Why talented coaches & creatives stay broke (and how to change that)
Click here for the audio and video version - read by the author herself.
The black ink glided across the page, and I knew instantly - I was in love. That night, I couldn’t sleep, replaying the soft encouragement of my teacher, Grace. She had no idea how much she stayed with me - or how much her story would shape this reflection.
That morning, I attended a beginner calligraphy workshop led by a young woman brimming with talent. She wore a bright yellow top, black pants, and sneakers. Even with her mask on, her smile was contagious. Let’s call her Grace.
The room was alive with creation - brush pens gliding, laughter rippling, and quiet focus thickening the air like incense. I reveled in the smooth glide of ink and the gentle precision of each stroke. Three hours flew by in what felt like a heartbeat.
At the end of the workshop, I approached Grace and asked if she offered an intermediate class. She hesitated, fidgeting slightly.
“Yes... um... just stay tuned...” she mumbled.
“Stay tuned, where?” I wondered.
Grace’s awkwardness lingered in the air, so I kept my questions to myself.
We gathered for a group photo, each of us holding our final artwork. Mine was a small card with a line from a Mary Oliver poem: “One wild and precious life.”
After the photo, Grace said cheerfully:
“You all did so well! After learning the basics, it’s just practice. You can find tons of videos online. No need to spend more money.”
She waved her hand and laughed.
I laughed too, but inside, I couldn’t help thinking: But it’s so much more fun to practice with others. And it’s much easier when someone guides you and helps you avoid mistakes.
When I got home, I set the calligraphy folder on my desk, determined to practice. Days passed. Then weeks. Eventually, I slid it into a drawer - where it still sits, gathering dust like an abandoned dream.
I appreciate Grace’s honesty. She probably believes that herself. But I also know that despite her sizeable Instagram following and six years of calligraphy experience, Grace still needs to hold on to her day job.
Unless she’s truly passionate about that day job (which I highly doubt), she’s unable to make a sustainable living from the thing she loves most.
After the workshop, I couldn’t stop thinking about Grace and her work. What if Grace’s story unfolded differently?
What if, instead of waving us off with free YouTube videos, she owned her role as a teacher and guide? Here’s the story she could be living…
The Story Grace Could Be Living:
Grace holds her workshop with a clear intention: to give attendees an amazing beginner’s experience and invite those who want to go deeper into an intermediate level where they could learn the real art of calligraphy and Grace could earn a fair and abundant income in return.
She knows that not everyone will say yes, but the right people will.
She prices her beginner workshop just enough to cover costs, attracting a full room. She promotes it on Instagram and sells out 20 slots quickly.
But behind the scenes, Grace has laid the groundwork to enroll committed students into the next step. She has clarity on her niche and mission:
“I help professional working women rekindle their creativity and find peace through calligraphy.”
She has created a framework that guides her students from total beginners to confident creators, capable of making calligraphy cards, large-scale artwork, and blending calligraphy with acrylics and watercolor.
Her intermediate course is a 7-week journey. Here’s what it includes:
An exact shopping list for art supplies and where to get them.
A weekly two-hour private class in an inspiring co-working space.
Direct access to her WhatsApp for questions.
A curated video bundle of the best online calligraphy tutorials.
A two-hour crash course on taking pictures of your artwork and sharing them online.
Grace knows the value of this offer and prices it at $700. Students can pay in two installments of $350, or make one full payment of $600 to save $100 and receive a bonus.
The Day of the Workshop:
Grace focuses on connection. Toward the end, she asks each participant to share their biggest takeaway. The room lights up with their reflections.
Grace gently says:
“I love how much you’ve learned in just three hours. I hope you’ll keep practicing and soon create beautiful art for yourself and your loved ones. It takes time to get good at calligraphy - and I made so many mistakes when I first started.”
She pauses, then adds,
“That’s why I created an intermediate calligraphy course for those who want to go deeper. It’s a one-on-one experience where I can guide you through the next steps.”
Grace holds up a few of her creations: intricate cards, framed pieces, colorful collaborations with watercolor.
“If you’re curious,” she continues, “fill out your details on this card. I’ll reach out to share more in the next few days. There are five spots available.”
A third of the room raises their hands, including me.
As I fill out my contact details, I feel excited.
The next day at lunch, my phone buzzes with a new WhatsApp message:
“Hey Milena, thanks for your interest in learning more about calligraphy with me. I’m honored. You have great skills for a beginner. With a little more support, you’ll soon be able to create so many beautiful things. I’d love to schedule a quick call to share more about the intermediate course. Would that be okay?”
“Sure,” I reply, smiling.
On our Zoom call, Grace doesn’t dive straight into details. She asks me thoughtful questions:
“Why do you want to learn calligraphy?”
“What’s holding you back from following your creative calling?”
“What’s your goal with studying calligraphy? What kind of artwork do you want to create?”
“How would feeling creatively fulfilled affect other areas of your life?”
As I answer, I discover insights I didn’t know I had. I feel deeply connected to her.
Grace listens carefully and says:
“Thanks for opening up, Milena. I loved when you said that art feeds your soul. I believe this course will make a difference in your creative journey. Would you like to hear more about it?”
