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Second-half-of-life thinking

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When I was a kid, one of my dad’s favorite sayings was, “You can’t put an old head on young shoulders.” I’m humbled at how strongly his words speak to me as I’ve grown older. This column is by no means meant to discount what young people bring to the table. In fact, it has been my youngest son Alex, now 26, who has kindled awareness of what I’ve come to refer to as “second-half-of-life thinking.”

Second-half-of-life thinking has less to do with age; it’s more about how we challenge and develop the thinking that gave shape to our earlier lives — first-half-of-life thinking. As the term suggests, first-half-of-life thinking comprises what we learned in the first stage of life, like how we engage in relationships, how we approach our work, how we run our firms, how we embrace our religious beliefs or non-beliefs, and even how we see other people as a whole. We tend to form opinions about each of these big concepts early in life and never revisit our thinking as life unfolds. Most people never leave first-half-of-life thinking; if it wasn’t for conversations with people like my son and a couple of other trusted friends, I would probably still be stuck in that first-half-of-life thinking.

I grew up in a mostly middle-class, mostly white, small town in southern Indiana. I’ve been married to my high school sweetheart for more than 35 years, attended the same church for more than 30 years and live about 30 miles away from where I grew up. I have three adult children and two grandchildren who all live in the same town I live in. If anyone is prone to getting stuck in the first-half-of-life thinking, I’m a leading candidate.

But I’ve also experienced a sense of restlessness whenever that which I consider to be my true self feels out of alignment with the way I’m personally engaging with the world. In the last few years, my restlessness seems to have increased. It’s due in part to deep philosophical, religious and business conversations with my adult children. And some has been the result of working with a new generation of young people and finally a couple of close friends with similar restlessness.

My response to this has been to indulge in reading. I’ve been an avid reader for the majority of adulthood, learning and evolving much along the way. I discovered self-help books in my early thirties; books like “The E-Myth” from Michael Gerber and “The Seven Habits of Highly Effective People” by Steven Covey. Books such as these taught me a lot about looking at my work and personal life differently. Lately, I’ve doubled down on my commitment to reading.

Poring over a couple of books a week, I’m learning that when we are not living out of our true self that there is an inner part of us that remains restless. I’m also learning that much of what we think we know about living is formed in the first half of life and that many people never come to the realization that it is only part of the story. Second-half-of-life thinking is about asking questions and challenging much of what we think we know about our first half of life.

It seems that the first-half-of-life thinking is required in order to get to second-half-of-life thinking. There doesn’t seem to be any direct flights from childhood to second-half-of-life thinking. I’ve learned from my years of helping people that you can’t force someone to move from first-half-of-life thinking either; many people get stuck there their entire lives. But generally speaking, second-half-of-life thinking is thinking that more aligns with your true self. It’s a more holistic and inclusive way of seeing life. It’s the realization expressed by Steve Jobs, who said, “Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma, which is living with the results of other people’s thinking.” First-half-of-life thinking is thinking that was passed on to you that you internalized as your own. Second-half-of-life thinking is asking questions and seeking answers to what you learned in the first half of life.

This topic is as broad and deep as the dimensions of our own lives. Suffice it to say, much of what we see as truths in our lives may not actually be truths, but rather other people’s thinking that was just passed on to us and accepted without question. The difference between those who stay in first-half-of-life thinking their whole lives versus those who embrace second-half-of-life thinking is the desire and the motivation to be a true seeker.

Do you ever have that restlessness about your firm? Do you ever think that your firm doesn’t truly represent who you are as a person? Do you treat employees and customers like real human beings with real lives, or are they just a means to an end? As a profession, are we just doing what has always been done, or are we actually changing people's lives for the better? If you’re interested in seeking second-half-of-life thinking, these are just a few questions you should be asking yourself. Second-half-of-life thinking is chipping away — some might call it shadow boxing — each of the pieces of our lives that do not align with who we are at our very core.

For a deeper dive on the topics discussed in this column, subscribe to Darren’s “Better Every Day” podcast on iTunes or at

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