For most of the last fifty plus years, the deal was simple. Get a job. Get safety. Trade upside for stability. If you wanted the upside, you had to take the risk. Entrepreneurship was the risky choice - sometime it paid off big-time but more often it did not.
That deal just broke. Quietly, but completely.
The 9-to-5 has become MORE dangerous. Without any increased reward.
And entrepreneurship - the thing your parents told you was reckless and a terrible idea - is now increasingly a sensible move.
The Frame Your Parents Taught You Just Broke
Common advice for most kids entering the adult world: get a job, work hard, don't take stupid risks. That advice was correct in 1995. It was correct in 2005. It was correct in 2015. It is no longer correct in 2026. Something shifted.
The reason it worked was simple maths. Jobs paid less but they paid forever. Businesses paid more but they could fail. You traded ceiling for floor.
But the floor is crumbling.
Something has gone horribly horribly wrong.
The Risk Flipped
This is the framework. If you only take one thing from today, take this.
In the OLD WORLD, the deal was clear. A 9-to-5 was small risk, small reward. Entrepreneurship was big risk, big reward. The risk-reward graph was symmetrical and the safe option was obvious. Most people picked the small risk. That was a rational choice for most - especially if you are risk averse.
In the NEW WORLD, the maths flipped. A 9-to-5 is now big risk, small reward. Entrepreneurship is still big risk, big reward.
The job didn't get less risky. It got more risky. AI is shrinking teams. Layoff cycles compressed from years to quarters. Skills that paid £80k five years ago pay £45k now or zero. Your industry can disappear in a fortnight - just ask anyone who was a stock photographer in 2023 or anyone who used to take Chegg gigs. Gonezo.
Business still carries risk, but business gives you upside. That's the entire point. That part of the equation hasn’t changed. It’s just now a LOT more sensible a risk to take than it was before.
Now I'm not telling you to quit your job tomorrow. In fact: keep it. Jobs are going to get rarer. KEEP your 9-5 for as long as humanly possible.
But you DO need to be thinking about what this means moving forward. What comes next.
Gen Z Is Already Doing It
The Guardian published a great pice on Saturday. Here’s the link: https://www.theguardian.com/technology/ng-interactive/2026/apr/25/gen-z-entrepreneurs-business-ai
Gen Z are getting hit hardest by shifts in the job markets. With insane joblessness levels and the painful task of sending out hundreds of applications for potential gigs only to be turned down (and ground down) by months of rejection.
The article focuses on the increasing number of Gen Z who realise its hopeless and have decided to go their own way.
When the traditional route is blocked it’s time to forge your own path. And that’s what they are doing.
These and more stories are in the article - highly recommend reading the original.
Importantly most of these young people didn’t PLAN to go this route. They all tried the traditional route first, hit a wall, and pivoted. This isn’t just Gen Z aren't being entrepreneurial because they're brave. They're being entrepreneurial because the alternative - waiting for a graduate scheme or finding a job that no longer exists - is worse. It’s necessity, not idealism.
Realise though that this is not just Gen Z. It’s just that Gen Z are the first to be affected. The canaries in the coalmine - sorry Gen Z. Because entry-level jobs are the first to fall to AI.
But … AI will roll up the chain. Unless you are within spitting distance of retirement you need to be ready for it to catch up.
I’ve been posting a lot recently about the need for everyone to wake up and realise what’s happening. It’s caused some consternation and (as is to be expected) argument. That’s good! We need to engage. Here are a couple of the objections.
Objection 1: "Not Everyone Wants To Own A Business"
I get this every time I post on this topic. "Not everyone wants to be an entrepreneur. Some of us just want a job. Why does everything have to be a hustle?"
Fair. I hear you. But you're answering the wrong question.
It's not about wanting. It's about the safety net being gone. Wanting a job is fine. Wanting a job in a market where the job is being deprecated is a problem. What you want at that point doesn’t really matter.
The question isn't "do I want to be an entrepreneur or start a business" The question is "what do I do when the thing I wanted to do isn't available."
Also, ownership is a spectrum, not a binary. Freelance is ownership. A side hustle is ownership. Consulting is ownership. Selling something you make is ownership. Multiple income streams is ownership. You don't need to "be an entrepreneur" with a capital E.
I’m not talking about becoming the next Steve Jobs, raising VC money and moving the San Francisco. I’m talking about carving out your own income to support yourself and your family.
