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Where to go from here with my life?

I’m working with numerous leaders who are in varying states of confusion about the next phase of their personal and professional lives. Four populations dominate this landscape:

  • Successful, late-career leaders, owners, or partners who see the time for their exits nearing. Commonly, they have given the lion’s share of their life energy to their organizations, businesses, or professions, and find themselves short on reliable friendships, family connections, and “next phase” clarity.

  • Mid-life leaders deciding whether to stay in their comfort zone, or take a leap of faith into a higher-status position that could bring unknown personal and professional challenges. In many cases, this involves a values struggle: “What will I be sacrificing in my personal life if I take on a more time-demanding level of leadership responsibility?” Those currently conversing with me from this crossroads include a respected manager who’s been offered ownership in her company, a police lieutenant who has the opportunity to become department chief, and a firm partner who’s been asked to become managing partner.

  • Talented millennial staffers who face this choice: Stay in their current role and gradually rise into positions of leadership, or risk taking a new, unforeseen opportunity – the chance to work in a different culture or setting, to join a friend in an entrepreneurial venture, or to accept a more meaningful job at lower pay.

  • Daughters and sons of family business owners who wrestle with whether or not to join the business. Often, subtle urging from a parent is part of the mix, and approval-seeking pressure comes into play. Tension between the pull to find one’s own niche, and the lure of financial security becomes palpable. What to do?

I’ve observed that all four populations share a common pattern: In general, they put more energy into asking others for advice or suggestions and less energy into personal reflection.

I’m not against seeking outside perspectives, but not at the expense of sober thinking based on rigorous self-honesty and discernment.

What are the specifics of that reflection process? No matter what your age, or the nature of the transition, consider starting with these three questions in the process of your life/work decision-making:

What am I good at?

“False starts” can be avoided by a high level of self-reflection on one’s unique skills. Everyone has a talent pattern – native or developed capabilities that show up throughout life. It’s important to pay attention to this dimension because usually what people are good at they also enjoy. To tease out your giftedness, ask yourself, “What do I get a kick out of that I can get paid for?”

Where is the greatest need?

It’s possible that you are good at something that is not required or widely appreciated. The sweet spot is unearthing where your talent meets a recognized, unmet need. Decide on the sphere you want to work in, then ask yourself what are the greatest needs in that sphere. For some, the sphere will be relatively contained: a firm, or even a department. For others, the sphere will be larger: a local community, an entire profession, or even the world. One window into assessing need is reflecting on what you care most about. “What problem most piques my interest or unsettles me, in my sphere of choice?”

What is my financial situation?

Every human requires resources in order to minimize financial anxiety. The key is accurately assessing the reality of your situation. Too easily, unfounded financial fear drives out the two important considerations mentioned above. Financial fear often masquerades as greed for more money without an objective assessment of what is actually needed. In determining what you need to earn, there’s always a trade-off to consider: “What’s most important to me at this juncture -- more money or discretionary time? ”Warren Buffet, one of the world’s wealthiest individuals, recently remarked, “I can buy almost anything I want, but I can’t buy more time.”

If you’re not in the middle of a transition now, you probably will be at some point. Reflecting before deciding can reduce the possibility of following wrong-headed impulses, taking bad advice, or holing up in your comfort zone.

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