Rethinking Your Career – The Possibility of Having Several Careers Throughout Your Life

Most of us have accepted the default that we must choose a single career to pursue throughout our life. 

The least people have career aspirations, which are singular and remain constant for their entire life. 

Most people I’ve encountered, find it hard to define what their ideal career would look like. 

Many people have a collection of career aspirations rather than a single one, but not everyone is willing to admit this.

They are afraid of being seen as inconsistent and unfocused. 

This is not necessarily the case. People who have a variety of interests and career goals are likely to be curious, creative, and ambitious people. The kind that wants to have it all and do it all.

Not possible, you say?

The good news is, that pursuing more than one career and having more than one career in your life is possible.

The key here is in your life.


Oftentimes people view career development as a straight line and process. 

As though you come up with your career goal when you’re 16 or 17, pursue it and stick to that same career goal until you’re 60, 65, and retire.

But that is not how career development works.

A lot of career development is personal development. 

To succeed in a career, you need to be devoted. But the career per se does not require your loyalty.

Unlike marriage, and your spouse, a career is not something that you commit to, but it is something that you develop and mold.

A career is the combination of your efforts, jobs, development of skills, accumulation of experiences in a certain area, that focuses on a purpose, or at least a goal.

The challenge is, that this purpose may not be crystal clear to everybody.

It usually requires experience and exposure to a lot of things, and a good understanding of oneself to arrive at a purpose.

Changing careers, or pursuing several careers is only a necessary follow-up step in the process of pursuing that purpose, or northern star, or whatever is guiding you. 

If you agree with this, then you’ll realize that a career is a living, dynamic thing. Something that evolves with your personal growth, development, and experiences in life.

Career change is oftentimes necessary. And sometimes, pursuing several careers, or multiple careers can be the best that you can do for yourself.

Having multiple careers means that you pursue more than one career either at the same time, also known as concurrent multiple careers (or ‘Portfolio Careers’ or ‘Slash Careers‘, or at different times or one after the other, also known as consecutive multiple careers.

The terminology is not important here. What matters is, that you open yourself up to an entirely different understanding of what your career can be. 

And that is, that just as there are different ways to build a house, there are infinite ways to have a career. 

If you are someone who has been struggling to choose one single career and feel that there is currently no single career path that will do it for you, then this might come as a relief. 

For some people, pursuing several careers concurrently can make sense. Take for example Violinmaker/Clinical Psychologist Bob Childs. An article by CNN revealed that

“The deeper he was drawn into what he calls the “mystery of what makes an instrument sound good,” the more isolated he felt, planing and sanding at his bench, alone for days on end. For Childs, concentration required solitude; there was no way around it, and “That really bothered me,” he says. “I wanted to figure out something I could do that involved working with other people.”

Pursuing two careers, as a violinmaker as well as a therapist, helped him to balance out his life. 

Bob Childs started making violins in his 20s, but only in his 40s, he became a practicing therapist.

This is a good example of how someone can have several careers by starting with one career and then adding a second career later on in life. 

People of generation X, Y, and especially Z, are very well positioned to have multiple careers, especially due to the increased lifespan which is likely to reach 80, 90, for generation X & Y, and even 100 years old for generation Z.

In ‘The 100-Year Life – Living and Working in an Age of Longevity‘, the authors point out that someone who is currently in their 20s has a 50% chance of becoming a hundred years old.

Contrast that with the life of our great grandparents. During their time, on average people only lived until 50 or 60 years old.

They would have 30-40 years from the time they graduated from school (if they went to school at all) or college, until death, to figure out and work on their career.

Normally, they would go through three life stages related to their work and career.

As touched on in ‘The 100-Year Life’ authored by Lynda Gratton & Andrew Scott, the first stage would usually be getting an education or training to prepare themselves for work. 

The second stage would be to get a job. And at that time most people would stay in one job or maybe just switch between a limited number of jobs.

Then the third stage at perhaps 50 plus, they would retire and spend time looking after their grandkids. 

Gen X-Z now has much more time. They finish their education between 20-25 years in most cases and have 50, 60, or even 70 years to develop a fulfilling and purposeful career.

More time simply allows for more possibilities. 

On the flip side, more time can also necessitate people to work more and longer. It all depends on how you choose to see it. 

‘Have to’ to versus ‘get to’ pursue a career and work longer.

For those people who always feel like they need to be working on something, the latter is likely to apply.

Longer time, better health, enhanced opportunities driven by digitalization enables more room to maneuver.

