It’s becoming increasingly common to have multiple careers in a lifetime.

People are rethinking what they want to get out of work. To many, work is no longer just a paycheck, but a way to pursue their passions or make an impact on the world.

“But I can barely manage my one career! Why would I want another?” Growing multiple careers concurrently can be complicated, but there’s a way to do it so they complement each other.

You might even find it fun.

Read on to find out what having multiple careers can look like, the pros and cons, and how to get started and grow your careers in a way that minimizes risk.

What Having Multiple Careers Can Look Like

Having multiple careers at once is actually an age-old concept. It’s the Renaissance Man and Woman. Or polymaths like Benjamin Franklin and Maya Angelou.

But, the popularity of having multiple concurrent careers has been increasing in recent decades.

It comes in all shapes and sizes, across all age groups.

It’s the lawyer who also is a chef. The teacher and art dealer. The writer/speaker/consultant. The mom, CEO, and business advisor. The marketing executive and house flipper. The developer/designer.

It’s thinking about your career not as a linear, single vocation but as a body of work crafted around your skills and interests.

The concept of this “portfolio life” was coined in 1989 by business guru Charles Handy and adopted by author/speaker/blogger/consultant Jeff Goins. Having a portfolio life means pursuing “a portfolio of activities – some we do for money, some for interest, some for pleasure, some for a cause.”

In her book, One Person / Multiple Careers, Marci Alboher coined the term, “Slash Worker” to describe the people who craft multipronged careers. Instead of working for one or two employers in the same industry their whole lives, these professionals care about diversifying their income sources and interests.

You are no longer your job title or where you work.

Your identity can be shaped by the results you create, the impact you make, and if you’re lucky – what truly excites you.

So, let go of your fears and spread your wings.

Types of Multiple Careers

In this guide, I address the “concurrent multiple career” – having two or more careers at once. You should know this is different from the “sequential multiple career” – those who change their profession over time, perhaps dedicating 10-20 years to one career and then making a career change. These people often fall in two camps: those who may be forced to make a career transition because of the changing economy, and those who choose to do so to pursue passions or find meaning later in life.

Here are a few common models of concurrent multiple careers:

  • One job to pay the bills, the other as a passion project or creative outlet (ie. lawyer and DJ)
  • Two or more complementary jobs (ie. author, speaker, and business consultant)
  • Two or more creative jobs in a similar industry (ie. actress, model, and photographer)
  • Two or more jobs across completely different industries (ie. engineer and bakery owner)
  • A combination of jobs generating passive and active income (ie. affiliate marketer, blogger, independent consultant, and author)
  • And many, many more

Benefits of Having Multiple Careers

Some reasons you may choose to have multiple careers:

  • For personal growth and autonomy. 40% of independent workers in a study by And Co said their main reason for becoming an independent freelancer was for “personal growth.” The second most-cited reason was “flexibility.”
  • To proactively diversify your income streams for financial security and autonomy. You can’t rely on your employer for a steady paycheck, no matter how sunny things seem.  
  • Because there’s a growing market for specialists and consultants. Companies are increasingly hiring independent consultants and specialists.
  • For fulfillment and freedom. Younger generations want to live to work on their own terms, not work to live.
  • To protect your mental wellbeing and identity. It can be painful if one identity is threatened – we’ve all seen the demise of the depressed retired athlete.
  • To become a more attractive, full-stack employee. The “full-stack employee” is extremely valuable to organizations because they’ve mastered a combination of skills. For example, the marketing executive with a technical background in data analytics and engineering.
  • To enter new roles and markets that didn’t exist when you started your career. Today, we have drone operators, artificial intelligence engineers, user experience psychologists, app developers, and countless more.
  • Speaking of artificial intelligence, to get ahead of the curve as jobs become replaced by working robots.
  • For improved pattern recognition and ideation. The more you know about a variety of topics and industries, the more creatively you can combine ideas, recognize patterns, and solve problems. James Altucher calls this “idea sex”.
  • To make more friends in different circles! You’ll meet more interesting people, be more interesting yourself, and be able to introduce people who might never meet otherwise.

The Downsides

Having multiple careers is not for everyone. Here are some reasons why:

  • It can be distracting, unsustainable, and lead to burnout. Multi-tasking is dangerous, and it’s better to do one thing well than 3 things badly.
  • Many employees sign a contract with their employer that prohibits working for another company. Even still, millions of people moonlight and keep it a secret.
  • Even if it’s not prohibited by contract, it can be frowned upon. Your colleagues and manager may doubt your professionalism and commitment to the company if you’re dedicated to more than one job.
  • You may actually reduce your earning power. For example, a freelance engineer who also runs a creative business on the side cannot focus on his programming career alone.

A Practical Guide to Having Multiple Careers

How to Get Started

Despite the risks, 68% of freelancers said their quality of life has improved since going independent and 45% said they feel more secure in their employment this year compared to last—twice as many who said they felt less secure.

Curious if a portfolio career can fit your lifestyle? You can do it in a way that maximizes your chances for success.

Here are a few things to consider:

  • Identify your strengths and what excites you.

If you know your interests and what message you want to deliver to the world, think about how you can develop that through complementary mediums. For example, as a consultant/writer/speaker, you can use many different formats to share your ideas around one theme.

