The Art of a Designing a Portfolio Career

Consultants Freelancers Entrepreneurs working independently

Co-Founders of the recent startup, THE JILLS OF ALL TRADES™, Megan and Corinne have been building portfolio careers over the past 25 years that have taught them to work smarter, live fuller, and carve their own niche. Here they share some of their learning.

Find a community. Working solo is great, but not if you’re siloed. The promotional power of a community will put a spotlight on you more than you can independently. So find your people, know your tribe, meetup, chat, join a board, volunteer, play a sport, coach, take a class.  It’s imperative for your personal and professional growth that you find a place of belonging - somewhere you can make a contribution. It is foundational, and can be the basis of establishing meaningful work.

Foster collaboration, not competition. There’s no corporate ladder to climb and no glass ceilings to shatter in your portfolio career so embrace this new work paradigm and shift the metaphor. There’s only space for one person at a time on that ladder anyway! Instead start lifting and linking others, and let your work life have the breadth and exploration of rock climbing, not ladder climbing. Mountains offer more; there’s more to see, more to explore, more to discover. So help someone find a new path, reach out your hand in someone’s aid, support a colleague from the bottom as you watch their ascent. Why? Because it feels great, and it’s more likely that they’ll do the same for you. You know what they say about that rising tide, all ships float. Plus those blue skies while you’re climbing together are just so much better than any ceiling, glass, or otherwise.

Connect by knot-working versus networking. Think about it. The best work comes when we don’t even feel like we’re working.  The idea of knot-working is to truly build authentic relationships in authentic ways, well beyond passing out business cards at happy hours and adding people to LinkedIn. So make friends.  Share your work. Tell your family about what you do. Display it. Write about it. Let others engage in it and engage with you. The power of personal connections is what builds sustainable professional relationships, so give knot-working a try.  It might be exactly what you want from your portfolio career.  

Establish an accountability partner. For real.  Having weekly check-ins, on the phone or in-person, can totally change the time you spend working. Set goals together. Create timelines.  Make lists. Then support each other. Offer feedback.  Learn to receive suggestions and critiques. And be generous to each other.

Set boundaries. You’re juggling this portfolio of work presumably so that you are empowered to determine how you work, when you work, and what projects you want to take on.  Portfolio careers are all about reconfiguring the work + life equation over and over to create the best you. In order to do this, take the time, every year, every month, or whenever it makes sense to write down your personal policies for work and your rules for engagement.  Seriously, write them down. Post them predominantly. Return to them often. Share them with your accountability partner. Then stick to them.  


The portfolio career truly offers the promise of establishing the right work life balance for you.  But be patient, good work takes time to build.