Squiggly Careers Podcast #464: Career Changers – How to Pivot and Create New Possibilities

Date: March 6, 2025
Hosts: Helen Tupper & Sarah Ellis
Guests: Jenny Blake (Author of Pivot), Ollie Kelly, John Rotherer

Overview

This episode of Squiggly Careers focuses on the theme of career change: how to make a pivot, navigate uncertainty, and create new possibilities for yourself. Hosts Helen Tupper and Sarah Ellis draw from their own “squiggly” career journeys and introduce actionable strategies for anyone considering a big professional move. The episode features an insightful interview with Pivot author Jenny Blake, followed by candid stories from two career changers, Ollie Kelly and John Rotherer, who trained with the tech bootcamp Makers.

Key Discussion Points & Insights

The Reality and Prevalence of Career Change

• Widespread Experience: Career change is common. “If we're going to have four or five different types of career during our working life, which is probably quite a conservative estimate, this is something that we'll all experience.” (Sarah, 02:42)
• Barriers: The biggest hurdles often aren’t motivation, but practical “how” questions and the fear of the unknown: “It's the unknown. You're moving from something that you've probably got some expertise in… into something new. Being a beginner in any area always feels hard.” (Sarah, 03:12)
• Statistics:
  • 61% of people consider pivoting, per LinkedIn (2023)
  • At least 50% have already pivoted once

Types and Scope of Career Change

• Small Changes vs. Big Pivots:
  • Change within the same organization feels more manageable due to familiarity (Helen: 04:13)
  • Entirely new ventures (starting their own company, switching industries) feel more risky and uncertain but potentially more rewarding (Helen: 04:37)
• Risk and Potential: “Changes can bring so many new potential and possibility for your career, and I guess we don't want to let the uncertainty or the fear hold you back from something that you might want to do.” (Helen, 05:15)

Jenny Blake Interview: Practical Steps for Career Pivoting

[06:04 – 17:08]

1. Feeling Overwhelmed by a Big Career Leap

• Start Small with Pilots:
  • “Identify a few small, safe to try experiments… [to assess] three E's: Do you Enjoy this area? Can you become an Expert at it? And is there room to Expand?” (Jenny, 07:42)
  • “You need to lift the starting gates, say, go. And your pilots will show you which ones take on a natural energy and momentum so that you can double down.” (Jenny, 08:25)
• Metaphor: “It's like lining up resources at the Kentucky Derby… You don't know which horse is going to win.” (Jenny, 08:15)
• Helen’s Reflection: “The process is about learning about what you can do rather than committing before you know what the right thing is to do.” (Helen, 09:01)

2. Overcoming Imposter Syndrome and Convincing Others

• Leverage Generative AI:
  • “Partner with AI, upload everything that you have about you, what you've done, your extended cv… So can you map my resume to this role and copy paste the job description.” (Jenny, 10:37)
  • “It's hard to read the label from inside the jar. Well, now here you have this, like, uber intelligent thought partner to help you read the label from the outside.” (Jenny, 11:23)
• Practical AI Tools: ChatGPT, NotebookLM

3. Building Confidence to Take the Leap

• Don't Expect Instant Confidence:
  • “Don't even expect to feel confident. In this environment… you're really not going to feel confident. Like, if you do, you're rare… My mantra for myself: 51, 49. I can be 49% insecure, worried, anxious… and then I just need to tip toward action. 51%.” (Jenny, 12:22)
• Action Over Perfection:
  • “Decisions are data. You really cannot know. That's, in a way, what makes them exciting.” (Jenny, 13:13)
  • “Nobody that I interviewed for the book about their pivots expressed regret no matter how they turned out.” (Jenny, 13:39)
• Regret Research: "People regretted the bold moves they didn't make much more than the ones they did that quote unquote, failed." (Jenny, 14:04)
• Let Go of Over-Control:
  • “May this unfold for the highest good for all involved. And I don't know what that is.” (Jenny, 15:20)
• Beware "Future Tripping":
  • “Future tripping is that you're too many steps ahead, you're too far out from where you are now. It takes you out of the present.” (Jenny, 16:24)

Real Life Pivot Stories: Ollie and John

[17:08 – 29:12]