  • If you don’t know yet, reflect on the work you enjoy doing now.

What unofficial ‘roles’ or side projects do you take on at your current job that may be outside your normal scope of work? Brazen suggests using one medium to explore multiple subjects. This may appeal to those who want to explore a variety of industries. For example, many authors and journalists use writing as a medium for developing expertise across new industries and ideas.

  • Pursue careers that complement each other and are mutually beneficial.

In Hawaii, I recently met an Uber driver and professional photographer who also runs his own tour business. He markets his tour business by word-of-mouth to his Uber passengers and differentiates his tour business by offering photography lessons and portrait prints to his customers.

  • Start small with passion projects and side projects and see what calls you.

Build your portfolio by working with one client who may be a friend or pro bono. See what resonates with others, what you enjoy doing, and follow your intuition. Know that you can always switch gears and iterate.

  • Negotiate contracts around the output produced, not time spent. 

Trying to juggle a full time job and a part time job, or two or more part time jobs where you’re on the clock can lead to burnout. Don’t trade time for money for more than one of your jobs. Ideally, your income does not have to depend on the number of hours you worked. For example, if you have a full-time desk job and you consult by night, lock in a retainer or project-based pricing for your consulting contracts rather than an hourly rate. Even better, have one or more jobs where you generate passive income.

  • Use your career to gain new skills and experience in an industry you want to enter.

Choose clients that are in industries that interest you, and take on projects that require you to build your skillset. It’s an MBA that pays you. Kabir Sehgal, a Fortune 500 corporate strategist/US Navy Reserve officer/author/record producer subsidized his skill development. His corporate job paycheck subsidizes his record producing career, and he invites his corporate clients to recording sessions to build rapport.

  • Leverage the halo effect and market yourself.

If you have proven experience in one field, it’s easier to gain credibility all around. Get very clear about how you tell your story and pitch yourself. Make sure to translate your prior successes and experience in a way that positions you as a uniquely valuable asset to your client or boss. Even if you’re a newcomer to the industry, your fresh perspective becomes a strength.

  • Leverage your network.

Because of the social power word-of-mouth referrals, your contacts will often be the ones to help you land your first clients or get your foot in the door in a new industry.

  • Don’t be a jack of all trades.

Focus on mastering a few skills that align with your strengths. Double down instead of trying to multitask. To differentiate yourself, show how you combine these two or three skills to create even more value.

  • Think of each of your roles as building blocks leading you to where you want to be in five to ten years.

Perhaps you’re a CEO and public speaker today, but you want to become a business coach, advisor, and investor once you have more experience under your belt. You can accelerate your trajectory and begin building credibility as a thought leader by contributing to outlets like Forbes or authoring a book.

Growing Your Portfolio Career

  • If you can, cut back on your main job to focus on growing your new career.

According to the Wall Street Journal, “successful portfolio careerists tend to first establish themselves in a specific field and then cut back to make room for something new.” If you have the flexibility, you can scale back on the number of days you dedicate to your job (ie. a dentist with his own practice hires another dentist so he can work three days a week and spend the other days starting a company).

  • Treat your other career like another big client.

Dedicate time to working for yourself, just as consultants juggle and prioritize their clients. Divide your time around your priorities and treat your own tasks and deliverables with as much care as you would for a landmark client.

  • Think about your entire career as a business.

Having multiple jobs creates more administrative and operational work. You need to juggle invoicing, understanding tax laws, structuring and organizing your business, keeping track of clients, finances, contracts, managing your personal brand, and more. Organize your portfolio life the way you would run a business.

  • Streamline the admin work with the right tools and technology.

If the last bullet gave you anxiety, it’s a good thing we have tools to help. Check out this epic list of free tools and software like AND CO to handle admin work.

  • Expand your market by thinking global.

Your income and audience is not limited to where you live. It’s fascinating how different professions are in high demand and respected in different cities. For example, translation services may be undervalued in the United States, but is extremely well-paid abroad. Or, your startup skills may be overshadowed in Silicon Valley, but celebrated in emerging tech hubs.

  • Track your metrics – both quantitative and qualitative.

It’s as important to measure metrics like revenue as it is to check in on your own sense of fulfillment. Is one job, client, or channel no longer fulfilling for you? Or does it not move the needle despite all the time or money you’re investing? Then get out of there! Know that you can always cut back and double down on what’s working, and on what you enjoy.


Is having two or more careers better than one? If you choose to pursue a portfolio career, it’s up to you to make it so. It has the potential to accelerate your personal and professional growth, and it can be incredibly fulfilling.

Start thinking of your career as a business of its own.

What are your values? Your life mission(s)? The “culture” you want to create in your ideal lifestyle? The types of people you want to interact with? And what projects, roles, industries, mediums/channels, or clients will help you make the impact you want to create in the world?

In the new era of work, we will see more and more people pursuing this path. You can do it too. Why not take the leap?

Start Creating

If you want to overcome your limiting beliefs and accelerate progress towards your dreams, check out the short thought experiment below.

6 Limiting Beliefs Keeping You From Your Dreams — And a Thought Experiment to Overcome Them:

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