My career isn’t a mess — I’m a Generalist!
By: Joey Chan
Tags: Personal Development, Creativity, Confidence, Design Thinking, Career Change

For the longest time, I wanted to be a specialist. I believed that a specialist is a be-all and end-all, the crème de la crème of any field. It’s a badge that you needed to earn if you wanted to be successful in your career and climb the corporate ladder. This was the reason why I felt very insecure for most of my career because I have changed careers 5 times in 5 years (now on my 6th). I’m often described as a ‘multi-purpose spray’ and someone who has lived many lives for a person in their early 30s.

Career “pivots”.

After I graduated with a double degree in law and commerce, I went on to become a corporate lawyer in a shipping company. That lasted for 1 year. I quickly realised that law wasn’t the career for me. I would always pop my head in to chat with my colleagues in marketing, or frequently stop by finance and IT to see what they were working on. I would annoyingly offer ideas to things I knew nothing about and get involved in a lot of extra-curricular activities. So, much to my parent’s disappointment, I gave up my career as a lawyer to do something I was actually passionate about even though I didn’t know what that was.

Image by cottonbro from Pexels

Leaving my job as a lawyer was like releasing the spring-loaded plunger on a pinball machine and I was the ball that randomly bounced off the sidewalls and bumpers. I bounced around from one job to another, trying to find that one thing I wanted to specialise in and I kept going until I could find it.

I co-founded a company in marketing, worked for a property developer to sell property, became a digital strategist for a film agency, helped freelancers and small businesses with strategy. While I was in these jobs, I also organised corporate events, did photography, volunteered at a legal centre, and mentored university students. All of that led me to my career calling: human-centred design.

Truth is, I had no idea what I was actually doing with my career.

Every time I updated my Linkedin, it was a reminder of all my insecurities:

What if people think ‘she doesn’t know what she wants’ because I look like I’m ‘job-hopping’;

No one will take me seriously;

I look like I’m a junior and starting a new career from scratch every time;

My career experience didn’t make any logical sense and was different from everyone else that graduated with a similar degree.

I lack focus because I have too many interests!

It wasn’t until I was funemployed for 4 months before my current job that I figured out how I could use all of my experience to my advantage and find the type of work where I can best apply my skills and interests. I reframed my stories and unlearned the idea I had to be a specialist in one field.

I‘m a specialised generalist.

The old saying goes ‘jack of all trades, master of none’ implies that you need to be a master of one thing. We often take this to mean one profession, one industry, one sector, or even one technology or platform. But ‘mastery’ should be broadened to include an approach, a way of working, an ability or trait.

Perhaps a better way to define myself is that I’m a generalist in business and a specialist in creative problem-solving. What I had collected throughout the years was a wide variety of skills across a number of business disciplines and in a number of industries. All the seemingly disjointed careers that I worked in actually worked in my favour because I could apply myself in many different roles because of these transferable skills:

How to communicate and influence people at all levels of an organisation. Ability to contribute meaningfully to discussions on a variety of topics and professions from the far left-brain logical professions (lawyers, accountants, IT developers) to far right-brain creatives (filmmakers, designers, artists), and everyone in between. An understanding of organisational structure and nuances of people in these departments: sales, marketing, finance, IT, people and culture, operations, and leadership. Ability to listen empathetically, use curiosity and inquiry to define a problem to be solved. Take knowledge from different disciplines to make new connections that lead to original ideas in problem-solving.

My intention isn’t to brag …but to tell you what I wish I knew earlier and save you the heartache of feeling like you’re not getting anywhere with your career.

Without realising, I had become a ‘T-shaped’ person — an expression that describes a person’s abilities in the workforce where the verticle line represents the depth of skills and expertise in a single field, and the horizontal is the breadth across other areas and disciplines. Specialists would resemble more of a ‘sword’ shape where they have a great depth in one thing, but little knowledge in other related areas.

In his book ‘Range: Why Generalists Triumph in a Specialized World’, author David Epstein builds a strong case for having a variety of experiences, experimenting and changing course every now and then to find your true passion. Through his research on the world’s most successful athletes, artists, musicians, and scientists, he found that while generalists often find their path late and juggle many interests rather than focusing on one, they are more creative, more agile, and able to make connections their more specialised peers can’t see.

“The more varied your training is, the better able you’ll be to apply your skills flexibly to situations you haven’t seen. You’re trying to learn how to match a strategy to a type of problem instead of just learning how to do repetitive patterns.” — David Epstein

I wish this book was published sooner because it would’ve been reassuring to know that generalists are just as important as specialists and that experimenting with different careers and having a broad range of experience is a good thing. Instead of feeling insecure about not having enough experience in one thing or be good enough for a job I want, or feeling like I don’t have any career direction, I can take pride in the fact that I am a generalist: a well-rounded person with an invaluable and diverse set of skills.

