What should trigger a leader to decide it is time to leave their role?

Christian Lanng · Sep 27, 2023

Something is seriously wrong when the thing you're supposed to love is the thing you can't bear to think about

He came to hate looking at the screen and even seeing the company logo, despite still believing in the company and doing the work

Scope: drawn from his own experience during the pandemic

4:59 20VC: "How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders | The Hardest Truths About Being a Founder Revealed | Why AI Co-Pilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng

Harry Stebbings · Sep 27, 2023

The signal that it's time to give up on a venture is when you're no longer excited to try anything new in it — no new projects, no new hires

13:19 20VC: "How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders | The Hardest Truths About Being a Founder Revealed | Why AI Co-Pilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng

Dominik Richter · Dec 1, 2023 · hedged

He expects to still be running HelloFresh in ten years, by then a company with many more business lines beyond meal kits and ready meals, and would only leave if the work stopped being about solving problems he personally finds exciting

What keeps him in the job is problem-solving at scale with very smart people; if his time shifted to other people's problems rather than ones he's excited about, the motivation would be gone

Scope: conditional on the work remaining fun and problem-solving oriented; framed as 'most likely'

51:44 20VC: HelloFresh CEO on Why When You Raise VC You Only Have Two Options, Why Your IPO Price is Irrelevant, Why Timing is So Important in Going Public & Why D2C is Not Dead with Dominik Richter

Micha Kaufman · Jun 9, 2025

A founder should audit annually whether they're still the right person to lead, and step aside if their contribution or energy is no longer maximized — even though the company feels like their baby

He measures energy, contribution, interest and curiosity; his rule is that five consecutive mornings of dread means he's done, because the company deserves someone who will do justice to the creation

Scope: one or two bad days are fine; it's the streak that signals; it has never happened to him

57:50 20VC: Fiverr CEO: 'If You're Not Adapting to AI, F* You. You're Done | Why "Time to Copy" is the Most Important Metric in Startups Today | Why 99% of AI Companies Today Will Die | Why Governments Will Take Control of AI with Micha Kauffman

Carles Reina · Feb 14, 2026

The moment you start losing passion for your job you should fire yourself and do something else

Without passion you will burn out extremely quickly

Scope: he also faults himself for doing too many things and being unfocused

57:07 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Carles Reina · Feb 14, 2026

One bad month is only a trigger to start reflecting; two or three consecutive months without motivation means you should seriously reconsider whether you're in the right place

If it persists for months everyone around you will start seeing it, so you have a real problem

Scope: one month alone is not enough evidence

58:33 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Becca Lindquist · May 2, 2026

Once a salesperson stops learning in a role, they begin to settle and keep settling further, so a flattened learning curve is a signal to move

People who stop learning start to settle, and it's a process of settling all the way to the bottom

Scope: typically applies to people 4-5 years into a software company

5:04 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Becca Lindquist · May 2, 2026

If you've plateaued after four or five years at a large company, you should leave rather than try to re-energize internally, because a next-gen AI startup offers far more learning and impact surface area

At a big company there's too much structure and process left to innovate meaningfully; at an AI startup the surface area you can impact is much higher

Scope: a move to a different role or subsector might work; people 12+ years at a place like Salesforce have had a great run and will likely stay

5:58 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Mike Cannon-Brookes · Oct 13, 2025

Founders must be self-aware about what they actually enjoy — if you don't enjoy the ups and downs of the founder journey itself, it isn't a journey you should be on

Being a founder is genuinely hard with bad days and weeks; you have to enjoy it as a source of learning rather than endure it

49:21 Self awareness about enjoying the journey itself is a prerequisite for founding

Gili Raanan · Mar 18, 2024

The moment you have to talk yourself into getting back up is the moment you should retire; standing up automatically is the signal you should stay in the game

Energy and drive should be intrinsic rather than self-manufactured

33:15 Needing to talk yourself into resilience rather than bouncing back automatically signals its time to retire

Carles Reina · Feb 14, 2026

Whether someone is a zero-to-one or scale person doesn't matter — if you still enjoy the job you should keep going

Life is too short to do something you don't enjoy, and most people are smart enough to figure out something else

57:53 Enjoyment not stage fit is the criterion

Phil Libin · Jan 4, 2017

He should not have been CEO of Evernote once it got big, because career development thinking must be the primary skill of someone running a big company and he doesn't think that way

Constant career conversations with employees felt like an alien concept to him; he's always been on a quest rather than a career path

16:10 Skill mismatch with the companys stage is the trigger

Patrick Forquer · May 11, 2026

Whether to stay in a role should be judged by a simple test: are you hitting your numbers, do you like your boss, and are you learning and making mutual impact with the company

If the answers are all yes you're in a good spot; two out of three or fewer means it's time to consider what's next

65:43 Three part test of numbers boss and learning

Harry Stebbings · May 11, 2026

On career and business decisions you should move fast but not be in a hurry — neither rot in a company nor jump too hastily

66:12 Move fast but never in a hurry