The Art of the ‘Squiggly Career’

When I look at career (so far) and compare it to both my late father’s career, and the career on my stepson that is just starting, I see a very different picture. My father was a Food Technologist and worked for only 2 organisations, in the same area of specialism, throughout his entire career. My stepson is only a couple of years out of University and, having started work in Property Investment, is already onto his second career – building his own business in the wellness industry.

I am somewhere in between – I trained as a Business Psychologist soon after graduating, applied those skills within several corporate and consulting roles for 30 years, but after hitting middle age, decided I wanted to try something different, and set up my own coaching business.

It has been acknowledged for some time that jobs are no longer for life and most people can expect to worked for several organisations throughout their careers, but I think what is less well understood is how many people have a broad range of skills, talents and motivations – which may not all be satisfied by one job. Charles Handy is often credited with coining the term “portfolio career.” Handy defined a portfolio career as one in which individuals have multiple sources of income and engage in a variety of different work activities, rather than relying solely on a traditional full-time job. In Handy’s view, a portfolio career is a way for individuals to build a more flexible and diverse career that allows them to pursue their passions and interests, while also achieving financial stability and security. He saw portfolio careers as an alternative to the traditional, linear career path, and as a way for individuals to take control of their own careers and create a life and work balance that works for them.

With a portfolio career, you have more flexibility to choose how you want to work, when you want to work, and where you want to work. Whilst not without its own challenges, this can be especially appealing to those who value work-life balance or who want to pursue multiple passions at once.

So, all we have to do is identify our passions as early as possible and find a job or portfolio of work that channels these passions in a way that delivers something the World wants?
Understanding what makes us tick and what we would like to do in life is a critical step on the path to having a fulfilling career. But that’s only half the battle. In his book ‘how will you measure your life?’ Clayton Christensen persuasively argues that we can draw lessons from how organisations have achieved success to help us navigate our navigate our career(s). Only a few lucky companies start with a strategy that ultimately leads to success. Christensen argues that, in a rapidly changing environment, a top-down, planned approach to strategy is often insufficient, and that organisations need to be flexible and responsive to changing circumstances in order to thrive. He argues that organizations can achieve this by embracing an emergent strategy that allows them to experiment, learn, and iterate over time.

One of my all time favourite quotes is by John Lennon:

“life is something that happens when you are making other plans”

The principle of emergent strategy applies to careers by recognising that career paths are often not linear or predictable, and that success is often the result of multiple factors coming together in unexpected ways. In an emergent career strategy, individuals focus on being open to new opportunities and flexible in their approach to work, rather than trying to adhere to a strict, pre-determined plan. This means being willing to take risks, trying new things, and adapting to changing circumstances as they arise.

By embracing an emergent approach to your career, you can be more responsive to new opportunities and challenges, and better equipped to navigate changes and uncertainties in the job market. You can also be more open to new experiences and learning opportunities that can help them grow and develop professionally. If you are so busy trying to figure out how to climb the next rung of a particular career ladder, you may miss potentially more fulfilling opportunities that life is presenting – maybe the ladder is lent against the wrong tree?

What might result from a more emergent strategy could also be describes as a ‘squiggly career’. A squiggly career refers to a career path that is non-linear, unpredictable, and has many twists and turns. It is a term used to describe a career that does not follow the traditional, straight-line trajectory of a single job or profession, but instead is marked by shifts, changes, and unexpected opportunities and detours.

A squiggly career may involve switching industries, taking on multiple roles within a single organization, starting and stopping work for family or personal reasons, or pursuing different interests and passions over time.

This type of career can provide a lot of flexibility and freedom, and it can be especially appealing for those who enjoy variety and change in their work. However, it can also bring its own set of challenges, such as the need for continuous professional development and the potential for income instability.

In any case, a squiggly career requires individuals to be adaptable, resilient, and proactive in managing their careers and finding new opportunities. With the right skills and mindset, however, a squiggly career can be a rewarding and fulfilling way to pursue one’s passions and goals.

Successful squiggly careers are often characterized by a few key traits:

1. Strong self-awareness: Individuals with successful squiggly careers have a deep understanding of their skills, interests, and values, and they use this knowledge to guide their career decisions and make informed choices about the work they pursue.
2. Continuous learning: With a squiggly career, it is important to be proactive in building and maintaining a diverse set of skills and knowledge. This can involve formal education, professional development courses, and on-the-job learning experiences.
3. Networking: Having a strong network of contacts and professional relationships can be invaluable in navigating a squiggly career. Building relationships with mentors, peers, and other professionals in your field can help you stay informed about new opportunities and connect with others who can support your career goals.
4. Resilience: Squiggly careers can be unpredictable, and it’s important to be able to bounce back from setbacks and handle change with grace and resilience. This includes being able to adapt to new situations, handle uncertainty, and maintain a positive outlook even when things are not going as planned.
5. Strategic planning: While squiggly careers are not always predictable, individuals with successful squiggly careers often have a clear sense of their long-term goals and a roadmap for achieving them. They use strategic planning to make informed decisions about their career and stay on track despite the twists and turns along the way.

There are many famous individuals who have pursued squiggly careers and achieved great success. Here are a few examples:

1. Oprah Winfrey: Oprah started her career as a news anchor and later transitioned into a successful talk show host. She then went on to launch her own television network and become a media mogul, with a diverse portfolio of businesses and investments that includes everything from books and magazines to her own production company.
2. Richard Branson: Branson is a well-known entrepreneur who started his first business, a student magazine called The Student, at the age of 16. He went on to launch several successful ventures, including the Virgin Group, which now encompasses more than 400 companies in a variety of industries, from music and travel to health and wellness.
3. Elon Musk: Musk is a tech entrepreneur and investor who has been involved in several successful startups, including PayPal, Tesla, SpaceX, and Neuralink. Throughout his career, he has taken on a variety of roles and tackled a wide range of challenges, from revolutionizing the payments industry to developing cutting-edge technologies that could change the world.
Overall, successful squiggly careers require a combination of self-awareness, continuous learning, networking, resilience, and strategic planning. By cultivating these skills and mindset, individuals can build fulfilling and successful careers that allow them to pursue their passions and interests over time.

Tags: career

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