When I think of my lowest, darkest moments in the past fifteen years, there’s one bright, summer evening that comes to mind. I was walking home from the subway after a big day at work. My walk took me down a harborside road past a park full of flowers and freshly cut grass, with families picnicking and kids playing on a jungle gym and sailboats passing by in the evening sun. Earlier in the day, there had been a celebration at the office. My team and I had just met a major deadline. An aggressive deadline that once seemed far-fetched, unachievable. 

Our success had been a team effort, and I had been leading the team. I had shown them a path. I had helped them follow that path. And I had worked alongside them to overcome one challenge after another. My colleagues appreciated what I had done and they thanked me for it. They toasted me, and I toasted them. Now I was returning home to a partner who loved me. I had good friends, helpful neighbors, a nice place to live, and enough free time to enjoy it all.

But as the birds chirped and the ice cream truck by the park played its happy tune, my mood took a downward turn. Excitement about the day’s achievement turned to gloom. I felt more worthless with each passing step. Hopeless. Angry. Why?

This software release had been a major success.

But it wasn’t the success I wanted.

Yes, I had reached for it, stretched for it, given it my all. This project had been one of the first major deals I had landed in my new life as an independent software consultant, running my own solo business, after years of having been someone else’s employee. Recently, I had been contracted by a promising startup to help them get their engineering efforts off the ground. My job was to set up shop. To mentor a team of ambitious but less-experienced engineers. To translate a slew of goals and requirements into a plan that could be carried out. To make things work. 

And guess what? I had made things work, I had guided the team to success, and doing this had given me great joy. I felt proud that I’d helped my colleagues be effective, that I’d helped the company reach its goals. The project hadn’t been easy and there’s no way I could have done it if I hadn’t really cared about it.

But this success hit me like a brick, because it reminded me of successes that I had wanted even more than this one.

If I had stayed in grad school, years earlier, and continued doing research, then I wouldn’t have been been celebrating a software release on this day. Maybe I’d be celebrating a research breakthrough, a new result, a published paper, a contribution to the world’s knowledge. I would have fulfilled the promise I had made to myself in my teens, that I’d commit my life to scholarship and mathematical discovery. 

And if I had stuck with writing after I quit grad school, if the novel I’d written had gone somewhere, helping me launch a literary career like I hoped it might, maybe then I’d be celebrating a book release. I would have fulfilled the promise I had made to myself in my twenties: if I wasn’t going to be making research discoveries as a professor, I would become an author, exploring inner terrain, making “discoveries” in the realm of fiction.

And if my own software startup had succeeded, the one I had launched after putting my literary ambitions aside, maybe then I’d be celebrating one of my own company’s achievements. I would have fulfilled the promise I had made to myself in my early thirties, that if the outlet for my creativity and passion wasn’t going to be literature, I would still forge something new, I’d make a difference in the world through entrepreneurship.

And if my lifelong efforts to create music had led to some kind of career, maybe then I’d be celebrating an album launch or a concert I had performed. In my mid-thirties, having quit grad school, abandoned a literary path, and failed to start a company, I had looked over my life and seen myself jumping from one thing to the next. I had asked, “What do I really want? What do I want to create more than anything else? What’s the one thing I would never give up?” And the answer was music. Among all the many dreams that had ever called to me, I recognized that creating new music is what mattered to me the most. I wanted to be a composer. But music was the domain where I felt the most “stuck” and the most afraid. No, I hadn’t succeeded as a researcher, writer, or entrepreneur but I had taken risks and gotten things started. As far as music, I had been practicing and studying for years, but I didn’t have a finished composition to my name.

Today’s software release had been a major achievement but I viewed it as the “easiest” of the kinds of things I had aspired to do in my life. I had failed at the hard things and now I was succeeding at an easy one. An “easy” one that still took a lot of time and effort – time and effort that I wasn’t putting into my true dreams.

I had been lucky in my life, and I knew that. Lucky with opportunities. Blessed with the freedom and the time to pursue each of the dreams that had called to me. And I had followed those callings. I had taken risks. I had reinvented myself and reinvented myself again. I had started bold new projects and given them my all – up to a time – up to a breaking point that always seemed to arrive.

