The Dream Job File
Start building your next career on paper before you ever make the leap
- Difficulty
- Easy
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 82%
Drawn from Harvey McKay's book Sharkproof, the Dream Job File is a simple, ongoing repository, originally a manila folder, now a Google Doc or notes app, where you accumulate everything relevant to the career you secretly want. Over months you pile in ideas, articles, names of people to talk to, notes from conversations, and observations about the field's technological edge. The act of building the file does two things: it converts an abstract fantasy into a concrete, researched plan, and it lets you begin the transition while still employed, dramatically lowering the perceived risk of the eventual leap. Gurley pairs it with a diagnostic: whatever curiosity already fills your downtime is a reliable tell about where the file should point.
Origin
From Harvey McKay's older book Sharkproof, which advised keeping your dream job in a manila folder. Gurley read it in business school and updates it for the Google Doc era.
Core principles
- 01You can begin the process of a career change long before you make the jump
- 02Accumulating notes, contacts and learnings makes a distant dream feel real and reachable
- 03A curiosity that occupies your downtime is a strong tell about your true direction
- 04Momentum and evidence lower the perceived risk of leaping
How to run it
- 1
Open the file
Create one dedicated place, a physical folder, Google Doc, or notes app, that exists only for your dream path.
Pro tip Keeping it separate from everything else signals to your brain that it is real and worth investing in.
- 2
Feed it continuously
Whenever you learn something, meet someone, or have an idea related to the field, drop it in. The pile grows over months and years.
Pro tip Notice what you research in your spare time; those are the highest-signal entries.
- 3
Add people and conversations
Log potential contacts in the field and notes from any conversations you have with them. Relationships de-risk the transition.
- 4
Let it become real, then leap
As the file thickens with evidence and a plan, the leap stops feeling like a gamble and starts feeling like the obvious next step.
Pro tip You can begin the process before you make the leap; the file IS beginning the process.
Watch out Don't quit until the file gives you a direction; a change with no destination isn't a plan.
In the wild
While working as a computer engineer at Compaq, Gurley spent his spare time learning about and trading stocks, reading One Up on Wall Street and poring over one-page stock write-ups. That downtime curiosity was the tell; it pointed straight at the finance and eventually venture career he later built.
→ Left engineering for Wall Street and ultimately a 25-year VC career.
A real estate lawyer who loved offensive football diagrams started a site to help people design plays, then built software, then launched a podcast. He effectively populated a 'dream file' around a hobby until it became a full career.
→ 900,000 followers and a full-time career talking football strategy with the best in the field.
Common mistakes
Waiting for one heroic leap
Treating the change as a single terrifying jump ignores that you can build the plan, network and evidence gradually while still employed.
Ignoring your spare-time signal
The curiosity that already fills your downtime is the clearest data about your direction; discounting it leaves the file pointed at nothing.
Is it for you?
Best for
Someone with an inkling about a different path who lacks the confidence or concrete plan to act on it.
Not ideal for
People who already have a fully-formed plan and just need to execute.
From the transcript
“he said to keep your dream job... keep it in a manila folder in a file but you could create it in a Google Doc…”
“if you have some curiosity that's occupying your downtime, that's a really interesting tell.”
From the episode
If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071
Bill Gurley