Reflections from a Recovering Maximizer

My journey to finding fulfillment amid everything imperfect, incomplete, and in process in my life.

Photo by Kyle Kesterson

Last Summer and Fall, I went through a season of deep sadness and withdrawal in my life. It was a challenging six months. I lacked my usual energy and drive and struggled to find joy or contentment in my day-to-day life.

Nothing in particular was missing or wrong. Nothing major had happened in my life to trigger this state of ennui—no death in the family or divorce. I hadn’t been laid off and I wasn’t going through financial hardship. 

So what was going on? I believe that I was transitioning off a fuel source that had energized and motivated me for most of my life, which left me feeling drained and mildly depressed. Let me explain. 

For most of my adult life, I have been a maximizer through and through. I’ve wanted to make the most money, have the best wife, buy the best house, live in the best town, build the most fulfilling and impactful career, have the most epic peak experiences… you get the point. In every area of my life, I was constantly striving for the best because I thought that maxing out these things would bring genuine happiness. Perhaps this was the result of mainlining Tim Ferriss for too many years in a row.

Maximizing isn’t inherently bad; in fact, it was the power source behind some pretty great things in my life. The impulse to maximize drove me to achieve some major successes and have some truly incredible experiences. But it also came with a major downside: the inability to rest content in the present moment, happy and fulfilled with my life, just as it was. Nothing was ever quite enough. 

Fear is another common fuel source. One I know super well and have benefited from over the years. The survival instinct that we all share is a powerful motivator. We humans are pretty good at not dying. Once I was able to have a couple of bucks in my bank account, this one seemed to fade into the background.

Looking back, the roots of my maximizing tendencies go back to my childhood. As a kid, I was pretty good at basketball. I thought that if I could just get into the NBA, I’d live a life of perfect happiness and all of my problems would be solved. And my father would finally provide all the love and acceptance I was yearning for.

That dream died when I was in college and quickly realized I wasn’t anywhere close to as good as I needed to be to reach that level. So I quit the basketball team to focus elsewhere, namely partying (making friendships and ‘romantic pursuits’) and business school. In my early 20s, my life revolved around music, it was everything to me. So I thought that if I could become a world-famous musician, I’d have the best life ever. A few years later, when I entered the world of entrepreneurship, I thought that if I could get rich from my startup, then I would live forever in peace. From there I moved on to thinking that if I could make the greatest impact on the world, then I would find deep and lasting fulfillment. If.. then. If… then. Happiness was always conditional on the next attainment. I was highly skilled in picking out ‘the next thing’ that society valued and would finally provide me lasting fulfillment.

You’d think I might have started to see the pattern by the time I was in my thirties and had spent over a decade engaged in relentless personal development work. But still, I fell back into the maximizing trap, thinking that if I could have the most successful coaching career, then I’d forever be blissed out living my purpose. When even meaningful work failed to bring me salvation, I turned my sights to my personal life.

If I could marry the most amazing woman I’d ever met, then I’d truly be happy. And if we left the grind of New York City and moved out to peaceful Boulder, Colorado, then I’d have a contented, spacious existence. But only, of course, if we bought the best house in the best location, close to nature with everything I wanted in it. Oh, and if we had the best dog to keep us company. But I’d also need to have the most healing plant medicine ceremony that would free me from my childhood traumas. Then I’d finally arrive at the perfect life. 

And then something weird happened. I did get pretty much all of these things: the coaching career, the incredible wife, the town, the house, the dog, and even some pretty liberating plant medicine experiences. (I never became an NBA superstar or a world-famous recording artist, but curiously, my failure to attain either of those things didn’t seem to diminish my contentment in life.) But I had successfully maximized my way to pretty much everything else I wanted in life. 

So there I was, the perfect wife, the money, the house, the dog, the spiritually aligned vocation, the great town, awesome friends, etc. But something still didn’t feel right. I was still struggling at times. I had plenty of ‘off’ days. And I still often felt a sense of discontent, seemingly for no reason. 

When my first company was acquired, I was shocked at how little of a difference I felt once the dust had settled. It was almost alarming. In hindsight, I can see that I just shifted my target for happiness. “Well, if it’s not a successful business and financial freedom,” I thought, “then clearly it’s the perfect partner.”

It was after finally settling into my ‘perfect’ life in Boulder that I started to catch on to the reality that attaining the things I wanted wasn’t doing what I thought it would do for me. I had achieved too many of these things to keep the charade up. There was now no better place where I could move the targets. These were my best choices. The strategy could no longer be maintained, it had to crumble.

