The Doubt Follows You to Every New Level.
Why the doubt never goes away, and what the founders who scale do about it.
I write for founders and executives navigating the inner game of scaling. Every week you’ll get one core idea, one tiny experiment, or one founder insight you can apply now.
Inspired by conversations with Alyssa Kushner, Celine Lightfoot, Sarah Kerin, Ayesha Kazi, and Maggie Blackburn. Founders and leaders who learned to keep building while the doubt kept showing up.
Have you ever looked at your own track record and still felt like you were about to be found out?
Sit with this for a moment.
The Belief Worth Challenging
There’s a quiet expectation that most founders carry: once you prove yourself, the self-doubt will go away. Hit the revenue target. Close the round. Ship the product. Earn the title. And somewhere on the other side of all that proof, you’ll finally feel like you belong in the room.
It sounds like a reasonable deal. Work hard, collect evidence, and eventually the inner voice that says “you don’t belong here” will get quieter.
Except it doesn’t work that way. Across five conversations with founders and leaders at different stages, the same pattern kept repeating. The doubt showed up early, when they were just getting started. Then it showed up again when they leveled up. Then again when they took on something new. The doubt never left. It just changed what it was about.
What separated the people who kept building from the people who stalled out was a specific shift in their relationship with that doubt. They stopped treating it as a signal that something was wrong and started treating it as a recurring companion to growth.
This issue is about that shift, and why the founders who scale are the ones who learn to move with doubt rather than waiting for it to disappear.
What It Actually Looks Like
Alyssa Kushner is a licensed psychotherapist based in New York. She leads women’s support groups, supervises other therapists, and runs her own practice. By any external measure, she’s established. But the doubt has come back at every single transition.
“I’ve had different waves of self doubt or imposter syndrome [...] being a therapist, then being a supervisor [...] then this new endeavor.”
What stands out about Alyssa’s experience is the layered quality of it. Each new professional threshold brought a new version of the same feeling. The content changed, the intensity stayed. Becoming a therapist triggered one set of doubts. Becoming a supervisor triggered another. Starting a practice triggered yet another. She described a pattern that most founders will recognize: the moment you feel competent at one level is often the moment you step into the next one, where you feel like a beginner again.
Her response to this pattern was practical. Rather than trying to silence the doubt, she learned to use her own track record as an anchor.
“I reminded myself that I’ve had this before and that I got through it.”
She also learned to turn her own tools inward. When the self-criticism got loud, she would pause and ask herself: “What would I say to a client right now?” That reframe created enough distance to keep moving. She reminded herself to give herself time, that mistakes are part of the learning curve, and that the beginning is always the hardest part.
Celine Lightfoot’s version of imposter syndrome looked different on the surface but ran on the same engine. She had been coding since childhood. Programming was the skill she’d built her entire career around. And still, she carried a persistent belief that she wasn’t particularly good at it.
“I never thought that I was unique in any way. I didn’t think that I was particularly good at it.”
She described trying to relearn how to code multiple times throughout her life, as if the skill she already had somehow didn’t count. The evidence was there. The belief lagged behind. Working with a coach helped her manage the vulnerability that comes with building a company. Having someone to talk through tough conversations and prepare for difficult moments gave her a framework to move through the doubt rather than sit in it.
Sarah Kerin, the CEO of efficientSC, experienced doubt as something closer to dread. When she entered an unfamiliar domain, she described the fear in visceral terms.
“I had this big fear [...] this was like a black hole and I would never be able to master it.”
What shifted for Sarah was incremental evidence. She didn’t wait for the fear to pass. She started collecting small data points: conversations that confirmed the problem was real, early signals that her approach was working. Over time, the fear of the black hole faded, replaced by a growing confidence rooted in the data she’d gathered herself. “I was like, okay, I can kind of figure this out.”
Ayesha Kazi, co-founder of ASL Aspire, faced a version of doubt that was grounded in a real gap. She had never built an app before. The technical demands of her venture were genuinely new to her, and the stress was constant early on. “I’ve never coded like this before [...] I was so stressed at the beginning.”