Throughout your long life, you can pursue and develop multiple careers.

Old model: 

Cram everything you want to do between the age of 24 and 50/55 (25-30 years). Likely to switch between multiple jobs, but likely pursuing one traditional career path.

New model: 

Distribute your career goals and efforts between the age of 24 and 70/75 or beyond (45-50 years). Start different careers at different life stages, and adjust the amount of time, the energy you spend on each at different times. 

These numbers are just examples. Important is the concept. 

Here is a simplified example, parts of it adapted from the same book ‘The 100-Year Life’. For more detailed examples I would highly recommend picking up this book! 

Klara graduates from university at 23. Instead of directly working for a company, she goes on an exploratory phase first. This could entail going overseas on a working holiday or live in another country to learn the language for a year.

Returning from that, she becomes an independent producer, doing something more entrepreneurial for 2 years. She opens a Mexican food catering business.

Then, still relatively very young at 26, Klara decides to get experience working for a company. With the hands-on business experience and foreign language in her pocket, she can offer something more unique and valuable than other fresh grads. 

Klara works for several years, and then at 29 goes back to get a second education. She gets a 1-year postgraduate degree in Marketing. 

The goal here is to sharpen certain aspects of her skill and knowledge, to gain a competitive advantage. 

Then Klara might go back to work for 3 years. On the side, she continues to run their catering business. After all, she already equipped with that skill and have the experience.

Since it’s running so well, at 32 Klara quits the corporate job and becomes a full-time entrepreneur. Having a family and kids now, she wants to have more time with her family. She becomes established and has a steady income source.

On the side, Klara has been writing. She always wanted to write a novel but couldn’t find the time and focus earlier. At 38, she takes an online writing course with a mentor and spends 50% of her time writing her novel and a blog.

At 42, Klara publishes her first novel. With her successful blog and a multitude of experiences, she manages to get hired at a marketing consultant by her former company.

At 50, she starts a new career in gardening. This is something she always wanted to do, but when she was younger she decided to prioritize other career goals first. Now that she is established as entrepreneur, writer, and consultant, she can find time and energy to add a new career. 

And so on.

The point here is, that there are so many ways to build a career. 

Many people, especially those who ‘grew up’ working in big corporations, see working for big corporations as the only way. 

Working for corporations is amazing. There is so much one can learn and experience in that environment. 

But many people just rely too heavily on corporations as the party to guide their career development and provide them (their only) an income. 

I remember the time when I was working for a large bank, where there were two performance reviews scheduled each year, with the opportunity to have a focused discussion to talk about one’s career path.

I realize now that I didn’t have a clear idea of what I really wanted, and neither did most of my fellow colleagues in the same age range. Everyone was young, ambitious, energetic. Everyone wanted a promotion, career development, and a higher salary.

But few knew what they really wanted for their career. And so they sort of ‘drifted’ along on a given path and followed the flow, instead of shaping their careers intentionally.

Some of my friends are even wondering what they are ‘still’ doing there, in the same job function for the past 15 years.

Some friends retained more or less the same job function and responsibilities, albeit with everchanging job titles which gave the illusion of change happening.  

No one is required to follow one given career path. That is just the default assumption of most people, because it may seem that sticking to one traditional career path is what most people do.

No one will or can tell you what the best career path for you is.

The career path that works best for any person needs to be figured out by themselves.

Other people, coaches, mentors, friends can help, but ultimately it’s the person in question who needs to spend time to figure this out.

And career development, as the word says is not a one-time static thing. A person needs to review their career regularly, latest yearly, and assess 

“Am I still on track?”

“Does the career path that I’m following serve me, my purpose, my aspirations?”

“What can I tweak/change/start/eliminate to make it a career that’s better for me?”

“Is this area I’m working in right now enabling me to make the contribution I want to?”

Whatever age you are at – and for you reading this blog post it’s likely to be somewhere between 20-50 – recognize that if you feel that you haven’t found the right career yet, you still have a lot of time and many chances to develop the right career. 

Even if you are in your 40s or 50s, you still have 30 or more years left. Even if you are 60 or 70, there is still a lot you can do to pursue the things that matter to you.

As long as that doesn’t include winning a gold medal in the Olympics or becoming an astronaut, chances are that you can do that. 

My mother became a Tai Chi teacher when she was in her 60s. My father wrote his first book on ‘Probiotics’ shortly before he turned 70.

And in case you’re just in your 20s or 30s, then don’t get me started. Life has just begun, and there are infinite ways to design your career. 

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