How do we design a work life that’s uniquely ours?
We’re trying a new thing for 2026: we’re always on — no long intro, no warm-up, just straight into the conversation. Which is perfect for this episode, because it’s all about dropping the script we’ve inherited about what a “proper career” is supposed to look like.
Alice Phillips and Dan Emery are joined by Charlie Rogers, founder of Undefineable Life Design and author of a new book (out March 4) rooted in one big idea:
We were never meant to be one thing.
In a world where job titles are unstable, AI is accelerating change, and the old social contract feels increasingly broken, Charlie makes the case that the safest and most fulfilling path forward is to stop forcing yourself into one label — and instead design a working life around what makes you uniquely you.
What is an “undefinable”?
Charlie defines an undefinable (ironically, by definition) as someone who lives beyond conventional labels.
It’s the person who gets slightly uncomfortable when asked, “So… what do you do?” not because they’re lost, but because the real answer is layered. They’re not just one role. They might have multiple income streams. They might be evolving fast. They may have outgrown old identities. And they’re more interested in leading with purpose and value than a one-word job title.
Charlie’s point isn’t that job titles are useless — it’s that they’re often a shortcut that triggers assumptions. When we move beyond them, we invite deeper connection and more accurate understanding of who someone is and what they bring.
Why this matters more now
We explore the push-and-pull forces making “undefinable careers” more common:
People who were always multi-dimensional, but never had language for it
People who followed a traditional path — and discovered it wasn’t theirs
And the wider shift in the market: AI, volatility, and the end of a single linear ladder
Charlie’s core thesis: your best protection in an AI world is not being average at one thing — it’s being meaningfully unique across several. He calls this the “automation of the average”: when everyone can generate competent output, your edge becomes your distinct blend — your lived experience, your voice, your taste, your synthesis.
The model: The Undefineable Ascent
Charlie’s book lays out a practical framework for designing a life and work identity you can actually sustain — financially and emotionally.
He uses a metaphor he calls The Undefineable Ascent, which begins with creating your destination: a Purpose Acropolis — the structure you want to build your life around.
It’s made up of five parts:
1) Your many interests (the raw ingredients)
Not just what you’re “good at” professionally — but the things that have been with you across life stages, including childhood interests, cultural influences, and recurring obsessions. The aim is expansion first: permission to name the full range of what’s in you.
2) Categories (grouping the chaos)
You then group interests into bigger buckets that give you room to grow — the kind of categories that can evolve as you evolve.
3) Your keystone: the Golden Thread
This is the connecting purpose — the underlying “why” that links your categories. It’s what makes your blend yours, not just a random set of hobbies.
4) Signature Expression (how it meets the world)
This is your distinctive way of delivering value — your style, your format, your lens. Charlie’s example: he’d rather design intimate spaces than big auditoriums, because that’s where he connects best.
5) Value streams (the pillars that fund and sustain it)
Not just direct income, but the whole ecosystem that supports your life — including family, rest, community, health, and time. Because the point isn’t to build a “successful” life that burns you out.
Semi-pro, not obsessed: the case for breadth with depth
One of the most useful distinctions Charlie makes is this:
Don’t aim to be “professional” in one thing and amateur in everything else. Aim to be semi-pro in a few things that combine uniquely.
He illustrates this through a personal story from endurance sport — reaching a high level, seeing what it would truly cost to become elite, and realising that identity obsession can kill joy. The lesson translates directly to work:
You can go deep enough to be credible and exceptional — without making one narrow identity consume your whole life.
The missing piece most career advice ignores: energy
Charlie’s framework explicitly pairs income strategy with what he calls an energy toolkit — a way to manage pace, capacity, and sustainability.
His point is blunt: if your body is signalling strain (the “blisters”), you can’t ignore it forever. A life design that only optimises for income, status, or output won’t hold.
Why Gen Z is especially drawn to this
Charlie shares why this thinking resonates strongly with younger workers:
Many graduated into disrupted conditions (COVID as a career cliff-edge)
Hybrid and remote work feel “default,” so presenteeism without purpose feels pointless
Traditional milestones (home ownership, stability) feel out of reach, creating a “what’s the point?” drift
AI adds pressure and uncertainty about what roles will even exist
Result: people get pulled to extremes — grind for high upside, or opt out and chase short-term freedom — because the “normal path” feels less believable.
Undefinable Life Design offers a third route: clarity without confinement.
What organisations need to learn from this
We end by zooming out to workplaces. If careers are becoming less linear, what should employers do?
Charlie suggests organisations should stop treating employment as the only relationship model — and start thinking in terms of ecosystems. He talks about an “advocate lifetime value” mindset:
An employee might work with you for 18 months — then become a referrer, a future client, a supplier, or part of your broader community. Companies that design for that long-term relationship (rather than trying to force loyalty through outdated structures) will be better positioned for the next era of work.
Where to find Charlie
Website: undefinablelifedesign.com
LinkedIn: Charlie Rogers
Book launch: March 4 (with a launch squad opening in early February)
