I intend to write here for my entire life. Aside from the tremendous value writing here has already provided me, I think it is truly important to have projects on the scale of an entire life rather than months or years. Those are important too, but I think you should have a consistent project that lasts as long as you do. And I intend for this blog and newsletter to be at least one of mine. I am not sure if here will always be here, but this blog as a continuous thing will last my lifetime.
First, I want to talk about why I think having lifelong projects matters.
You build confidence in your ability to sustain momentum / persist. With short term projects, even when they are successful, you never get to test your endurance. It is a skill to endure.
You develop a compounding skill or set of skills. In twenty years, skills you develop by working with them frequently on a long term project will seem like an unfair advantage. I believe that what we are capable of on the scale of decades will surprise most us. For example, when thinking about the question “what if you kept doing what you’re doing for another decade?”, I wrote the below tweet:
You get to experiment, analyze, and refine your creative process. Shorter projects don’t provide the opportunity to switch your approach while maintaining the core project (you end up jumping from one project to the next instead of iterating). By experimenting with process while keeping the overall goals of your product or project constant, you get solid data on how to build well. Especially for someone like me who tends to bounce from exciting project to exciting project, I value the challenge to consistently iterate on a single project and find ways to keep it interesting over longer time scales.
When you intend to do something for decades rather than months or years, you make different decisions than you are accustomed to making day to day. My theory is that these long term decisions are more authentic, and possibly even more ethical than shorter term decisions. The things I write about, titles I give to my posts, approach to growing, ways I share my writing, and more are all informed by my understanding that I don’t need rapid growth or “viral posts”.
Longer term projects often produce less anxiety than shorter term projects with some pressing goal. With my blog, I am in no rush to gain readers (though I do set goals around this) because I feel confident that over two decades growth will take care of itself.
You get to create worlds. Creative people, tend to collect many inspirations and influences. They also accumulate opinions, aesthetic and otherwise. Synthesizing these in one grand project is important, because you are likely the only person alive with that precise mixture of influences and opinions. It also creates a cool network of referenceable work, even fairly early into the project. That means when I learn something new I have more previous work for the new concepts to build upon and it makes it easier to learn things. This has routinely been demonstrated as vital to the learning process.
You experience the unknown. Most of us work on things that take months or years, so we don’t get to see how we perform on longer time scales. I bet unique skills and insights are on the frontier, and the mystery of what might come of working on a project for decades is exciting.
A lifelong project frames your own thinking about your work. I feel permission to iterate and a lack of pressure to get things perfect on the first pass. The project becomes more of a “playground” for your ideas which is freeing.
Particularly with writing, working over decades gives you a true sense of your past selves. I look forward to seeing the opinions, likes and dislikes, and the worries and hopes of past Jake. This connection with my previous selves helps me build a durable (and accurate) narrative for myself, which I think is very important.
Longer projects also help improve self-esteem and trust in my own capabilities. From launching the various projects that I have, I’ve noticed a sharp decrease in my desire “to prove myself” to anyone other than myself. When I produce work I genuinely think is good, I feel deeply fulfilled from that alone. “The reward for good work is more work.”
Having a lifelong project gives you a “container” for your ideas. In my day to day life, I am constantly noticing things I think I would have otherwise overlooked because I am always running a “could this work as an essay?” algorithm in my mind. This can become a bit stale if you allow any old mediocre idea to creep into your container, but on the whole makes my experience of the world richer and gives me an enduring sense of purpose. I wrote a bit about this when summarizing the value from coding for 30 days in a row.
Now, I want to talk about why I chose my blog specifically as a lifelong project. There are several reasons why a blog is a great choice, but I should also acknowledge that in many ways I never made an active decision here. I enjoy writing very much, so in some ways a blog being my longest continuous project was a very passive decision.
The first reason a blog is a good choice for a lifelong project is that writing has been something I have loved from a very young age. I began writing songs and short stories very early in my life, and even took a crack at a Lord of the Rings style fantasy epic around fourth grade or so. I launched my first blog a little later (an embarrassing political project) and in high school (or maybe early college?) submitted several poems to the New Yorker. When I think about what things I’ve most consistently enjoyed throughout my life, writing is at the top spot. The fact that I have always enjoyed writing, reduces the chance for burnout and makes it likelier that I can keep at it over decades.
But even setting my natural affinity aside, I have become convinced that writing improves thinking. I wrote about that here if you want to check it out, or if you want to read about this topic from a more accomplished writer, I suggest Orwell’s piece on this. In many ways, writing is the foundational skill for knowledge. Writing makes learning new things much more thorough and durable. This is because writing reveals the errors in your current thinking more effectively than any practice I know of and it actually generates new thoughts so it helps identify new approaches or innovations. Furthermore, to communicate that learning at scale, writing is essential. So by picking a writing project to be one of my long term projects, I am investing in a skill that improves nearly every area of my life. Even if I never succeed at writing in the ways many people think of as success, I still “win” new ideas, clearer thinking, and the power of explanation. This is what some people call Systems Thinking, avoiding binary “win-lose” pursuits.
A third reason for choosing this blog as my first lifelong project is simply my love for documentation. I am inspired by things like Buckminster Fuller’s Dymaxion Chronofile, Wolfram’s obsessive self-documentation, family photographs or home videos, historical letters and diaries, and reading my Grandfather’s PhD thesis. It is that kind of record of my own interests and thinking that encourages me to continue writing here throughout my life. This record is more than an interesting time machine for myself (though that aspect is very fun for me), it also creates a trove of material for generating new ideas and for seeing the evolution of my thinking over time (my thinking process and my thoughts on specific topics). Rereading my past writing routinely inspires new writing, and often times when I reread a post I see many gaps where I feel I could have elaborated more, communicated something more clearly, or have changed my mind entirely. That shows that I have improved at writing and learned since the time of the original post. That reminder is valuable. I have also started including more photographs in my posts for this same reason. My Roundup posts also provide my future self a source for possible renewed interests and re-explorations over time, and a journal like glimpse into my own past to see what sorts of reading, art, and schools of thought I was into.
What are some other categories that can make good lifelong projects? The more I think about that question the more the answer seems to be anything. It almost doesn’t matter what the category is, so long as you actually enjoy it. Pursuing a single thing for decades probably leads to the same insights regardless of what the thing is. The tangible “hard skills” will differ, the types of audiences and opportunities differ, and the actual experience of the work will of course differ. But my theory is that whether your lifelong project is photography, music, cooking, coding, or woodworking the true benefits transcend category. It is about self-esteem, iteration and innovation, self-expression, endurance, self-mastery and discipline, and creative fulfilment.
Thank you to those who have read my posts so far, and I hope you will continue to, as we all grow old.
I love this and it inspires me to do the same. Over the last two years I’ve filled many journals and I enjoy the boundless growth and introspection in each of them. Here’s to a life long project of pure self expression and creation, whether there’s one reader or millions- your work is valuable.