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

Summary

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

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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.

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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)

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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

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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

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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.

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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.

Transcript

[A]

Hi, I'm Sarah.

[B]

And I'm Helen.

[A]

And this is the Squiggly Careers podcast. And we are on day five, final day of our Squiggly Career Skills Sprint. If you are starting here, it's also fine, but for lots of people, we know that you will have been working your way through the sprint. And so firstly, like, well done for spending some time on your development every day. We know it's not easy, we know there are loads of demands on your day. And just as you were about to get started, someone will ask you an annoying question. But the fact that you have stuck with it, you should. You should feel really good about.

[B]

And we will send those people, everyone, today. You will also get your. I've completed. You'll get a badge. I've completed the Squiggly Skill Sprint badge. So if you put that on LinkedIn and tag us, we can celebrate your sprint success.

[A]

And remember those daily summaries, I'm sure you're all really used to them by now. In today's summary, for example, you'll get an example of a mind map, our first mind map, I think, of the week. You'll get a link for a tool that Helen's going to talk about and loads of prompts, which, again, cut and paste the prompts. Use our prompt as a starting point, and by now maybe you can just use our prompt and then make it even better for yourself.

[B]

So we're talking about future possibilities, so let's just talk about why this matters. In a Squiggly career, when we looked at careers like ladders, you basically just had a plan, you were looking at the next step, you weren't really looking much beyond that, and you definitely weren't looking in different directions. In the world that we are working in today, where there's lots of change, lots of uncertainty, there's. That approach is risky and it doesn't help you with your career resilience. We don't want either of those things for you. We want you to have lots of opportunity, lots of options, so you have more control in your career. And that is why future possibilities matter. It means that you'll be able to explore different directions that you can develop in. It means that you can get more curious and open about your opportunities and that that just gives you more choice. There's also a useful Squiggly stat here to support this point, which is that people now have 10 to 15 jobs on average in their working life. So lots of different jobs and potentially lots of different companies, and that 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. That's what this skill is all about.

[A]

And you want to create, not wait when it comes to your future possibilities. You know, I think we are all guilty at some point in our squiggly careers of suddenly realizing, I want to do something different now and then. We've not really been proactive or very intentional about it. And then you default to or just start applying for jobs. And sometimes you can be lucky and, you know, you apply for the right one and it all kind of works out. But certainly in my own career, when I think about all of the different squiggles and the moves that I've made, all of the best ones have been quite a while in the making. You know, I've had curious career conversations. I've explored different ideas. I've almost been thinking about it and acting on it for a while.

[B]

Even like this job, this was a while in the making for us.

[A]

So an AI prompt to get you to zoom out. I think we want to start here by not limiting ourselves, almost ignoring constraints, and thinking about the art of the possible. That's why I enjoy this section. And I like mind maps. I'm like, oh, what? What could be? What might happen? And so your prompt here is give the AI a bit of context about you. But remember, don't share anything sort of really personal or individual. So don't say, my name is Sarah. This is my job at this company. More like, I'm a finance manager in a large organization in the retail sector. So specific enough, but without being kind of too personal to you, I'm curious about where my career might take me next. Act as a squiggly career mentor. I went for mentor today, slightly different to coach, hopefully for a good reason. Act as squiggly career mentor who's worked in lots of different roles and industries. Generate a mind map showing me three obvious possibilities, three ambitious possibilities, three. Three pivot possibilities, and three dream possibility for my career. So quite a lot, quite a long prompt, and then it just does it.

[B]

I mean, you would have to, if you were doing that yourself, that would take you a good. I mean, a good 10 minutes to do. And it just did it quite quickly for you.

[A]

And what I liked about this was, I mean, you could use this to build. So what you could have done was put in the ideas you'd already got and then said, give me some new ideas. So ones you've not Already thought of. Or you could use it as a starting point, you know, like as a springboard. So I think you can use it in either way. I like the fact it gave me mini definitions, which again, I'd not given it that, but it sort of gave it back to me. So it said for ambitious possibilities, for example, bigger leaps, but they're still rooted in your strengths. So I was like, oh, I like that, I like that little reminder. Oh, but this is still about, about you and your strengths. It does give you a visual. You can download it as a PDF, you can kind of print it out. And it did. It was sort of specific about like roles. An ambitious one, for example, could be to move into strategy. And I was like, oh yeah. I mean, I'm not in finance for a start, but I was like, but I wouldn't mind going to work in kind of strategy. It talked about dream possibilities. I thought, oh, this is interesting. How has it decided what my dreams are?

[B]

Whose dream is this? Yeah, whose dream does it give you?

[A]

Well, I mean, so one of them was founder, co founder. And I was like, oh, it's so smart. They're so smart. Which I was like, oh, that's interesting. Right? Because these things do learn, which, you know, scary slash smart, creative finance educator or coach. So I was like, oh, it, it has learned about me even though I'm not in finance. And then the other one was head of impact, social enterprise leader.

[B]

I think you probably also would quite like that.

