6 podcast covers later… how messy, imperfect action built my six figure coaching business
the case for starting before you've figured it out
“if you’re not embarrassed by your first draft, you started too late.”
- Reid Hoffman
I shared that quote it in the very first episode of my podcast because hearing those words, helped me to finally press publish.
It was July of 2021. I was my apartment in Florianopolis, Brazil trying to record the first episode. Starting and scrapping and starting again, watching myself spiral into compulsive perfectionism and thinking: this is exactly what I tell my clients NOT to do.
I had just niched into healthcare professionals. I still wasn’t sure any of this was going to work.
Five years and six podcast covers later — here we are.
and before we get into it, if you want to build a coaching business that replaces your clinical income… the $100K Healer is your new home.
I want this post to be your permission slip. To start before you’re ready. To show up imperfectly. To let yourself be seen while figuring it out.
Because… frankly, there’s just no other choice. If you keep waiting until you have it all figured out. You will quite literally never begin.
I didn’t wait until I figured it out to start building my business. I built it by showing up as the messy, in-progress, version of myself. publicly, repeatedly, and long before I felt ready.
Recently I was updating my podcast cover art and I realized… the journey of my business can be told through the evolution of my podcast covers.
Every single cover tells a story and marks a pivotal moment in the journey.
and I want take you bts. to show you what it looks like to build a business while you're figuring things out.
what it looks to build a business while you’re finding yourself (and sometimes losing yourself)
so you can realize… its not only safe to start before you're ready, but it's the only way you can actually make an impact.
girl shares her heart online (2021)
life after medicine v1.
my first instinct is to cringe at the horrific design, but i’ll save my canva critique for another day.
because the truth is: I am SO proud of this little baby chelsea.
she was scared. she was not making much money yet. she had no clue if this podcast thing was going to work. but she felt this pull to buy a mic from a random electronics shop in brazil, and start sharing her heart online.
for months i had felt this nagging pull to start a podcast. when I sat down to give it a proper brainstorm the idea for “life after medicine” dropped it like a vision. I immediately knew this was bigger than me.
even though I had doubts and insecurities, when I get a pull like that… I listen.
its like the Audre Lorde quote says:
“when I dare to be powerful, to use my strength in the service of my vision, then it becomes less and less important whether I am afraid.”
girl hits six figures (2022)
ok… can you already see the massive shift’
the letters are bolder. the font is bigger. the colors are brighter. i’m taking up more space. both on the cover and in my business as a whole.
this is the era where i first hit my stride. my confidence was growing. my income was growing. it was all finally working. you can see it in the photo too. i’m smiling in my full Enneagram 7 exuberance. pure joy.
this is when my business hit six figures (2022)…. and then it hit six figures again (2023)
so yes, I was feeling more confident and successful, but also behind the scenes, i was starting to get scared.
I took two weeks off to go on Nomad Cruise, had my lowest sales month, and panicked.
I took 2 weeks off my business at the end of 2023 to go on nomad cruise, and had my lowest sales month in almost 2 years.
I started to feel a bit freaked out. Like the success was built on shaky ground and could all disappear at any moment. Which was kind of true.
my business had no real systems for reliably generating income. it was running because I was running it, and the moment I stepped away, revenue dried up.
I def had some work to do to stabilize my business. So thats what brought me into my next era..
girl loses herself to copy-paste bro marketing strategies (2024)
this is the only cover without me in it…. which is a perfect metaphor for what was happening inside my business at that point.
At the start of 2024, I went into what I can only describe as med student controlling mode.
I started outsourcing the strategy. Following other people’s playbooks. I wanted someone else to give me the exact play by play.
And somewhere in that process, I stopped trusting myself entirely. It happened slowly overtime. Little by little, I stopped looking inward. I looked everywhere else for the answers.
The result? A podcast cover with a stock photo of a doctor on it.
I learned a lot in that phase, and at the end of the day I’m grateful for it. Because it grew my discernment. Now I’m much more skilled at learning from someone else’s strategy, but putting it through the filter of my own intuition.
girl says YES to jumping into limbo (2025)
the good news is, I eventually found myself again. which then led me to what felt like the most chaotic, messiest, rebrand of all times.
June of 2025 I hosted a virtual summit called Pivot Potentials: a career reimagining summit.
and it ended up sparking a “brand reimagining”. By the end of June I was feeling a big shift coming on.
In July I hosted “July Re-align” where I wrote to my intuition every single day for 31 days.
Somewhere during that time, the vision for spiritually ambitious entrepreneur started to form.
It wasn’t fully fleshed out. I didn’t fully know what I wtf i was doing, but I knew I was moving in the right direction. Mainly because…. I wasn’t following someone else’s playbook anymore. I was trusting myself again.
i didn’t really know it at the time, but this cover was really me saying YES to being in limbo for a while. I said goodbye to Life After Medicine, and started The Spiritually Ambitious Entrepreneur podcast.