What made the difference for Ayesha was external support. “If we didn’t have that support, I would be so stressed [...] truly, from every step of the way.” Having mentors who committed to helping at every stage turned what could have been paralyzing doubt into something manageable.
Maggie Blackburn’s doubt hit hardest during a domain switch. After years in consulting, she moved into tech and lost the footing that had made her confident in her previous career. “I remember just being very stressed and had imposter syndrome, didn’t know how to navigate certain situations internally.”
She was honest about what that period felt like: “I feel like I was pretending sometimes like how to do something or that I knew the answer to.” Looking back, she recognized what she needed most was permission to be a beginner. “It’s a new role. You don’t have to do it all. Take baby steps.” Over time, a more supportive manager and growing familiarity with the pace made the difference.
The pattern across all five stories is consistent. The doubt showed up when things were changing, when these founders and leaders were growing into something new. And in every case, what mattered was how they responded to the doubt, whether they treated it as evidence of failure or as a signal of growth.
If this resonates, forward it to a founder or a leader who’s been carrying more doubt than they’ve been admitting.
From the Coaching Room
Every founder I’ve coached has expressed doubt about something. Getting funding. Meeting new revenue milestones. Managing the team. Feeling like they have the skills they need to build the product or company. The specifics change, but the pattern is always the same: a founder who is clearly capable, clearly doing the work, sitting across from me and wondering if they’re enough for the stage they’re in.
What I’ve noticed is that the doubt rarely shows up when things are going badly. It shows up when things are growing. A founder closes their first major client and immediately starts worrying about whether they can retain them. A founder hires their first team and wonders if they know how to manage people. A founder hits a revenue milestone they set for themselves and moves the goalpost before they’ve even sat with the accomplishment.
The doubt follows the growth. And in coaching, the work is almost never about eliminating it. The work is about helping them see the pattern: that this feeling has shown up before, at the last stage, and they got through it. That the doubt is a response to new territory, not a reflection of their ability.
Once they see the pattern, they stop waiting for the doubt to leave. They start treating it as a familiar signal that they’re doing something that matters.
What the Research Actually Shows
The Impostor Pattern Was First Documented in High Achievers
Pauline Rose Clance and Suzanne Ament Imes published the first formal study of what they called the “impostor phenomenon” in 1978 in the journal Psychotherapy: Theory, Research & Practice. They studied 150 high-achieving women, including PhDs, respected professionals, and students with top academic records, and found a consistent pattern: despite clear evidence of accomplishment, these women did not experience an internal sense of success. They attributed their achievements to luck, timing, interpersonal relationships, or overestimation by others.
The finding that matters for founders: Clance and Imes identified this as a cycle, not a one-time event. Each new success created a new opportunity for the impostor feeling to return, because the person’s internal framework kept discounting their own evidence. This maps directly to what Alyssa described. Each professional threshold, from therapist to supervisor to practice owner, triggered the same doubt pattern. The accomplishments accumulated, but the internal experience of “I’m about to be found out” kept resetting.¹
Impostor Syndrome Shows Up Across Every Demographic and Career Stage
Dena Bravata and colleagues published a systematic review in the Journal of General Internal Medicine in 2020, analyzing 62 studies with a combined 14,161 participants. They found that impostor syndrome prevalence ranged from 9% to 82% depending on the population studied. The variation is itself revealing: the phenomenon shows up across gender, age, race, and career level. It is not limited to any single group or stage.
Two findings from the review are worth sitting with. First, impostor feelings were strongly correlated with anxiety, depression, and reduced job performance, meaning the doubt itself has a measurable cost when left unaddressed. Second, the review found no evidence that impostor syndrome naturally resolves with career advancement. People at senior levels reported it just as frequently as people early in their careers. For founders, this confirms what the stories in this issue suggest: waiting for the doubt to leave on its own is not a strategy. The doubt persists. What has to change is how you respond to it.²
How to Keep Moving When the Doubt Shows Up Again
These are practices drawn from what actually worked for the founders in this issue. Each one addresses a specific moment in the doubt cycle.
