Guilty-Pleasure Career Bet
Find the thing you feel guilty getting paid for, do the hell out of it with intensity, and take non-linear risks.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 88%
Schillace's theory of extraordinary careers: linear, tightly-managed effort yields a linear, boring return (climb the ladder over 30 years). Outsized returns come from doing extraordinary things — bigger risks and more interesting shots. The lever most people miss is that we undervalue what we're good at, assuming work must be unpleasant to be valuable. His prescription is to find the work you'd feel guilty getting paid for, pour disproportionate intensity into it, and stay open to others seeing value in you that you don't see yourself.
Origin
Sam Schillace's reflection on his own 35+ year career, reinforced by Charlie Munger and Warren Buffett's 'go big when you find an advantage' philosophy and Seth Godin's advice to do the best version of whatever job you're in.
Core principles
- 01Linear, tightly-managed work returns linear, boring career results; extraordinary returns require extraordinary, riskier shots.
- 02You get ahead because you had impact; you had impact because you did something you're good at with a lot of intensity.
- 03We undervalue what we're good at because we assume valuable work must be unpleasant.
- 04Being unwilling to embarrass yourself or fail caps how far you can go — 'you cannot dance if you're afraid to embarrass yourself'.
- 05Others often see high-value capabilities in you that you dismiss because they come easily — stay open to those signals.
- 06From error comes virtue: make mistakes into something creative rather than avoiding them.
How to run it
- 1
Find your guilty-pleasure work
Identify the thing you get real pleasure from that people will pay you for — the work you feel almost guilty accepting money for. If such a thing exists for you, that's the target.
Pro tip Watch for the moment someone is happy to pay you for something that doesn't feel like the thing you 'should' be doing — that surprise is the signal.
Watch out Don't dismiss easy, fun work as low-value; that instinct is exactly the trap that pushes people toward needless grinding.
- 2
Do the hell out of it with disproportionate intensity
Once found, pursue it as hard and as well as you can. Impact comes from intensity applied to something you're genuinely good at.
Pro tip Munger/Buffett: when you find a real advantage, go big rather than buying a little at a time.
Watch out Extreme intensity isn't for everyone and can make the people around you less comfortable — Schillace is candid that his all-in/all-out style has this cost.
- 3
Take non-linear risks and tolerate failure
Choose bigger, more interesting bets that could produce outsized results, accepting that many will fail and some publicly. Build a tolerance for embarrassment as the price of extraordinary outcomes.
Pro tip Adopt a motto that reframes failure — Schillace uses 'virtue from error': make something creative out of every mistake.
Watch out Beware filtered content that presents rare five/six-sigma successes as normal and makes ordinary failure feel shameful.
- 4
Stay open to pivots others see in you
When someone lets you do something you're surprisingly happy to do, or values work you'd have dismissed, lean into it and let your role shift.
Pro tip Schillace couldn't understand why he was paid to manage instead of writing code until his boss said 'everywhere you go it gets better, keep doing whatever you're doing' — a pivot he'd have missed if closed off.
Watch out Earlier career stages often demand compromise jobs for income; the advice is to stop those as soon as you reasonably can, not to refuse them outright.
In the wild
Schillace tied his self-worth to lines of code and couldn't understand why his boss was thrilled with him for managing instead. The boss told him everywhere he went things got better and to keep doing whatever that was.
→ He leaned into a people-and-leadership role he was surprisingly happy in — a pivot enabled by staying open to a strength he hadn't valued.
Schillace carved an instrument from an 80-year-old piece of forest redwood; the knots became 'cat eyes' and the arch came out slightly too high so it's a bit hard to play — a partial failure he kept as a passion project on the wall.
→ A literal 'virtue from error' — he embraces experiments that don't fully work as worthwhile creative acts rather than wasted effort.
Common mistakes
Grinding at unpleasant work to prove worth
Believing valuable work must be unpleasant pushes people to grind through careers they dislike, when the highest impact comes from intense work on something they enjoy and are good at.
Playing it linear and safe
Tightly managing to avoid surprises yields a slow, boring, linear return; extraordinary results require accepting bigger risks and the failures that come with them.
Is it for you?
Best for
Mid-career-and-beyond builders with enough stability to take bigger swings, deciding how to allocate risk and energy for outsized impact.
Not ideal for
People early in their careers or under acute financial pressure who genuinely must take compromise jobs for income — Schillace explicitly flags the advice as privileged and stage-dependent.
From the transcript
“you should go do the thing that you feel guilty to get paid for if there's a thing like that and do the hell out…”
“the way you get extraordinary returns is you do extraordinary things right you get you know you have to have you have to take bigger…”
“we tend to undervalue the things we're good at we tend to think work has to be unpleasant and so if something is easy and…”
“you cannot dance if you can't if you're you know afraid to embarrass yourself you cannot succeed if you're afraid to fail”
“I have this personal motto which is like from error comes virtue”
“everywhere you go it gets better so like just keep doing whatever it is you're doing”
From the episode
How to be more innovative
Sam Schillace (Microsoft deputy CTO, creator of Google Docs)