Squiggly Careers FAQs
What is a squiggly career?
Career ladders and jobs for life are a thing of the past. Today, we’re living in a world of squiggly careers, where moving frequently and fluidly between roles, industries, locations, and even careers, is becoming the new normal. Squiggly careers can feel stressful and overwhelming, but if you know how to make the most of them, they can be full of opportunity, freedom and purpose.
What’s the difference between a squiggly career and a traditional career path?
Careers used to be linear and ladderlike. They were about following in other people’s footsteps, and focused on getting to the top. A squiggly career is characterised by change and choices, by potential and possibilities.
Who coined the term “squiggly career”?
Helen Tupper and Sarah Ellis created the concept of squiggly careers in 2013 and found that it quickly connected with many people who felt it reflected their experiences and ambitions. Since then, they’ve written three bestselling books, run hundreds of training programs across the world, and produced over five hundred weekly podcasts of The Squiggly Career with over 5 million downloads.
Who are Helen Tupper and Sarah Ellis?
Helen Tupper is the CEO and co-founder of Amazing If. She has held senior leadership roles at Microsoft, Virgin and BP. She is the co-author of three Sunday Times bestsellers and a regular contributor to Harvard Business Review. She is part of the LinkedIn Top Voices program, an invitation-only group of experts across the professional world. She sits on the board of the CMI and is an alum of the EY Winning Women programme. Helen is a Fellow of The RSA, has lectured at MIT and her love of learning has led her to study at Henley, Cranfield and Cass Business School. She lives in the UK with her husband and two children.
Sarah Ellis is co-founder of Amazing If. Her career has spanned financial services, retail and the creative industries with roles at Sainsburys, Barclays and Gravity. Alongside Amazing If, Sarah sits on boards of REC and MoreThanNow. She is the co-author of three Sunday Times bestsellers and a regular contributor to Harvard Business Review. Sarah is an alumna of Harvard, London, and Warwick Business Schools and in 2024 was named in Management Today’s inaugural Women in Leadership Power list. She lives in the UK with her partner and bug loving 8-year old.
What books have Amazing If published?
Helen Tupper and Sarah Ellis have published three Sunday Times bestsellers. The Squiggly Career, You Coach You and Learn Like a Lobster as well as the Pound Project publication Gremlins. They are regular contributors to Harvard Business Review, writing on the topics that matter to senior leaders – from making learning a daily habit and reimagining employee retention, to building a culture of feedback at work.
What organisations does Amazing If work with?
Amazing If partners with organisations across the globe who want to make career development a shared responsibility between employer and employee. Clients include: The Lego Group, KFC, Sky, HMRC, Google, B&Q, Laing O Rourke and Visa.
How many people have listened to the Squiggly Careers podcast?
Squiggly Careers is a weekly audio and visual podcast that helps listeners take control of their career development. Hosted by Sarah Ellis and Helen Tupper, together they cover all things work: from how to manage stress and overcome confidence gremlins to micro-aggressions and discovering strengths. With over 5 million downloads, each episode is full of ideas, actions, hints, and tips that can be put into practice straight away.
How do I manage my career when there’s no clear promotion path?
Promotions are a career focus for lots of people, but they are not always possible for everyone. Whether a promotion is motivating because of pay or more power, the opportunity to work with new people or do more of the work you love (and less of the work you don’t), there are other alternatives you can explore to get what you want from work. Episode 323 of the Squiggly Careers podcast helps you respond to the challenges and feel like you’re still making progress.
What is a strengths exercise for career development?
Strengths are the things that give you energy, pull possibilities towards you, and shape what you want to be known for. As part of our AI Skills Sprint we’ve got a 10 minute exercise to help you understand your strengths.
How do I find a career sponsor or mentor?
Mentors and sponsors are both people who can help progress in your career. Mentors typically have experience you want to build and sponsors unlock access to new career opportunities. We’ve got two podcasts to help you build these relationships – one on mentoring and one on sponsors.
