Get a job if you love risk
Think getting a corporate job is safe? AI changed the game: stable careers are now for risk-takers.
This week I hosted three Substack Live calls. Viewers could leave comments in real-time and even join the conversation, which made it more fun than podcasts!
When Lawyers Use AI with
There will be more Live streams next month; I’ll announce them in advance.
Employment was once the norm, entrepreneurship the exception. Soon, it will be the reverse.
I’ve been reflecting a lot on this recently. We’re so used to seeing the job as a default. My entrepreneur friends would say things like, Well, if my startup doesn’t work out, I’ll go and get a boring corporate job — at least the pay will be better.
My parents were understandably alarmed when I decided to start a business after uni instead of trying to join a company like Google — or any reasonable company, getting a job instead of a share certificate.
A job feels safe. It might not be perfect, but it’s there. Being an entrepreneur feels like a bold, daring choice for all the obvious reasons. You get all the trouble and insecurity upfront, and the business might start making money only much later, if at all.
But I wonder if this is changing, thanks to the AI impact.
Jobs are already hard to find. I could find some boring statistics, but I’ll cite some anecdotes.
Friends are forwarding CVs of people with good degrees in whatsapp groups with messages like, “in a tough spot” or “happy with a free internship”. A highly successful entrepreneur confessed that his daughter has struggled to find anything at all to start her career after uni, despite a good degree and his formidable connections.
Software developers I know who got used to be treated as royalty, started struggling to find jobs once big companies executed massive layoffs 2-3 years ago. I suspect the worst is yet to come.
When I talk to my founder friends, no one’s saying they’re struggling to hire, and if they do, it’s for rare specialist roles, often on contract or freelance, not perm.
This post from
is very long, but very entertaining, if I may use such word in this context, and despite colourful language, serious:even the people, perhaps especially the people, who have done everything right by interning, getting a good degree from a top university, networked, worked hard, are screwed. The only way to get a job now is through a connection, and much of that is timing, luck, and class.
The author’s in LA but I guess it’s not that different in London, or anywhere.
What’s the big deal, you might ask. After all, jobs, especially first jobs, have always been hard to find. Sometimes it’s easier, sometimes it’s harder. What’s the big deal?
The big deal is that jobs as we know them are not coming back and I have a strong intuition AI has something to do with it.
There are plenty of reasons why the job market feels hard, and I’ll leave it to economists. But going forward, a big, maybe the biggest factor, will be the impact of AI on employment that we’re already seeing.
Part of it is that AI can automate most work, so companies are, at best, stopping hiring because they can grow by leveraging technology, and, at worst, reduce headcount proactively.
Part of it is that much value creation these days and especially going forward requires an understanding and experience working with AI, regardless of the industry, role or seniority. This means more demand for people who know who to apply AI to existing problems, but less demand for people who don’t — and that’s the vast majority. The skills that were valuable in pre-AI world look less valuable going forward.
Part of it is that junior work is often the easier to automate. Junior lawyers who could once get experience reviewing contracts don’t get a chance now that solutions like DraftPilot (I had a Substack Live with its founder
this week) use AI to do this for lawyers.What a senior decision-maker could have delegated to their team to research, now can be done by Deep Research in minutes. A senior decision-maker wins, but now they don’t need their junior analysts anymore.
And a very big part of it is that we’re beginning to see just the very first, timid signs of where it’s going. The AI progress is exponential and unstoppable. (Btw, an excellent book that I wish were a required reading for everyone today is The Coming Wave: it outlines what’s coming and why.)
Looking at these signs, I believe that employment was once the norm, entrepreneurship the exception; soon, it will be the reverse.
By this I don’t mean that everyone will literally become a sole trader or register a limited company and raise funds from investors. No, most people will still have jobs with employment contracts and a salary at the end of the month. But the nature of these jobs will change.
Consider my friend James McAulay who joined ElevenLabs, one of the hottest AI startups in London, in a Growth role. He’s one of the few people I know who got a really cool job recently.
James wrote 11 Lessons from my first 11 weeks at ElevenLabs. The entire post is worth reading, but look at this gem:
Just before I joined, ElevenLabs announced that it was doing away with formal job titles. Instead of spending time negotiating a fancy title for myself, I simply joined the Growth Team and added "Growth at ElevenLabs" to my LinkedIn.
Working without a title means you rarely come across a piece of work and think "This is above me" or "This is below me" - if you see a problem to solve, you solve it.
