What does your map to the future look like?

Monday 18 November 2019
A linear, ‘staircase-like’ career path doesn’t necessarily work in the modern working world. Nowadays, it’s all about being squiggly.
a person pushing a pin into a piece of paper on a board

Helen Tupper spent the first half of her career in marketing, working in management positions for brands such as BP, Virgin and E.On. She eventually became commercial marketing director for Microsoft, before calling an end to that career altogether.

Since 2013, Tupper and Sarah Ellis had been running Amazing If, a career development business with a difference, alongside their day jobs. The pair now have a long-running podcast and a book coming out early next year, both called Squiggly Careers.

It all spawned from Ellis and Tupper’s changing philosophy about the world of work – that a linear career model just doesn’t really cut it anymore. “That was the expectation of a good career,” says Tupper. “It was all about going upwards, that you'd be happy when you made it into a senior position. What we know now from our own research and from the organizations we work with is that model doesn’t really feel like the careers that many people are experiencing or really want to experience.”

There are several factors that influence what a good career looks like nowadays. As people are working longer, we have a broader range of generations working together in the workplace – sometimes four or five. This makes the workplace more complex – a linear model is no longer viable if people are staying in their roles for longer.

Technology is also changing how and when we're working: you're competing with people that you weren't competing with before as companies increasingly dip into a geographically broader talent pool. On top of that, people are looking for more purpose in the work that they do beyond earning a salary.

So how do you plan your career in such a complex environment? Tupper says that you need to think about five different elements to identify what career possibilities are open to you.


What do you really care about when it comes to work? What motivates and drives you? If you know what your values are, you can make better decisions about your career.

“When you understand your values, you can start to craft your job in a way that might be more fulfilling for you, which will make you happier in the long term. And you can also build better relationships with people when you know your values, as you tend to empathise better with other people’s motivations.”


People struggle to know their own strengths, says Tupper. This is an issue in a modern career, where it’s essential to be self-aware, be able to articulate your strengths, and know the value you bring to a role or workplace.

“You can really start to take control of your career if you have that knowledge. We've trained 10,000 people now, and the vast majority of people don't know what they're best at.”

One way to tap into your strengths is to start with your weaknesses, which people find much easier to identify. Write down three things you aren’t as good at and ask yourself why you aren’t so good at them. Think about how they relate to things that you do. Your strengths are likely to be the other side of the coin to your weaknesses.


Part of the reason that people struggle to come up with their strengths is a lack of confidence. Even people who know their strengths aren’t always confident when talking about it, Tupper explains. “They've got what we call ‘confidence gremlins’ that hold them back.”

One way to be more confident in talking up your strengths is to manufacture some personal distance. “If I said to you: what would your partner say you do best or what would your manager say that you do best? There's something in the psychological distance which that question creates that allows you to see yourself from a different perspective.”


This is not necessarily traditional networking as you might think of it. As Tupper puts it, it’s about people helping other people. You want to build a strong network of mutually beneficial relationships, where you can share your strengths and values. It doesn’t matter if you have a very large and broad network or a smaller and more focused one, as long as it’s active.

“Maybe I can help people by connecting you to somebody else. Maybe I can help you by contributing my time or my expertise as a coach or my expertise from working in these different businesses. You're always thinking: what are your challenges and how can I help you personally?”

Career possibilities

Once you have an understanding of your core strengths and values and have built your confidence, you can start to map out what Tupper calls career ‘possibilities’; you need to think about what you might want to do before you need or want a new job.

“What's it like to work [at that business]? What are the jobs? Are they a good use of my strengths? What would I need to learn to be better? Doing that proactively will help you break out of the ‘staircase’ thinking, so you can really position yourself to succeed in a squiggly career.”

On CMI’s Career Development Centre, we have all the tools you need to evaluate your current professional situation and see if there are any areas you want to develop in.