The Elusivity of Fulfillment

When was the last time YOUR life felt meaningful and rewarding?

“When was the last time you felt really fulfilled? When your life felt meaningful and rewarding, or aligned with some deeper purpose of motivation? Take a moment to really think about that and observe what comes to mind.”

That sentence, sitting at the top of an article about purpose by wellness expert Cortland Dahl, was one I’d already read more than once. And I didn’t know how to answer it. I felt like a proverbial deer in the headlights.

I got up and walked around a little. I went to the bathroom. I refused to look at another screen until I’d contemplated it, and to be honest, I didn’t think I was going to come up with anything, and that bothered me. My thought process got a little panicky:

It’s been that long. You don’t even remember what fulfillment feels like. That’s not good.

I grabbed a dry-erase marker and went to work on the large glass mirror that covers one wall of my office; a remnant of the house’s previous owner. I don’t even know why it’s there, but sometimes, it gives me a space to work out my thoughts away from my computer.

Maybe it was something about writing in large format, the motion of writing out the words, but as I made my way through my first bullet point — something to do with professional success — I found an idea forming. I put a question mark after point one, and then dropped down a line, and then it came to me.

“When I got back on my feet in 2011, and Jamie” (my wife) “called to thank me for the house.”

She’d done it in a voicemail, and I’m grateful for that. If it had been just a conversation, it might be nothing but a hazy memory now. But because it was a recording, and because it meant so much to me, I’ve held onto it for ten years. I just listened to it again while writing this:

“Hi! I just thought I’d call…to thank you. We’re just enjoying our day out here, and the sun is being filtered so beautifully through the trees, and it’s gorgeous, and the house looks great, and I’m just happy and thought I’d say thank you. So thank you. And I wish you were here to enjoy it with me. It’s a beautiful day. A beautiful fall day. And we’re playing in the leaves, and we’re hanging out, and it’s cool. And that’s all. Alright, bye!”

It’s a simple message, taken at face value. But it wasn’t just the words that she said. It was the way she said them. The contentment in her voice, the almost musical quality in her tone, that to my ears at least signaled deep satisfaction, happiness, and sincere gratitude. It was one of the most meaningful things anyone has ever said to me.

Even so, I asked myself why this, of all moments, was the one I chose. To answer that, a little backstory is in order.

In late 2010, we were in a rough spot as a family. We’d just spent a year in Arizona so Jamie could manage and grow the businesses of and care for her elderly father, who had fallen ill. After a ton of effort, a significant increase in revenue, and a never delivered-upon promise of a small business loan so we could start our own thing, she asked for a financial stake in what she’d just single-handedly built as her father had slowly convalesced. Instead, she was literally told not to let the door hit her on the way out. It was a staggering show of ingratitude and rejection from a man who had begged us to drop everything in our lives and move across the country with our growing family and move in to take care of him.

Several months later, we had moved out of her dad’s house and into our own place. I managed to find a job with an IT and web design company, and though I enjoyed the work, I was underpaid and putting in too many hours to have time for a second job. Even at about 60 hours of work a week, I wasn’t making enough for us to afford all of our necessities. We sat on a leaky air mattress on our living room floor because we had no money for a couch. We had to choose between paying all the rent and utilities or buying a sufficient amount of fresh food for our family of six — which, we had just found out, was about to be a family of seven. When one of the threadbare tires on our minivan spontaneously blew out as we pulled into church one Sunday, we’d hit our limit.

In desperation, I posted something on my blog about our situation. I didn’t have a lot of readers at the time, but a young man in Canada who’d followed me for a while — a medical student I’d never met in real life — offered to loan us $2,000 to get us back on our feet. We took it gratefully, and used it to get new tires and rent moving pods. We broke our lease, and limped back East to lick our wounds in the 1-bedroom basement suite of my parents’ Northern Virginia townhome. We had the new baby just four months after moving in. Two parents and 5 kids, including both a newborn and a 14 year old, in what amounted to a tiny 1-bedroom apartment that was already partially used as storage.

For a year.

Don’t take my commentary on the challenge of the situation as ingratitude. I’m very thankful for my parents’ hospitality. I know it wasn’t always easy for them either. And it wasn’t the first time we’d had to go crawling back to them to start over after a failure.

The upside was that I quickly got a decent job. I was hired as the Director of Community Relations at a professional association within a month of returning to the DC metro area. And better yet, as I paced that cramped basement doing a final phone interview, I negotiated a starting salary of $80,000 a year. I was 33 years old, and it was more money than I’d ever made in my life.

That year in the basement was a long year. But in October of 2011, the sacrifice paid off, and I was able to buy a four bedroom house on three acres — which led to that heartfelt voicemail from my wife about the kids playing happily in the autumn leaves.