67% of Gen Z say they want multiple income streams. Not because they all want to be founders. Because they've worked out, much earlier than my generation did, that single-income employment is structurally fragile. They know how fragile the system is and (correctly) want protection.
Objection 2: "AI Isn't Really Creative"
The other pushback I get: "Sure AI can do some stuff but it can't be truly creative. My job needs human judgement."
Two responses.
One: most jobs are not 100% creative or requiring judgement. Even very creative jobs are probably 60-70% routine. Drafting briefs, formatting decks, scheduling, processing email, writing the boring sections of a report.
Most jobs are full of boring BS.
AI does not need to be perfect to shrink a team. 70% is enough. If AI takes the routine 70% off ten people's plates, you don't need ten people anymore. You need three. Maybe. The other seven are unemployed despite being "creative."
Two: even the genuinely creative work is being commoditised. Look at what Claude Design and ChatGPT Images 2.0 did to "good enough" graphic design last week. Average is no longer a differentiator. Only the top 5% of taste-makers survive that compression. Are you in the top 5%? Be honest. If you are: great! You are genuinely going to be fine - congrats. But for the remaining 95% that’s no comfort.
I'm not saying creativity is dead. I'm saying "I'm safe because my job is creative or requires judgement" is the cope a lot of knowledge workers told themselves in 2023, and the data from 2025-26 has not been kind to that argument. If your defence against AI is that AI can't quite do what you do, that defence has a short half-life.
Objection 3: "I'm Out. Going Homesteading. "
The other end of the response curve: people who do believe that AI is capable. And for that reason are opting out. This comes in a few forms like "I'm out. I'll grow vegetables and raise chickens." Or a milder alternative “I’m going to work with my hands” / “learn a trade”.
Awesome!
I have so much time for this! A homestead is ownership. If you've already pivoted to a trade or running a smallholding, you're not the audience for this newsletter - you're already where I'm trying to get people. You’ve done it! You’ve taken control and made a decision.
The version I have less time for is doomerism as a strategy. "We're all going to be unemployed and money won't matter" is not a plan. It's a way of avoiding having to do anything. Even if you genuinely believe AI will collapse the labour market in five years, are you just going to sit and wait? What if you are wrong?
Agency beats passivity in any future.
You don't have to believe my version of the future to take action - you don’t have to start a business. But you have to do SOMETHING. Just waiting and hoping for the best (or the worst!) isn’t really a strategy!
What To Do This Week
Here are a few options. Start with whatever seems easiest - don’t think about what’s best. Best gets in the way of starting.
Sell your time. Freelance. Consult. Take on a service contract. Generally the easiest path to your first non-employer income. Start here to PROVE to yourself it’s possible.
Sell your knowledge. Coaching. An info product. A workshop. Take what you already know how to do and turn it into something other people pay you for once.
Sell something you make. A digital product. A physical product. A piece of software. A template, a notion doc, a course. Something you can ship that has your name on it.
Build an audience and monetise. Pick a platform. Show up daily. Two years in you've got something nobody can take away from you.
Build a tool with AI. This used to be the top of the ladder for technical people only. Now it's available to everybody. Vibe code a product, ship it, charge money.
Pick the smallest version. Start this week.
And here's the picture I keep coming back to. There's a guy in Lisbon with a folding table, a tablecloth, and some booze in a doorway. That's his entire “business”. He didn't wait for the perfect setup. You don't need the perfect setup either. You need the smallest possible version to start.
The single biggest blocker I see in entrepreneurs trying to start is "I'll launch when X is ready." The Portuguese booze seller has a folding table. You don't need a website. You don't need a logo. You don't need an LLC. You need to do the smallest version of the thing and find out if anyone wants it. Everything else is procrastination dressed up as preparation. It’s roleplaying business.
The New Safe Is Ownership
Doing the “safe” thing is now risky.
Experimenting with entrepreneurship and starting something is now the play.
Not entrepreneurship-with-a-capital-E. Not "quit your job and become a founder."
Just: own something, anything, even small. Even 5% of your income from something you own changes your psychology, your risk tolerance, and your options. The first £100 you earn outside your salary unlocks a different version of you.
Oh and if you want help working your precise next steps I built FreedomOS for exactly this. Diagnostic, framework, action plan. Sign up at Freedom OS.
Kyle