Flirting with Your Possible Selves

…Instead of working backward from a goal, work forward from promising situations. This is what most successful people actually do…” ~ Paul Graham, co-founder of Y Combinator

Are you doing now, professionally, what you planned at the beginning of your career?

Are you looking to change from what you’re doing now to something not yet defined?

Many of us, throughout our professional lives, change our careers – not just our jobs – depending on where and who we are at any particular time.

In his book, Range: Why Generalists Triumph in a Specialized World (Amazon Kindle link), David Epstein disputes the 10,000-hour path to expertise in favor of a meandering path that provides a variety of experiences over time.

You’re probably familiar with the 10,000-hour “rule.” It asserts that to gain expertise and competitive advantage, one must devote 10,000 hours to a highly specialized endeavor, regardless of the domain (sports, music, chess, art, etc.). Tiger Woods is often cited as a prime example. At the tender age of 10 months, he was learning the elements of the perfect golf swing, and by the time he was two, he won the ten-and-under division of his first tournament, on his way to becoming one of the greatest golfers of all time and one of the most famous athletes in the world.

The belief that the more complicated and competitive the world becomes, has pushed many people to specialize early in their lives. This belief ignores the reality that our work preferences and our life preferences change over time because we change. We’re not the same people at 40 that we were at 21. And we’re not the same people at 70 that we were at 40.

Modern life, with “wicked problems” (where the “rules” are unclear or incomplete), requires range — making connections across far-flung domains and ideas. Successful adapters and creative achievers tend to have broader interests and can take knowledge from one pursuit and apply it to another.

“Slow Bakers”

This was the term Epstein applied to what is often referred to as “late bloomers” – people who achieve success after a meandering career path, as opposed to the result of early and narrow specialization.

The ultimate example he offers is the career path of Frances Hesselbein, who management guru Peter Drucker called the best CEO in the country. Hesselbein had four professional positions, all as president or CEO, and never applied for any of them. In fact, she tried to turn down three. And she began her first professional job at the age of 54 as the executive director of her local Girl Scout council in Pittsburgh. Six years later, in the mid-1970s, she was recruited as the CEO of the U.S. Girl Scout Council.

During her tenure as CEO, Hesselbein completely changed the culture of the organization, growing a more diverse membership, establishing more relevant programs and merit badges to meet girls’ interests and needs, revamping the Council’s leadership team to better reflect its membership, and growing the cookie business to $300 million a year.

The morning after she retired from the Girl Scouts in 1990, Hesselbein was invited by Mutual of Omaha to be the CEO of a leadership foundation it offered to establish. As she enters her second century, she is CEO of the Frances Hesselbein Leadership Institute that she has grown from the ground up.

When asked about her leadership training, Hesselbein explained that in lieu of formal, specialized training, she just did whatever appeared to teach her and enable her to be of service, and the accumulated experience added up to leadership training. Hesselbein had no long-term plan, only a plan to do what was interesting or needed at the moment. “I did not intend to become a leader, I just learned by doing what was needed at the time.”

Dark Horses

There’s an organization called The Dark Horse Project. It’s focused on working with people who perceive themselves as following unlikely career paths – they’re “dark horses.”

Dark horses focus on their interests of the moment. They examine their current motivations and preferences and seek the best matches for right now, recognizing that a year from now, they could well be on to something different.

Dark horses embody short-term planning and apply the lessons they learn to a series of pivots that move them forward.

Why It Matters

Career goals that once seemed safe and certain tend to blow up as our life and work preferences change over time. The precise person we are now is fleeting, just like all the other people we’ve been.

This may be never more prevalent as employees push back against returning from remote work and being asked to perform beyond reasonable work requirements without added resources, training, and development.

We need to be able to adapt to accelerated changes in the workplace and in our lives. We need to apply our accumulated experiences to new situations, which may look very different from the past.

If we’re in a highly specialized field that rarely considers outside influences, and we’ve been in that field since the beginning of our career, we may have difficulty adapting to systemic change.

Those of us who have traveled a long and winding road (nod to The Beatles), may be more facile in dealing with fundament changes as we’ve “seen that road before.”

What are your thoughts? How have your career preferences changed over time? How have you handled those changes?

Let me know, I’d love you hear from you. I can be reached by email at

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