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Are You A What-If Person?


Wondering if you’re a “what-if” person like Jasmine?
Jasmine (not her real name) and I met during a delayed flight from San Jose to Honolulu. Crammed into a lounge area filled with people none too pleased with the delay, we carried on a philosophical conversation about what it means to live a full life.
I don’t know about you, but for me the right people show up in my life when I need to hear what they have to say. It often works in reverse as well. 
Returning to school in her early forties, Jasmine believed that an MBA would be a good professional move for her as she grew older. But now she’s having doubts about this career strategy and second thoughts about even remaining in Silicon Valley.
But even worse than a flawed career strategy, she worries that too many of the dots she’s connected in the past five years have been in a straight line. No big risks, no big career moves that could have put her MBA to better use. 
She’s now struggling with what to do with the rest of her life. 
Our conversation turns to honoring our choices in life, whether they’re twisty-turvy decisions full of adventure and risks, more A-to-B-to-C straight lines, or a life that plays it safe. 
Her conflict takes me back to a choice that absolutely altered the trajectory of my life, a decision driven by a promise to myself as a teen that I wouldn’t look back on my life and wonder “what if”. Now, I can’t honestly say that I’ve kept this promise 100% of the time, but I’m pretty comfortable knowing that I’ve honored change that has been thrust on me as well as those times when I’ve reached out and grabbed hold of it. 
“It sounds like you’re worried about becoming a what-if person.”
“What’s a what-if person?”
“Someone who’s maybe too careful about their choices in life.”
For decades I’ve walked a fine line between that of a project manager and change practitioner skilled in the art of Plan B’s—the what if situations—preparing teams for twists and turns that require pivots and mitigation plans in order to land on their feet, while also being the guide and navigator in taking on big adventures, as well. 
It’s been the creative tension in my professional life. 
And here I am offering advice to Jasmine on how to avoid becoming a what-if person!
“How will I know what too careful looks like?”
“Ask yourself, ‘Will I look in the rearview mirror at the end of my life and wonder whether or not I should have taken a different path, embraced the adventure instead of playing it too safe’. Maybe include some topsy-turvy choices along with straight lines—trust yourself—mix things up! But at the end of the day, honor your choices without harsh judgement. Make decisions without regrets.” 
As the gate agent announces our boarding call, Jasmine and I quickly exchange business cards and head towards our mutual destination that will certainly take us on different life paths.