Squiggly Shortcut: You Don’t Need a Perfect Plan to Change Careers — Here’s What to Do Instead

6 Nov 2025 · 7 min · 8 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

How to start and succeed at a “squiggly” career change without needing a perfect plan, using small experiments, networking, transferable skills, and bridging roles.

Key claims

Don’t overthink—take small action (experiments, projects, volunteering) and build relationships while stress-testing fit. Have many curious career conversations and ask for introductions with a clear “ask.” Emphasize talents over titles by identifying how you work (e.g., listening, collaboration, cross-functional problem solving) and mapping them to target roles. Don’t let job descriptions discourage you. Use bridging roles to move incrementally.

Notable examples

The host and partner took seven years to shift from corporate jobs to running Squiggly Careers/Amazing If.

Guests

No guest is interviewed in this episode; it’s hosted by Sarah.

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

Chapters

Tap a time to open that second in VO

Start with Progress Over Perfection

0:00 to 0:22

Learn the importance of taking action, no matter how small, to initiate career change.

“And for a limited time, college students get the best of both worlds.”

Start with Progress Over Perfection

1:34 to 2:49

Learn the importance of taking action, no matter how small, to initiate career change.

Curious Career Conversations

2:49 to 3:56

Understand the value of networking and having conversations about different careers.

“Number two, have as many curious career conversations as you can.”

Focus on Transferable Talents

3:56 to 5:10

Identify and articulate your transferable skills to enhance your career transition.

“Number three talents over titles you have to figure out your transferable talent and talk about them clearly and with confidence.”

The Role of Bridging Jobs in Career Change

5:10 to 6:33

Explore how transitional roles can facilitate your journey toward a new career.

“But think about those transferable talents, have those career conversations, do the progress over perfection.”

Lessons from Personal Experience

6:33 to 7:27

Sarah shares her own career transition story and the lessons learned along the way.

Further Listening on Career Change

7:27 to 7:59

Get recommendations for additional resources and episodes on career change.

“April Ryan all about career change she's written and researched lots about career change she's also done it herself.”

Further Listening on Career Change

8:02 to 8:51

Get recommendations for additional resources and episodes on career change.

“You think you know a browser, but Gemini and Chrome, that's new.”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Study and play. Come together on a Windows 11 PC. And for a limited time, college students get the best of both worlds. Get the Unreal College Deal. Everything you need to study and play with select Windows 11 PCs. Eligible students get a year of Microsoft 365 Premium and a year of Xbox Game Pass Ultimate with a custom color Xbox wireless controller. Learn more at windows.com slash student offer. While supplies last, ends June 30th. Terms at aka.ms slash college pc. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more.

0:42Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. Good sleep is everything. That's why Oli's Science Back Support is made with a blend of melatonin and L-theanine for both kiddos and grown-ups. So when your mind won't switch off, you've got something that can help. Erasing thoughts and restless nights won't stand a chance. Find Oli's sleep solutions for the whole family at Oli.com.

1:20That's O-L-L-Y dot com. Hi, I'm Sarah and this is a Squiggly Careers Shortcut on Career Change.

1:34now we know that within a squiggly career you're likely to have at least four or five different types of career so this will feel relevant for all of us at some point we're all going to change careers at some point it can feel both motivating and exciting but also quite daunting and difficult to do so if you are thinking about doing something different in your squiggly career what can help you to get started whether it is a really significant squiggle so doing something quite dramatically different or whether it's a squiggle and stay move so maybe a move within the organization you're already in.

2:10One start with progress over perfection you can't think your way to career change as much as I might like to as somebody who enjoys thinking and reflecting you have to take action and this action can be really small experiments small projects volunteering find as many ways as you can to try before you apply get involved even if it's a really kind of small opportunity doesn't need to feel big or time consuming but the closer that you get the more relationships you will build and also it's a good stress test for does this feel like the right fit for me. Number two, have as many curious career conversations as you can.

2:55It will help you understand the reality of different teams, different areas, what challenges they've got, whether that's something that you're interested in. So you'll get a feel for fit. And also you never know who knows who or who knows what. Now we know with really big career changes, so if you're looking to do something very different from what you do today, you need to find some new people to talk to. And that can feel really hard if you're more introverted like I am. So ask for introductions. Remember, people really like helping people. So have clarity on what do you need? So what is your ask?

3:30And it can just be something like, I'm exploring a move into sales and marketing at some point in the next few years. Do you know anyone who could give me some insights into that or who might be prepared to share a bit about their experience and usually you will find someone will be able to help you and people really enjoy talking about what they do so never apologize for asking for a bit of help. Number three talents over titles you have to figure out your transferable talent and talk about them clearly and with confidence. My top tip here is think about how you do your job rather than what you do.

