Squiggly Careers Podcast

Episode: AI Skills Sprint – How To Design Your Future Career Using AI

Hosts: Sarah Ellis (A) & Helen Tupper (B)
Date: September 19, 2025

Episode Overview

This episode marks the final day of the Squiggly Career Skills Sprint, a week-long journey aimed at empowering listeners to shape their own career development. Sarah and Helen focus on harnessing AI to design future career possibilities, urge proactive career planning, and introduce practical tools and prompts that anyone can use to discover new directions. The conversation is upbeat, supportive, and full of actionable advice for anyone keen to future-proof their “squiggly” career in a landscape of uncertainty and change.

Key Discussion Points and Insights

1. Why Focusing on Future Possibilities Matters

• The Squiggly Career Approach:
  • Traditional career paths ("ladders") have given way to squiggly, non-linear journeys.
  • Simply relying on the next “logical” step is risky—today's environment demands agility and career resilience.
  • Stat: “People now have 10 to 15 jobs on average in their working life… [with] an average career… around 40 years.” (01:04–01:54, B)
• Intentional, Not Accidental Progress:
  • The best career moves are not luck—they’re the result of curiosity, exploration, and deliberate, long-term planning.
  • “You want to create, not wait when it comes to your future possibilities.” (02:08, A)

2. AI Mind Map and Prompts for Career Design

• Zooming Out with AI:
  • Use AI as a “squiggly career mentor.”
  • Provide it with specific but non-personal context (e.g., “Finance manager in a large organization in the retail sector”).
  • Prompt AI to produce a mind map: “Three obvious possibilities, three ambitious, three pivot, and three dream possibilities for my career.” (02:49–03:45, A)
• Benefits:
  • AI-generated mind maps save time, offer unique insights, and can expand your thinking beyond the obvious.
  • Useful as a brainstorming springboard or to inject new ideas.
  • AI’s responses may surprise you with their breadth and depth, even suggesting roles like “Founder/co-founder, Creative Finance Educator, Head of Impact, Social Enterprise Leader.” (04:54–05:17, A)
• Quote:
  • “Sometimes the obvious possibilities are not always the most motivating ones, so this gets you beyond the obvious.” (05:17, A)

3. Using AI for “Curious Career Conversations”

• Bridging the Knowledge Gap:
  • Instead of immediately applying for jobs, prioritize learning and discovery via “curious career conversations.”
  • AI tools (like Udlie, see summary link) can simulate these conversations, helping you clarify questions, test interests, and boost your confidence before engaging with real people.
  • “No one has to see this. This is just you. But you put the profile in... [and] it will generate you a role play.” (06:47, B)
• Practical Example:
  • Helen describes a simulated conversation with “Rebecca,” an AI avatar representing a career in Microsoft Sales, which provided feedback on her skills and conversation style.
  • “Nice job. Growth areas: slow down and sharpen points... Balance elaboration with brevity... Focus on delivering concise, impactful answers.” (07:45–08:08, B)
• Value:
  • Practicing with AI builds confidence, reveals areas for improvement, and makes real conversations more productive.
  • “I’d ask better questions in my real career conversation because of the practice. So... it made me more thoughtful.” (08:28, A)

4. Team Exercises: Identifying Squiggly Career Role Models

• Bringing It Into Teams:
  • Encourage team discussions about inspiring “squiggly career” role models.
  • Sharing stories of people forging unconventional paths invites fresh perspectives and fosters resilience and curiosity within teams.
• Hosts’ Own Role Models:
  • Helen: Aviva Wittenberg Cox, for her advocacy and generosity in the areas of generational and gender diversity in work. “She uses her space… to support other people, and I love that she wins, but helps other people win.” (09:12, B)
  • Sarah: Margaret Heffernan—admired for her credibility, curiosity, resilience, and her outspoken commitment to improving the world of work. “Everything she writes, I read, and I think, oh, I’m a bit smarter because I’ve spent time with her.” (09:31, A)

Notable Quotes & Memorable Moments

• “You want to create, not wait when it comes to your future possibilities.” – Sarah, 02:08
• “People now have 10 to 15 jobs on average in their working life... and our average career is around 40 years, so we're working for a longer time. We are having more roles, and we want you to have more resilience.” – Helen, 01:37
• “Sometimes the obvious possibilities are not always the most motivating ones, so this gets you beyond the obvious. It just gets you into generating ideas.” – Sarah, 05:17
• “The action isn't ‘I'll apply for a job,’ the action is ‘I'll go and learn more.’” – Helen, 05:45
• “Fake Rebecca is not getting me a job in the sales team. Real Rebecca might, but this could give me the confidence to have an even better conversation with the person who is actually in sales.” – Helen, 07:32
• “Everything she writes, I read. And I think, oh, I'm a bit smarter because I've spent time with her.” – Sarah, 09:31

Timestamps for Key Segments

• 00:45: Recap of the week’s skill sprint and overview of today’s focus
• 01:04: Importance of future possibilities in a changing career landscape
• 02:08: The need to be proactive in career planning
• 02:49–04:52: Guide to creating AI-powered career mind maps and what to include in prompts
• 05:17: How AI expands your view beyond obvious options
• 05:39: Transition from ideas to informed action (“curious career conversations”)
• 06:47: Demonstrating AI simulations (Udlie) for safe practice
• 07:45: Sample AI feedback and its practical value
• 08:39: Reflections on the benefits of AI practice for real-life conversations
• 08:40–10:14: Bringing role model discussions into team development
• 09:12–09:31: Helen’s and Sarah’s personal career inspirations

Final Thoughts & Call to Action

• Celebrate Your Progress: Listeners are encouraged to take pride in committing to their own growth, share their “Completed the Squiggly Career Skill Sprint” badges, and spread the word to support others in their journey.
• Listeners’ Community: Join future sprints, stay connected, and keep exploring new ideas with the Amazing If community.

This episode is a practical, uplifting guide for anyone looking to leverage AI for future-focused career design, and encourages a spirit of curiosity, safe experimentation, and personal celebration.