Why Your Biggest Moves Stay Stuck in Drafts
How to turn high-stakes founder moves into small, asymmetric experiments with guardrails—so you move faster without blowing up the downside.
New here? The Inner Game is a weekly note for founders and startup leaders about the psychology and practice of building.
Every week you’ll get one core idea, one tiny experiment, or one founder insight you can apply now.
Founders don’t usually stall because the idea is bad, they stall because the move feels too big to risk.
You’re staring at the cold outbound list, the potential partner intro, the scary “what if we focused?” strategy doc. You tweak, polish, reword… and then don’t send, don’t ship, don’t ask.
In this issue, you’ll get a simple way to turn those scary, high-stakes moves into small, asymmetric experiments, including how designer Julie Mollo turned one cold email and a six-month pop-up into a decade-long business.
The Inner Game in 3 Lines
Most founders treat big moves like pass/fail exams on their identity, so they wait for certainty instead of running experiments.¹
When you turn those moves into small, reversible tests with clear questions, you get data, momentum, and fewer 3 a.m. spirals.²
This week’s tiny experiment: design one “nothing to lose” test with a clear question, tiny downside, and a date on your calendar.
Brain Stuff for Builders
An experimentation mindset is choosing to run small, time-boxed tests with clear hypotheses instead of making giant, all-or-nothing decisions.
A few things we know from the research side:
Experiments beat opinions. Lean Startup work popularized the idea that a startup is a portfolio of hypotheses, not a smaller version of a big company. Your job isn’t to be right in advance; it’s to move through a build–measure–learn loop quickly enough that you find what’s true before you run out of runway.²
Small wins change how your brain feels about hard work. Studies on “the progress principle” show that the single biggest day-to-day driver of motivation and creativity is simply making progress on meaningful work, even tiny progress.³ Small, well-designed experiments create those “I’m moving this forward” hits.
Organizations that treat change as experiments adapt faster. Experimental organizational development (ExOD) is basically “test-and-learn for orgs”: instead of huge change programs, teams run bounded experiments, collect local knowledge, and scale what works.⁴ That’s exactly what you’re doing as a founder, only with less safety net.
Fear of failure is real, but trainable. Research on entrepreneurs finds that fear of failure is linked with lower well-being unless founders build resilience and reframe failure as information rather than a verdict on their abilities.⁵ An experiment frame (“What will we learn?”) literally changes the meaning of a “no” or a flop.
Put simply:
Your nervous system hates pass/fail, identity-level tests.
It can tolerate small, reversible experiments.
That’s why the structure of your moves matters as much as the content.
From Dorm Room to VMAs: What Julie Actually Tested
Julie didn’t sit down with a 40-page business plan and a fundraising deck.
She made a series of experiments that looked, from the outside, like wild luck.
Experiment 1: The “Nothing to Lose” Email
She was a college student in Massachusetts, working 3–4 jobs, sewing a collection on the side.
On the way to a DIY photoshoot, a Katy Perry song came on the radio and she had that “I just know she’d love these clothes” jolt.
She found a “Book Katy Perry” link on MySpace, and sent a cold email to Katy Perry with her portfolio site. Within 24 hours she heard from Katy’s stylist, then Katy herself!
Julie’s line that stuck with me:
“If she didn’t email back, nothing would have changed. Because she did, everything changed.”
That is a textbook asymmetric bet:
Upside: life-changing client, proof, press.
Downside: 10 minutes and maybe a tiny ego bruise.
Most founders probably have a “Katy Perry email” sitting in drafts right now, take this as a sign to send it.
Experiment 2: Six Months of Live Market Research
Years later, Julie was tired of piecing together income from custom clothing.
She had a clothing line, Retroversible, and a handful of glitter vinyl clutches made from scrap fabric. When she signed a two-week pop-up, followed by a six-month pop-up lease, she treated both as experiments, not a forever store.
Question: What actually sells when I put this in front of real people?
Constraints: 6 months, one tiny space, whatever she could sew overnight.
Method: Don’t replenish clothing as it sells. Do replenish clutches and keep adding new styles.
By the end of the six months:
The walls that started out with mostly clothing were almost all bags.
That experiment answered a huge strategic question:
“Am I a clothing brand or a clutches brand?”
The data said clutches.
No survey, no whiteboard offsite. Just a real-world test.
Experiment 3: Constraints as a Feature, Not a Bug
Julie didn’t have a giant production budget.
So she designed with constraints:
All bags share the same core materials: glitter vinyl and glitter appliqué.
New designs often start with scraps from custom pieces, not new fabric orders.
She watches what custom colors and motifs keep getting requested and then turns those into standard products.
Those constraints are the experiment design:
Costs are bounded.
Brand is consistent (fun, flirty, retro, rock-and-roll).
Each new motif, such as lipstick, tennis rackets, dogs is a low-risk test, not a reinvention.
The Hard Lesson: Experiments Still Need Guardrails
During the pandemic, Julie was hit with a lawsuit tied to a law in another state, tucked away on “page 95” of a retail packet she hadn’t fully read.
