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Take the Long View

NB: This is part of a series of entries regarding lessons learned in the years since I quit my job in search of a life more intentional. These are also being posted at LinkedIn. This particular entry can be found here.

Fifteen years ago, I worked as a network administrator and after a few years in the job, realized it was not the best use of my talents and I wanted out. However, I lacked a full accounting of those talents and what their better application might be. After months of anxiety, I did what many dream of doing: I walked out. I quit, which, had a new job awaited me, would have been rather pedestrian. But I had arranged no new job. The only things awaiting me were mortgage and student loan payments. Regardless, I recognized the “now or never” nature of the moment and that I could take the risk because I had no major responsibilities. No one but me would go hungry for lack of my paycheck.

A snippet from an earlier incarnation of the first blog.

The months leading up to my decision, and the immediate aftermath, were agonizing. A friend suggested I start this blog and share it with friends and family who were eager to support me. The journey that followed has been, in my opinion, fortuitous, if not slightly unconventional. As I continued jotting down new ideas and thoughts from my experience, the blog’s focus evolved into examining ways, big and small, people can live with more intention, more awareness, and an increased sense of fulfillment. After all, that is a large part of what I was initially missing all those years ago.

I have learned a lesson or two – the hard way as always – as I’ve explored this idea, at least enough to share a few dos and don’ts. In fact, in the last year, a modest number of people have sought me out for advice on making big transitions in their lives, some of it exacerbated by the COVID-19 epidemic, which has inspired soul searching for more than a few of us. As a result, I have been invited (read: challenged, dared) to share some of those lessons through a series of brief posts. Therefore, in the coming months, I intend to do just that. If you are contemplating similar changes in your life, big or small, I hope you find them of good use. As always, thanks for reading.


As the title above suggests, an important first step is long-term thinking. In my experience, changes made or actions taken to increase a sense of fulfillment are best evaluated through the lens of what we will be remembered for. More simply, legacy. These actions don’t have to be grandiose, but they should create, over time, the person we want people to remember. In my experience, these actions are an expression of your authentic self, proportional to your situation, and adjustable.

Your Authentic Self

Taking action to increase a sense of meaning in life requires knowing who we are at our core. When I began, I had barely an inkling of my authentic self. As I wrote back in 2010, even though I knew I wanted to do something else, I had to first envision what that might look like. So, I turned to two resources. The first was the well-known book by Dr. Stephen Covey, The Seven Habits of Highly Effective People. Covey’s second habit, Begin With the End In Mind, includes a visualization exercise wherein the reader imagines their funeral and the things their family, friends, and community say about them. The result is a starting point for examining our personal values, which can inform our thoughts on what comprises a meaningful life, which in turn leads to legacy. I discovered I want to spend my life in service to positive causes larger than myself, in leadership roles where possible, even if I won’t see the full impact of my work in my lifetime.

The meaning of life: Take risks.

After that exercise, I reviewed a paper I wrote for a required introductory philosophy class at Marquette University, the purpose of which was to examine what we believed the meaning of life to be. I will spare you direct quotes because my writing, which has never been Pulitzer Prize-winning material, was even worse back then. Suffice it to say, I surmised that life’s meaning lay in stripping away the unnecessary and taking risks because death, even if decades away, will be here before you know it.

I began reflecting on whether or not my life aligned with those elements that I concluded were authentic expressions of who I am. It did not, so I took an important first step in course correction. Ever since, that has been the primary lens through which I evaluate life’s big decisions.

Make It Proportional to You

Five years after quitting, I found myself working with developing countries on renewable energy and climate change issues, and I believed I had found the better use of my talents that I originally sought. And whenever people learned of my striking out to find a more meaningful use of my life, they asked if I thought they should do the same. At first, I always said, “Yes! Quit your job, take the leap and trust the net will appear.” Over time however, I realized I was giving very dumb advice. I was prescribing a course of action suited to the parameters of my then-life. That did not mean it was suitable for everyone. But as the saying goes, when you have a hammer, everything looks like a nail.

Hammer: Quit Your Job. Nails: Everyone

This led me to question if taking such a dramatic step was necessary, or if I could have started smaller and arrived at an end that, although different in form, would have been similar in substance. I will never know. And lest I be charged with hypocrisy, I am not advising people avoid big risks. I am suggesting that many roads do in fact lead to Rome. Quitting a job and jeopardizing your family’s livelihood in order to find more meaning in your life might not be the best strategy. Baby steps might be more appropriate. Perhaps your job is very gratifying but something as simple as volunteering with a local service initiatives fulfills the desire to give back. The key is to identify and take meaningful action best suited to your circumstances. For the record, when people now ask my advice about quitting an unfulfilling job, my answer is a measured, “Maybe.”

Stay Flexible

Like life, the means and result of this process are not static, and therefore require periodic evaluation. Circumstances and beliefs may change. In junior high school, my long-term vision was as a power forward for the Boston Celtics. I had the drive and desire to play at the NBA level, but, as I discovered, I lacked the key ingredient: raw athletic talent. Therefore, I had to reassess. Similarly – and more seriously – when I began searching for a more meaningful application of my talents, I pictured it taking place in Chicago. Immediately after quitting, I was hired to organize and open a community center in a predominately Latino neighborhood. I also helped my then-girlfriend launch a non-profit aimed at erasing the stigma around mental illness. I felt I was on my way.

If taking an unexpected left feels right, trust it. (Photo Credit: Joe Thorn, Flickr.)

Things changed, however, when I had a chance to volunteer with Catholic missionaries overseas. This experience added a global element to my journey that I had never considered. Upon returning home, I re-ran some of the visualization exercises and reflected on whether or not continued work abroad was in-line with who I was and what I wanted to do. It was, and I adjusted my short- and long-term choices as a result. The broad strokes of my initial epiphany remained, but I had found a different stage on which I wanted to pursue them. It was difficult leaving Chicago. I’m rather attached to it. But, adjusting my understanding of what my work would look like (or where it would take place) allowed me to maximize the opportunity to find that higher and better use of me.

So What? (I frequently end with that question.)

In the end, we are our own limits to living with a sense of increased meaning and fulfillment, and those experiences can come from myriad corners of our lives. For some, it’s the job. For others, it is being active in their local community. Some may burn for that vocation that has them fired up before their feet even touch the floor in the morning. If you are anywhere along that spectrum of wanting to increase the intention with which you live your life, start by defining that that long-term view. Explore what comprises your authentic self, size your actions to the circumstances of your life, and remain flexible as you go through the process. Above all, take that first action, no matter how small. Get a sense of what that risk feels like. Notice if the world looks marginally different as a result. Those first steps are often more than most people take and they have some of the biggest impact. Then, go back and do it again. And again. And again.

Next n the series: Know the difference between supporters and cheerleaders, and who in your life fits which role.



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