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The career pivot playbook: how to know when it's time for a change

4th Sep 2026

Around 4 million people have changed careers since the pandemic, CIPD estimates, but the pathway to making a professional change isn’t always clear. That’s why we brought together experts who’ve navigated their own career pivots to share their experience, alongside tips that’ll help you do the same. 

Almost half of UK workers (42%) expect to retrain or pursue multiple careers. That’s according to Canda Life’s Life100+ research programme, which also found that 65% of UK workers agreed that there’s no longer a linear path from learning to working and retiring, and that we need to consider more adaptable approaches. 

When people do decide it’s time for a career change, half (46%) don’t know which path to take, LHH found

Our webinar panel of career-change experts have their own experience of this topic: 

  • Webinar host Gee Foottit helps people make their own career changes at St. James's Place Financial Adviser Academy
  • Isla Brown moved from law to financial advising in her late thirties by retraining through St. James's Place's Financial Adviser Academy. 
  • Sam Cross left teaching and took an exploratory approach, trying coding bootcamps, cyber security, and project management courses in the evenings before settling on project management at BAE Systems.
  • Rob Fulford left academia after 12–18 months of deliberating and pivoted to a career in talent, employer branding and diversity and inclusion at SAP.

They discussed what it really takes to know when to leave, how to find what's next, and how to make the leap without losing yourself in the process in our webinar, which you can replay here.

Why people stay too long

Rob described the pull of investment and guilt: years of deep, specialised academic study had gone into the career he eventually left, and stepping away felt like letting down the people who had supported him along the way. He estimated it took 12 to 18 months from first having the thought of changing careers to actually acting on it, something the panel agreed is a fairly typical timeline for a genuine career pivot.

Sam's version of guilt came from the gap between the idea of teaching and the reality: long evenings marking, weekends lost to school trips, and a toll on her health and relationships that built up gradually rather than all at once.

Isla spoke about a different kind of resistance: the fear of having "wasted" years of study and training by changing direction, and the nagging sense of being too old to start something new in her late thirties.

"I think people stay in their comfort zone out of fear and uncertainty… and that's why these conversations are so important." — Isla Brown, St. James's Place Financial Adviser Academy

Telling a rough patch from a real signal

Sam described noticing a shift in her own priorities and what she called her "moral compass," realising she wanted to be present for the small, ordinary moments with her children rather than only seeing them on weekends. She was clear that talking about it early, rather than bottling it up, made all the difference.

Rob's experience was more instinctive: paying attention to the kind of work that genuinely energised him, and trusting that even a career built in one narrow field would transfer elsewhere. Isla's advice was to take the long view: picture yourself decades from now, looking back, and ask honestly whether you'd be happy with the choice to stay.

"Sometimes you only know what the job is like when you're in it… as that began to dawn on me, that was when I began getting this sense of what is right for me versus not right for me." — Rob Fulford, SAP

Working out what's next

Sam took a deliberately exploratory approach, trying coding courses, a government-run skills bootcamp, and cybersecurity and project management courses in the evenings, at her own pace, before eventually landing in project management. 

For Rob, there were two very different ways to pivot: the first meant actively advocating for a role that didn't exist for someone with his background, and the second meant deliberately starting at the bottom in a small, unglamorous recruiter role to learn a completely new craft from the ground up.

Isla's advice was simpler still: talk to people. She described reaching out to women already working in finance, including cold messages on LinkedIn, and encouraged anyone considering a pivot to do the same rather than trying to figure it all out alone.

Naming your transferable skills

A recurring theme was that people chronically underestimate the skills they already have, often because it takes someone else pointing them out for them to notice. Sam described a moment on her project management course when her tutor told her to look back at her time as a teacher, at which point she realised she'd effectively been running scheduling, budgets and stakeholder management in the classroom the whole time.

Rob's advice for identifying transferable skills leaned on tools as well as reflection: using AI to help extract skills from a CV, then pairing that with genuine, personal storytelling in interviews.

Isla made the case for prioritising EQ, or emotional intelligence, over technical credentials, arguing that the ability to build trust and communicate well is what really carries someone through a pivot, while technical knowledge can always be learned along the way.

"People buy from people, and they always will. They won't remember what you say, but they'll remember how you make them feel." — Isla Brown, St. James's Place Financial Adviser Academy

Using AI without losing your voice

Rob was candid that AI is reshaping recruitment and can genuinely help identify patterns and common threads across a career history. His caution was about output, not input: whatever tool you use, the final result needs to reflect an authentic, individual voice, not a generic version of "why I want this job" that a hiring manager has seen a hundred times before.

Talking about a pivot with confidence, not apology

Isla encouraged people to reframe a pivot as a genuine USP rather than something to explain away: investing time and money into retraining is proof of commitment, not a gap to be justified. Sam echoed that authenticity matters more than a perfectly matched CV, adding that employers increasingly want people who will challenge the status quo, not simply follow it.

Facing the financial reality

Rob was upfront that a pay cut is a real and valid concern for many candidates, not something to just dismiss, and said he managed it by focusing on the longer-term trade-off in work-life balance and opportunity. Sam described a significant hit to household income when she left teaching, offset in part by building small additional income streams alongside her apprenticeship. Isla framed it as a household decision rather than an individual one, involving a genuine reset of financial and domestic responsibilities with her husband, and offered a reframe worth sitting with: sometimes short-term financial pain is simply the price of long-term gain.

One thing to do this week

Asked for a single, practical next step, Rob's answer was to simply make a first move, and not to wait until it feels perfect. Sam's was research paired with honest conversation with the people closest to you. Isla's was to extend that conversation further, including to people outside your immediate circle, since many people will be happy to share their own career story if asked.

The question worth sitting with

Closing the session, each panellist offered a single question to take away. Isla's was to fast-forward to old age and ask: would you be happy with the journey you’ve taken? Rob's was more immediate: what is actually keeping you in your current role? And Sam's tied the two together: is what you're going through right now actually worth it?

Key Takeaways

  • The pull to stay in the wrong career is usually made up of investment and guilt, and is not necessarily evidence that change is the wrong move. Recognising that pull for what it is can free up the decision.
  • A genuine signal to change (rather than a passing rough patch) often shows up as a shift in priorities or values, not just a bad week at work.
  • Exploration takes time. Trying multiple courses, conversations or small moves before committing is a normal part of the process, not a sign of indecision.
  • Most people underestimate their own transferable skills until someone else names them. Getting an outside perspective, whether from a mentor, tutor or peer, is often the turning point.
  • AI can help surface patterns and common threads in a career history, but the final story told in an application or interview needs to stay personal and authentic.
  • Financial concerns around a pivot are real and worth planning for, but they are rarely permanent. Treating a pay cut as a temporary trade-off for long-term gain, rather than a fixed reality, changes the decision entirely.