[A]

Yeah, I mean, I can't do the finance bit that I said in the actual prompt, but I would quite like some of those things. So I just think this is a great way to get you started. And you know, sometimes the thing that we see is that the obvious possibilities are not always the most motivating ones. So this gets you beyond the obvious. It just gets you into generating ideas. And then I think you move into like. Right, okay, the so what now?

[B]

And so on. The so what now? All these ideas about your possibilities, you really want to put them into action in some way. And we always talk about the value of curious career conversations. So the action isn't I'll apply for a job, the action is I'll go and learn more. Always kind of let the sort of learning lead you. And so we often say, go and have curious career conversations. Now the good thing about AI is you can have a curious career conversation with, with AI about one of your possibilities. So the tool that we played with here is Udlie and we'll put the link to that in The Squiggly career summary. So you can just click through and give it a go. There is a page in there where you can design your own role play. Please do not cringe at the word roleplay. No one has to see this. This is just you. But you put the profile in. So I actually did. The profile that I used here was I said, I want to have a curious career conversation with someone in sales in Microsoft about potentially making a move in that direction. I currently work in marketing and would like to practice my conversation skills so I learn and make a good impression. So you're going to have to just put in there, you know, maybe use Sarah's prompt first. Pick one of those possibilities that you're interested in. Create a profile of a person you want to talk to and what it will do is it will generate you a role play so you will literally have an avatar. I had someone called Rebecca who works in sales and she.

[A]

How was Rebecca? She was great. Yeah. You said this. You sounded like you'd like made friends with Rebecca.

[B]

It's so good. So I was chatting to Rebecca and she was saying, oh, you know, what is it that interests you about sales? What skills do you think you could bring? What do you want to learn? What are the questions that you got? It was really, really useful. Now, I don't think that replaces meeting the real Rebecca, because the real Rebecca, if there is a real Rebecca in sales at Microsoft. But the reason being we talked yesterday in the skill sprint about the role of networking and how that leads to new, often new opportunities. So fake Rebecca is not getting me a job in the sales team. Fake. Real Rebecca might, but this could give me the confidence to have an even better conversation with the person who is actually in sales. Really give this a go. Also, it gives you feedback. That's the brilliant thing about this and it gives you quite clear feedback. Like, I got strength. Helen, you showed up with enthusiasm for exploring opportunities and engaged with a professional and had relevant insights into their field. Nice job. Growth areas slow down and sharpen points. Some answers felt a bit rushed or slightly disjointed. Balance elaboration with brevity. Focus on delivering concise, yes, Impactful answers. So I think it gives you feedback so that when you have the real conversation, you can show up even more effectively in it and it's just safe. It's a nice, safe place to practise what could feel a bit like a scary conversation.

[A]

So I think it can either increase your confidence or it could just be an. And I'm going to have some curious career conversations that are sort of pretend or practice ones, and I'm going to go and do the real ones as well. I think I would. I had a play with it because you were very enthusiastic about the fake Rebecca. And I was like, I think I'd ask better questions in my real career conversation because of the practice. So I'm already confident enough to have them, but it made me more thoughtful.

[B]

Yeah, agreed.

[A]

So how could you talk about this together as a team? I think we've got quite a nice exercise here. Well, we enjoy doing it, basically. So we were thinking, actually, when you're thinking about possibilities, it's nice to think about who are your squiggly career role models. So someone who is progressing in a way that feels inspiring for you, and actually talking about that as a team, I think, is really nice. It's really nice to hear people's examples of who they find interesting and inspiring and, like, what is it about what they do? Who would you pick?

[B]

The first person that came into my mind was Aviva Wittenberg Cox.

[A]

Brilliant.

[B]

Aviva and I really. And then you just go into a why? Why is it? And I admire the changes that she's making in both generational and gender diversity at work. She's very generous. So. So she uses her space, I think, to support other people, and I love that she wins, but she helps other people win with their work, too. Love that. What about you?

[A]

Margaret Heffernan, longtime fan, and she's been on the podcast as well, basically, because I fangirled her until she came on the podcast. And I think the reason I find her an inspiring role model is her credibility, her expertise. She's not afraid to share her points of view. And again, probably similar to Aviva, I feel like she just wants the world of work to be better and so she'll call out things that are making it worse. But she's also really curious. She's been, like, working for a really long time, and she's just stayed curious and relevant and resilient, and she just always. Everything she writes, I read. And I think, oh, I'm a bit smarter because I've spent time with her. And I think, oh, that's. That's an amazing thing to inspire me.

[B]

It's a nice chat to have together as a team. So that is the end. Yay. Well done for sprinting. Well done. It isn't easy to commit to your development, and if you've got this far on the sprint, like, that is a commitment to yourself and your learning and we really hope that it's been useful. Energy and useful are two of our values, so let us know if it's done that for you. Please share your badge. You should celebrate this with pride. Make sure that you stay connected for amazing if, because we will be doing another sprint. And just a big thank you for us for being part of the community and all of your kind of support and love of squiggly careers as well.

[A]

Of course, please share the sprint with other people if you fancy giving us a rating or a review. Those things really help us. So if you've got time for a five minute favor today, that's one way you can say thank you to us.

[B]

Thanks so much everybody.

[A]

Bye.