Tiny Career Experiments for Founders (Without Quitting)
A framework for testing new roles and finding your next chapter without blowing up your current traction.
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.
You can feel completely done with your current path and still stay stuck for months.
Maybe you’re a founder who built yourself into every role and now secretly wonders if the business needs a different version of you. Or you’re still in consulting or big tech, building on nights and weekends, and you keep telling yourself you’ll leap “once things are clearer.”
In this issue, you’ll get a simple way to turn big, scary career questions into tiny experiments you can run alongside your current work, plus how used that approach to move from Deloitte and Slack into a portfolio career of retreats, events, and self-designed work.
The Inner Game in 3 Lines
Most founders treat career moves like all-or-nothing bets on their identity, so they either stay too long in misaligned roles or blow things up in one dramatic jump.
When you treat your next chapter as a portfolio of tiny, time-boxed experiments, you get data, confidence, and traction without burning your runway.
This week’s experiment: design one “job as playground” test, small enough to run in a few days, meaningful enough to teach you something about your future work.
Brain Stuff for Builders
An experimentation mindset means you treat your next move (product, market, or role) as a hypothesis to test, not a verdict on who you are.
A few pieces from the research and practice side:
1. Big, irreversible decisions activate your threat system.
Behavioral economists Daniel Kahneman and Amos Tversky showed that we’re loss averse: we tend to feel potential losses about twice as strongly as similar gains.¹ Quitting a job, walking away from a “good” title, or changing your role inside your own startup sounds like a permanent loss, so your nervous system quite reasonably says: “Not yet. Later. When it’s safer.”
2. Small wins are rocket fuel for motivation.
In a well-known Harvard Business Review piece, Teresa Amabile and Steven Kramer found that the single biggest day-to-day driver of motivation and creativity was simply making progress on meaningful work, even tiny progress.² When people logged their workdays, small steps forward (“I finally got feedback on that draft”) mattered more than big events. The Power of Small Wins is literally their term.
Tiny experiments give you those small wins: you send one uncomfortable message, host one small event, test one new positioning line, and suddenly your brain has evidence: I can move this forward.
3. Lean Startup applies to your career, not just your product.
Eric Ries’ The Lean Startup popularized the idea that a startup is a portfolio of hypotheses, not a smaller version of a big company. Your job is to move through a build–measure–learn loop until you find what’s true before you run out of runway.³
You can apply the same loop to your own role:
Build: try a small version of the work you think you want (facilitating one offsite, leading one partnership, piloting one “head of X” responsibility).
Measure: notice what energizes you, what drains you, and whether anyone would actually pay for it.
Learn: use that feedback to design the next experiment, not to write a 5-year plan in stone.
4. Tiny experiments help you escape the “perfect path” trap.
In Tiny Experiments: How to Live Freely in a Goal-Obsessed World, Anne-Laure Le Cunff argues that we often trap ourselves in what she calls the “self-consistency fallacy”: I’ve always done X, so I have to keep doing X. Tiny experiments become a way to explore alternative selves without burning everything down.⁴
Instead of asking “What’s the perfect next role?”, you ask:
“What’s a 1–2 week experiment that would let me test a version of work I might want more of in the future?”
Put together:
Your brain hates pass/fail, identity-level tests.
It can tolerate small, reversible experiments with clear guardrails.
For founders, that’s the sweet spot: experiments that create both traction (real signal, not just vibes) and optionality (more than one viable path forward).
Maggie’s Portfolio of Experiments
Not One Perfect Leap, but a few tiny experiments
On the Little Pursuits Podcast, Maggie Blackburn described a career that looks, from LinkedIn, like a clean ladder: Deloitte to Slack to product marketing to retreats and events. Underneath, it was a string of small experiments that let her trade prestige for alignment without jumping off a cliff on day one.
Here are three patterns worth stealing:
1. From “good on paper” to “something feels off”
Early on, Maggie did what many high performers do:
Chose the practical, prestigious path (business and Big Four consulting) over creative work after an offhand “you can’t really draw” comment that left her doubting her skills.
She landed a rare sophomore internship at Deloitte, and then eventually was offered a full-time role. The brand, pay, and travel all looked great on paper.
Internally, the work felt… flat. Long client projects, lonely travel, and a sense that she was grinding toward a partner role she didn’t actually want.
Founders get a similar version:
The company looks good on paper: raised, growing, impressive logos.
Internally, you’re lonely, bored, or stretched across work you don’t care about, but you tell yourself: “This is what success is supposed to look like.”
2. Curiosity and Relationships as Experiments
Maggie’s first experiments weren’t dramatic quits; they were curious pivots:
Inside Deloitte and Slack, she followed her curiosity toward more creative, visible work (digital, product marketing, launches) by talking to people doing roles she found interesting.