4:09Often we see ourselves in kind of what we do day to day, like the tasks and the jobs that we need to get done. But think about if you were doing a very different job next week, what would you take with you? It's usually your house. Are you a really good listener? Are you an amazing collaborator? Do you work really well cross-functionally? Are you really good at creative problem solving? What are those transferable talents that you've got and then start to connect the dots between those talents and where you want to go. How will they be useful for that team, for that organisation, for that department that you want to move to?

4:44And one word of caution, just watch out for job descriptions putting you off making those moves. Sometimes job descriptions can read a bit like wish lists and so if you read a job description you wouldn't apply for any jobs whether that's similar to what you do today or if you're trying to do something different. But I think particularly when you're in that career change mode, you can look at a job description and think, well, I just don't have enough to apply. But think about those transferable talents, have those career conversations, do the progress over perfection. And if you can, if you're thinking about a career change, if you can have conversations with people beforehand, that often puts you in a much better a position to at least be considered or hopefully get an interview.

5:28And final thing to think about with career change, and this has definitely worked for me every time I've made any kind of career change, is bridging roles can be really useful. So a bridging role might not be exactly where you want to go, but it gets you much closer. So maybe there's a bit of what you do today. So maybe it is within a similar team or some of the skills that you've got both your what's and your how's still stay relevant but there's there's some newness there that's getting you a bit closer to where you want to go successful career change does tend to happen incrementally and bit by bit unfortunately there's no sort of silver bullet of going from one thing to something very different overnight and for most of us we also need to make sure that we are still earning enough and kind of we've got all of those kind of basics in place.

6:21And so often, you know, having a kind of bridging role and in between role, and it might be one or it might be a couple, but where you feel like you're moving in the right direction, you're getting closer to where you want to go can be a really good thing to do. You know, when Helen and I were, when we first created Squiggly Careers and our company Amazing If, we didn't move from our kind of corporate jobs to running Amazing If overnight it actually took seven years and we were doing loads of different things during those seven years but that's the biggest career change and the biggest career move that I've ever made and I think one of the reasons that it worked out so well and that I'm still doing it today is that we did all of those things that we just talked about we did a lot of testing and learning lots of curious career conversations really thought progress over perfection now it might not take you seven years but just kind of be kind to yourself and you know think about your own expectations around kind of how to make these things happen we're all going to be working for a long time in our squiggly careers so don't feel disheartened if you can't make it happen straight away I hope you found that useful if you'd like a longer listen on career change episode 379 of squiggly careers podcast I interview April Ryan all about career change she's written and researched lots about career change she's also done it herself.

7:41So if you want some examples and some more stories to bring to life some of the things I've talked to you about today, that might be a useful listen.

7:59This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required, compatibility and availability varies 18 plus. You can't reason with the sun. Trust us, we've tried. This summer, it's time to put that angry ball of fire on mute.

8:32Columbia's OmniShade technology is engineered to protect you from the sun's harsh rays that can burn and damage your skin. The sun is relentless, but so is our gear. Level up your summer at Columbia.com to spend more time outside and less time slathering on aloe lotion. You're welcome. Columbia. Engineered for whatever.

From the publisher

Most of us will change career up to 5 times in our squiggly careers. In this shortcut, Sarah shares why career change isn’t about having the perfect plan — it’s about getting started. She gives three practical ways to make progress without pressure, from small experiments to curious conversations that open new doors.


Episode 509


🦞 Pre-order Learn Like A Lobster:

🇺🇸 PRH US – https://bit.ly/3KxTeBn

🇬🇧 Amazon UK – https://amzn.to/3KcRZaR


⏱️ Timestamps


00:00 Welcome to Squiggly Shortcuts

00:28 Why “perfect plans” hold us back

01:05 Idea 1

02:15 Idea 2

03:35 Idea 3

04:50 Why small actions build big confidence

05:10 Where to learn more


🎯 What You’ll Learn


- How to stop overthinking your next move

- Why progress matters more than perfection

- How to turn small steps into big opportunities

- How to reframe uncertainty as growth


🎧 For more ideas, listen to Episode 379, where Sarah interviews April Rinne about navigating career change with confidence.


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/

🏃‍♀️ Join the Skills x AI Sprint: https://youtube.com/playlist?list=PLNQl9gsac8BXnWe2qoGuHkLKwsygjP_Ma&si=l7kODG3JpopH0Irz

📮 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.

More from Squiggly Careers

All 129 episodes
Squiggly Shortcut: You Don’t Need a Perfect Plan to Change Careers — Here’s What to Do InsteadSquiggly Careers · 7 min
Listen in VO