Of course, I do.
Grace walks me through the course. Her framework is crystal clear, each step guiding me closer to mastery. The bonus crash course on sharing artwork online feels like icing on the cake.
I say a big YES - and opt for the full payment option.
I’m so excited to gift this to myself.
When I get home, I pull out the calligraphy folder. Motivated by the journey ahead, I open my notebook and write with my brush pen: “Let the soft animal of your body love what it loves.” - another Mary Oliver verse I adore.
I snap a photo and send it to Grace.
Her reply comes quickly:
“Wow! Well done for practicing!”
I smile, already thinking about the artwork I’ll create for my best friend's birthday.
Meanwhile, Grace celebrates enrolling another student. The more students she enrolls, the more confident she feels - the more faith she has in her path as an artist, teacher, and entrepreneur.
Within a few months, as she continues to enroll students and generate reliable income, Grace can quit her day job and devote herself fully to the work she loves.
If you’re a coach, you might see yourself in Grace. You have a gift - one that could transform lives. But are you inviting people deeper into your world, or are you unintentionally sending them away with a 'just watch free videos' mindset? Let’s change that.
Know your niche: Fill in the blanks: “I help ____ to do ____, so they can ____.” If you’re struggling, there’s work to be done to define your niche.
Know your framework: Transformation takes time. What’s your clear roadmap to guide clients through their desired transformation?
Create an in-depth offer: How long will it take to walk clients through your framework? This is the length of your coaching program. (For new coaches, I recommend a 12-week program.) What support elements can you include that complement the coaching sessions and give the extra value you know the clients want? (Think of 5 support elements that are not coaching sessions. Example: meditation tracks, direct access to your Whatsapp, etc.) How much is the investment? (Because coaching tends to solve more complex problems, you can genuinely price your first program from $1,000. The first coaching program I launched 6 years ago was $2,000. If you want to hyperventilate and feel extreme resistance towards this, you probably need to work through some major money blocks.) What are the payment options? Refund policy?
Decide on a launch strategy: Pick what feels easiest - online masterclasses, DMs, or posts. Remember you don’t need a website, a mailing list, an ads budget, or a big audience to enroll your first batch of highly committed clients. Your current connections and network are enough.
Enroll clients: Offering free Discovery Sessions - Clarity Calls, Strategy Calls, Breakthrough Sessions, however you want to name it - is a great way to let people explore your coaching with no strings attached. Discovery Sessions - when done right - give you and the potential client a beautiful opportunity to gain clarity on whether or not working together is for the highest good of everyone involved.
Bonus Tip: One of the biggest mistakes new coaches make is exhausting themselves on the social media treadmill. Stop wasting your time posting a reel a day without knowing who you’re talking to, what you’re offering, and how you can serve them.
That is the fastest path to burnout. Your social media efforts need to align with your enrollment strategy. Otherwise, it’s all wasted time.
For example: If you’re clear that your enrollment strategy is doing events, you can map out a social media calendar to promote your events. So you can convert the audience to workshop attendees and ultimately to highly committed clients who are willing to invest in their growth with you.
Finally, picture this: You, at your desk, heart full, guiding clients who light up with breakthroughs. Your inbox, not filled with uncertainty, but with messages from people eager to work with you. Your gifts - no longer a side note, but a thriving, breathing reality. Your story deserves this unfolding.
There’s an old Japanese proverb: “Brush your ink with the weight of your heart.” Like calligraphy, building a coaching business requires every stroke - every decision - to carry clear intention. Half-hearted strokes create shaky lines. Hesitation leaves gaps. But when you commit - when you pour your whole heart into the movement - your work flows with strength, inspiration and undeniable beauty.
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PS: FAST-TRACK YOUR COACHING BUSINESS TODAY!
Here's a secret most new coaches don't know about building a sustainable coaching business: the key is knowing exactly who you’re serving.
Having absolute clarity on your ideal client allows you to approach them, communicate your message effectively, and enroll the right clients for your business - confidently and effortlessly.
That's why I created Unlocking Your Coaching Genius - a course that guides you through my proven, step-by-step process to locate your unique genius as a coach, define your soul-aligned and profitable coaching niche, and make your communication a magnet to the clients you were born to serve.
SHARING = LOVING
The freedom you want is possible!
Hey, fellow purpose-drive human!
I’m Milena. When I was 24, I said no to corporate job offers to “do my own thing.”
9 years, some major fumbles, 3 TEDx Talks, 1 published book, 50,000 followers, and hundreds of clients (from 15+ countries) later…
I make a multi-six-figure living as a coach while spending most of my time walking barefoot in my apartment. #introvertgoal
I know you want to make a difference.
I’m here to help you turn that calling into a financially sustainable coaching business — while staying away from the hustle, and skipping the pitfalls that trip up most new coaches.
Quit your 9-to-5. Move to a paradise island. Slow yoga every morning. Work from sunlit cafes. Make time for loved ones (including yourself). Grow your influence. Wake up excited about your day. And serve only the clients who light you up…
All of that (and more!) is possible, once you have the right support.
Let me help you shine.