She treated those conversations as experiments: “What do you actually do all day? What parts light you up? Is there a shadow project I can help with?”
When she moved into product marketing, it was after shadowing, doing a test project, and building trust with a manager who could sponsor her.
This is pure Lean Startup:
Hypothesis: “I might like X more than my current role.”
Experiment: “Do a small slice of X for someone who already does it, in service of their goals.”
Metric: “Do I like the work enough to want more of it?”
3. Using her job as a playground, not a prison
The bigger shift came before she quit:
While still employed, Maggie taught Pilates at a local studio, then asked if they needed marketing help, which turned into her first small-business marketing client.
She bought a place that became an Airbnb project.
She started helping design retreats and events with people she’d met years earlier.
None of these were “the new job.” They were live experiments on questions like:
“Do I actually enjoy working with small business owners?”
“Do I like being on-site and orchestrating experiences?”
“Does it energize me to bring people together in real life?”
By the time she left her last PMM role, she hadn’t replaced her income, but she had evidence:
People would pay her for marketing and events.
She liked that work more than internal decks and stakeholder politics.
Her fear around money and uncertainty was real, but she’d handled other big risks before and come out okay.
That’s the core idea for founders:
Treat your current role, whether that’s “CEO of a 20-person startup” or “PMM at a Series D company” as a playground for experiments, not a life sentence.
The Tiny Experiment Sprint (Career Edition: 30 Minutes)
Here’s a way to turn Maggie’s story into something you can actually run this week.
You can do this solo, with a co-founder, or with a trusted friend.
1. Name the real tradeoff you’re stuck on (5 minutes)
Write down the question that’s actually haunting you. Not: “Should I quit?”
But something more specific, like:
“Do I want my next 3 years to be mostly operator, mostly builder, or a portfolio of both?”
“Is my highest leverage as CEO in sales, product, or people, and what do I do with the rest?”
“Do I want to keep optimizing this startup, or start building a second income stream as a creator or consultant?”
Circle the one that has the most emotional charge.
2. Design one tiny, asymmetric experiment (10 minutes)
Ask Maggie’s question: “What would it look like to use my current setup as a playground?”
Constraints:
Takes ≤ 60–90 minutes to set up.
You’d be okay if it “fails” (mild embarrassment allowed; existential shame, no).
If it works, it creates new options, not just dopamine.
Some examples for founders:
Operator vs builder:
Join one product working session this week as a “guest PM” and actually own one small decision.
Or, step out of one standing meeting and delegate it, just for a month, to test whether you really need to be in the weeds.
New market / offer experiment:
Host a tiny, 10-person virtual roundtable for the kind of customer you think you might want more of, and treat it as research and signal for potential future work.
Put a “coming soon” landing page or pricing card up for a new offering you’re curious about, and see who clicks / replies over two weeks.
3. Set guardrails (5 minutes)
Before you run the experiment, answer:
Downside: What’s the real worst likely outcome? (Write it down; our brains love to catastrophize.)
Time & money: How much time and cash are you actually willing to burn on this? Be specific.
Ethics & capacity: Does this experiment risk breaking trust with your team, your investors, or your current employer? If yes, shrink it or get advice first.
This is the “read the fine print” lesson from our previous issue on experiments: experiments are for discovering product-market truth, not for discovering legal or ethical landmines the hard way.
4. Decide what you’ll measure and when you’ll stop (5–10 minutes)
For it to be an experiment (not just a vague intention), you need:
A time box: “I’ll run this for 7 days, until the end of the month.”
A simple metric: replies, intros, sign-ups, people who say “this was helpful,” etc.
A review moment on your calendar where you’ll ask:
What did I actually learn about the work, the demand, and myself?
What surprised me?
What’s the next tiny experiment that builds on this?
Then hit send, publish, or schedule.
Community & Share Loop
If this made you think of a friend who may be curious about their next chapter, or a founder who keeps talking about leaving but hasn’t designed any experiments yet, forward this to them and ask:
“What’s one tiny experiment you’d be willing to run in the next 7 days or a few weeks?”
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.
The Founder Circle is 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 “portfolio career” idea you’ve been quietly sitting on. I read every response.
References
¹ Daniel Kahneman & Amos Tversky, “Prospect Theory: An Analysis of Decision under Risk,” Econometrica, 1979.
² Teresa M. Amabile & Steven J. Kramer, “The Power of Small Wins,” Harvard Business Review, May 2011.
³ Eric Ries, The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses, Crown Business, 2011.
⁴ Anne-Laure Le Cunff, Tiny Experiments: How to Live Freely in a Goal-Obsessed World, HarperOne, 2024.
⁵ Little Pursuits Podcast (2026). Conversation with Maggie Blackburn.
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