When I considered the “why” of that moment’s importance this afternoon, it was pretty simple to answer:

Because I no longer felt useless. Because I felt like I’d done something of real value.

I’d spent most of the year we lived with my father-in-law in Arizona alternating between doing menial tasks to keep him happy and having nothing to do. I knew nothing about how to manage what were essentially slum properties in a bad neighborhood in a town I’d never lived in, and was thus unable to be of much help to my wife. Instead, I tried — and failed — to be a stay at home dad to a handful of little kids while searching desperately for a path to a new career. And when things went to hell, my wife wound up pregnant, and I went back to work, it hadn’t been enough to take care of everyone who was depending on me.

I hadn’t always been a good provider, and I was extremely self-conscious about that. But that day that Jamie called me, I knew I’d made it. My wife and kids were happy and taken care of. They had everything they needed. And I’d overcome some very serious obstacles and insecurities to get them there.

When I talked to my wife about that voicemail today, she said felt the way she did that day because she was “finally somewhere I could just be a mom and a teacher and … we could just hold hands on the porch and watch lightning bugs in the yard.” She also worked as a real estate agent on the side, and for the first time in our lives together, we didn’t feel like we were financially drowning.

In the Spring of 2012, just a few months after buying the house, I lost 40 pounds - and my wife lost nearly as much. We were eating healthier. I was up and moving every day. I felt better and was happier and more energetic than I’d been since I was a teen. My blood pressure and cholesterol, which had both been creeping up, dropped precipitously. My mindset, naturally disposed toward negativity, was incredibly positive. Instead of spending my nights sipping whiskey and watching television, I was reading books, learning, and talking to Jamie about self-improvement and business. I was more productive than I’d ever been.

Looking back, I think it was because of that sense of fulfilment that I was able to make additional positive steps in my life. It was a snowball effect that had started with digging out of a bad situation, getting a good job in the midst of adversity, finding success, and then building on it. A series of small steps that led to a dramatic improvement overall.

But not all successes are equal. Some can actually derail you. Which is why I’m left asking: what happened between then and now that the last time I felt that fulfilled was a decade ago?

Well, a lot. Much of it is too personal to go into here. We went through some rough years as a family, facing a number of challenges both internal and external.

After three years in the job that got me the house, I left to do my own thing. When I started my publication in 2014, I was sucked into the entrepreneurial lifestyle pretty quickly. Long hours, late nights, less and less time spent with the family. My work became all-encompassing. The website audience was growing very fast, but the money didn’t immediately follow. In 2015, we almost lost everything — our house, our family vehicle — but I believed in the mission, and I dug in even harder. In 2016, that effort paid off, and my new business was doing well enough to pay all of our bills. Our financial situation had improved sufficiently that I was able to be the sole provider for the first time in our marriage. We weren’t taking our large family on fancy vacations, but we had upgraded our lifestyle enough that we could afford to pay for all our needs with some wants and upgrades thrown in for good measure. My parents’ basement felt pretty far away. I had millions of readers, lots of influence, and had become fairly well-known within the sphere my work focused on. By every objective metric, I was more successful than I had ever been.

But my workaholic tendencies had borne bitter fruit. I hadn’t realized it, but I’d pulled away from my family quite a lot. I went from being the dad who gave the kids baths every night and read them bedtime stories to being the dad who distractedly said goodnight to them from my desk as they came by in their pajamas to kiss me goodnight. When I finished work, I’d stay up late trying to squeeze in some leisure time, not getting to bed until after my wife was asleep. My marriage suffered. My teenager started making bad decisions. I had given up drinking alcohol entirely when I’d started losing weight, but now it had returned as a constant companion as I sought to manage my the stress of work, which was not only intellectually demanding, but often extremely negative, as the news and commentary business tends to be. I grew more and more unhappy, and put back on all the weight I’d lost, and then some. We moved across the country again hoping to address certain familial needs, but all it did was create a whole new set of problems and regrets.

In hindsight, I can see that all of this was building to a crescendo. When 2020 finally happened, the center could no longer hold. Things fell apart, and I had a reckoning. I was forced to face how off track I’d gotten. Years of bad habits, hurtful behaviors, and avoidance strategies had finally come home to roost. I couldn’t have been further from the guy I was ten years ago, and I didn’t like who I’d become.

It was time for a reset — and it wasn’t optional. Now, here we are.

So the big question I’m asking is: how do we rediscover meaning and purpose when we’ve lost it? How do we find fulfilment when it has escaped our grasp?

Maybe you’re asking that too, for reasons of your own.

I don’t have all the answers yet, but I’ve been out hunting for them. And I’m going to tell you what I’ve found so far in the next installment, so stay tuned.

(See Part II of this post right here.)

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