… which spoiler alert didn’t last too long.
girl says YES to leadership (also 2025)
I had literally just rebranded to the Spiritually Ambitious Entrepreneur months before, which was a big deal for me. Changing the name of the podcast felt SO permanent.
But after just a few months, I started to feel this pull towards a new name. The $100K healer. It started off as a free training I did. Then I rebranded the paid tier of my substack to that name. Every time I shared the name with someone there was an “oooh” reaction.
The $100K healer felt clearer, more specific, more activating, and really just more aligned with where I wanted my business to go.
But, you’re not supposed to change your podcast name 2x in one year. That’s insane.
I put a message in my client Telegram and floated the idea: what do you think of spiritually ambitious entrepreneur vs $100k healer.
Unanimously, they said: “We prefer Spiritually Ambitious.”
But as I read through their responses I knew… I have to change it to the 100K Healer.
Partially because…. the reasons they preferred “spiritually ambitious entrepreneur” were rooted in money mindset issues. Which was exactly the work I wanted to lead them through.
But also because hearing their definitive responses, created a definitive response within me. It suddenly felt clear: if I don’t change it, I’m actively holding myself back.
Listening to the market is obviously important, it’s something I teach and fully believe in. But you don’t listen so that you can react to the market. You listen so you can LEAD the market.
I wasn’t going to name my podcast from other people’s limitations, I was going to name it from my vision.
I wanted to change the name of the podcast immediately…so I whipped together a “good enough” cover while sitting in a café in Namibia. But I always knew it was just a placeholder.
girl has quantum leaped from the inside out (2026)
when I look at this cover I just feel…. LFG energy. I’m looking straight at the camera like “come at me breh”
And the coolest part is…. this version of me only exists because I was willing to show up as every version before her.
The baby entrepreneur in the jean jacket. The copy-paste girl who lost herself trying to scale. The dancing sparkly rebrand that didn’t have it all figured out but committed anyway. The good-enough placeholder made in a café in Namibia.
If I had waited until I was ready…. none of this would exist.
what i’ve been releasing to get here
There’s a Hafiz poem that has been guiding my inner work over the past year:
“The wind and I could come by and carry
you the last part of your journey
if you become light enough,
by just letting go of a few more things
you are clinging to
that still believe in gravity.”
The phrase “things that still believe in gravity” keeps playing in my head over and over again. Like a refrain.
Its become my inquiry.
What within me still believes in gravity?
What am I clinging to that’s weighing me down?
And little by little
I let it go.
Everything that feels heavy.
Every part of me that believes in limitation, in lack, in not good enough.
Every pattern that holds me down.
Every story that keeps me from taking flight.
That’s what you’re seeing in this new cover.
That’s what’s shaping this new era.
Its the defying gravity era.
Where the only thing I’m interested in, is experiencing my infinite potential. And holding the vision for YOU to experience yours as well.
And none of this came from waiting until I had it all figured out. It came from showing up messy, again and again, and letting each version of me exist long enough to become the next one.
the oak tree and the acorn
There’s a Zen Buddhist concept I first heard in Eat Pray Love that I keep coming back to:
“The Zen Buddhists say that an oak tree is brought into creation by two forces at the same time. Obviously, there is the acorn from which it all begins, the seed which holds all the promise and potential, which grows into the tree. Everybody can see that.
But only a few can recognize that there is another force operating here as well — the future tree itself, which wants so badly to exist that it pulls the acorn into being, drawing the seedling forth with longing out of the void, guiding the evolution from nothingness to maturity. In this respect, say the Zens, it is the oak tree that creates the very acorn from which it was born.”
Many of us feel that longing from our future oak tree. The version of us that wants SO badly to exist.
We feel the pull to launch the offer, start the podcast, show up more consistently. The pull to go ALL in on our business, and finally quit our day job.
But we ignore the pull because we’re not “ready”. Because we haven’t figured out exactly what it means yet.
But when you refuse to show up until you’re ready, your acorn never has the chance to grow into the oak tree.
The only reason my current oak tree self exists is because I let my acorn be messy af (idk if this analogy is holding up, but just go with it)
I followed the pull of my oak tree.
I showed up before I was ready
I let myself be seen as a work in progress.
So here’s the reflection I’ll leave you with:
What is your future oak tree self pulling you towards right now?
What could be possible be if you stopped trying to figure it all out first?
if you gave yourself permission to honor the pull of your oak tree?
if you showed up messy and let yourself be a work in progress all along the way?
if you let yourself be seen — messy, evolving, figuring it out as you go?
I pinky promise you.
Doing it messy. Doing it imperfect. Doing it scared.
is infinitely better than never doing it at all.
if you are reading this and you know your oak tree is pulling you to take your coaching business full-time, I’m opening up some 1:1 coaching spaces to support you. send me a message at hello@coachchelseamd.com or find me on instagram @coachchelseamd.
oh and stay tuned… next week the inner circle (substack paid tier) becomes the $100k catalyst. a weekly audio drop for clinicians building a coaching business to turn overwhelm into focused action that moves the needle.