Motivation for Change

• John: Ran an independent music venue for 8 years; burnout and lack of reward led to seeking something completely new.
  • “I didn't really want to step sideways. So, yeah, I just really wanted a complete change.” (John, 18:41)
• Ollie: Tech recruiter with a humanities background; passion for tech and curiosity drove the change, despite initial fears it was “out of reach.”
  • “I was a bit of a technical nerd and I just wanted to understand how things worked… what held me back from taking a leap of faith was just a fear that it wasn't for me.” (Ollie, 19:04)

The Challenge of Starting Over

• Learning Curve:
  • John: “You’re building, like, tiny little functions and it’s like, oh, my God, this makes sense. But then you’re shown some massive program… I literally don't understand… I suppose I could kind of compare it to learning an instrument.” (John, 21:37)
  • Ollie: “I got a little bit of whiplash almost from shifting context into… an engineering environment… It's just too vast and it's changing too quickly… You need to get comfortable with the ambiguity and be able to trust in your cognitive abilities.” (Ollie, 22:17)

What Makes It Work (Support Systems)

• Community:
  • “One of the things that's helped me the most is kind of finding a community of people who were in the same boat as me and making sure I kept in touch with those people. Job hunting and career changing can feel really lonely.” (Ollie, 23:25)
  • Makers bootcamp provided ready-made peer groups; technical meetups and online communities are key
• Mentorship:
  • “Try and get yourself some sort of industry mentor… People are more open to helping and giving you their time than you might think.” (Ollie, 23:25)
• Feedback and Resilience:
  • “I've improved a huge amount through this job search… asking for feedback from interview processes and putting myself out there and feeling uncomfortable quite a lot of the time, but still learning.” (Ollie, 24:33)

Most Rewarding Aspects

• John: “The sort of team working mindset, that is my favourite thing currently.” (John, 25:20)
• Ollie: “The favorite thing for me at the moment is just like the learning. I wanted a career that was going to keep pushing me.” (Ollie, 25:33)

Hindsight and Advice to Others

• Use Your Network:
  • “The more I put myself out there and, like, ask for feedback, the more I got actionable insights as to what wasn't working in the CV that I put together or the project I'd done or the interview that I'd gone and done.” (Ollie, 26:20)
• Expect Setbacks and Have Patience:
  • “Some of it is luck… There’s also another 10 reasons why it didn’t work out for you that time and they're not to do with you.” (Ollie, 27:54)
• Don’t Give Up:
  • “Try and be as prepared as possible. Trust yourself, trust your instincts and don’t give up… I’m so glad I didn't just completely quit because I wouldn't be here now.” (John, 28:50)

Notable Quotes & Memorable Moments

• “You just want to help us to make it happen.” (Helen, 01:54)
• “It's hard to read the label from inside the jar. Well, now here you have this… thought partner to help you read the label from the outside.” (Jenny, 11:23)
• “My mantra for myself: 51, 49. I can be 49% insecure… and then I just need to tip toward action.” (Jenny, 12:38)
• “Job hunting and career changing can feel really lonely… it’s so crucial to find the people that are going through it with you.” (Ollie, 23:25)
• “I was at a point where I thought, just don't think it's going to happen… I’m so glad that I didn’t just completely quit because I wouldn't be here now.” (John, 28:50)

Timestamps of Key Segments

• 00:00-04:00 Introduction, overview of the series, setting the context
• 04:00-06:00 Helen and Sarah’s personal career change stories
• 06:04-17:08 Helen’s interview with Jenny Blake (Pivot): pilots, AI, confidence, regrets, and mantras
• 17:08-29:12 Ollie & John—real-life experiences with Makers bootcamp, feelings, challenges, community, resilience, and advice

Conclusion & Further Resources

• Take Action: The hosts encourage listeners to explore the episode’s accompanying guide, full of reflection questions and tools.
• Network: Follow Amazing If on LinkedIn to connect with others interested in career change.
• Final Words: “Patience with the process. But patience with yourself is a matter of time as much as it's a matter of ability and practice.” (Ollie, 28:24)

This episode is filled with practical steps, honest stories, and reassuring advice for anyone at a crossroads in their career, reminding you that change is normal, community is vital, and bold moves bring growth—regardless of outcome.