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When most of us tell the story of our career journey, it’s often a very linear tale. “And then, I left that job and took this one. Then, I decided to step away for a bit and start something new. Then, I took a role with a marketing firm.” However, the reality is much more complex.

Most of our lives and our career journeys are much more circuitous in nature. My friend Mitch Joel calls it “the squiggly path”, meaning that it veers left and right and doesn’t seem to have a rhyme or reason looking forward, but looking back it all begins to make sense.

My career path was definitely “squiggly”. As I discuss with David duChemin in this week’s episode about his book and podcast A Beautiful Anarchy, twenty years ago I could never have imagined the career I’m in now. However, looking back, the clues were there all along. (There weren’t many early-twenty-something musicians dragging personal development books along to gigs or tracking creative productivity in notebooks…)

Careers Usually Only Make Sense Looking Backward

There are two dynamics present early in your career: (1) there are clues all around you as to what you might be great at and enjoy, and (2) you lack the wisdom, self-knowledge, and foresight to be able to put those clues together. So as you move forward, you do your best to navigate according to what you know. Many people eventually figure out the pieces some time in their early to mid thirties, and are able to begin assembling a life and career that brings more meaning and opportunity to contribute. However, by that point many people are often more encumbered by things like mortgages and family responsibilities, making shifting a career more of a challenge.

If you find yourself in a place where you might be ready for a change, I challenge you to take a hard look at the clues in your past successes and try to identify any patterns that stand out to you. Where were you (a) fully competent, (b) deeply driven, and (c) well-received by others? That’s the very definition of a “sweet spot”.

You Need To Bring Stakeholders Along

In any career or life move, you must ensure that your stakeholders are fully considered. The general rule of thumb for family decisions is that the least risk averse person gets to determine the threshold for action. In other words, if one person is ready to leap, but the other says “we need six months of savings in the bank first”, the more risk-averse person gets to call the shots. That way, everyone feels good about the move.

Are there any stakeholders you need to include in your planning? Are they aware of your present thinking?

Be Responsive, Not Reactive

Many people are reacting to the present circumstances without fully absorbing the implications of their actions. In any stressful moment, I find it best to take a pause, consider everything that’s happening, consider the all of the possible consequences of my actions (first, second, and potential third order consequences), consider my values, and then act in a meaningful way. I find that by taking this approach, I am much less likely to jump into something I’ll regret later. Be responsive, not reactive.

As you consider all of the effects of our present situation on your life and work, where are you tempted to react instead of meaningfully responding? Take some time to pause, to reflect on the consequences, to consider your values, then to craft a strategic plan of action that moves you forward.

Embrace the beautiful anarchy that is a life well-lived and work well-crafted. Use this time we all have to respond to your circumstances, to strategize, and to embrace the possibility of what awaits on the other side.

This episode is sponsored by Freshbooks . See how Freshbooks can save you time and boost your creativity at Freshbooks.com/Accidental.

The intro music for the AC podcast is by Joshua Seurkamp. End remix is by DJ Z-Trip.


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