For one reason or another, each of my efforts to pursue a dream had resulted in insight, discovery, experience, personal development, but still a sense that the dream hadn’t come to fruition, that it hadn’t turned into a viable path forward. So time and time again, I had fallen back on my skill as a software developer to support myself. Software knowhow was the one thing people kept calling me for.

I had done what I thought people were supposed to do to find meaning in life, but now my life felt meaningless. Nothing had worked out and I was again back to software.

After all the attempts I’d made to forge a new path for myself, milestones like the one I had celebrated today were my most public accomplishments. To the extent that I was interacting with “the word,” the world knew me as someone who could build a good software system. No one really knew or cared about the other stuff, the researcher I had wanted to be, the author I had wanted to be, the entrepreneur I had wanted to be, or the musician I had wanted to be. No one was calling me for those things.

So today’s milestone counted against me. The extent to which I had dedicated myself to this achievement and struggled to make it happen was the extent to which I had sold out, given up. For all my efforts to build the life I wanted, I was again doing someone else’s work.

What happened next? 

I arrived home in quiet rage against myself. My partner asked me what was wrong and I couldn’t explain it. I sulked. Maybe that triggered a quarrel.

But then… nothing happened, not immediately. My bad mood blew over. I went back to work. I stuck with the company I’d been working for and I helped them through more releases after this first one. In my free time, I kept pursuing my creative projects. And over the years some of those projects did come to fruition.

What really happened next, happened little by little, over the span of ten years. What happened next is that I slowly found ways to take a gentler and more wholesome view of my life. Reflecting on that miserable walk home – thinking back to it from time to time over the years – I learned some lessons from that gloomy moment. Lessons that would help me avoid the same anguish today, I think, if I were to take that same walk again, in similar circumstances.

Here are five of those lessons:

The first lesson is that you can practice your deepest values in whatever you’re working on at the time. Which means you can find fulfillment in whatever you’re working on, even if it’s not your “top choice” of all things to work on. 

I had the idea that writing software for someone else’s businesses wasn’t what I cared about the most in life. In the grand scheme of things, making fundamental research discoveries, or creating new art – these things were more valuable to me, and to the world. But there’s something to question here. 

In order to help a team build a good software system, I had needed to exercise the virtues that mattered, and still matter to me the most. I care about teamwork. I care about vision. I care about clarity. I care about precision. I care about effective communication. I care about creative problem solving. I care about getting things done. 

I want to be helpful. I want to be creative. I want to be effective. I want to be kind. I want to be inspiring.

So while that software milestone, years ago, was not the single victory in life I would have chosen if I’d been given a free pick, it was still a chance for me to manifest the qualities that are most important to me. These are the qualities I would choose to have, if given a free pick. And this was a chance to apply them and develop them further. The success wouldn’t have happened without my practicing those virtues, so I can see it as a success in which I harnessed the best of myself. A full-fledged success. Not any lesser than any other kind of success.

The second lesson is that moments in life are interconnected. Our experiences are ready and waiting to network with each other, to communicate with each other in pursuit of a larger meaning, if we allow them to “mingle” in our hearts. So we shouldn’t see past failures as endings, isolated from everything else, removed from all conversation, leading nowhere.

I was choosing to see each of my failures as an ending but I could also have seen that it was the beginning of something else. And none of my failures had been pure, absolute ones. I had learned something significant in each endeavor, so I had benefited in every case.

The software victory that I’d pulled off had surprised people, even me. How had I been able to do it? Maybe the answer is that I’d been able to do it because of everything I had learned in being a grad student, then writing a novel, then launching a startup, all while refining my musical craft. And maybe if I hadn’t done all those things then I just wouldn’t have known how to take a hopeless, impossible software situation and bring clarity to it and steer it towards a good outcome.

The third lesson is: Stop insisting on meanings and interpretations that don’t serve you. Stuff that happens to you doesn’t “mean” anything until you ascribe it meaning.