Being a generalist isn’t enough.

By Tino Renato

What’s going to give you an edge in your career is knowing how to apply all the things you’ve learnt from your different careers in new contexts and situations. Let’s use this example of a head chef who studied business and previously worked in hospitality as a casual and has a side hustle doing photography. Being able to integrate her knowledge and experience means she would be able to run a kitchen efficiently, deliver a great dining experience, manage the business profitably, and be able to contribute to the marketing collaterals and strategy to appeal to new customers.

Acquiring new skills and knowledge is the easy part; true mastery is in application and execution.

Experiment more.

“If we treated careers more like dating, nobody would settle down so quickly.” — David Epstein

Like dating, the goal is to use the shortest amount of time to learn as much as you can because time is your most valuable asset. If something (or someone) isn’t right for you, wouldn’t you want to know sooner rather than later?

Through experimenting with different careers, I found my true calling in human-centred design. Not only does it combine my love of creativity and business strategy, but also a field where I was able to apply everything I had learnt from all my different careers — the attention to detail from my days working in law, the interpersonal and organisational skills from running a business, through to creativity and storytelling from my time working in the film industry.

Experimenting doesn’t necessarily mean quitting your job.

You can become a generalist wherever you are. In fact, it’s probably the least riskiest way to experiment because if you end up hating it, you just go back to what you were doing before! In small organisations, you’re often required to wear multiple hats and do things outside of your position description to get stuff done. While you may feel overworked at times, this is one of the best ways to accelerate your growth and broaden your skill set across different business functions.

Large organisations tend to hire for more specific and specialised roles, so getting exposure to other functions may require more proactiveness. Good organisations who value employee growth and wellbeing would support an employee’s desire to learn. This may take the form of learning and development programs, secondment to another department, and structured and unstructured learning opportunities.

The only waste of time is when you’re stagnant.

Far too often, people have great fears about changing careers or pursuing their passion. The more senior you are in your current career, the harder it is to step out of your comfort zone and away from what you already know. You think you’re going backwards by starting something new and all the years put into becoming a specialist would be a waste. That is just your ego getting in the way. Every time I felt it was time to change careers was when I felt stagnant and I wasn’t learning anything new. I felt like staying in a job just for the paycheck was the real waste of time — time that I could be spending elsewhere, learning something new.

Specialists can become generalists too.

Regardless of how specialised you are in your field, change should be seen as building blocks. I came across this story about a paramedic who became a service designer so that he can help build a better health system. He didn’t “start over” as a service designer; he built design skills on top of his 7 years of specialised knowledge as a paramedic. Before, he was saving lives as a paramedic. Now, he improves the larger health system that impacts thousands of people.

Some people stay within one field of work because of the belief that they’re not creative enough, smart enough, or *whatever* enough to pursue something else. I call BS on this because I believe you can learn any skill whether or not you’re a ‘natural’ at it. Dr. Carol Dweck calls this the growth mindset — the belief that you are in control of your own ability as opposed to purely relying on natural talent. People with a growth mindset know that they can learn and improve with hard work and effort. They don’t see failures — only lessons.

Find the common thread.

So, you have a bunch of transferrable skills under your belt. BUT it’s not enough to land your next job if you’re not able to communicate how the skills acquired in one role can be valuable in the new role. Start by asking yourself:

What’s the overall theme or commonality that is true across all of the jobs you’ve had?

Looking at my track record, I was in the pursuit of understanding people — why we do what we do, how we make decisions, and what we feel. When I tell people about my career path, I get confused looks and questions like “How did you go from being a lawyer to being a designer?!” Two very different professions on the surface but when you distill it down, it’s all about being able to understand people and solve problems. The common thread in my career is my curiosity for human behaviour and psychology. In each job role and industry, I was able to see how people behave in different contexts and therefore gained insight into the underlying human experience:

Law = Conflict and risk

Startup = Resilience and adapting

Marketing = Influence and desire

Film = Empathy and storytelling

Consulting = Creative problem solving and deep listening

So which is better: generalist or specialist?

At the risk of sounding like a therapist, neither is better than the other — you need both to work together in organisations to get the best outcomes. Generalists’ broad skills make them best placed to know who and what they need to solve a problem. Specialists’ deep knowledge and understanding of the intricacies of a particular solution are necessary for it’s implementation.

The point is not to argue which one is better but to elevate the importance of the role a generalist plays in teams and organisations.

For people looking to change careers and find a career that aligns with your passion: Do a stocktake of your work experience and find the common thread. Focus on the transferable skills, rather than the job title. Show how you have mastered and can apply your common thread in a new context. Everything you do adds to your knowledge bank.

For leaders and managers: Identify the generalists and specialists in your teams, encourage and support those who want to experiment in a new field or job function. You’ll have a more diverse team and your staff will be more excited and motivated at work. It’s a win-win!