Why founders fall out of love with the problem
A performance psychologist on stress, the right support, and how founders lose the plot
Building or leading anything is a long grind of one step forward and what feels like two steps back. The calendar is full, the pressure is constant, and the wins keep arriving later than you wanted or expect. The question that decides whether you last is how you keep performing, and keep leading well, over years consistently.
Stephanie Simpson has spent her whole career studying how people do exactly that.
She started in dance and theater as a kid, danced professionally for a WNBA team, and earned an MFA in dance before going back for a master’s in clinical psychology at Columbia. Along the way she studied the psychology of performance across sports, positive, and clinical psychology, and trained as an ICF-certified coach through iPEC. Today she runs Stephanie Simpson Coaching, a consulting and coaching practice helping founders, executives, and teams do their best work under pressure.
Ask her how anyone sustains that over years and every answer points the same direction: stay in love with the problem, get honest about your stress, put the right support around you, and measure yourself against what you actually value.
Here are five takeaways from our conversation
1. Stay in love with the problem.
The most useful thing Stephanie carries from her entrepreneurship training is a line from her professor: “you have to be in love with the problem, not the solution.” Her read on why that matters is blunt. “Most people’s businesses fail because they’re in love with their solution and they’re not actually really getting into the problem like they maybe did originally, but they’re not listening to their target market.” This can happen slowly as you invest more time and effort on the solution. You start by caring about the people you are serving, and somewhere along the way you start defending the thing you built for them instead. The fix is to keep going back to the problem, and to keep listening to the market that owns it, long after you think you already understand it.
To Coach yourself:
When did you last sit with a customer and let them describe the problem in their own words?
Notice when you are defending the solution or you might be tuning out the customer.
Pick one real user and get on a call with them this week, and go in with no pitch.
From Stephanie: “How are you listening to the feedback? What lens are you looking through right now?” Staying in love with the problem is a habit of listening, and you can lose it without noticing.
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2. Untangle the knot one strand at a time.
Stephanie spent a second master’s thesis expecting to prove that stress is the enemy, and came out the other side arguing the opposite. “We don’t want to get rid of fear and stress completely because they actually help us get to a place of flow or peak performance,” she says, and yet “not having a healthy relationship with it could actually kill us.” The work is turning a vague sense of overwhelm into something you can act on. She describes the way most of us carry it: “we just kind of mush them all together into this like knotted little ball.” So she names the strands one at a time, sorts them into what she can and cannot control, and spends her energy only on the first group.
To Coach yourself:
Here’s Stephanie’s framework to navigate these moments:
Name the source of the stress
Prevent what you can (what’s in your control)
Regulate your body in the moment (breathework, movement, get outside)
Manage the thought that sets off the trigger in the first place
3. A mentor hands you a map. A coach holds up a mirror.
Stephanie is precise about a distinction most people blur, and she thinks the blur costs founders. A mentor is an expert in their own life who gives you advice from what they have done. A coach does something different: “[in] a good coaching session, the coach is only talking 20 percent of the time.” They ask powerful questions, they mirror back what they’re hearing, they notice patterns that keep resurfacing, and they leave you in the driver’s seat to make decisions on how you want to move forward. She makes the case for why every founder needs a coach, on top of a mentor, is about perspective you cannot get from inside your own head. “Your coach is there to remind you that you’re actually not in love with the problem anymore. You’re falling into the trap of you’re only seeing your solution.” The job, as she puts it, is to “champion them, and also hold a mirror up to them.”
To Coach yourself:
Where in your work do you need an answer, and where do you actually need to hear your own thinking out loud?
Who do you turn to for sound boarding and getting clarity?
What would shift if, this week, you asked one person to ask you questions instead of handing you advice?
From Stephanie: “We’re on a road trip together and I’m in the passenger seat with you as your co-pilot, but you are driving this car.” A mentor would take the wheel; a coach keeps you in the driver’s seat, which is the only place real ownership grows.
4. Find the person who says your name in the room.
When Stephanie maps out career support for people inside organizations, she adds a role most people never name for themselves: a sponsor. It is not your manager and not your mentor. “[A sponsor is] someone in the ecosystem of your workplace that has access to different meetings and tables and knowledge that you don’t have, but knows who you are, respects what you do, sees your talent and potential and says your name in those meetings.” A sponsor advocates for you when you are not in key decision making meetings about your career. For most individuals, the decisions that shape a career often happen in rooms you will not be invited to, which makes the person willing to speak for you there worth more than another piece of advice.
To Coach yourself:
Which key meetings are you not part of when decisions about you get made?
Who already knows your work well enough to say your name there, and have you built the type of relationship in which they would advocate for you?
Pick one person this month and make sure they know exactly what you are working toward.
Also ask yourself whose name you are saying when they are not in the room, how can you advocate for others that are not in spaces you have the privilege to be in?
5. Count the wins your business mentor would ignore.
Four years in, Stephanie still runs a practice every Friday: she writes down her celebrations and wins. At first the list was all clients signed and revenue booked, and she noticed it left her flat. “This is not making me feel good,” she remembers thinking, before going back to the reason she built the business at all. So the list changed. Now it holds the hour-and-a-half walk in the middle of a Tuesday, the nap she took because she was exhausted, the friend’s show she got to see on a Wednesday afternoon. “I’m measuring them by these other things that a business mentor would tell me I need to measure my success by,” she says, and that is the point. Money still matters, but a scoreboard built only from someone else’s metrics manufactures its own stress. “If you’re not living in alignment with those values, you’re creating distress.”
To Coach yourself:
What did you start your business for, underneath the revenue and the milestones?
What wins from the past week would never make a standard scoreboard but actually matter to you?
Start a Friday list this week, and put the first one on it.
From Stephanie: “There are other things that I can measure my success by that are really aligned with who I am and what’s important to me.” The scoreboard you inherited and the scoreboard that keeps you going are rarely the same one.
Resources Stephanie mentioned
iPEC, the coach-training program she went through for her ICF certification, built on its Core Energy approach and an attitudinal assessment she wanted so she could actually show a client’s shift.
Armchair Expert, the podcast she keeps coming back to. Her habit: when a guest grabs her, she goes and reads that person’s book or finds them elsewhere.
Brené Brown, whose books she names as directly influential on her work.
Leaving you with this question: when you sit down this Friday, what would make your list of wins if you stopped counting only the ones a business mentor would approve of? Share it with me.
If anything in this article resonated with you, share it with one more person that could also use these insights.
Ways Work with me
I’m Dar Patel, an ICF-certified executive coach (PCC), I have worked with founders and executives, and am the writer behind The Inner Game, the weekly newsletter of Little Pursuits.
My goal is to support founders, executives, and individuals doing one of the hardest things we can do: build and scale something from the ground up.
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