On Obsession

Success is a result of obsession

Posted on January 21, 2024

Obsession is an interesting phenomenon.

You give up everything, all other desires and purpose, for one thing. That sounds bad. Scary even.

It can be, but it can also be the key to obtaining everything you want to achieve in life. History has proven to us, whether it’s through conquest, capitalism, or competition, that in order to be successful you must be relentlessly obsessed with one goal.

Why does obsession make us successful? When we are entirely focused and devoted to one goal, it creates a never-ending desire to learn, which leads to new abilities, new thoughts, new ideas, and new innovations that otherwise didn’t exist. The longer you’re obsessed and learning about a topic, the further in-depth you go, which leads to the bleeding edge where all the new great ideas reside.

You can’t make it to the bleeding edge without doing the leg work to get there first. Think about recent examples like Kobe Bryant (of basketball fame), Wayne Gretzky (of hockey fame), Steve Jobs (of Apple fame), Steve Walton (of Walmart fame), Steve Altman (of OpenAI fame): they were/are all obsessed with one objective, their craft, and wildly successful because of it. Kobe would watch and rewatch tapes of basketball games, analyzing every move to perfect his game, get up early and train for hours on-top of his team’s practices; for years. Walton would visit retail stores across the world with a pen and paper, talk to every store clerk he could find, all to collect more information to better his retailing; for decades. These two are not the exception; all of the greats I named, and pretty much every other one in history, has focused and devoted themselves to one goal, which pushed them to pursue further than anyone else had gone before in their crafts, and it lead to excellence.

Another interesting note, if you asked any one of them what they were obsessed with, they would likely answer in one word; Kobe: basketball, Gretzky: hockey, Jobs: consumers, Walton: retailing, Altman: intelligence.

I think that’s a key to an obsession. It should be described in one word. “I am obsessed with B2B SaaS”, “I am obsessed with finding the best influencer marketers for brands”, and “I am obsessed with building great teams” are all examples of disingenuous obsessions.

When I talk about obsession, I mean in the pursuit of excellence; not in the pursuit of money or fame. The more words you use to explain your obsession, the more disingenuous I think it is. Either that’s on purpose, or the more likely case, because you just don’t know what you’re obsessed about yet.

So that begs the question, how do you gauge what is an obsession? Or even more importantly, what’s a good obsession?

Gauging what is an obsession is a very personal task, but you can probably identify a few candidates just by asking yourself: What do I think about while I’m mindlessly driving? What about when I’m working out? Sitting at home alone? Walking to the bus stop?

If you are thinking about a topic all the time, it’s a pretty good indicator that you’re already obsessed with it. Now, is it a good obsession? That’s another personal question that truthfully I don’t really know the answer to; this is something I am still ideating and thinking through. Generally though, I think a good obsession is a broad category.

I actually think niching down with your obsession is a bad idea because it ends up becoming a situation akin to trying to use a specific tool to solve a problem, since it’s the tool that you know how to use, instead of picking the best tool for the job. Imagine if Sam Walton decided that his obsession was discount stores, which was his first chain of businesses before starting Walmart, just because he decided that discount stores was his obsession, not retailing as a whole. He would have missed out on the biggest opportunity of his lifetime, and as history has shown, likely had his discount stores driven out of business by Walmart-type big box stores like Costco. By leaving his obsession open to retailing, he could keep an eye on the craft as a whole and adapt as needed.

On top of being general, I also think the obsession should be non-technical in nature. What I mean by that is that I think it’s important to understand what are skillsets you leverage for your obsession versus what are actual elements of your obsession.

A personal anecdote to better illustrate this point: for a long time (over 10 years now), I decided that I was “obsessed” with software engineering, architecture, and computer science. I studied the entire stack, from RAID microcontrollers, hard drive caching, networking, all the way up to the animation timing of cards swiping on dating apps. I have a very full and complete working knowledge of software and computers. I can build and ship products starting from bare metal, as I have many times; but that isn’t an obsession. It’s a tool. I’m very effective at using that tool, but what is it that I’m working towards?

That’s where your reasoning comes in, and you have to ask yourself questions to figure out where your obsession truly lies.

Your work should be an intersection between your obsession and your skillset. From this I’ve realized that my skillset, not obsession, was my technological knowledge, and over the years my obsession has changed: it was social for a long time, then healthcare, now it’s creators. The intersection of my skillset and those obsessions lead to RU Mine, my work at MyChart, and now Creator Check, respectively.

This isn’t to say that niching down is bad, as Naval says, “the riches are made in the niches”. You have to niche down to build a product, a business, or provide a service. Without a clear understanding of who you’re helping a why, you’ll never end up building effective solutions. My argument is that your overarching obsession should not be so niche that you saturate it quickly; an element of what makes obsessions great is how open-ended they can be.

Think of basketball and Kobe, and bring some set theory into this. The set of possible actions that can occur in a game of basketball is effectively endless, which means you really can never saturate that obsession. If you decide that “dating apps for dogs” was your obsession, I think you’d very quickly find out that the set of possible actions is finite and small. You will very quickly saturate the obsession, leading right back to aimlessness.

A great obsession example is healthcare. It’s broad enough that you could be designing better ambulatory stretchers, providing better access to patient records, or designing footwear for patients that can’t bend down. Your options quickly become endless when your pursuit is bettering healthcare as a whole rather than just one specific category. This endlessness is exactly what allows you to explore and build great solutions to problems that ultimately pushes your overarching goal of bettering healthcare forward.

Social, healthcare, and now creators — you may ask yourself, isn’t that weird to change your obsession that often? And maybe it is, I’m not really sure. I’ve thought about the idea of having multiple obsessions at once, if it’s feasible and if you give up anything by dividing your attention across two different crafts. I think Elon has proven that you can attend to more than one at once, but are we all Elons? Naturally I like to think that I am one, but it’s probably far too early to tell.

So, I think the best advice I can give myself is to pick one goal that eclipses all the others and make that my main obsession. Honestly, will I listen to it? I am not sure, but there’s the advice.

What about changing your obsession? Is that okay? I think so, and so does Richard Hamming. He has a fantastic speech called “You and Your Research” where he argues that you should actually be changing your research, and conversely obsession, every 7 years or-so. This prevents you from becoming stagnant in your work, keeps ideas fresh, and keeps you learning which is the number one most important aspect of life.

The final piece of the puzzle is to focus. Focus, focus, focus, FOCUS.

That’s as much for me as it was for you.

You have to be relentlessly focused on this obsession. Steve Jobs famously said, “People think focus means saying yes to the thing you've got to focus on. But that's not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I'm actually as proud of the things we haven't done as the things I have done. Innovation is saying no to 1,000 things”.

If you jump around between topics constantly, you run the risk of never truly being able to become the best in one-specific thing. It’s useful being a generalist, and I would argue that you really should be good at many things, but it’s the specialists that make the world turn.

Many people in their 20s with great potential have sputtered out and become cogs in the system for spreading themselves out too thin and being unable to say no.

You have to say no. You have to focus. You have to be unapologetically obsessed.

Understand what you’re aiming for and become a heat seeking missile that does not stop until it hits its target.

This is the most important part of all of this. Focus, focus, focus, FOCUS. Do not become a cog in the system. Become the best in the world at one specific thing.

To summarize all of this in a few thoughts:

  1. Throw yourself into a topic that you are excited about, is impactful, and has lots of opportunities to grow and develop.
  2. Separate your skillset from your obsession.
  3. Go all-in, say no, and focus.