Five Skills to Help You Succeed in a Squiggly Career

08 Apr 2022

This blog is based on the talk ‘The Squiggly Career’ by Helen Tupper at the 2021 Agile Business Conference. We’ve placed Helen as the narrator, so you can read it in her voice. Members can also hear her voice by watching the full one-hour talk.

“There was a time when careers looked a bit like ladders. You started on the lower rungs and climbed your way up, with your steps marked by a series of promotions and new job titles. It was assumed the goal was pretty much the same for everyone – clearly you wanted to move ‘up’ the ladder. Careers were thought to be linear and deterministic; yet that model was created in a world that was very different.

“100 years ago, the world of work really was more predictable, comprising similar functions, similar roles and similar routes to ‘the top’. Compare that with today, where people are not motivated by conformity and work is a bigger part of our identity than it’s ever been. The idea that everybody wants the same thing, and that success means the same for everyone, no longer feels right. That ladder concept can now be holding people back.

“Now we can talk about squiggly careers as a replacement for that ladder. No two squiggles are the same. There aren’t good squiggles and bad squiggles, only your squiggles. What's needed is for you to have the skills to take advantage of opportunities as they arise.

“Here are 5 skills that help people succeed in a squiggly career:

1. Values

“Values sit at the core of any career. Values are what motivate and drive you, and understanding your values means you can understand what ‘makes you you’. This immediately gives you 3 benefits:

  • It makes you happier at work because you’re more connected to your work and are more authentic. There’s no need to take on a persona when you’re at work
  • You can make better decisions about your career because you understand what works best for you. You don’t need to adopt other people’s ideas and expectations
  • You’ll be able to build better relationships, identifying where your values align or differ from those of your colleagues. You’ll be able to be curious about these differences to create more connection”

Check out the video and you’ll find an actionable tool to find out what your own values are and to explore how these may be influencing your career.

2. Strengths

“Marcus Buckingham, founder of ‘The Strengths Revolution’, describes a strength as anything that gives you energy, even if you’re not good at it yet. Conversely, a weakness is anything that takes your energy away even if you are good at it.

“This can be seen repeatedly in situations where people don’t love doing the things they’re good at and end up being disengaged and demotivated. We need to work on those things that give us energy. We can make progress on this by doing simple things like asking colleagues when they have seen us working at our best. Or you can work through an energy audit (Helen describes how to do this in the video). The key to understanding your strengths is to recognise when your intent is aligned with your impact. When these two things are synchronised, that builds your career.”

3. Confidence

“The reason confidence is important is that if you don’t have that belief in yourself, it can hold you back from taking action. Building self-belief is needed so we can do brave things and use our strengths.

“A lot of work on confidence focuses on the stuff above the surface, offering tips and tricks such as smiling, projecting your voice, looking at the lens of a camera. These things may impact how you look, but they have less impact on how you feel. ‘Imposter syndrome’ can still creep in – causing you to worry whether people think you know what you’re talking about, for instance. We need to feel confident to take chances, and to build a deep and authentic confidence.

“This is a long-term endeavour and there are habits we can build that will help. One is to regularly reflect on successes. A great start is to build a mindset of everyday confidence by reflecting on all the small things that have gone well:

  • Recognise 3 successes at the end of every day
  • Continue until you have forty successes collected over 2 weeks
  • Make sure you record them – write them down
  • Reflect over your successes

“This balances our brain’s negativity bias to gain a true perspective of our impact and helps prevent imposter syndrome creeping back in.

4. Network

“When we think about networking, we tend to think it’s about who we know – people knowing people. Yet, this isn’t a sign of a good network. A good network is built from people helping people!

“Start thinking about how you can help people; how you can build meaningful relationships, and then be clear about the help you need as well. This way, we can build a community around us to support us in our careers.

“When you start with what you’ve got to give, you’ll most likely get more in return. Here are 4 ways to contribute to your community:

  1. You can be a consumer of information – reading and learning, and also with a view of sharing this or turning it into something that helps other people
  2. Be a contributor – giving generously of your expertise, your experience and your energy!
  3. Be a connector – introducing people to one another, to build a sense of community
  4. Be a creator – start something from scratch that fulfils a need

5. Future

“When we’re shifting from ladders to squiggles, we also shift from the idea of planning to reach a destination, to the idea of opening up new possibilities. We’re not looking for a destination but a direction for our development.

“We need to stretch our thinking in different directions by asking ourselves:

  • What is the obvious move to make in our career?
  • What is the ambitious move – to something we find interesting, but feels just out of reach?
  • What is the pivot possibility – do we switch to something different, or even go back to something we’ve done before?
  • What is our dream? It’s worth exploring this, to find out if the reality meets our expectations and to find out what may be needed to make it happen.


We’d like to thank Helen Tupper for her contribution to our 2021 Agile Business Conference.

The world of business agility is extremely squiggly, and we recommend Helen’s guidance to navigate its complexity, and to develop the deeply rooted growth mindset on which our agility depends.

As the professional body for business agility, we focus on giving you the networking and connection opportunities to build your career and share your learning and experience with others – so we can all play our part in building business agility worldwide.