Vibe-Based Career Decisions
Exploring how to put trust in what feels right, not what looks certain
Hi friends, it’s Tom 👋 back from two weeks in Portugal where everything was glorious until the power went out on our final day. Behind the scenes I’ve been working with a pal to create an exciting new offering, which will run alongside my coaching practice. I’ll share more soon, but for now, know that the tips in this post are fresh and have helped me work through where to invest my own energy. I hope this is useful for anyone else working through a big career decision at the moment.
I used to have two rules of thumb for my career:
Follow the conversations you wish could continue, and the roles that enable them.
Leave jobs after two years, plus or minus a year. Because after this point your rate of learning hits diminishing returns and you’ll grow overly familiar with a single environment, making it harder to adjust to others.
Since striking out on my own I’ve found myself re-visiting and expanding these to build a set of tactics that make sense for where my world is today and the clients and projects I take on tomorrow.
While I initially leant heavily on data to make the ‘right’ decisions, I’ve increasingly found myself drawn to intuition and gut feel on my biggest moves. And it’s liberating.
‘Vibe coding’ has drawn both fans and skeptics. But to me, the underlying idea is about leaning into intuition as a way to move forward at pace, in a world increasingly caught up in change. The most authentic path, is one that’s liberatingly human: just follow the vibe.
I figure at this point one of two things will be true:
Your eyes have glazed over and you’re about to open another tab OR
You’re curious to read about some of the tactics I’m trying
Let’s get tactical. If you’re weighing up a career decision, here are prompts I’ve found useful.
Where does your mind wander on holiday?
When you’re away from your day-to-day, where does your brain go to recharge its creative juices?
I’ll admit, I’m terrible at beach reads. Many years ago, as I laid on a picturesque beach in Portual, I found myself pulling out ‘Design is a job’ by Mike Monteiro. A book on design ethics and moral frameworks for design leaders. Of course, my wife laughed at me. But at the time I had recently transitioned into people management and felt deeply inspired by soaking up as much of the literature in this space as I could. This was energising for me.
I wouldn’t recommend business books on holiday, but if you reach for one anyway, ask yourself: Why this? What’s it nourishing in you?
Lean into what expands you vs contracts you
You’re probably familiar with the idea of reviewing your calendar for what activities bring you energy or drain you. If not, here’s a great overview from Carly. I’d highly recommend trying it. But depending on the amount of reflection you have space for, there’s a risk of focusing too heavily on the surface-level, short-term feeling, rather than long-term sustainability.
For comparison, let’s consider going to the gym for the first time. That first day probably feels extremely draining and unfun, but give it enough time and momentum and there’s a good chance you’ll be on track for it to feel energising for you. In other words, how comfortable you already are with the activity has a large impact on how energising it can feel afterwards.
A clearer model for personal growth: Which activities expand you, and which ones contract you? Going to the gym for the first time might still feel draining, but approaching the activity with a gentle, growth-oriented mindset can help position this experience as ‘expanding’ your future growth.
Where possible de-couple your current environment from your next move
Beyond the job itself, context matters. Your environment—ways of working, team support, org culture—shapes how work feels.
In other words, an activity you find energising or draining in one context can be the opposite in another.
I’ve seen this in folks who jumped from big tech to startups but miscalculated the lack of support they’ll get in hiring or growing their team; or from founders joining scaling companies who miss the total autonomy they didn’t realise they craved.
Another layer is the influence your calendar plays. Back-to-back meetings make it hard to know what’s truly rewarding, and what just offers momentary relief from stress.
It’s great to try new roles of course, but if there’s even a hint that you could be over-correcting, it’s worth leaning into that feeling as part of deciding your next step.
Type 1 vs Type 2 fun
On a recent podcast Monzo CEO, TS Anil explained how he thinks about Type 1 vs Type 2 fun. I’ve only respect and admiration for TS, and his analogy really resonates on this theme.
Essentially, Type 1 fun is something immediately and obviously fun, like laying on the beach or eating a delicious snack. Type 2 fun can feel more challenging in the moment but leads to longer-term ‘fun’ in the future and a richer life story. For instance, skipping that Netflix show to train for a marathon or staying inside to write another chapter of your novel while missing the beautiful sunshine outside.
Both types of fun matter. But Type 2 fun is often most nourishing for the future you want.
Decide with your body
“If you find yourself caught up in your head, get into your body”
This wisdom comes from Vuokko, my pal and former partner-in-crime (so to speak) at Monzo. It’s a mantra I increasingly find myself reaching for when there’s a big decision to work through. Whether it’s long walks through the forest or a speedy 5K before the kids wake up. I find that getting my body into a state where my intuition can flourish makes decision making infinitely easier. Decisions I’ve been weighing heavily quickly come into focus and start to ‘snap to grid’. Another Vuokko-ism for when the boundaries around a decision becoming clearer and more aligned (or misaligned) to the larger system you’re making sense of.
Interview yourself
Of course, there’s always a way to incorporate AI. Especially when it comes to vibes.
The tactic I’ve found most helpful in working through big decisions is having it interview me in voice mode. I’ll explain the decision I’m looking to make, as much context as I can, and then have it ask one question at a time to help me work through and unpack which path feels most intuitive.
I find voice mode much better at activating intuition because it encourages your immediate stream of consciousness, not a blank page with your inner editor popping out from behind your shoulder to sense check every word.
Don’t expect AI to give you the answer. Use it as a mirror to hear yourself more clearly. Of course, you can also do this with an actual human too, but AI is often the quickest path to getting unstuck and building forward momentum.
Key takeaways
To recap, here are six tactics to try the next time you’re making a big career decision:
Tune into your intuition during downtime
Ask yourself: Where does your mind wander when you’re on holiday?
Reflect on the books, ideas, or topics you gravitate toward when you’re not “supposed” to be thinking about work, they might reveal where your deeper interests lie.
Map what expands you vs. contracts you
Try this exercise: Review your calendar and activities to assess which ones feel expansive (growth-promoting) vs. contracting (limiting).
Distinguish between what drains you now but expands you long-term (like going to the gym) and what drains you full stop.
Separate the work from the workplace
Ask yourself: Is this activity inherently draining, or is it just this context?
Consider whether the environment—culture, support systems, calendars—is skewing your experience of the actual work.
Reflect on your personal “fun” mix
Ask yourself: Am I investing enough in Type 2 fun, the kind that leads to longer-term fulfilment?
Make conscious trade-offs between short-term comfort and long-term reward in your career and side projects.
Make decisions with your whole body
Try this practice: Go for a walk, run, or movement session to help decisions ‘snap to grid.’
If a choice feels like a ‘whole body yes,’ it’s probably worth paying attention to.
Use voice to bypass your inner editor
Try this prompt with AI or a friend: “Can you ask me one question at a time to help me work through this decision?”
Talking out loud (especially in voice mode) helps bypass overthinking and lets your intuition surface more naturally.
You made it to the end! I appreciate you! Until next time,
— Tom