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Lion in a what?

Digital Media, Organizational, and Personal Development

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Sisyphean Dread in the Pursuit of Greatness

I like working off my calendar because it helps me stay focused. By chunking tasks into hours-long blocks of specific errands, chores, or activities, I can also fit goals like my New Year's resolutions into slots of time when I'm focused doing only those things. But truth be told, I feel like I need a bigger why.

Why do I need a bigger why? I've felt uninspired by the work I do outside of my day job - and I've always had a side project to distract me from improving products or writing tests. The purpose of this blog was to highlight my personal journey in a professional light. I decided to focus on the themes of technology and leadership, and this blog was built from scratch as a labor of love. This lack of inspiration may be more closely related to a sense of impatience in terms of my own growth, which I characterize by a sense of child-like excitement contained within the body of a slightly disgruntled man.

By open-sourcing my New Year's resolutions, I felt more compelled to stick to my word. Recently I fostered a dog for 48 hours. I have also started working on the non-profit business model canvas for an environmental non-profit that has yet to be formally named. Yes, I am bragging - and rightfully so. It takes a lot of work to be this awesome all the time. But truth be told - I fear that when I do the thing and make the stuff and be the person - when that journey is over - I will return to a state of deep existential despair. Also known as boredom. And I hate being bored.

I subscribe to a newsletter called Breaking Smart, which has the tagline "seeking serendipity through technology." Venkatesh Rao, the writer of Breaking Smart, wrote about this existential despair in a post titled "What Entrepreneurs Can Learn From Regular People." He says many entrepreneurs view everything in their universe as things that either do or do not contribute to their goals with varying levels of risk to obtain those things. Without a purpose or sense of instrumentalism about the things they encounter in their day-to-day lives, these people experience a similar level of existential crisis after both success and failure. I consider my dog fostering experience to be my most recent failure. I had originally signed a form to keep him for many weeks, but even after housebreaking him and taking him to the office for half a day, the amount of stress overwhelmed the level of fun I had from having a dog, and I took him back to the shelter I got him from on my lunch break after just 48 hours of taking him home. My next dog will be smaller.

That night, I wrote a journal entry about my experience, what I had learned, and then took more notes on dog behavior. Even with a system of under-stimulating, academic-style knowledge acquisition, I apply my knowledge and exercise curiosity. Once again: even with experiences that promote growth, why do I feel a need for a bigger why? Well, for about 10 hours a day, I am either working, eating, working out, or getting ready to do any of the previous three things, and my energy is limited. One of the ways I work out is by doing yoga and meditating, and while I exercise mindfulness and staying present in my day-to-day life, I experience the doubt and sense of idleness expressed in this post at very innocuous moments. Ironically, I've even started to soak in experiences with greater appreciation than I did when I was younger. I have traveled to different countries, gotten lost in my own city on foot, and I have gone to one hip-hop dancing class. Instead of appreciating all the texture of what I've experienced, I fear something that hasn't happened yet - mastery - and feel a lack of inspiration, but is truly doubt of my own self-efficacy.

I need to do this right the first time - and then every time after that.

This becomes a self-fulfilling prophesy, and I become more likely to abandon my goals. Which answers my original question.

I think that's part of being human, though. In hindsight, it actually makes sense. When I realize that I'll get used to any skill level or life experience over time, as long as I repeat it, I begin to wonder when I'll get used to it or when the next time I plateau will be. That uncertainty intimidates me when I look in the face of the goals I've set for myself. During the mundane process of honing my skill in a disciplined fashion, I crave spontaneity in the absence of a quick feedback loop. However, by applying those skills and seeing their impacts - with a new dog and new adventures with old projects, like this blog, I motivate myself to do more inspiring things and give myself permission to bask every now and then.