I brought this alarming realization to my therapist, who suggested that I spend some time tracking my urge to maximize. He advised me to pay close attention to what was present when I started chasing happiness in some new attainment. Could I come to a deeper awareness of what was driving all this? 

“Be warned,” he said. “I suspect that something might have to die in the process.” 

I finally got it. I believed that the attainment of any of these things was going to bring me the true peace and happiness that was missing in my life. It was going to protect me from any harm, ruin, or loss. Life would be blissful as soon as I got there. 

But happiness was always a point on the horizon. Like a mirage in the desert, it receded further into the distance whenever I came close to approaching it. True fulfillment was always just around the corner, once I attained the next thing that I had been chasing.

As I became more aware, I began to see how constantly this urge to maximize was triggered. Seeing a Zillow posting of a nice house or a beautiful couple at a party. A magazine with successful people in it. Hearing friends talk about some incredible adventure they just went on. Seeing someone I know launching a new business. It was everywhere. 

My therapist was right, something in me did die—and then came the six-month mourning period. I gave up the belief that salvation existed at the destination. I stopped looking to the mythical ‘next big thing’ for fulfillment. Giving up the illusion that more attainment would bring true satisfaction, I found myself deep in a cocktail of sadness, despair, and apathy. Without my usual fuel source, my batteries ran dangerously low. I was sleeping much more than usual, being avoidant in my relationship, and feeling generally checked out and unenthusiastic about life. It took me into a pretty existential place of What’s the point? If I could maximize my way to happiness, then of course I was motivated to do anything necessary to make that happen. If right now was pretty much as good as it gets, then why bother to strive for anything?

To get through this period of disillusionment, I had to make contact with the sadness and grief I was experiencing. It was painful. And it was deep. Seemingly never-ending (there were 35 years of unwinding to do). And yet, nothing lasts forever.

After rounding the corner, I’m proud to say that I’m in a whole new relationship to this. I care way less, in a wu wei kind of way. I’m sleeping better. I’m less wound up. I’m less militant about achieving. I don’t need to fill my days to the brim, although sometimes it still happens. I spend less time doing and create more space for just being. I actively work on feeling gratitude every day. I make an effort to bring joy into everything I do. I remind myself that this moment is enough. It feels like growth. It feels like maturity.

The thing about being a maximizer is that you can never just be satisfied. The Buddha said that “life is suffering” (dukkha). Interestingly, some Buddhist scholars have suggested that the term dukkha is more accurately translated as “dissatisfaction.” Think about that—the same word can mean either suffering or dissatisfaction. The wisdom here, I think, is that when we can’t be satisfied, we suffer. We need to recognize that our striving won’t eradicate the underlying suffering inherent in existence. Being aggressive against our reality might drive business results, but it has the potential to make you miserable.

I share all of this because I want you to reflect on what your fuel source currently is. What drives you forward? What pushes you ahead in life? If you’re a highly successful person, there’s a good chance that you are a maximizer to some degree. 

Consider where you’re maximizing in your life. What is the if/then statement in your mind about what will bring you happiness? Can you track the urge or impulse that’s underneath the fantasy of the thing you’re chasing? What are you looking to feel in attaining that thing? If you’re a founder, is reaching the pearly gates of an exit going to make you feel the way you want to feel? 

As a recovering maximizer, what I now use as my fuel source is something more sustainable. It’s love. It’s the energy of the present moment. It’s gratitude for what I have. Enjoying the small pleasures. Committed to meaning. Committed to nourishing relationships. Committed to growing a beautiful family. I’m here to build. I’m responsible for my inner state. I orient towards what’s going well.

The takeaway? Getting what you want isn’t going to make you happy. It’s also not going to solve all your problems. Life is like a game of whack-a-mole: As soon as one problem is solved, another one pops up. If we are looking for some magical solution to our problems to come along and make us happy—more money, more success, the right relationship—we’ll never get there. As soon as we ‘arrive,’ we’ll find that something else is missing. We’re forever kicking the can down the road, waiting for the conditions to finally be right for us to be happy.  

I hope that you’re able to find a new fuel source in present-moment awareness, love, and gratitude for the magic that is your life right now and the people in it. I love what author Susan Cain recently said: “The heart of humanity is that there is a perfect and beautiful world out there, and we are not in it. We all long for a different world.”

Be in the beauty of this world, this life, this moment. Stop searching for a different world. Right here and now is about as cool as it’s ever going to get—enjoy it!