Happy & Not in Jail

Last week, I explored the competency of Knowing Self, and this week, I was inspired by Clayton M. Christensen’s thought-provoking article, “How Will You Measure Your Life?” Christensen is widely recognized for his pioneering work on disruptive innovation, which shows how technology can radically transform markets and topple well-established companies that fail to adapt. His insights on how nimble businesses outpace slow adopters are nothing short of brilliant.

What strikes me, even more, is Christensen’s ability to distill complexity into simplicity, and his reflections on measuring life’s success are, in my view, even more, profound than his disruptive technology theories. When teaching MBA students at Harvard, Christensen encouraged them to answer three critical life questions before delving into management theory:

  1. How can I ensure my relationships with my spouse and family bring enduring happiness?

  2. How can I ensure I’ll be happy in my career?

  3. How can I ensure I stay out of jail?

These questions may seem straightforward, but they carry profound depth. This week, I found myself focusing on the second question. Over the past 25 years, I’ve transitioned through four distinct careers. Interestingly, Generation Z (my kids’ generation) is projected to experience up to 17 jobs and seven different career paths in their lifetimes. My career trajectory, with just four major changes, is already considered unusual among many of my Gen X peers. I often wonder what the professional lives of my children will look like and believe that thoughtfully answering all three of Christensen’s questions will help us navigate life’s many transitions. Question #2, in particular, offers invaluable guidance for career changes.

In another influential piece, "Managing Oneself," management guru Peter Drucker lays the foundation for truly understanding how we function best. Drawing from Drucker’s wisdom, I’ve designed a simple worksheet to help people begin answering that pivotal second question.

Know Self Worksheet:

  • Are you a READER or a LISTENER?

  • How do you learn best?

  • Do you work better with people or independently?

  • Are you strongest in decision-making, advising, or as a task completer?

  • Do you thrive on stress and variety, or do you prefer predictable consistency?

  • What are your personal values?

  • What are your personal strengths?

After gaining clarity on these personal insights, the next step is to apply them to the specific task or job at hand. This requires addressing three further questions:

A) What does the situation/task/job require?

B) Given my strengths, working style, and values, how can I contribute most effectively?

C) What results must be achieved to truly make a difference?

I firmly believe that a deep understanding of both personal characteristics and the task’s requirements will set people up for success, satisfaction, and a meaningful contribution to their work. Leaders, the more we understand these aspects of ourselves—and our team members—the more effective and engaged our teams will be.

So, leaders, here’s the question: Do you know these things about yourself? More importantly, do you know them about your people?

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Individual Path…Stronger Destination

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