Five Strategy Questions to Ask Today

CareerRFL "Insight"

Three unexpected questions to help you find work you love

By June 5, 2014 2 Comments
By Ben Sands – For additional insights, tools, and leadership resources, click here

At 22, my life strategy – the mantra that guided my day-to-day decision-making – was shockingly, alarmingly, embarrassingly simple:

“I want to tell a great story…” 

I wasn’t interested in a “dream” job, “living my purpose,” or making a pile of money.

All I cared about was telling a better story.

More accurately, I wanted to enjoy talking about the work I was doing and the life I was living. If I didn’t find it interesting, who would? If I wasn’t proud to talk about it, what was the point of doing it at all?

Simple yes, but here’s the thing: my unconventional approach (i.e to “prioritize the story”) worked.

What’s more, it’s still working for me today.


To me, a great story has three common characteristics: excitement, risk and growth (and a bit of romance, too – but that’s material for another article).

Accordingly, prior to each major personal or professional decision, I ask these three questions to ensure that my next step is consistent with the story I want to tell:

1. Does this excite me?

To me, the opposite of happiness is boredom. The next opportunity – personal or professional – must excite me. Seems obvious, right?

Unfortunately so many talented men and women choose safety, security and boredom over excitement, every day.

Granted, there are times when things have gotten a little too “exciting” (like the time my friends and I overestimated how quickly we could learn how to sail and subsequently sank our boat in the BVIs) but, for the most part, the pursuit of an exciting life has resulted in some of my favorite stories: of teach skiing in Aspen, tending bar in Nantucket and, most recently, relocating to Charleston, SC.

2. Will this expand my comfort zone?

From an early age I sensed that there there was a direct correlation between the amount of risk and uncertainty one could comfortably tolerate – and the quality of their life.

For someone who had as a teenager and young adult been obsessed with risk, I new I had to actively work to expand my comfort zone and grow. For the most part that meant actively seeking out situations and opportunities that made me uncomfortable…and wading in, regardless.

Like excitement, there can be such a thing as “too much” when it comes to growth but, again, this attitude has led me to some remarkable experiences. Among them: starting 3 new businesses and (ehem) a short, uneventful cameo on ABC’s The Bachelorette.

3. Will I learn something new, rare and/or valuable?

Will this experience bolster my existing skill set? Will this experience be additive to what I have already seen and done? Most importantly, will I be stronger personally and professionally as a result?

My “regret-free role models” – the men and women who are living life the way I would like to live it – all possess some rare and valuable ability that has served as the foundation for their personal and professional success.

In pursuit of my next opportunity, I remain mindful that each new experience must not only be exciting and growth-oriented, but also accretive to my existing skill sets and experience. I don’t change simply for the sake of changing, the “next thing” must create opportunities for me to refine – and master – new, core skills.

The pursuit of learning guided my professional transition from tending bar in Nantucket to selling consulting services to Fortune 500 CFOs and then, a few years later, to co-found a new management consulting company.

Even more important than the professional learning, however, has been the personal.

In prioritizing my story, I have been able to learn a great deal about who I really am, what I really want and what stories I want to tell going forward. And at the end of the day, only with that knowledge can you truly find work you love.

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