How should founders and leaders deal with self-doubt and imposter syndrome?

Sebastian Siemiatkowski · Mar 1, 2021

Self-doubt is healthy and should be welcomed; the worrying case is a leader who reports having none, because it means they are not reflecting on or learning from their actions

Self-doubt represents continuously questioning whether you are doing the right thing and taking the right decisions

Scope: acknowledges it is painful to experience

17:54 20VC: Klarna Founder Sebastian Siemiatkowski on Scaling Europe's Most Valuable Private Tech Company, How To Motivate and Challenge Your Team Most Effectively & The Biggest Lessons From Working with Mike Moritz

Harry Stebbings · Sep 14, 2021 · hedged

Insecurities can have positive effects, helping drive a person forward, though they have pros and cons

Those thoughts have driven him forward personally, so there are pros as well as cons

Scope: acknowledges there are cons too

41:49 20VC: Sequoia's Doug Leone on What Has Been Instrumental To Scaling Sequoia Over Generations, How Sequoia Think About International Expansion and What They Learned From China and India & Why When You Lose Pre-Seed You Become Private Equity

Raaz Herzberg · Dec 12, 2025

Imposter syndrome should be embraced rather than fought, because it fuels motivation and prevents complacency

Feeling you know less than others keeps you paranoid and never complacent, whereas some people wrongly think they know more than they do

3:47 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Gili Raanan · Mar 28, 2026

Maturing as an investor requires greed and determination to keep going while feeling like the worst investor in the room for years

Surrounded by super achievers at Sequoia, he felt like the shittiest investor every day and it took a long time to mature; only persistence gets you through the bad days

46:28 Persist through years of feeling like the worst in the room

Gustav Söderström · Oct 12, 2022 · hedged

Everyone has impostor syndrome, and in a hypergrowth company you feel like an impostor continuously because the job changes every year even if the title doesn't.

You go from being CPO of a tiny Swedish company to a Scandinavian one, then a global one, then a New York listed one — each time it feels like there's no way you can be that person.

46:23 Hypergrowth companies produce continuous impostor syndrome since the job changes every year

Kim Graves · Jun 27, 2025

Working with a professional coach is highly valuable for navigating career crises, because a coach helps you reframe what is actually true versus what you fear

Her coach walked her through 'what's the worst that can happen' and challenged her false belief that she had no advocates, which let her see the situation clearly

68:28 Professional coaching helps reframe fear versus truth in career crises

Harry Stebbings · Jun 27, 2025

Women in sales should second-guess themselves less and trust their own intuition rather than seeking validation

The many women he works with continuously check themselves and ask him to validate decisions where their original intuition was already right

70:29 Trust your own intuition rather than seeking external validation especially for women in sales

Kim Graves · Jun 27, 2025

Confidence and self-belief are the highest-leverage career assets — you should just go for it, since the worst outcome is failure or a no

The downside of trying is only failure or rejection, which is small relative to the upside

70:47 Confidence and willingness to ask is the highest leverage career asset

Matan Bar · Feb 11, 2021

A strong leadership team is the foundation that makes hyper-growth scaling possible and defuses founder self-doubt

Trusting leaders with decisions and consulting them on an ongoing basis, plus an inclusive culture with open, honest, direct conversations about dilemmas, makes founders comfortable with their doubts

19:04 Trusted leadership team absorbs founder doubt

Doug Leone · Sep 14, 2021

At his age, lingering insecurity and the urge to look smarter than he is counts as a character weakness rather than a useful driver

By 64 those residual proving-yourself impulses no longer serve him

41:55 Insecurity that persists after success is a character weakness not a useful driver

Harry Stebbings · Jun 17, 2024 · hedged

Founders wrongly disqualify themselves by comparing themselves to today's great leaders at their endpoint rather than at the start

They look at incredible leaders ten years in and conclude 'I'm not that'

48:02 Comparing yourself to leaders at their endpoint not their start causes self disqualification

Matt Murphy · Jul 27, 2026

Doubt — self-imposed or from those around you — makes an investor dramatically worse, so firms should build high-trust environments

He has personally experienced periods of doubt in his career that degraded his performance; everyone fails in this business and needs to be built up

51:59 Doubt degrades performance so firms must build high trust environments

Matt Mochary · Mar 9, 2020

The self-critical voice can never be made to go away, but you can stop acting on it and add a second, self-appreciative voice alongside it

Tracing when the voice first formed in childhood lets you see it made sense for a five-year-old and served you to get where you are, and then ask whether it still serves you as an adult

17:17 Add a second appreciative voice rather than silencing the critic

Matt Mochary · Mar 9, 2020

Almost all self-critical thoughts are formed before age five, probably before memory begins, and essentially none are created after five or six

He knows of no case where such a thought was truly created post age five or six

18:42 The critic is a pre age five artifact to be traced

Matt Mochary · Mar 9, 2020 · hedged

Imposter syndrome is fear, and an 'energy audit' — marking each hour of your past two weeks' calendar red or green by whether it energized or depleted you, then outsourcing, eliminating, or redesigning the reds — will help overcome it

Marking the reds reveals patterns; for each you have only three options (outsource, stop doing it, or specify conditions that would make it energizing), and repeating the cycle monthly compounds

19:24 Energy audit and redesign the calendar