The cheapest time to take a risk is when everyone tells you not to
Everyone around you tells you to play it safe early in your career.
Take the Big 4 graduate offer! It'll look good on your CV! It keeps your options open...
That advice in my view is backwards, and I've got a slightly painful story to explain why.
Earlywork almost didn't exist
A month before I was meant to start my dream graduate job at AWS, I pulled out of the offer to go full-time on Earlywork.
It was one of the hardest calls I'd made.
Plenty of people told me not to renege, that I should honour the offer and give the grad role a proper shot before betting on something uncertain.
I did it anyway.
About a year later, the AWS role I would have taken got made redundant... funny that.
I'm not telling that story to look clever, because I had no idea that would happen at the time. The way I made the call is the useful bit, not how it turned out.
The maths of being early
Early in your career is when your downside is smallest and your upside is the largest.
You have no mortgage, no family depending on you, and plenty of time to "recover" if things go sideways.
When I looked at Earlywork honestly, the worst case was that I learned a huge amount and went back to a "safe" graduate job a year later.
The best case had no real ceiling.
That's an asymmetric bet, where the downside is capped and the upside isn't, and asymmetric bets are always worth making.
The strange thing is that people take the least risk exactly when risk is cheapest.
Ten years later, with a mortgage and a team relying on them, the same risk costs a lot more.
Stop trying to be 0.1% better
Most people early in their careers spend their energy trying to be 0.1% better than the person next to them.
You see it most clearly in banking, consulting and law. A clear ladder, a fixed number of promotions and a culture built around comparison.
Whether you get the next promotion usually comes down to marginal stuff:
- Who put in a few more late nights
- Who built slightly better client relationships
- Who played the game a little more strategically
It's competitive, intense and crowded.
Now picture a different game, where you don't have to win by 0.1% because you're not playing on someone else's board.
Maybe that's starting something of your own, joining an early-stage startup or going deep on a niche most people overlook.
Yes, it's riskier, less structured and less predictable.
But you're mostly competing against yourself, and sometimes the race with fewer runners is the one most worth running.
A messy resume is a good sign
Before starting Earlywork, I never held a job for more than 9 months...
Different industries, different-sized companies, internships, part-time, full-time, all of it. Some I loved, some not as much.
I had this itch to work in a big company, so I did, and I hated it (sorry!).
But now I know with certainty that I love working in small businesses, and I didn't hypothesise my way to that conclusion.
The number one question I get asked is "how do I know what I want to do?"
The honest answer is you probably don't, and that's fine. The only way to figure it out is by trying stuff.
If your resume looks a bit all over the place in your early 20s, good. It means you're out there figuring it out rather than sitting on the sidelines waiting for certainty that's never going to come.
You don't have to quit tomorrow
None of this means everyone should resign on Monday morning.
Earlywork actually started as a side hustle. It was nights and weekends for a long time before it became my full-time work, and I know plenty of others whose stories followed the exact same path.
AI has taken the cost of building to almost zero, so there's never been an easier time to get started on something that's truly your own.
With so many people worried about what AI does to their job, having that thing might honestly be the safest career move going right now.
The catch is it has to come from real passion.
After a tough day at work you need to feel a pull to go work on it, not a push, and that pull only shows up when you're solving a problem you actually care about.