How to Choose a Career Path When You Want to Do Everything

A lot has changed over the last two years in the world of work due to the pandemic. Months of lockdown, working remotely, and never-ending Zoom meetings have caused so many people to reexamine what's important in their lives and careers. 

For the midlife professional who has been working for 20 years or more, it's easy to assume that even amid this unpredictability, you know how to manage your career. However, a study by Harvard Business Review found that midlife career professionals need greater help and support if they want to avoid being undervalued and overworked.

Researchers noted that professionals 45 and older were more likely to have made bad or less successful career decisions earlier in their careers, which have led to less than successful outcomes. I've found two contributors through my work and research: (1) following traditional career progression advice and (2) building a career based on titles and income and not meaningful and satisfying work.

The excellent news is midlife career professionals don't have to follow the status quo and can now take control of their careers. Now is the perfect time to design a career and life you love. Whether you're looking to pivot, transition, advance, or start a side-hustle, you also have the option to dive into the gig economy and create a portfolio career.

A portfolio career is a working style where you combine multiple income streams through a mix of full or part-time employment, freelancing, passion projects, or working as a consultant. It's an excellent option for the multi-passionate person who has always struggled with choosing a singular career path. A portfolio career allows you to showcase your gifts, talents, and brilliance while creating your own economy, which is why 24 million U.S. workers want to leave their jobs and become their own bosses.

More and more women today prioritize freedom and flexibility over the security of a "stable" traditional job.  The resurgent of the gig economy makes a portfolio career a viable and exciting option for many midlife career professionals. If you've fine-tuned your ability to self-manage after working these last several months remotely and are looking to branch out and try something new, you may want to explore a portfolio career.

Pros and Cons of a Portfolio Career

I always tell my clients if they can find a job or career that allows them to absolutely love at least 80% of their work, they're in a great place. There are always things you don't love in your work, and it's usually related to working outside of your zone of genius. 

One of the benefits of a portfolio career is that it lets you do more of the work you love because you're making the decisions about when, how, and for whom you'll work. Freedom and flexibility are other advantages because you won't be limited to company vacation days, holidays, or sick leave. You'll also determine your salary by setting the price for your services, which can provide significant financial security for some. Finally, the versatility of experience, along with career satisfaction and growth, can have you looking forward to Monday mornings instead of counting the days to your retirement. 

It's essential to be clear that a portfolio career isn't synonymous with being an entrepreneur. You can hold a series of part-time positions as an employee or even keep a full-time job with one or two part-time positions. The key idea is that you have multiple streams of income doing multiple similar or varied tasks. 

A portfolio career isn't for everyone. You'll need strong time management skills to juggle the multiple roles and responsibilities of a portfolio career. Brand development will be necessary, so the people you want to work with you are clear on what you're offering and know how to find you. This will require deep self-awareness so your network can show up for you and support your efforts. 

In addition, to calendar management and tax implications for reporting multiple income streams, it's vital that you have a cohesive strategy for your career trajectory before you consider a portfolio career. Holding various jobs to make some extra money to manage your finances should not be your reason for doing this. Instead, know your career goals and your "why" for going this route; otherwise, you'll find yourself overwhelmed, overworked, and frustrated by taking on too many disparate roles.

While specializing in just one thing can be risky in our current economy, it's still not the norm to do multiple jobs and hold various positions. As a result, you may be perceived as a flake or just unable to land on the "right" career for you. It takes a true rebel persona to embrace this career path.

Launching Your Portfolio Career

You'll first want to determine if you're genuinely a multipotentialite, a term psychological and educational term popularized by Emilie Wapnick. 

Do you have multiple talents, gifts, and ideas that could be applied to various projects, roles, or even businesses? If you've found yourself changing positions every few years and have excelled at doing them all, you're most likely ready for this type of career.

It's always good to have at least one steady stream of income, so if you're currently employed and enjoy what you do, by all means, stay. Think about this as your "anchor" career. You may want to look around your organization to see if there other opportunities for you.

You may best utilize your unique gifts and skills during certain times of the year. For example, working seasonally during certain times of the year, sharing your work, craft, products, or services to the world gives you time to plan and prep throughout the year.

Lean into your networks to explore your options and share your ideas. Others may approach you to leverage your skills in a way that you haven't previously considered. It's also a good idea to talk to others who live that portfolio career life and learn how they got started, the challenges, the benefits, and the advice they may have for you. 

Check out And What Do You Do? 10 Steps to Creating a Portfolio Career. In it, the authors share over 40 stories of individuals who have joined the portfolio revolution. 

The best thing to do if you're interested is to test it out and see if it works for you. 

Bottom line, if you're the type of person that loves to dig into your career, master your craft and advance to the upper ranks, then a portfolio career may not be the right path for you. 

However, suppose you've never quite found the right thing, have enjoyed bits and pieces of each of your positions, have a ton of ideas, talents, and opportunities, are great at time and self-management, and could care less what others think. In that case, a portfolio career could be exactly what you've been looking for.

Frankly, I believe it's time we expand our idea of the word career. It doesn't have to be the only choice or journey to find your one true career. Your career is just a part of the ecosystem of your life. As you grow and evolve, your needs, interests, and desires will also grow and develop. So why not allow your career choices to change and evolve as well?

Check out my segment on Portfolio Careers on AM Northwest: