Episode 389 - Planning a Career Change When You Do Not Know Where to Start (2026)
Sunday evening, with the light fading and the weekend nearly over, has a particular way of surfacing a quiet, heavy feeling for people whose work, while not disastrous, simply is not what they are meant to be doing, paired with the genuinely uncomfortable fact of having no clear idea what the alternative even looks like. In this episode, Robin speaks directly to that specific, common feeling, and shows how artificial intelligence can help structure the genuinely difficult, often paralysing early stage of a career change, before any concrete plan exists.
The episode walks through practical, non-generic ways to use AI for career exploration, including identifying genuinely transferable skills from your current role that you may be undervaluing or not recognising as marketable elsewhere, researching unfamiliar industries or roles in plain language before committing time to exploring them further, and drafting a realistic, staged transition plan rather than expecting a single dramatic leap. Robin explains how to use AI to prepare thoughtful questions for informational interviews with people already working in a role you are curious about, how to reframe and rewrite a CV to highlight relevant experience for a different field, and how to manage the financial and practical planning that any serious career change requires, without pretending the process is quick or risk-free.
The episode is honest about the emotional dimension of feeling stuck in the wrong career, including guilt about wanting change when "nothing is technically wrong," and fear of the unknown that keeps many people scrolling job listings they have no real intention of applying to. Robin frames AI here as a low-stakes exploration partner, useful for research, structure, and rehearsal, while being clear it cannot make the decision for you or replace a qualified career counsellor for anyone facing a particularly complex transition.
This episode suits anyone feeling quietly unfulfilled at work, people considering a significant career pivot without a clear plan yet, listeners overwhelmed by where to even begin researching alternatives, and anyone tired of scrolling job listings without ever applying. It speaks to search terms including planning a career change, finding transferable skills, career pivot for beginners, using AI as a career coach, and overcoming career uncertainty in 2026, closing with a specific, manageable first research task to try this week.
Robin offers a specific research method within the episode: listing every task currently performed in your role, asking an AI assistant to translate each into transferable skill language relevant to a target field, and using that reframed list to identify roles that genuinely fit rather than roles that merely sound appealing from the outside. The episode also covers preparing for informational interviews, including specific, thoughtful questions to ask someone already working in a field of interest, and how to interpret their answers honestly rather than through rose-tinted assumption. Robin closes with a single, manageable first step: one informational conversation booked within the next two weeks, treated as research rather than a job application, in 2026.
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