More people in midlife are creating a livelihood from a blend of a variety of sources. Job security no longer comes from an employer, but from your marketable and transferrable skills. They’re creating their own portfolio career, which, according to Penelope Trunk, is:

“Not the same thing as holding down three bad jobs and wishing you could figure out what to do with yourself. Rather, it’s a scheme you pursue purposefully and positively, as a way to achieve a mixture of financial and personal goals.”

You might be executing a portfolio career without knowing it, even if you are looking for a “regular job.”

Your Portfolio Career: You, In A Briefcase

Think of your portfolio career as a briefcase that contains the talents, job skills and capabilities you need to craft a suitable work/life blend. Here are two brief examples from “And What Do You Do?” by Barrie Hopson and Katie Ledger:

• “I have three jobs…I am a lawyer for several small companies, a professional cook, and a food writer.”
• “I spend three days a week working on a project for the elderly, one day doing admin for a charity, and two days building up my upholstery business. I love how these activities challenge different parts of me.”

The Internet has transformed where and how we work. Solo encore-entrepreneurs all over the world are creating jobs and businesses for themselves, finding happiness, fulfillment, and income -“passion, purpose, and a paycheck”- as a result. Research from the Ewing Marion Kauffmann Foundation reveals that people over 55 are almost twice as likely to found successful companies as those between 20 and 34!

Consider A Portfolio Career If You’re…

• Frustrated with your current employer
• Starting a new, encore career in midlife
• Seeking less-stressful work
• Self-employed or starting your own business
• Unemployed and need paid work
• Retired and considering some paid work
• Balancing other responsibilities, but want paid work

Expand and Manage Your Portfolio

Your portfolio career, just like a financial portfolio of investments, needs to be expanded and managed. Maybe you’ve been on a single career train that derailed in the recession and now see the wisdom of a portfolio career as your future. To begin creating this portfolio you’ll need to examine several areas including:

• Your strengths you enjoy using, are good at, and proud of.
• The market demand or need for what you do.
• Your work values.
• How many job “investments” you are able to manage in your portfolio.
• If you want to have multiple employers or start your own business.
• Your ability to manage your finances in the transition.
• The level of stress and energy required.

Look for more tips in future posts on how to develop your answers for these key areas to create your own portfolio career.


Laura Schlafly is the founder of Career Choices with Laura in Lake Oswego, Oregon, and with an MBA from the University of Michigan and 20 years of serial entrepreneurship she's a Boomer eminently qualified to help others with their own encore careers. As if that weren't enough, she's also a professional speaker, private pilot, dancer, and student of Asian culture and languages.You can find out more about Laura and what she does at her website,