaries "later," once I was more established. Spoiler alert: "later" never came.
Lesson Reframe
How you start your business is how you’ll continue it. Set boundaries early. Honor your time, your energy, and your well-being from the start. Boundaries don’t just protect you; they protect the love and passion you have for your work. You deserve to rest and enjoy your life as you build your dream.
Mistake #5: Waiting for Perfect
In everything I did, I aimed for perfection—whether it was creating social media content, launching my podcast, or building my coaching practice. I thought my work had to be flawless before I could share it. That mindset kept me stuck, delaying my progress and robbing me of the chance to learn and grow.
Lesson Reframe
Forget perfect. Aim for what I call "B+ work"—work that you’re proud of, but that doesn’t hold you back in the pursuit of some mythical idea of perfection. B+ work gets you out there, connects you with people, and lets you refine your craft over time. The key is to just start and trust that growth comes from action, not endless preparation.
Final Thoughts: Embrace the Mess
Every mistake I’ve made has taught me something invaluable. They’ve shaped the coach I am today and the business I’ve built. Mistakes are part of the process—they’re signs that you’re trying, growing, and moving toward your dream.
If becoming a coach is your dream, I hope my messy journey inspires you to take the next step. Mistakes will happen. Perfection is impossible. But the life and career you’re building are so worth it.
Applications for the Wholehearted Coaching Certification are open until December 15. If you’re ready to embrace your purpose and start building your dream, I’d love for you to join us. Head to wholeheartedcertification.com to learn more.
Here’s to messy beginnings and beautiful growth.
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About your host, Shirin Eskandani
Hi, love! I’m Shirin.
Coach, speaker, writer, and life alchemist.
I teach you how to listen to your intuition again, tune out all the BS, and let your heart lead the way.
Because once you strengthen your inner GPS, decisions become easier, boundaries become clearer, and belly laughs become a daily thing.
A LITTLE BIT ABOUT ME:
I’m a certified life coach (accredited through the International Coach Federation)
My husband and I met on Instagram and we live in Brooklyn, NY with our plant babies
I have a masters degree in Music and was a professional opera singer for twelve years. I worked all over the world singing on stage at Carnegie Hall and the Metropolitan Opera (more on that later…).
I believe in the woo just as much as I do the work (internal and external). No amount of crystals and affirmations will make up for a lack of a healthy mindset and aligned action.
I love all the Real Housewives franchises. Don’t make me choose one… seriously, don’t.