Why careers are becoming like showbiz
From linear careers to constant experimentation
Most people are still planning careers like it's 1995.
Five-year plans. Linear progression. Build expertise, climb the ladder, retire with a pension.
But time itself has compressed.
Dror Poleg, economic historian and author puts it bluntly:
“The predictable 'paint by numbers' career path is getting shorter and shorter.”
This compression of time is fundamentally changing how a career will form.
As Dror explained on this week’s Ollie on Work podcast:
“It looks much more like showbiz. You have to accept the fact that you're facing much more uncertainty than you thought.”
At first, this sounds terrifying. But it's actually liberating.
Think about how actors, directors, and producers actually work:
Project-based: They move from project to project, building different skills and relationships each time.
Portfolio approach: They're simultaneously developing multiple opportunities - some will fail, others will succeed unexpectedly.
Reputation-driven: Success comes from a track record of delivering, not from climbing an organisational hierarchy.
Network effects: Who you know and who knows your work matters more than your job title.
Constant reinvention: They adapt to new technologies, audiences, and market demands rather than perfecting one skill forever.
Sound familiar?
This is exactly how the most successful people in tech, consulting, and creative industries already operate.
The difference is they're doing it intentionally while everyone else is still pretending the old model works.
Why this matters now
Three forces are driving this shift:
1. AI is commoditising knowledge work. What took teams months now happens in minutes. The value isn't just in knowing how to do something - it's in knowing what's worth doing.
2. Companies can't predict what they'll need. When technology changes every six months, hiring for "five years of X experience" makes no sense. The skills you need to add value are fundamentally changing.
3. Remote work broke geography. You're no longer competing with colleagues down the hall. You're competing with talent worldwide.
And, Dror points out:
“AI doesn't just replace workers - it replaces institutions.”
The structures built for the industrial economy - including how we build careers - need complete rethinking.
The practical framework
If careers are becoming like showbiz, here's how to approach yours:
Think in projects, not jobs
Instead of asking "What's my next role?" ask "What's my next project?"
Your project might not look like a traditional job - it might be a podcast, a niche app, or a paid community.
Projects have clear outcomes, defined timelines, and measurable results. They also end, forcing you to continuously prove your value rather than coasting on past achievements.
Build a portfolio of experiments
“Everyone will need to experiment constantly rather than following set career paths.”
This means running multiple small experiments simultaneously:
A side project that tests new skills
A different type of client or industry
A collaboration with someone outside your usual network
Learning a complementary discipline
The thing is, not all of this will be clear cut. As Dror points out:
“More and more of our work will seem useless until it is useful.”
The work that looks pointless today might be the thing that changes everything tomorrow. Momentum comes from constant output, not perfect planning.
Most will fail. One might change everything.
Optimise for stories and network
In showbiz, your next opportunity comes from the story of your last success and who knows about it.
Stop optimising for job security (which doesn't exist anyway) and start optimising for compelling stories you can tell about problems you've solved.
Your network isn't just professional contacts - it's your career infrastructure. These are the people who will know about opportunities, recommend you for projects, and collaborate with you on experiments.
What to do this week
1. Audit your current ‘experiments’ What are you testing outside your main role? If the answer is “nothing,” that's your first problem to solve.
2. Identify one showbiz-style project Something with a clear outcome, timeline, and story you could tell afterward. Start it.
3. Practice explaining your value in stories Stop talking about your job responsibilities. Start talking about specific problems you've solved and results you've created.
The showbiz career model feels uncertain because it is.
There's no guarantee that your next project will lead to anything. Your experiments might fail. Your network might not come through.
But AI is in the process of disrupting everything. Take this as an opportunity to start building something new. And embrace the fact that experimentation - discovering new opportunities, meeting new people - is exciting.
If you start building your showbiz-style career today, you'll have options when everyone else is scrambling to figure out what happened.
The stage is yours…
Ollie
Listen to my conversation with Dror Poleg on this week’s Ollie on Work podcast, here.
Interested in me sharing insights on these topics with your team? Book a free consultation - HERE