Explore Four Career Possibilities
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 7
- Confidence
- —
The ladder makes people reactive, and the most proactive thing they usually manage is a fixed plan — 2023 this role, 2024 that one — which leaves them blinkered and stuck when it doesn't materialise. Tupper's alternative is proactive career curiosity: instead of fixing the future, explore four kinds of possibility through conversations, not applications. The obvious possibility (the move everyone assumes you'll make), the ambitious one (interesting but currently out of reach), the pivot (who needs what you want to be known for, viewed through talents rather than job titles), and the dream (what you'd do with the constraints removed). Each is tested against your values and strengths, because a role that looks perfect on paper but doesn't need what you want to be known for will not energise you. Talking about them is the engine: possibilities become probabilities, which become positions.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Stop trying to fix your future with a plan
A linear plan of roles and years narrows what you notice and leaves you frustrated when those roles don't appear. Swap the goal from fixing the future to being flexible about it, and from planning to being proactively curious.
Watch out The plan itself is what makes people blinkered — they stop exploring around the roles they've written down.
- 2
Explore the obvious possibility
Everyone has a move that appears to make sense — your manager's job, the next grade up, or simply staying where you are because it's growing. Explore it properly rather than defaulting into it: talk to people doing it, sit in their meetings, observe it from a different angle.
Pro tip Test it against your values and what you want to be known for — if the role doesn't need that, it won't work for you.
Watch out Assuming that because a move is obvious it must be right is how people end up in roles that look good on paper.
- 3
Get close to the ambitious possibility now
The ambitious possibility is the interesting one that feels out of reach — more senior, or a sideways move into something you've never done. Have a conversation, make a connection, get close to the context. The closer you get, the sooner it becomes a reality.
Watch out The longer you leave it — 'I'm not ready yet', 'people will think I'm too ambitious' — the further away it will always feel.
- 4
Look at pivots through talents, not job titles
Job-title thinking forces every option to sound senior and similar. Instead ask who needs what you want to be known for — in your company, outside it, in this community, outside it. You start matching on talent, which opens options a title search never surfaces.
Pro tip This is the most enjoyable of the four to explore precisely because it isn't constrained by hierarchy.
- 5
Don't discount the dream
The dream is the unconstrained choice: what would you do if the real constraints — earnings, location, knowledge — were removed for a moment? Many people skip it because it scares them. Sit with it and ask a smaller question instead: what would you need to know about it, and who could you find that out from?
Pro tip Speak what you seek until you see what you said — if it only exists in your head, it is very unlikely to happen.
- 6
Have curious career conversations, not applications
Exploring does not mean applying for jobs — that's the opposite. Go and talk to people who are in or near each possibility to collect data for your development. Ask the questions that reveal fit: how much freedom do people have in what they work on and how they work?
Pro tip Listen for the answer that flags a mismatch as clearly as the one that confirms a fit.
- 7
Rule possibilities in or out, and let them compound
Some conversations will make a possibility sound amazing; others will rule it out, which is equally useful. Either way, you get closer to the possibility and the people connected to it become more aware of you — so possibilities turn into probabilities and then into positions.
Watch out Exploring without ever deciding is just another way of staying stuck.
In the wild
After concluding she couldn't develop the way she wanted in one organisation, Helen made sure her next move was informed rather than hopeful. She had curious career conversations with people in different positions and different companies, asking a question aimed squarely at her core value: how much freedom do people have in what they work on and how they work? She was explicit about the disqualifier — if the answer had been 'we have processes we have to follow', a flag would have gone up. What she actually heard was that everyone had their own project. She joined Virgin knowing the environment was likely to fit.
→ A move chosen on values-fit evidence gathered before joining, not after.
At Microsoft, the obvious possibility for Helen was her manager's job — the move everyone assumed she should make. Running it against her own criteria exposed the problem: the role didn't need what she most wanted to be known for. She had already chosen career development, not marketing, as her talent, and had been told in feedback that she spent more time understanding the people who worked for her than the company she worked in — harsh but true. The sensible-looking promotion would have looked good on paper while moving her further from the work that energised her.
→ The obvious next rung was consciously ruled out rather than defaulted into.
Common mistakes
Applying for jobs instead of having conversations
Exploring a possibility means getting closer to it through people, not submitting applications. Applications force a yes/no decision before you have any real data about whether the role needs what you want to be known for.
Defaulting into the obvious move
People take their manager's job or the next grade because it's the sensible-looking step. If it doesn't fit your values and doesn't need your strengths, it will look good on paper, drain you in practice, and reduce the impact you could have had elsewhere.
Waiting until you feel ready for the ambitious one
'I'm not ready yet' is a confidence gremlin, and it's self-defeating: the longer you postpone the conversation, the further away the ambitious possibility will always feel. Proximity, not readiness, is what closes the gap.
From the transcript
“that's the skill here really is to be practically curious about your career”
“the longer you leave it the further it will always feel away”
“speak what you seek until you see what you said”
From the episode
5 Skills To Succeed in ANY Career - Helen Tupper (Squiggly Careers)
Helen Tupper (Squiggly Careers)