Ditching the old career ladder
5 lessons from a squiggly career
I have a confession to make. Over the last 26 years, I’ve had 21 jobs.
I’ve been a banker, a bartender and a boathand. I’ve worked in classical marketing, commercial design and entertainment. I’ve co-founded a perky little design company and managed ops at a digital start-up. I’ve worked in PR, direct marketing, advertising and digital agencies. I’ve been a leader, a manager and a trusted adviser. I’ve worked inside and alongside organisations with three staff, three thousand staff and thirty thousand staff, across different sectors, different countries and different time zones.
For a long time I was embarrassed that my career journey wasn’t a clean and tidy trajectory. At one point I was even told that my CV looked ‘like a dog’s breakfast’. The worst thing about that (particularly unhelpful) feedback? I believed it. And I was embarrassed about it. That’s because, I had always believed my career should be a nice tidy ladder, progressing up towards a sparkly destination. In reality, it’s been messy and squiggly.
I didn’t have a plan
Back in high school, I could never answer that Frequently Asked Question - what do you want to do when you grow up / leave school / get a job? Some of my friends were clear. They had a career goal in mind. They were planning to be a policewoman, a physio, a builder and even a vet. They were sorted! But me? No clue. I quite liked the idea of being a Boss one day, but that was about it. So, I decided to do a business degree and kept my options open by majoring in two subjects. After graduating I stepped into a junior marketing role. Still without an ultimate destination in mind. I just took it one step at a time and grabbed opportunities that came my way. And 25 years later, I ended up a senior leader, and The Boss.
No - I didn’t have a clear plan from the outset. But if you ask around, you’ll realise very few people do. It’s not easy to stand at the bottom of a mountain and clearly see the path to the top. Nor is it easy to make decisions about some vague future version of yourself. Some of us need to start climbing and be prepared for detours, dead ends and u-turns along the way.
And we’re not alone.
“A career is a journey, not a destination”
Vincent Van Gogh had 5 careers before becoming an artist. Roger Federer played more than 12 different sports before settling on tennis. I’ve met plenty of people who’ve had diverse and interesting career journeys, and achieved great success. These people learned as much from their failures as their successes. They all achieved success in their careers - some in multiple different careers. Yet, like me, they were often apologetic about their messy career paths.
Why are we conditioned to think that a ‘good’ career path is one that involves goals, a plan and a tidy trajectory? Why do we apologise when we don’t fit that mould?
The definition of ‘career’ is changing
In the 50 years after World War II, long and stable career paths were the norm. The workforce was comprised mostly of men and career options were limited. Here, the way to success was to start in an entry-level position and incrementally move up a ladder over time, working 9 – 5 (with someone supporting the family at home). Many people would work at the same company for 10, 20, or 30 + years, eventually earning a gold watch or a pension for their efforts. The options were even more limited for women (typically a choice of teacher or nurse) and there was no career progression for them.
That was 75 years ago. Times have changed.
Work is dramatically different today. But our mental models haven’t necessarily changed, which has confusing implications for us all. A few decades ago, nearly all workforces across the globe consisted of permanent employees. These days, more than 40% of employees are considered non-permanent workers. And this is expected to rise as people fully embrace more remote, distributed and gig work. In fact, the very definition of “career” is in major transition. The traditional view of career trajectories is out of date - it is widely acknowledged that very few professionals are on a ladder-like path anymore. Most of us will follow a more disruptive career path that consists of a series of discrete “gigs” or “tours of duty”. And because we’re not following traditional pathways in these new careers, we can’t always see the end from the beginning.
Lessons from my squiggly career
Hindsight is 20:20 right? When I look back over my career journey, I can now see themes emerging. My natural empathy and strengths in collaboration and relationship building, have drawn me to jobs that relate to serving people – be it in client service, marketing or leadership. While I didn’t realise it at the time, I was attracted to roles where I could use those strengths. Another theme is problem solving - the wide range of roles and organisations I’ve worked in gave me the chance to tackle lots of different problems. So I also became skilled at lateral thinking and adaptability. As a result, I now have the benefit of ‘range’ to offer any organisation. I’ve come to appreciate that my dog’s breakfast is neither a bad thing, nor a rare thing. It has shaped me into the leader I am today, and I’m not done yet.
“The path is rarely a straight line until hindsight selectively connects the dots.”
As a leader I am often asked to mentor young people who are uncertain in their job or struggling with career decisions. As a mother, I’m supporting my teenager with her high school subject choices and her worries about the future. As an adult I have often had to make scary decisions to step sideways or back in my career. I’ve come to realise there is no ‘one right way’ to design a career, and there’s definitely no playbook.
My own squiggly career has taught me some valuable lessons -
It’s a journey, not a destination ~ This is a big one. I’ve learned that some travellers have a clear destination in mind and their journey takes them on a direct route to get there. Others take a different approach. They end up taking side roads, the scenic route, wrong turns and u-turns. Sometimes they re-route entirely. Both of these approaches are ok - there’s no ‘one right way’ to map a career and there doesn’t need to be a definitive end point. It is your journey to travel your way.
Job titles don’t define us ~ We’re not defined by our job title or job description. Doing a particular job right now doesn’t mean that’s all we’re capable of in the future. Dave Evans & Bill Burnett reckon “there are lots of great versions of you”. Your current role might be a stepping stone or learning opportunity before you move on to the next thing. We don’t need to change who we are as a person, but we can absolutely change and evolve what we do in our job (Who I am vs What I do will be the subject of another blog for another day!)
Our strengths travel with us ~ your skills, values and experiences travel with you from one job to the next. They are not attached to the job, they are part of you as a person. They are transferable. And they can be just as (sometimes even more) valuable in different jobs at different places at different times.
Range is good - In his book and TED Talk, David Epstein makes the case for ‘Range’. He argues that people with a breadth of experiences and a range of skills will be uniquely placed to solve the messy, human, wicked problems we’ll face in the future. It might feel counter-intuitive but science has proven that people who sample a variety of activities, gain broad general skills and know their own interests and abilities offer huge value to organisations. What’s more they’re also more likely to feel fulfilled at work. Yes - it’s important that we have people who are specialists in their field. But being a ‘jack of all trades’ is also something to value and celebrate.
Take one step at a time ~ Life is looooooong. Our careers are long. There is always time and scope to change. Humans are never done evolving - or Becoming as Michelle Obama says. Detours, failures, false-starts and fresh-starts are all learning opportunities. Stay curious and try new stuff. Even if you have an idea of your dream job - you might change your mind when you get there. It’s never too late to get started and it’s never too late to change. So, keep an open mind and take it one step at a time.
The final piece of good news for us messy career people is that we’re trending! We’re now living in an era of portfolio careers, hybrid working and the gig economy. The smart women behind The Squiggly Career podcast argue that the good old career ladder is outdated and no longer works for people or organisations. According to them, we should ‘ditch the ladder, and embrace the squiggle’.
Bring it on!
“Ditch the career ladder, and embrace the squiggle.”