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

19 Sep 2025 · 11 min · 4 chapters

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In short

Day five of the “Squiggly Careers” AI Skills Sprint focuses on using AI to expand “future possibilities” for career resilience, then practicing conversations to act on those ideas.

Guests

Christy (Lululemon employee; shares a “Shake It Out” shorts product segment). Main hosts: Sarah and Helen (run Squiggly Careers podcast; Sarah and Helen discuss prompts and tools).

Key claims

Traditional “career ladder” planning is risky amid uncertainty; people average 10–15 jobs over ~40 years, so you need options and resilience. AI can generate mind maps of career possibilities and role-play practice conversations.

Notable examples

Sarah’s prompt context (finance manager in retail) generates three possibility types plus dream roles (e.g., founder/co-founder; head of impact/social enterprise leader). Tool: Udly role-play with “Rebecca” (sales at Microsoft) for feedback on strengths and improvement areas. Team exercise: discuss squiggly role models like Aviva Wittenberg Cox and Margaret Heffernan.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Importance of Future Possibilities in Careers

1:07 to 2:15

Discussion on the significance of exploring future career possibilities.

“We don't want either of those things for you.”

AI Prompting for Career Exploration

2:15 to 3:40

Using AI prompts to explore various career opportunities.

Engaging in Curious Career Conversations

3:40 to 6:26

Utilizing AI for role-playing career conversations to gain confidence.

Identifying Role Models and Inspirations

6:26 to 11:00

Discussing the importance of role models in career progression.

“And so we often say go and have curious career conversations.”
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Transcript

Automatic transcript. May contain errors.

0:00Hey, it's Christy from Lululemon and I'm here at the office checking out the Shake It Out shorts. These have been my go-tos and I kind of think of them as a middle ground between a true run short and a more playful, athletic, sporty short. They have all the performance you want for running, so a comfy liner, our lightweight, swift fabric, even a pocket for your keys. But what I really like is the flowy fit and layered hem. It gives it a little bit of volume, a little bit of fun, so they feel as good on a run as they do just at coffee afterwards. You can find the Shake It Out shorts in-store now or online at lululemon.com.

0:30Hi, I'm Sarah. And I'm Helen. And this is the Squiggly Careers podcast. And we are on day five, final day of our Squiggly Careers 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, 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 have asked you an annoying question. or um but the fact that you have stuck with it you should you should feel really good about and we will send those people everyone today you will also get your i've completed you 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 and remember those daily summaries i'm sure you're really used to them by now um in today's summary for example you'll get an example of a mind map our first mind map i think of the week um 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 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, that approach is risky and it doesn't help you with your career resilience.

1:55We 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 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 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 even like this job this was a while in the making for us so an ai prompt to get you to zoom out i think we want to start here by not limiting ourselves almost ignoring constraints i'm 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 um 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 and 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 so I went for hopefully for a good reason act as a 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 pivot possibilities and three dream possibility for my career so quite quite a lot quite a long prompt and then it just does it 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 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 is it decided what my dreams are yeah whose dream did it give you well I mean so one of them was founder co-founder and I was like oh it's so smart they're so smart um 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 I think you probably also would quite like that 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 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 it the action isn't I'll apply for a job and the action is I'll go and learn more always kind of let the sort of learning lead you.

6:26And 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 AI about one of your possibilities. So the tool that we played with here is Udly, 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 role play. 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 can 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 how was Rebecca she was great yeah you said this she sounded like you'd like made friends with Rebecca it was so good so I was chatting to Rebecca and she was saying oh you know what is it that interests you about sales what what skills do you think you could bring what do you want to learn what other questions have you got it was 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.

7:48But the reason being, we talked yesterday in the skills 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. 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 a 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 it's just safe it's a nice safe place to practice what could feel a bit like a scary conversation 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 yeah agreed 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 like hear people's examples of who they find interesting and inspiring and like what is it about what they do who would you pick uh the first person that came into my mind was aviva wittenberg cox the brilliant aviva brilliant and i really but and then you just go into a why why is it and i admire uh the changes that she's making in both generational and gender diversity at work she's very generous 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 i love that what about you margaret heffernan yeah um long time fan and she's been on the podcast as well basically because I fangirled her until she came on the podcast.

10:07And 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 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 an amazing thing to inspire. It's a nice chat to have together as a team.

10:45So 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, 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 of course please share the sprint with other people um if you fancy giving us a rating or a review those things really help us um so if you've got time for a five minute favor today uh that's one way you can say thank you to us thanks so much everybody bye

11:31Thank you.

From the publisher

This is the fifth and final episode of the Squiggly Careers x AI skills sprint series.


Today, Helen and Sarah talk about exploring Future Possibilities in your career. As careers become less linear and more unpredictable, having multiple options and directions is essential for resilience and control.


In this episode, they show how to use AI prompts to generate a mind map of career possibilities, from obvious to ambitious, pivot, and dream options. They also introduce an AI tool for practicing curious career conversations through role play, helping you build confidence and get feedback first.


With people having 10-15 different jobs on average throughout their working life, embracing a variety of possibilities actually reduces career risk and builds long-term resilience.


🥇 Sign up for the sprint here: https://bit.ly/41jasYO


⏱️ Timestamps

00:00 Introduction

01:07 Why future possibilities matter in a squiggly career

02:48 AI prompt to explore different types of career possibilities

05:40 AI Tool: Yoodli

08:39 Team activity: who are your career role models?


🎯 What You’ll Learn

* The importance of having multiple career options

* How to use AI to generate a mind map of career possibilities

* Why creating rather than waiting for opportunities matters in modern careers

* How to practice curious career conversations


📚 Resources Mentioned

Future Possibilities Daily Summary - https://bit.ly/scss-ai-day5-summary

Yoodli - https://yoodli.ai/


For questions about Squiggly Careers or to share feedback, please email helenandsarah@squigglycareers.com


More ways to learn about Squiggly Careers:

📩 Download our free career tools: https://www.amazingif.com/toolkit/

📮 Get Squiggly Careers in Action in your inbox: https://bit.ly/SquigglyCareersInAction

📚 Read our books: The Squiggly Career and You Coach You: https://www.amazingif.com/books/

Hosted on Acast. See acast.com/privacy for more information.

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