I had the idea that my software success “meant” that I had been a failure at the other things I had tried to do. Harnessing my energy for someone else’s project “implied” that my true dreams had not been fulfilled, otherwise I would have been putting that energy into my own projects. But that was only an idea in my mind that I was insisting upon. It had no objective substance to it. Looking closer, I can see that I was still pursuing my dreams – practicing music, writing essays, and more – as I worked my job as a software consultant. In fact, it was my software work that gave me the stability and freedom to pursue those dreams. What did I have to thank for all that time I’d been able to spend writing prose and studying music? My software career.

I was the one telling myself that my software success was a sign of a larger failure. I was the one giving it that meaning. But there’s always an option to stop narrating for a moment. To stop telling ourselves what things mean. To stop drawing connections that don’t serve us. If I had done that, I could have seen my software success as just that. A simple success. A thing to celebrate. A thing that was good for me and good for others involved. A thing that could be good without taking away from anything else. 

The fourth lesson is that any time you do something, it’s a triumph of optimism – even just getting out of bed in the morning. You might not think of yourself as an optimist, but if you’re alive, you’ve been practicing optimism on a regular basis. So you’re probably better at optimism than you think.

In my case, my software victory had been the result of daily optimism – believing, believing, believing it could be done. Yes, part of my job had been to be a pessimist – to raise alarms about goals that were at risk. To identify pitfalls. To give early warnings about deadlines that could slip, costs that hadn’t been properly identified, new issues that could crop up. But to be a pessimist in the service of optimism. To identify problems so the team could avoid them. To point out risks… with the conviction that we could mitigate them. To forecast ways we could fail… with the confidence that we could eventually succeed. I was being paid to maintain the confidence that we could succeed, and to prove it right. I was being paid for my optimism. And I kept getting paid because I was good at optimism.

But I wasn’t applying that same optimism to my own life. I was interpreting each of my failures as evidence that I couldn’t succeed rather than as evidence of my courage, and as proof of the experience I had gained. I was being a pessimist about myself, for no good reason.

If I had taken the optimism that I was harnessing at work and applied it to my life, I could have seen a few things. My grad school career had been a failure but my desire to study and acquire knowledge was ongoing. My first novel was a flop but I was still writing. My startup failed but I had already used the lessons I learned from the startup in launching other projects that had succeeded. And in music I had just confronted a lifelong fear and signed up for voice lessons. I was learning how to sing.

The fifth lesson is to let yourself accept the fulfillment that comes from helping others. Accept it as primary. Not secondary to other kinds of fulfillment.

In my case I was really proud that I’d helped my teammates succeed. I was really proud that I had helped the company move forward. I was really proud that I had helped the company’s founder realize his entrepreneurial vision. But I was undervaluing that satisfaction, because I was thinking of my own success as more important.

There was a hierarchy in my mind, where doing something for others was of course very good and very commendable, but doing something for me was secretly better. Yes, I was happy I had helped someone else with their company but if given a choice, I would have succeeded at starting my own company. Yes, I was happy to have mentored a young engineer but if given a choice, I would have published a book, or made a research discovery of my own.

But if I flipped that around – if I could see helping others was just as valuable as succeeding in my own projects – my whole view of the situation would have changed. Instead of feeling like I’d failed to achieve what I wanted most – success in my personal endeavors – I could have noticed what I’d been giving to others all along, and counted that as a primary form of “success.”

In conclusion, if I were to take that same walk home today, knowing I had been victorious in a big project at work that didn’t match my dreams for how I was going to be spending my life, I would have some new techniques at my disposal to make sense of it. Techniques for finding happiness in the moment and avoiding the patterns of thought that can lead to misery. 

I’d think about the virtues that I had practiced in achieving this success (first lesson). I’d see this success as interconnected with, and enabled by, all my previous experiences including my biggest failures (second lesson). I’d avoid looking for implications in this success that don’t serve me (third lesson). I’d recognize the role of optimism in achieving this success and I’d be willing to apply that same optimism to my life overall (fourth lesson). And I’d notice the ways I’d helped others on the path to this success. I’d look to what I had given to others as a measure of what I had achieved. And I’d embrace the satisfaction that comes with giving as a primary kind of satisfaction (fifth lesson). With these five lessons in mind, I know it would be a happier walk. ■

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