It gives everyone the autonomy to run towards the highest-impact problems they can find, without needing to run everything through a team lead. I think it's created a very fluid and flexible organisation, which might not be right for everyone, but it's producing good results for us.
This is entrepreneurial behaviour and skillset. Sure, it may be a job on paper, but what James is doing is looking for problems to solve and solving them, even without a formal title, in a “very fluid and flexible organisation”.
The entire company is growing like wildfire because it’s full of people like James who look for problems to solve and solve them like entrepreneurs. And maybe it’s not a coincidence that before getting the job at ElevenLabs, James was a founder and CEO at Encore (check out the podcast I recorded with James about how he sold Encore).
This is what I mean that we’ll all be entrepreneurs going forward. People who can act and think like entrepreneurs, will be part of “very fluid and flexible” organisations like ElevenLabs or maybe start their own companies or go freelance. And people who can’t do that, who need a job spec and clarity on what’s needed to deliver and how it needs to be done, will be competing for an increasingly small pool of good, old-fashioned jobs.
Have you seen the recent memo from Shopify CEO? It’s worth reading in full because it’s where things are going for everyone, but here are a couple of highlights:
Using AI effectively is now a fundamental expectation of everyone at Shopify. It's a tool of all trades today, and will only grow in importance. Frankly, I don't think it's feasible to opt out of learning the skill of applying AI in your craft; you are welcome to try, but I want to be honest I cannot see this working out today, and definitely not tomorrow. Stagnation is almost certain, and stagnation is slow-motion failure. If you're not climbing, you're sliding.
Before asking for more Headcount and resources, teams must demonstrate why they cannot get what they want done using AI. What would this area look like if autonomous AI agents were already part of the team?
“Learning the skill of applying AI in your craft” here doesn’t mean “I’ll use Figma AI instead of Figma”. It doesn’t mean “I’ll use ChatGPT instead of Google to find answers”. It means doing what James is doing at ElevenLabs: using all power of AI tools evolving at breakneck speed to find innovative solutions to emerging problems before your employer tells you what to do or how to do it. This is entrepreneurial skill set.
The reason it’s happening is simple. Companies can’t tell you what to do or how to do it anymore. Tobi at Shopify and his senior team can’t just cascade down quarterly goals anymore. Leaders know intuitively that the world and AI move faster than they can respond with traditional structures, so they are giving up a great degree on command-and-control, letting go of structures and doing what ElevenLabs are doing: defining the mission, defining the context (what matters and why), building basic infrastructure (see James’ post for some details) and letting internal entrepreneurs run wild learning, building, shipping and winning.
And that’s why employment was once the norm, entrepreneurship the exception. Soon, it will be the reverse.
Maybe it already is the reverse in some industries, but all industries will be forced to catch up soon. As I’ve said when I compared the coming AI impact on employment to USSR collapse:
First, resilience, entrepreneurship, and adaptability will be paramount. By entrepreneurship, I mean the broader mindset of proactively creating and adapting, not just owning a business. Those capable of quickly pivoting careers, continuously learning, and creatively solving problems will thrive, much like post-Soviet entrepreneurs. Creating our own opportunities and not relying on others to offer us a job is going to be a must-have skill.
Ten or twenty years ago, I would have said that getting a job is a safe choice. Those who are adventurous and like risks, can go and open their own business. Today, I would probably give the opposite advice to most young people starting out.
The safe choice going forward is learning how to find your own clients, sell your own products and services, send your own invoices and maintain a diversified client base. It’s safe because it makes you resilient in a rapidly evolving environment. You’ll apply this skill set either on your own or inside a company like ElevenLabs.
But if you feel adventurous and like risks, go get a job with a large company in a specialist role, expecting the HR team to send you to corporate training, and climb a career ladder. It might pay off, but hey — you’ve been warned.
Great post, and a discussion that isn’t being had enough.
It’s such a special time to be building, that apart from a very few small number of exceptions, taking a job right now feels like short term gain exchanged for long term pain.
This is exactly the conversation we need to be having.
The middle class is not just being “impacted” by AI. It was always a systemic function—part buffer, part myth, part subsidy. And now that function is dissolving.
Jobs are disappearing not because there’s no work left, but because the value chain has been digitized past the need for middle-tier cognition. We are witnessing the soft disintegration of economic legibility for millions of people whose roles were always more infrastructural than meritocratic.
I wrote about this collapse here:
🧾 The Middle Class is a Semi-Meritocratic Pseudo Universal Basic Income
https://sonderuncertainly.substack.com/p/the-middle-class-is-a-semi-meritocratic