What does it mean to “own” your career development?
Owning your career means taking 100% responsibility for your own professional growth rather than relying on someone else. If you’re feeling stuck, unsure of your next step, or craving more direction, episode 519 of the Squiggly Careers podcast has simple clarity-creating strategies to help you find focus, feel more in control, and move forward with confidence.
What is the Squiggly Careers Toolkit and who is it for?
The free toolkit is there to help you talk about Squiggly Careers in your organisation whether you and your company are familiar with our work or not. Inside you’ll find ideas, insights and tools to help you to support people to progress. It’s a great place to start your squiggly journey.
What is Squiggle & Stay?
Squiggle & Stay is a programme designed to support organisations who want to Reimagine Retention. In a Squiggly Career progression means much more than promotion and people develop their careers in different directions. The challenge for organisations is how to make it possible for people to move internally in a way that’s available to everyone. So far we’ve worked with more than 15 ambitious organisations and over 7000 employees to experiment with how to remove the barriers to people transferring their talents and discover new ways to help people progress. We’ve taken an open approach to the programme with everyone involved committing to sharing what works and what doesn’t as we all learn as we go. You can read about the experiments and insights so far in the Squiggle & Stay Playbook.
How can organisations work with Amazing If?
We can support you in lots of different ways – from conference keynotes on topics like ‘the five skills you need to succeed in a squiggly career’ or ‘how to use AI for career development’ to accelerator workshops, programmes, learn-a-longs and week-long sprints. You can get in touch with us at helenandsarah@amazingif.com and find out more on our website.
What are Squiggly Skills Sprints?
Learning is an essential part of succeeding in a squiggly career, but we know it’s not always easy to fit in. The purpose of our free Skills Sprints is to make learning easy to do and something that you can add in to your day. You can sprint by yourself or in a team in less than 10 minutes per day. We have sprints on: accelerating your self awareness, increasing your impact at work, using AI to build your squiggly career and learning like a lobster.
What’s involved in an Amazing If workshop?
Amazing If workshops are designed to be enjoyable, inclusive and interactive — and deliberately different from standard corporate training. Every session uses live drawing rather than slides, combining storytelling and discussion to make learning memorable. All content is bespoke to the audience, but every experience shares the same goal: practical ideas people can put into action immediately. Depending on your needs, workshops can range from 30-minute keynotes to long term programmes, and can be paired with self-led learning toolkits, video series, and playlist resources so the learning lasts beyond the room. There’s more information on our website.
What skills are most important for career development?
The most important career skill right now is learning how to learn. In a world where roles, industries and technologies are constantly changing, the ability to stay curious, adapt quickly and build new skills continuously is what separates people who thrive in their careers from those who feel left behind. Helen Tupper and Sarah Ellis call this being a “learn-it-all” rather than a “know-it-all” and explore the science and practice of lifelong learning in their book Learn Like a Lobster, including how to make learning a daily habit rather than an occasional event.
How do I have a career development conversation with my manager?
Career conversations work best as a series of regular chats rather than one big annual event – little and often beats saving everything up. Come prepared with an agenda and focus on possibilities rather than plans, since possibilities open up thinking while plans can limit you to today’s reality. The most useful conversations include asking for “even better if” feedback, being clear about what you want to learn and why, and making it easy for the other person to help you. And don’t stop at your manager – a broad network of career conversation partners will give you richer and more varied insights. Episode 109 of the Squiggly Careers podcast has lots of useful ideas for action.
What is psychological safety and why does it matter at work?
Psychological safety is the belief that you can speak up, share ideas, ask questions, and make mistakes at work without fear of embarrassment or punishment. It was first defined by Harvard professor Amy Edmondson and is now widely recognised as one of the most important conditions for high-performing teams. In a squiggly career world, psychological safety matters more than ever – people need to feel safe enough to explore new directions, have honest career conversations with their managers, and take the kind of risks that lead to real growth.