Why Everyone Should Consider Building A Portfolio Career

After business school I kept my side hustles going, first as an MBA admissions consultant while working full-time at the Boston Consulting Group, then as a freelance writer and career coach when I left consulting to become an entrepreneur. Over time I added public speaking, startup consulting, and podcasting to my portfolio of side hustles. It wasn't easy to manage, but it helped smooth my sometimes unpredictable cash flow in the startup world, accelerated paying off my student loans, and gave me peace of mind that I had a breadth of marketable skills even if I lacked a financial safety net.

Then two years ago, when the moment finally came that I didn't necessarily need the extra cash, I realized I also enjoyed the creativity and breadth of work my side hustles gave me. These were opportunities to build skills that were outside my day-to-day role and expand my network orthogonally, which paid dividends when my zig-zag career took another turn last year.

The rise of the side hustle – and its sibling, the gig economy – have been colloquially attributed to the post-financial-crisis job market and the Uber-fication of everything, though of course the second job was in no way created by millennials (or the employers who first decided internships should be unpaid and "entry-level" jobs should require previous experience). My grandfather delivered office supplies on the side while working 40 hours a week on the assembly line at General Motors so he could support his family of five. My mom picked up extra shifts at Sam's Club after her full day as an administrative assistant to make ends meet as a single parent.

No, millennials didn't invent the idea of multiple income streams. But the rise of the Portfolio Career is more than a stop-gap against the ballooning ratio of student debt to stagnant wages. It's a framework for the future of work that openly admits three things:

1. It is unlikely that we will spend our entire careers in one industry, let alone one company. The world is changing faster than ever before, and entire industries are at risk as AI, machine learning, autonomous vehicles, and other technologies go from the fringe to mainstream. Specializing in just one industry could be limiting at best and catastrophic at worst (c.f. law, media, truck driving, and more). Diversification across skills and industries is the only way to stay nimble and relevant.
2. There is no such thing as a perfect job. And that's okay. It is unlikely that one job will provide everything you need to be happy: a healthy (and growing) salary, inspiring colleagues, opportunities for growth, creativity, mentorship, and meaning. Rather than jumping around indefinitely in search of the fairy-tale role, find something that meets some of those needs, then pursue side projects to fulfill the rest.
3. This is not about work-life balance. It's about work-life integration. As with a financial portfolio, a career portfolio can (and should) be rebalanced from time to time. Perhaps a life change (like a new child) or the current political climate makes an employer-provided healthcare plan more attractive than the flexibility of a freelance career. Or perhaps a hobby grew into a side hustle and is now strong enough to become a small business, creating a less risky path to entrepreneurship than quitting a job and going all-in from the beginning. A Portfolio Career provides more on- and off-ramps to match shifting priorities and risk tolerance, making work-life integration more feasible.

I believe Portfolio Careers are the future of work, and employers that want to attract top talent need to adjust accordingly. Contracts that prohibit side hustles (or worse: that claim ownership over any intellectual property generated during the term of employment) will hurt recruiting and retention. Businesses that expect lifetime commitment (while making no such commitment in return) rather than understanding "tours of duty" will be unprepared when employees "rebalance their portfolios" and leave. The tax industry is also advised to pay attention, as the proportion of filers who need to calculate estimated quarterly taxes (while taking into account W-2 salary) continues to rise.

The Portfolio Career may have been conceived out of financial necessity, but for many, it provides a sense of control and a roadmap for professional fulfillment in a world that feels ever more volatile and unpredictable.