The concept of living a Portfolio Life excited me enough that I created a new blog to chronicle my journey. I had high hopes when I wrote my first post back in April 2015, but then reality hit. I didn’t have time to develop one more blog, so I never published it.

I forgot about that cyber real estate until WordPress reminded me of its existence after an automatic update. I re-read A Freelancer’s Manifesto and decided I’d been possessed by an overly-enthusiastic street preacher the day I wrote it. I’m glad I wrote it, however, because I needed to hear that sermon again.

With major financial outlays on the horizon for our family, the siren song of the “secure,” full-time paycheck once again had me fishing for a job. I threw out my line and got a nibble—an interview. On top of that I had an unexpected offer to teach a class with the possibility I could do both the class and the full-time job. The class was a bonus, but what I really wanted was that full-time security blanket.

To put a long story short, I’m teaching the class, but I’m not working full time. The first twenty-four hours after learning I’d snagged a blue gill rather than a trout stung. That experience, however, gave me a fresh reminder of how much moxie it takes to be a job hunter. Putting yourself out there time after time with no results can chip away at your self-confidence and self-worth. I’ve had to relearn that job hunting is a bit like a game of poker. Only one person can win each hand, but no matter how much you want to win, don’t ever throw your self-worth and self-confidence onto the table as part of your bet. No job is worth gambling those away.

With a few days of hindsight under my belt, I’m thankful for the way things turned out. The three-hour class fits into this portfolio life I’ve been fashioning since April. It provides a bit of income, allows me to keep my teaching muscles in shape, and won’t derail the other projects that I have in the works.

I had to recommit to the choice I made to live a Portfolio Life after spending a couple of weeks backtracking and doubting that choice. It’s not the first time this has happened, and it may not be the last. But every time I’ve chosen to follow the “safe route,” it turns out to be a detour that brings me back to the path where I started. It’s easy to look at those rabbit trails as failures, but when you’re living a portfolio life, the detours simply add another page of experience to your life’s portfolio.

How about you? Have life circumstances ever caused you to doubt your chosen destination? What have you done to turn yourself back around?


The original concept of a portfolio worker is credited to Charles Handy who wrote about it in his book, The Age of Unreason. Jeff Goins builds on Handy’s idea of a portfolio worker in his book, The Art of Work, and applies it more broadly to a person’s life–a portfolio life .

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