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She painted 100 watercolors during the pandemic. Then she burst into tears when someone told her what they were worth.
ashley jablow · life design school
Ashley Jablow
Life Design School
A facilitator, coach, and accidental entrepreneur who spent years asking who she was becoming and finally turned that question into four beautiful journals.
Ashley Jablow never planned to run her own business. She grew up in a family of women entrepreneurs – her mother’s retail business has been running for 45 years, her grandmother’s antique store before that – and somehow none of it sounded exciting when she was young. She moved through nonprofit work, open innovation, corporate consulting, and government consulting. Then she got laid off, started freelancing, and a few years later looked up and realized her body had started a business before her brain did.
She does not go anywhere without a flip chart. She loves a two-by-two. She has spent her career helping people think visually, move through transition, and design lives that actually fit them. During the pandemic, when her in-person facilitation business disappeared overnight, she picked up a paintbrush and started making something. 100 watercolor postcards – life design frameworks, quotes, concepts – that she never quite knew what to do with. Until someone told her exactly what they were.
Stop sitting on a body of work she had no framework for. Trust the thing that made her different from every other coach. Find the format, get out of perfectionism's way, and build in public - messy, brave, and one pre-order at a time.
A hundred pieces of original work — and no idea what to do with it.
Ashley had something genuinely rare: 100 original watercolor illustrations of life design concepts, created over two years, each one paired with the writing and thinking from her coaching practice. She had something no other coach had. And she couldn’t see it.
01
The Pandemic Wiped Out Everything
Ashley’s business in early 2020 was built almost entirely on in-person facilitation – traveling to client sites to teach and train. In one fell swoop, in March of that year, it was gone. She didn’t rebuild immediately. She picked up watercolor brushes and started making 3×5 postcards of life design frameworks, quotes, and concepts from her coaching practice. She wasn’t sure why. She just knew she needed to make something. It took two years to finish all 100.
02
A Differentiator She Couldn’t Recognize in Herself
When Ashley first connected with the CEO Collective, she was trying to figure out how to get clients into a group coaching program. She brought her Instagram and her content. Racheal looked at the watercolors and saw what Ashley couldn’t: a hundred pieces of original content, completely distinct from every other coach in the industry. Ashley’s response, when Racheal pointed it out, was to burst into tears. She knew it was true. She wasn’t ready to believe it yet.
03
Waiting for Clarity Instead of Creating the Conditions for It
Ashley describes the two years between finishing the watercolors in 2022 and launching the journals in 2024 precisely: waiting for clarity to arrive. She considered planners, card decks, calendars, mugs. She thought about it, sat with it, let it evolve. Her insight from living through it: clarity doesn’t come when you demand it. It comes when you create the conditions for it and sometimes you have to let the idea find you in a wine bar on your birthday before you’re finally ready to move.
“The community and the mentorship were so instrumental in helping me first see that I had something uniquely valuable — and to really practice believing it. Almost metabolizing it.”
Ashley jablow · life design school
What the system – and the courage to build in public – actually built.
Ashley didn’t write a word before telling the world she was writing four journals. She tagged 200 people on LinkedIn, took pre-orders before a single Google Doc existed, and finished all four books in seven months. The CEO Collective gave her the structure, the accountability, and the community proof that she was not making this up.
Phase 01
The Forcing Function: Announce Before You’re Ready
“Once I let people know I was doing this, people started getting excited. They started asking about pre-orders. That was: oh shoot, I’ve got to do this now. People are paying me money for this.”
Phase 02
One Volume at a Time: The Rinse and Repeat Launch
Phase 03
The CEO Structure: Finally Feeling Like She Was Doing It for Real
What it looks like when you finally let yourself do it messy.
I never planned to run my own business. I come from a long line of women who did – my mom has run a retail business for 45 years, my grandmother had an antique store before that – and somehow none of it appealed to me.
Then I got laid off and started freelancing and looked up a few years later and thought: oh. I accidentally started a business. What am I doing with this?
During the pandemic, my entire business disappeared in a week. All of my revenue was in-person facilitation. Instead of rebuilding immediately, I picked up watercolor brushes and started making postcards – life design frameworks, quotes, concepts from my coaching practice. I finished 66 out of 100 before life got in the way. It took me two more years to complete all hundred. And then I had no idea what to do with them.
"Clarity will arrive if you create the conditions for it to come. You can't demand it. You have to wait for it — and sometimes it finds you in a wine bar the day after your birthday."
Racheal looked at those watercolors and told me I had a year of content. I burst into tears. I knew she was right and I was completely freaked out. It took years of the CEO Collective – the retreats, the community, the mentors – to help me move from knowing it to believing it. To metabolize it.
February 24, 2024, in a wine bar in New York with my mom, the journals clicked. I walked out and said: I’m writing these. I announced publicly before I’d written a word. Pre-orders started coming in. I wrote all four journals in seven months. What started as an idea over a glass of wine became four physical books in my hands by October. The lesson: do it messy. The only person who expects perfection from you is you.
WHAT’S DIFFERENT NOW
Ashley’s biggest wins.
Result 01
Idea to 4 Published Journals in 7 Months
Result 02
50 Pre-Orders Before a Word Was Written
Result 03
A Community That Celebrated With Her
Result 04
Real Impact: At Dinner Tables, With Teens, In Marriages
Featured Episode · Promote Yourself to CEO®
From 100 Watercolors to Four Published Journals — Do It Messy
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CEOs Building Unshakeable Businesses.
You already have something. Do it messy.
Whatever is sitting in your drafts folder, your notes app, your Instagram feed that you don’t know what to do with – it’s probably already the differentiator you’ve been looking for. The CEO Collective is where you get the framework, the community, and someone to sit across from you and tell you what you can’t see in yourself. Then it’s up to you to believe it.