Do the Thing You Feel Guilty to Get Paid For

Sam Schillace

CVP Deputy CTO, Microsoft (Google Docs Creator)

NOV 2024

The Insight

The Work You Feel Guilty
Getting Paid For

"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 of it. If you get pleasure from doing something that people want to pay you for, do it as hard as you can."

We undervalue what comes naturally to us
We conflate unpleasant work with valuable work
The paradox: your easiest skill is often your most valuable skill
Guilt signals misalignment between interest and career

Disruptive Innovation Framework

Why-Not vs What-If Questions

Why-Not questions: People asking about limitations ("browser wasn't ready," "no connectivity," "cloud not secure")
What-If questions: Asking about possibilities and implications ("what if cost drops 10x," "what if we can collaborate in real-time")
The shift: Move from problem-finding to possibility-finding
The pattern: Every good idea looks dumb at first, even the dumb ones

Google Docs Story

Early critics called it a "toy in the browser." That's a signal. When people dismiss something as a toy, it's often a sign they sense something threatening.

The Binary Test

If people either love it or hate it with few in between, you've got something disruptive. If opinions cluster in mild indifference, it's incremental.

Optimism as Practice

Being Optimistic is a Choice, Not a Trait

Not natural: Sam admits he's not naturally optimistic; it's a deliberate habit
Growth mindset: Look at possibilities over limitations; suspend disbelief
The math: Over a career, you lose more by being pessimistic than you protect yourself
In tech: The industry rewards creative, curious, open, optimistic people trying new things
First principles: Everything humans use today was disruptive once; every innovation looks threatening

The career perspective

Sam spent 10 years not realizing he had a career. Optimism would have helped him see the opportunity earlier in tech rather than planning for med school as a backup.

The Renaissance engineer

At Google, Sam was one of only two people who had code readability across all three tiers (backend, middle, frontend). Broad curiosity compounds.

Building North Stars

Play with Purpose

Pick interesting, buildable north stars rather than aimless tinkering
Example: "Can I write a word processor in a browser?" was both play and goal
Current work: Multi-agent systems that self-monitor and self-correct
Weird combinations of tools often unlock novel solutions
Breadth prevents tunnel vision; depth prevents spinning wheels

The full-stack advantageUnderstanding multiple layers (backend, middleware, frontend) gives you perspective that specialists lack. It's rare because it's uncomfortable.

Contrarian

Sam's Provocative Truths

✗Work has to be hard to be valuableINSTEAD →✓ Do what's easy and fun for you. That's your edge. Everyone else has to grind through it.

✗Being pessimistic and right protects youINSTEAD →✓ Being optimistic and wrong costs less than missing the upside. The math doesn't work the other way.

✗Good ideas feel obviously good at firstINSTEAD →✓ Good ideas feel threatening. If nobody's upset, you're probably just iterating, not innovating.

✗Features are the future of softwareINSTEAD →✓ Intention and interactivity are. Users will feel it's broken if software can't understand what they're trying to do.

Based on Sam Schillace's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube

Every sketch here began as a transcript.

Send us yours and we’ll draw it. $1 a transcript.

Sketch mine →

0:00

The Work You Feel GuiltyGetting Paid For

Why-Not vs What-If Questions

Being Optimistic is a Choice, Not a Trait

Play with Purpose

Sam's Provocative Truths

The Work You Feel Guilty
Getting Paid For