Prove the Side Hustle Before You Quit
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 6
- Confidence
- —
A de-risking sequence from an affiliate marketer who left a London marketing job at 36 after a year of evenings and weekends. The mechanism is that quitting feels like risking your whole salary, but the real exposure is only the gap between your current pay and the job you could reasonably get again — a few thousand pounds, not thirty. You compress that gap further by refusing to quit until the side income is real, banking a stripped-down runway from the side income itself, and setting an explicit deadline with a named fallback. The year of practice does double duty: it produces the money and the confidence, because small wins arriving at intervals prove the model works before you have anything at stake.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Find people already doing it and check they are not geniuses
Go to events and meet the people earning what you want to earn. If they are bright but not rocket scientists, you have evidence the constraint is effort and learning rather than raw talent.
Pro tip Meeting them in person is the point — it converts an abstract income figure into a person you can benchmark yourself against.
- 2
Learn by practising, not just consuming
Learn the skill by listening to podcasts, reading online and actually starting projects — building the websites, running the campaigns — while still employed. Bodge your way through at first.
- 3
Work the evenings and weekends for a bounded season
Run the side hustle in the hours you have — 7pm to 11pm on weekdays plus weekends — treating it as a defined period rather than a permanent way of living.
Pro tip Keep the season explicitly time-boxed; the guest worked one crazy year and then deliberately finished at 2 or 3pm afterwards to make up for it.
Watch out This is genuinely outside your comfort zone and harder than is healthy over a long period. It is only defensible because it ends.
- 4
Hit a real monthly number before considering the jump
Continue until the side income is materially real — in his case roughly £1,000 to £2,000 a month — and until you can honestly say you know how to do this and that more hours would produce more money.
Pro tip Track the leading indicator, not just revenue; with SEO he could watch rankings move on extra effort, which sustained belief between paydays.
- 5
Bank a stripped-down runway
Save enough from the side income to cover the mortgage and bills for six months. Stripped of everything but housing and food, that number is far smaller than people assume.
Watch out Fund the runway from the side hustle during the practice year rather than from savings you would otherwise need.
- 6
Set a deadline and name the fallback
Give yourself a hard window — six months to match your old salary — and state the fallback explicitly: if you miss it, you go back and get the same or a similar job. Experience makes that fallback credible, which makes the leap low-risk.
Pro tip Say the deadline out loud to a partner or friend so it becomes a commitment rather than an intention.
Watch out If you talk about it and practise at it forever you are never going to do it. At some point the hard decision has to be made.
In the wild
Living in the countryside near Aylesbury and commuting an hour and a half each way to London, the guest needed to work from home for personal reasons and found no marketing jobs of merit locally. He set his computer up in the lounge with a mirror angled so he could watch TV while working, ate dinner with his wife at six, worked from seven to eleven, and did the same at weekends for nearly a year. He saved enough to cover the mortgage and bills for six months, told his wife he would give himself six months to match his salary, and quit. He was earning more than his salary within three.
→ Replaced a full salary in three months and permanently reclaimed three hours a day of commuting.
Ali reframes the arithmetic that stops most people. Someone in a £30,000 job treats resigning as putting £30,000 at risk. But if they could realistically get a £28,000 job next week, the true exposure is the £2,000 gap between the job they hold and the job they could get back — and even in a worse case, a £25,000 to £28,000 role is very reasonable. Set against the upside of going all in on yourself, the calculation changes shape entirely, and he notes he doesn't know anyone who made that jump and regretted it.
→ The decision reframes from an all-or-nothing gamble into a small, recoverable downside.
Common mistakes
Quitting the job before proving the side hustle
Ali's repeated advice is not to quit until you have done it for a while in evenings and weekends. The guest is explicit that he would never have jumped without a year of practising and learning first — the practice is what produced both the income and the confidence.
Treating your salary as the size of the risk
Quitting a £30k job is not a £30k risk when a £28k job is available next week. Sizing the downside as the gap between jobs, not the whole salary, is what makes the move rational.
Letting the crunch season become permanent
The guest's defence of the crazy year is that it was one year out of a fifty-year life, followed by deliberately shorter days. The other guest on the same episode describes 110-hour weeks for months that led to burnout and hating the thing he loved — the difference is whether the season ends.
From the transcript
“so i used to get home from work at say six o'clock on a work day um have my uh meal with my my wife…”
“i'm going to give myself six months if i can't get the same amount of money i get my salary within six months i'll go…”
“but yeah i put enough money to one side to pay the mortgage pay all the bills for six months which is not a lot…”
From the episode
6 Lessons That Improved My Life - Season 2 Round Up
Season 2 Round Up