Rejecting the Idea of “Shoulds”

In defense of following your interests

In my present environment, 21st-century America, there are increasing returns and opportunities available to idiosyncratic people. Or, as Tyler Cowen put it, the age of average is over.

I’ve been thinking about this idea as I ponder the person I want to be in my new quest for agency. My surprising self-revelation was that I hadn’t thought deeply about what I desired. When I thought I was thinking about what I wanted, I was mirroring back what other people wanted and trying to figure out how to get it, too. Maybe that’s a place to begin, but any sustainable path needs to come from within, or you’ll give up at the first sign of boredom or struggle.

Let me share where I arrived, as forcefully as possible, and then I’ll use the rest of this post to expand on the idea and offer a few caveats. Here we go: 

To the greatest extent possible, you remove “shoulds” from your life, formulate your own opinions, and follow the path of your passions/interests from moment to moment.

I

Let’s start with the advice to follow your passions, which has significantly fallen out of favor. Today, it’s rejected mainly as 1) too much of a cliche or 2) downright unhelpful. I don’t disagree with these claims. In specific contexts, they are absolutely true.

In fact, I’ll offer my first caveat here, and this should apply to any counsel I give: there’s a chance you should be following the exact opposite advice. I don’t actually know. You need to try it out and see what it does for you.

My hunch is that the advice to follow your passion or interests would be helpful to anyone suppressing that part of themself, even a little bit. If you’re a diligent rule follower and have the slightest inkling towards a passion project— I think you should do it. You have very little to lose. 

Perhaps slightly more controversial; if you’re the kind of person who can’t NOT follow their passions/interests, I think you should surrender to that impulse as well. Any failure points you’ve experienced thus far in life might be because you’ve only done so with hesitation, guilt, and without the full enthusiasm of freedom that such an endeavor deserves.

I give this advice for two reasons— the first is that passion, defined as a barely controllable desire, is one of the closest things to free energy that the universe offers. People deeply interested in a topic, project, idea, or whatever seem to possess other-worldly energy levels to pursue these areas. I’ve experienced it myself, sitting for hours and hours on the couch, into the wee hours of the morning, following a rabbit trail of reading or writing an article. 

The other reason is that many successful and interesting people follow this advice. Many of my readers thus far have come from Marginal Revolution blog, so I’ll use an example we’re all familiar with— Tyler. Do you think Tyler Cowen is far more disciplined than you, and that’s why he can read so many books and articles and still have time for his rather large output of podcasts, books, articles, and papers, not to mention his teaching role and running Emergent Ventures? No! His impulses simply run in that direction, and he’s given into them like a raging hedonist. At this point, I’m sure he can’t stop himself and wouldn’t want to anyway. 

II

My next idea is to remove all the “shoulds” from your life. This is, in effect, permission to break every rule you don’t want to follow. Of course, moral and ethical considerations still apply. 

The best way to illustrate this point is by describing all the rules I’m breaking with this blog post. You might say the result is complete rubbish, but that’s okay. I’m probably not writing for you. I’m optimizing for a small slice of the human population that thinks like me and finds my voice intriguing. Digital writing is one of the greatest ways to increase your surface area of luck and draw like-minded people to yourself. 

Back to my point on rule-breaking:

I didn’t outline this post. When I started, I really had no idea where it was going to end up. I stewed on the idea over a few long walks, but only to the extent that I couldn’t stop thinking about it. Exploring the idea is the fun part for me, and so I have to save as much of that fun part as possible for my actual writing. I can’t unwap that gift too early, otherwise, it will feel like a homework assignment—writing a summary of thoughts I’ve already had.

I hate editing and rewriting. The opportunity cost of those activities seems so high. My first draft is the most authentic, and any time I put toward rewrites could be spent on understanding a new idea or more writing. So, I do the minimum possible and run my work through Grammarly—which helps me clean up the rough spots in a quick, gamified manner that barely feels like work. 

What else? I didn’t publish this when I thought I should, but rather when I had something bursting out of me. I’m not trying to write in a way that sounds smart or literary, but just in the way I think. When an idea seems done or is getting boring, I move on to the next point. In this way, I’m applying my aesthetic to the piece in a way that doesn’t feel forced but pushes me towards a state of flow and greater output.

The advice boils down to this: in any domain of life, do more of the stuff you want to do and less of the things you’re only doing because you “should.” You’ll be shocked at how much you can get away with and how unusually effective the approach can be.

III

Of course, I’m going out of my original order, but that’s another rule you’re allowed to break. You should strive to think independently. This is another price of trite advice that is actually quite useful. Here’s what I mean: 

Some people out there will discourage you by making good things you like sound lame or unsophisticated. Maybe everyone is saying that reading the news is the equivalent of metal junk food, but you think it gives you a unique perspective. Or you like a certain category of books, food, traveling, etc., that most consider uninteresting but you find fascinating. These are precisely the areas you should lean into.

A good rule of thumb is to pursue anything in the following categories: 1) interesting to you but boring to others, 2) play to you but works to others, OR 3) insightful to you but uncool to others. The limits to contrarian thinking are further out on the curve than most people dare go.

IV

It should be clear by now that the strategy I’m suggesting is riskier than the classic advice. It’s high variance, which is good if you’re like me and motivated by possibilities and want upside, but it could also be bad if your life runs off the rails. That’s why I suggest a couple hedges. These hedges will, in effect, raise the floor of worst-case possibilities while still retaining a huge amount of the upside compared to the way most people live.

Hedge #1 - Avoid toxic addictions. If you’re going to live more impulsively, in a sense, it’s essential to put up a few guardrails. For me that means staying off social media sites (Twitter, Reddit, etc) and pretty much anything with infinite scroll (TikTok, Instagram, YouTube shorts, etc). Those sites are so addictive to me that if I genuinely gave into them, I would waste an excessive amount of time and walk away feeling drained instead of energized. Blogs, essays, and articles, on the other hand, inspire me to want to join the conversation, and they engage a more active part of my brain.

Once you cut out the addictive bad habits mentioned above, you’ll discover your natural level of ambition. Most people want a balance of productivity and fun in their lives and won’t feel satisfied without making some progress on meaningful goals. I think a similar thing happens with diet—we only overeat because we’re surrounded by hyper-palatable junk food. Most of us would be a healthy weight if our primary options were the foods available 100+ years ago. 

Try to create that sort of environment, and I think “eat what you want” is much safer advice. The same thing applies to “productivity.”

Hedge #2 - Always be creating. One thing I’m not saying in this advice is that all humans naturally err in the direction of productive activity. I think the ship of your life still needs to be steered in that direction. Looking around at the world and the people I see, the most honest assessment is that we naturally drift toward passive consumption. If left to our rawest impulses, many of us would spend most of our days being entertained and titillated in a way that doesn’t benefit ourselves or others. 

There’s so much I could say on this topic from a philosophical or moral perspective, but my advice today will be practical and apply to the average person. Most of us improve our behavior when we’re aware of it. So, hold a mirror up to your life and observe yourself. For me, this simply means keeping a list of what I produce each week. This doesn’t always have to be an artifact, per se, but it could be a great in-person hangout with a friend, a good conversation with a spouse, an article you wrote and published, or a project you shipped at work. All of your passion and energy should be channeled in the direction of real-world fruit. Growing wise or intelligent is no use if you don’t have better relationships or valuable work to share with others. 

This is the ultimate litmus test for whether your “passions” lead you to apathy or agency. Don’t live by other people’s opinions, external “shoulds,” or willpower alone— instead, channel your unique impulses to leave a dent in the world that only you can.