It forced a painful, expensive shift:
Changing how and where she sourced materials.
Relabeling products for different markets.
Being much more rigorous about legal and logistical details.
Her advice now is simple: “Always read the fine print.”
From an experiments perspective, this is about setting boundaries:
What legal, compliance, or trust lines can your experiments never cross?
Where do you need a lawyer, accountant, or domain expert to sanity-check the plan?
Experiments are for discovering product-market truth not for discovering the hard way that you’ve violated a regulation.
The Tiny Experiment Sprint (30 Minutes)
Here’s a simple way to turn Julie’s story into action this week.
You can do this solo, with a co-founder, or in a short working session with your leadership team.
1. Pick one question that actually matters
Not “Should we pivot the company?” , which is too big.
Think:
“Can we get 3 non-warm intros to ICP buyers in the next 7 days?”
“Will people say yes to a 20-minute user interview about this new workflow?”
“Will our audience click on this more specific positioning line?”
Write one question at the top of a doc.
2. Design a tiny, asymmetric move
Ask: “What’s my version of Julie’s email to Katy Perry?”
Requirements:
Takes ≤ 60 minutes to set up.
You’d be okay if it totally flops. (Mild embarrassment allowed. Existential shame, no.)
If it works, it creates new options: intros, data, traction, not just dopamine.
Some examples:
Email 5 specific people with a very clear ask (“Can I test this draft landing page with you for 10 minutes?”).
Put a rough “coming soon” feature on your pricing page and track clicks for 2 weeks.
DM 10 podcast hosts/newsletters with a tight, non-spammy pitch tied to their audience.
Run a 24-hour discount or “pre-order” card for a very specific new offer and measure responses.
3. Set the guardrails
Before you launch, answer:
Downside: What’s the real worst likely outcome here? (Be honest, but don’t catastrophize.)
Ethics/compliance: Is there any realistic way this breaks trust, violates a policy, or uses data in a way that would make Future you cringe? If so, adjust or get advice.
Capacity: What happens if it over-performs? Do you have a simple way to handle the “good problem”?
If you’re experimenting with contracts, pricing, or regulated spaces, this is where the “always read the fine print” lesson lives.
4. Decide what you’ll measure and when you’ll stop
For a test to count as an experiment, you need:
A time box: “We’ll run this for 7 days.”
A simple metric: replies, signups, calls booked, interviews scheduled, clicks, etc.
A review moment: 15 minutes on your calendar where you’ll ask:
What did we actually learn?
What surprised us?
What’s the next tiny experiment?
If you want a companion piece to this, pair it with our earlier Founder OS issue on choosing one cleaner decision each week — experiments + decision clarity work well together.
If this made you think of a designer, maker, or founder who’s stuck polishing instead of testing, forward it to them and ask:
“What’s your one ‘Katy Perry email’ experiment for this quarter?”
Founder Circle
In speaking with 100+ founders, I’ve noticed how lonely building can feel: constant pressure, high stakes, and very few spaces where you can be fully honest about what’s working and what isn’t.
I created The Founder Circle to provide this space for founders. We have a small cohort (6 founders max) for early-stage, funded, or serious bootstrapped founders who want clearer priorities, better decisions, and a peer group (plus two coaches) so they’re not carrying everything alone.
Sign up is easy! Enter your information in the form below and I’ll add you to the next circle for free so you can try it out.
Here’s what past participants have said:
“Hearing other people’s stories and what they’re going through… now I don’t need to wait until I get there. I already have a good idea how I’ll act when I do.”
“Talking through the dilemma I had and having someone ask a few questions… that made all the difference.”
“Knowing there are so many founders out there makes me feel I’m not alone and I don’t need to worry. Anything can have a solution.”
P.S. Hit reply and tell me one tiny experiment you’re willing to run this week or the “Katy email” you’ve been overthinking. I read every response.
If you want to go deeper to check out the references used in our research:
¹ Joe Sanok, “Building an Experimenting Mindset to Overcome Fear of Failure,” 2017.
² Eric Ries, The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, Crown Business, 2011.
³ Teresa M. Amabile & Steven J. Kramer, “The Power of Small Wins,” Harvard Business Review, May 2011.
⁴ Philipp D. Schaller & Arjan Kozica, “Experimentelle Organisationsentwicklung: Perspektiven eines zukunftsfähigen Veränderungsansatzes,” Organisationsentwicklung: Zeitschrift für Unternehmensentwicklung und Change Management, 2021.
⁵ Soheila Esfandiar et al., “Entrepreneurship and Fear of Failure: Understanding the Mechanism through Resilience,” Sustainability, 13(10), 2021.
I try some in social media
I've seen this exact pattern with agency owners who over-polish and never ship. The perfect pitch deck becomes the excuse. Tiny experiments force you to commit before you're "ready"—and that's when you actually learn if the idea has legs. What's one tiny experiment you shipped recently that moved the needle?