The Three-Lens Quit Decision
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 6
- Confidence
- —
How Alex decided to leave a Morgan Stanley sales and trading seat — the only career he had ever imagined — for a newsletter with 10,000 subscribers and no revenue. He deliberately ran the decision through three separate lenses rather than one. First, regret comparison: which future version of himself would be more upset, the one who stayed and watched someone else build his idea, or the one who left and failed. Second, worst-case laddering: state the worst outcome, then keep asking 'then what' four or five layers deep until you either find a survivable landing spot or discover that you have an options problem rather than a venture problem. Third, the countdown-clock test, sharpened by losing his father at 49: if the clock hit zero tomorrow, how would you rather have spent the time.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Name the fork explicitly
Establish that this genuinely is a binary inflection point, not a 'do both' situation. For Alex and Austin the fork was full-time or the project becomes a shell of itself — working nights after a trading desk or an investment banking analyst schedule had a ceiling.
Watch out If you have not confirmed the fork is real, you will burn months optimising a false compromise.
- 2
Run the regret comparison
Ask which you would regret more: staying safe and watching someone else succeed with your version of the idea, or leaving, failing, and having to find a new job. Alex found the answer obvious — regret at watching someone else win purely because they risked their time when he wouldn't.
Pro tip Frame both branches as a specific scene you would be living in, not as abstract outcomes.
- 3
State the actual worst case
Not the catastrophised version — the realistic one. For Alex: quit the job, work on the business, and it fails about six months later, because the vast majority of businesses fail.
Watch out A vague fear cannot be tested. If you cannot write the worst case as one concrete sentence, that vagueness is doing the deciding.
- 4
Ladder 'then what' four or five layers deep
Take each worst case and ask what happens next. Maybe the old employer takes you back for the entrepreneurial experience. If not, maybe it becomes the story that gets you into business school. If not, maybe the people you met in the startup scene lead to founding or joining another company.
Pro tip Kill each option deliberately as you go — assume the bridge is burned — so the ladder tests resilience rather than optimism.
- 5
Classify what the ladder reveals
If four or five layers deep you still find no viable landing option, the problem is not the venture — it is that you have not kept your options open as a professional. That is a different problem with a different fix.
Watch out Do not fix an options problem by staying put; staying put usually makes it worse.
- 6
Apply the countdown-clock test
Ask what you would rather be doing with your time if your life countdown clock hit zero tomorrow. Alex found it a no-brainer: he far preferred building his own thing to sitting in front of a screen trading mortgages.
Watch out Used alone this lens over-romanticises quitting. It works because the two prior lenses have already established the downside is survivable.
In the wild
Alex started at Morgan Stanley in July 2015, waking at 5am, on the desk by 6:30, trading until 7pm, then working on Morning Brew from 8pm until he fell asleep with the laptop on his lap. When his co-founder Austin hit his own fork — an investment banking offer — they met over beers in one of New York's oldest bars and agreed it was full-time or nothing. Alex ran the regret comparison, laddered the worst case four or five options deep, and applied the countdown-clock question. He quit just after Labor Day 2016.
→ Both founders went full-time; the business was eventually sold to Axel Springer in October 2020.
Common mistakes
Stopping at the first worst case
One layer of 'what if it fails' produces a scary, unresolved image. The value only appears at layer four or five, where you either find a survivable landing or diagnose that your options were too narrow to begin with.
Deciding on upside fantasy instead of downside survivability
None of Alex's three lenses required predicting success. The decision turned entirely on whether he could live with the worst case and which regret he preferred — both answerable today, unlike the odds of winning.
From the transcript
“i thought about things in terms of regret what would i regret more”
“i always use things as like the worst case scenario framework in a decision and can you live with the worst case scenario”
“i basically got like four or five layers deep of options and i was like if none of these are options after morning brew fails…”
From the episode
Lessons From Selling Morning Brew For $75 Million At 28 - Alex Lieberman
Alex Lieberman