Build an evidence file you can return to.
Alyssa’s approach was to remind herself that she’d had doubt before and gotten through it. Make this concrete. Keep a running document of decisions you made that worked, problems you solved, and moments where you operated beyond what you thought you could. When doubt shows up at the next level, the file becomes your anchor. The goal is to interrupt the pattern Clance and Imes identified, where each new threshold resets your internal scorecard to zero.
Replace self-judgment with a single reframing question.
Alyssa asked herself, “Would I judge a child this harshly?” You can adapt this to any version that creates distance from the inner critic. The question works because it shifts you from evaluation mode to compassion mode. When doubt turns into self-punishment, the punishment becomes the bottleneck, not the doubt itself. One question that interrupts the spiral is more useful than trying to argue your way out of the feeling.
Collect small data points before the big fear shrinks on its own.
Sarah Kerin didn’t wait for confidence before acting. She gathered evidence: conversations, early signals, data that confirmed her direction. The fear of the “black hole” didn’t disappear through willpower. It faded as concrete information replaced abstract dread. If you’re staring at a new domain or challenge that feels overwhelming, start with the smallest testable question. One conversation. One data point. The doubt starts losing ground the moment you stop imagining and start measuring.
Give yourself, or someone else, explicit permission to be a beginner.
Maggie Blackburn’s manager told her: “It’s a new role, you don’t have to do it all. Take baby steps.” That single statement changed her trajectory. Ayesha Kazi’s mentors did something similar by committing to support at every step. If you’re leading a team, consider how often you give this kind of permission to the people around you. And if you’re the one carrying the doubt, consider that no one else is requiring you to have all the answers at the new level. That expectation is usually self-imposed.
The Bigger Picture
Clance and Imes documented the impostor cycle nearly fifty years ago. Bravata’s systematic review of 62 studies confirmed it persists across career stages, regardless of how much evidence accumulates. The research is consistent: the doubt does not resolve on its own.
But here’s what the research doesn’t capture, and what the founders in this issue show clearly. Alyssa built an evidence practice she could return to at each threshold. Celine Lightfoot found that coaching gave her a space to move through vulnerability rather than sit in it. Sarah collected small data points until the fear of the unknown lost its grip. Ayesha Kazi leaned on a support system that showed up at every step. Maggie Blackburn gave herself permission to be a beginner again.
“I’ve had different waves of self doubt or imposter syndrome... being a therapist, then being a supervisor... then this new endeavor.” ~ Alyssa Kushner
None of them found a way to make the doubt disappear. Each of them found a way to keep building while it was there. That’s the shift. And it’s available to anyone willing to stop treating doubt as a verdict and start treating it as part of the job.
Founder Circle
There’s probably a moment in this essay you recognized as yours. Founder Circle is a live, small-group coaching session where ten founders each work through one real challenge and leave with clarity they didn’t have walking in. Join us for our next circle by reserving your spot.
P.S. What’s the last thing you doubted yourself on that turned out fine? I read every response.
I’m Dar Patel, an ICF-certified executive coach (PCC) and founder of Little Pursuits. I partner with founders and executives through the leadership inflection points: the identity shifts, the hard conversations, the decisions you keep carrying alone. This newsletter is where that work meets the page. Find me on LinkedIn.
If you want to go deeper to check out the references used in our research:
¹ Clance, P. R., & Imes, S. A. (1978). The Impostor Phenomenon in High Achieving Women: Dynamics and Therapeutic Intervention. Psychotherapy: Theory, Research & Practice, 15(3), 241–247.
² Bravata, D. M., Watts, S. A., Keefer, A. L., et al. (2020). Prevalence, Predictors, and Treatment of Impostor Syndrome: a Systematic Review. Journal of General Internal Medicine, 35(4), 1252–1275.
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