The Shadow Career Test
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 7
- Confidence
- —
Nat Eliason's method for detecting when profitable work is standing in for the work you actually want to do. Borrowing Steven Pressfield's idea of the shadow career from Turning Pro, he defines it as a career taken on because you are afraid of the real thing, which pays some other benefit large enough to blind you to the true cost. Money is the most corrupting version of that benefit, because success at the wrong thing brings social validation that reads as confirmation you are on the right path. His test runs on motive rather than outcome: if the primary reason you are doing something is money, interrogate it with the wealth thought experiment and the thirty-year question, then structurally remove the alternate income paths so you cannot drift back.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Ask what the primary reason is
For each significant commitment, name the main motive. If the honest answer is money, flag it for scrutiny rather than proceeding. Ali's version is to think twice, then three times, then four.
Watch out Legitimate money-driven work exists — Nat's SEO agency genuinely paid the bills. The flag is a prompt to examine, not an automatic no.
- 2
Run the wealth thought experiment
Ask whether you would still choose to do this if you had a hundred million in the bank. If the answer is no, ask whether you actually need the money. Usually the answer to that is also no.
Pro tip Ali describes calibrating this over time rather than getting it right immediately.
- 3
Apply the thirty-year question
Ask whether you could do this every day for thirty years and be happy even without a big financial outcome — whether it would be worth doing for its own sake. Work that passes is your infinite game.
- 4
Recover what the money was originally for
Trace back why you started earning in the first place. Nat took the SEO work in 2017 specifically to afford writing later, and somewhere along the way forgot that was the point.
Pro tip Write the original purpose down at the moment you take the funding work, so the drift is detectable later.
Watch out The forgetting is the failure mode, not the earning.
- 5
Cut at the peak, not at the trough
Exit while the money is still good, because the pull only strengthens with success. Nat quit crypto at the point where doubling down could plausibly have made him far more.
Watch out Waiting for a natural stopping point means waiting for failure, which never arrives on schedule.
- 6
Close off the escape hatches structurally
Forbid yourself from doing anything else that could make money until the real work supports you or the reserve genuinely runs out. Nat committed to writing as his only income path unless he had to go get a normal job.
Pro tip A hard rule beats case-by-case judgement, because each individual opportunity will look reasonable.
- 7
Pre-commit against the shiny objects
Expect lucrative adjacent opportunities to keep appearing — Nat cites a writing-with-AI course he estimated at six or seven figures — and refuse them on the rule rather than re-deciding each time.
Pro tip Ask what state you would be in two years from now if you took it and made no progress on the real work.
Watch out Each shiny object is individually defensible; the damage is cumulative years.
In the wild
Nat entered crypto to make money quickly so he could return to writing. Instead it consumed him — unhappy, worse relationships, worse health, and not fulfilling work, but extremely lucrative. At the decision point he could either go all in, become a full crypto influencer or join a VC firm and be positioned for the next cycle, or quit outright. He judged that the desire for money was blinding him to why he had started, and stopped. The reserve he retained was enough to fund several years of writing while spending it down.
→ Full-time writing, a published book and a sci-fi novel in progress, instead of a lucrative career he did not want.
Once committed to writing, Nat watched the AI tools boom arrive and immediately saw an opening: a course on writing with ChatGPT and Claude that he estimated could make six or possibly seven figures. He describes it as genuinely hard to refuse. The deciding frame was not the revenue but the counterfactual — going down that path for two years and then waking up with no progress on the writing. He declined it on the standing rule that nothing other than writing was allowed to make money.
→ The rule held and the writing kept moving, at the cost of a plausible six-to-seven-figure detour.
Common mistakes
Reading success as evidence of fit
Succeeding at the wrong thing generates social validation — you're so good at this, you're winning — which tells you to keep going precisely when you should stop.
Waiting for a clean exit point
The shadow career gets more attractive as it succeeds, so there is never a moment when leaving feels obviously correct. The exit has to be taken while the money is still good.
Keeping a side income open 'just in case'
Any remaining money-making option becomes the thing you drift back into whenever the real work gets slow or unrewarding.
From the transcript
“it sucks to try something and have it fail but sometimes it sucks more to try the wrong thing and have it succeed because success…”
“money is like the most corruptible tool for getting you stuck on the shadow career”
“I run the the thought experiment of like let's say I had 100 million in the bank would I still choose to do the thing”
From the episode
Chasing Success vs True Fulfilment - Nat Eliason
Nat Eliason