Taking Stock of Your Life

Taking Stock of Your Life

The phrase, ‘taking stock of your life,’ seems to apply to those of us in the second half of our lives, probably because that is when most of us think to appraise our past. After all, you cannot take inventory of your life until you have something to measure.

The flaw in this thinking is the presumption that we know how much time we all have, or that taking stock is a one-time task instead of an ongoing, self-correcting process.

I was reminded of the importance of taking careful stock when I met Dave Cotter, the CEO and founder of a startup called SquareHub, who recently spoke at GeekWire’s Startup Day on the subject of work-life balance. The subject intersects with the larger themes of my personal blog and with the mission of my company, so naturally I listened carefully. I was in the audience when Dave spoke, and I talked with him afterward.

In Dave, I saw a real-life example of all the concepts our firm is built around: living life fully and with authenticity, making meaningful connections, being generous, and allowing yourself to be vulnerable to life’s possibilities. In many ways, Dave exemplifies the kind of person I had in mind when I constructed our company’s mission statement.

He is a leader, someone who has held high-profile positions and handled high-pressure situations. He is ambitious and successful in his career, and he has a lot to show for it. He also has a family he cares about, and values he lives by. He is young enough to have much of his life’s work ahead of him, but old enough to know that time is less of a commodity and more of a luxury; in other words, he understands his mortality, perhaps better than most of us.

At age 41, he had a stroke that nearly killed him. His life was not perfect. His marriage of 10 years had ended. He was not as actively involved as he would have liked in the lives of his three daughters. He could say that he started and sold a successful company. He could say he worked at a high level for one of the most admired companies in the world.  But he could not say that he was happy. In fact, he said he felt empty, alone and unfulfilled.

The trigger to act, to become vulnerable, to change your path, is different for all of us. For Dave, the trigger was the simple fear of death. From that fear came courage, the other half of vulnerability.

Part of having courage is standing fast even when you know others might view that courage as something else entirely. If Dave returned in his present state to his former, senior position at Amazon, he said, they would tell him he should go play in the over-40 league. Letting go of his warrior mentality was part of becoming vulnerable.

One Sunday afternoon, he walked into a coffee shop in his neighborhood and spotted a former colleague hard at work on his laptop, headphones clamped to his head. His friend had left his family at home so he could concentrate on work. It was as if he was looking at a years-younger version of himself. When you’re on a treadmill that never stops, sometimes you don’t know you’re on one.

He wanted to tell his friend to go home, that work will still be there Monday, that sometimes “saying no” won’t impact your job nearly as much as you think it will.

For those at the beginning of their career trajectory, this is the kind of advice that is perhaps best filed away for use later with more life experience. Most of us, including Dave, need to build and perform before we understand the cost of our attention and resources, and what makes us feel truly rich.  While most of his financial resources are tied up in his latest, fledgling startup – more on that later – Dave would say his life is richest in relationships. Today, he spends more time with his daughters, makes them lunch every day, and takes them to school.

“I have an interesting sense of joy and ease that is foreign to my prior way of life,” he told me. “Five years ago I would have been extremely stressed out and needed sedation. Instead, I’m happy, having fun and feel fulfilled.”

One of the most significant changes in his thinking after his stroke was shifting his mentality from “get” to “give.” The force of generosity was always part of his life. Once he chose to focus on it, he realized the instinct came easily because he is largely the product of the generosity of others.

A beneficiary of the foster care system, he was adopted by caring parents. Once in the business world, he was guided and boosted by supportive mentors. By focusing on helping others – he wants to help fund the ventures of those who don’t have access to capital for example – he focuses more on relationships than on stuff.

Dave did not let a good crisis go to waste. After his stroke, he created SquareHub, whose namesake mobile app acts as an online organizational tool for families. You can use the SquareHub app to privately send messages, share photos, and coordinate schedules and activities. It combines and streamlines the functions of texting, email, and other tools. The company is the direct product of Dave’s desire to connect in a meaningful way with his family, and for the first time his work has lined up completely with his priorities in life.

Taking care of your important, personal relationships is where your life should begin, he realized. His failure to do so earlier cost him his marriage and compromised his performance at work.

My mistake was I set a trajectory and expectation for my life early on and then went into grind mode, Dave said to me. “Money can insulate you, but it also creates different problems.”

Compared to his “warrior” self, Dave would say he lives his life now with much more authenticity. Playing the role of the warrior was exhausting – even if he didn’t want to admit it. The stroke was clear proof of the toll his work life was having on his health. 

When we advise our clients at Highland, we don’t just assess our client’s assets. We examine the broader life picture including their goals, relationships and community. We try to understand the kind of legacy they want to leave while impressing upon them that wealth is not the end goal, but a tool and a responsibility. It is a resource to be stewarded thoughtfully, not owned or spent without conscience.

Like myself, Dave believes in a higher power. He was raised Lutheran by very religious parents who instilled in him a sense of generosity and caring. He recovered from his near-fatal stroke with one clear, simple desire in mind.

“I want to be remembered for raising three amazing daughters, and for helping people,” he said.

Is it time to take stock of your life?


John Christianson
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