Anyone who has progressed upwards in their career knows the cadence. You start off as an individual contributor, whether intentional about your craft or industry, or just luck of what was available and convenient at the time you were looking. Be it an assembly line, box, code editor, or spreadsheet – your hands were on the actual work product. If you are good at what you do – and potentially good at looking good too – you’ll be given the opportunity to move up and have more impact. Similarly, if you’re an entrepreneur, you’ll hear the magical words “leverage” and “scale” start to arise.
Whether driven by our ego to seek higher status or by capitalism to increase our effective hourly rate, we take the bait. We leave the world of the individual contributor, believing that your time could instead be spent managing six of them – their hands on the assembly line, box, code editor, or spreadsheet. Hopefully, it works. Then you start managing managers who, in turn, have their hands on the assembly line, box, code editor, or spreadsheet. All being well, despite all the communication and personnel management items that start to fill up your calendar and inbox, the leverage you have led to greater outcomes – more money, more respect, more power.
The only thing that you’ve sacrificed is the joy of doing the work you really enjoyed. The kind that got you to jump out of bed in the morning. We put kids and adolescents through such a regimented life up through college graduation and then launch them out into the real world with enough momentum to propel them through their first few years. They get their first job, start building their career and paying rent, and then… In Stanford professor Adrian Daub’s words – “I met 24- and 25-year-olds who had gone as far in life as they possibly could in some ways … I got to see a lot of the other side of this — people entering their 40s and realizing that no one had even the faintest outline of where their journey should go.”
If there’s one flashing warning signal about our society that we’re not paying attention to, it’s that our achievement of greater wealth has not made us collectively any happier. Nicer stuff, bigger houses, a bigger title, fancier restaurants have not made life better lived. One of the frequent stats that are often eagerly volunteered is the quantity of people managed, as if that’s an indicator of self-worth. As a society, we are “stuck” chasing the wrong things.
Having had enough time to look at both the diverse tracks of my friends and colleagues, as well as my own experience, the distinction has revealed itself. While some colleagues have risen up in their career ladder and loved the increased responsibility and delegation capabilities, others look at the “legos” they’ve given up and realized that is what they were seeking all along.
I saw this myself. By the latter years of Contactually, despite the thriving business, I found myself personally less enthralled. I had an incredible love for the founding mission, product, users, and team, but my day-to-day was disengaging and exhausting. My own role and purpose in the company veered towards managing the company, limited spurts of business development, putting out fires, keeping the engine running. When one is fully engrossed with a sense of mission, there’s an otherwise common emotion that disappears. Boredom. Every hour of every day, unless intentionally giving oneself a sabbath, is to serve the purpose. Even in moments of downtime, the resting mind is evaluating and running scenarios and planning the next steps. As Eric Hoffer wrote, “When people are bored, it is primarily with their own selves that they are bored. The consciousness of a barren, meaningless existence is the main fountainhead of boredom.” It’s hard to believe now, but I was bored. OK, Eric is being a little harsh on me here, but I did not find the passion in the work I was doing.
I pushed through, assuming it was a myriad of routine factors associated with a growing business (it was). This was further amplified post-acquisition. On my departure, “back to zero” as I called it, I was given the rare opportunity to completely rewrite not only what I was working on, but what I worked on. How could I craft my new roles?
What are the moments when we feel we are resonating at our highest frequency? Forget the marketing speak of “leading a team” “coming home to my kids” – where do we feel we’re most in our element? For me, it’s the peak flow states of product development, presentation, and other creation. Where everything else falls away but the product I’m working on – the model is in my head, all I need is to translate it into code. My love has led me to ensure that a substantial portion of my time is devoted to that work. Yes, I’ll manage a team. Yes, I hope to see scale. But I know that my own personal joy and excitement can only aid the fire I bring to a venture. Further than that, partially inspired by Daniel Pink’s excelled analysis of daily rhythms in When, I’ve crafted my own daily schedule to best reflect the types of work I can best achieve given my own energy cycles.
It’s often insufficient to keep our pursuits clandestine, and rob others of the same energy that we feel. Rather, it can be a calling in of itself to share it with other people – younger generations in their upbringing, peers via shared experiences, or the complete strangers who happen across your book a hundred years from now. My love of creating can be credited to the crate of my father’s Lego building blocks, and the ongoing romance with the internet, the day my parents brought home our first computer before there was any real utility. Or, in William Wordsworth’s words – “What we have loved, others will love, and we will teach them how.”
Some are best in the navy, and some go back to being pirates.
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