The Power of Obsession: Harness Your Inner Drive for Success

Hassan Karimi
7 min readDec 10, 2022
Bob Dylan performance in NYC in 1963
Bob Dylan performance in NYC in 1963

When Bob Dylan arrived in NYC he spent long hours days on end in the New York Public Library. He was mostly reading accounts of life in the 1800s, more specifically, the Civil War.

Why? Because he wanted to know what life was like then and how this country got through an era where society was torn at the seams. What were people talking about? What were there day to day concerns? Most importantly, how did people talk and what was the language?

When living in Italy as a child, Kobe Bryant would spend hours daily pouring through NBA game tapes with his father. He looked for all the key subtleties, the footwork, and the various offensive and defensive styles of NBA teams. He intensely studied the stars from Magic Johnson to Larry Bird to Dominique Wilkins. “I used to watch their moves and then I would add them to my game.”

He would just as intensely watch films from his own performances and of his opponents. It’s not unusual for an aspiring athlete to watch videos of other great athletes or even of their own performances, but it’s exceptional for anyone, especially as a child, to be that diligent about it.

Legendary music producer, Rick Rubin describes Eminem as obsessive. He always has a notebook with him and he’s always filling them up with writing. Rubin quotes Eminem:

I write constantly, to the point where while I’m writing my books I know 95 percent of this stuff, 98 percent of it’s never gonna get used. But by writing all the time it’s like I’m sharpening my tools. And I’m more able to draw upon that skill-set when needed. And sometimes a reference that I wrote two years ago might come back and find it’s way into a record completely unrelated just because I was doing this homework and coming up with a new rhyme scheme or just hearing a word I liked and thinking about how that could rhyme.

The examples above are habits of some of the best. Mythical figures of our time and the obsessive dedication that drove their craft. You don’t have to be the next Eminem or Kobe Bryant, or even care to be like them.

But identifying and honing your own obsessions can pay dividends.

1,000 die-hard fans (Midjourney generated)
1,000 die-hard fans (Midjourney generated)

Founder and former executive editor of Wired Magazine, Kevin Kelly popularized the idea that “a craftsperson, photographer, musician, designer, author, animator, app maker, entrepreneur, or inventor” can make a good living by building only a small audience of 1,000 true fans. Kelly describes a true fan as a die-hard fan that will essentially pay $100 a year for products, art, or services that you create, resulting in $100,000 for the year. The essay was originally written in 2008 and rings true louder today than it did back then.

However, the path to 1,000 true fans doesn’t happen overnight. Jack Butcher, a designer who has grown notoriety through his unique designs, illustrates it perfectly in the tweet below. The path involves going for a long time with little or no results for a long time.

Today we have people like Mr. Beast who has one of the most popular YouTube channels at the age of 24 with 115 million subscribers. His recreation video of the sensational show Squid Games generated more revenue than the original! He didn’t just accidentally stumble upon his success. He got there by obsessing over every element of content creation on YouTube. He met daily with a small group of friends that would share every day about what they were learning about successful videos on YouTube. He obsessed over every detail from the thumbnail image to the sequencing of events to crafting titles, leaving no stone unturned. Everyone in the group went on to grow channels with over a million subscribers and Mr. Beast became the juggernaut he is today.

David Senra hosts Founders Podcast, a show where he summarizes biographies of the greats. He found himself obsessed with reading biographies about people’s lives and one day decided to start sharing about it on his own podcast. For years he was doing a solo podcast talking about the biographies he was reading. He spends 20+ hours of reading and note-taking for about an hour-long episode. He’s now turned an obsession into a viable business.

Archimedes’s lever
Archimedes’s lever

How to follow suit

The most interesting and the most important form of leverage is the idea of products that have no marginal cost of replication. This is the new form of leverage. This was only invented in the last few hundred years. It started with the printing press. It accelerated with broadcast media, and now it’s really blown up with the internet and with coding. Now, you can multiply your efforts without involving other humans and without needing money from other humans.

Almanac of Naval Ravikant

The simple lesson here is to find your own obsessions. Identify the things you are already doing naturally.

Whether it’s cooking, reading, hunting down the best deals in town, whatever it is, start there. Trung Phan, a business writer known for his viral Twitter threads, advises people to find something they would be willing to keep working at for 4 or 5 years before seeing any major results.

Common wisdom suggests asking yourself “What would I do if I couldn’t fail?”

But the better question is “What’s something I would be doing even if I knew it would fail?”

That’s how you identify what’s worth pursuing yourself. Something you will persevere at regardless of the circumstances.

Maybe you don’t have a specific thing.

Start with your interests. Are you drawn to something super-specific like mid-century modern Italian furniture or light-roasted coffee beans from Hawaii?

It’s hard to determine how long your interests will last in a particular area, so don’t get caught up in picking the right one. Just find a starting point and go from there. An interest in mid-century modern Italian furniture can reveal a greater interest in furniture design or interior design. Maybe something else entirely.

After establishing a starting point, choose a medium. Will it be social media posts? Will share illustrations or launch an e-commerce shop? Will it be a personal blog?

I suggest starting with low stakes and a low barrier to entry. The important pieces are starting, getting feedback, and doing the work. The quality will come over time with dedication. Quality is not the starting point.

George Lucas, inspired by the comic series Flash Gordon, set out to write a space opera.

He locked himself in his office 8 hours a day and kept it at until he wrote the first draft of what came to be Star Wars. The process went through multiple drafts of receiving feedback and revisions.

In The War of Art, Steven Pressfield draws a clear distinction between the amateur and the professional.

The amateur protects and treasures each of their unique ideas while the professional brings no significance to their work. The professional shows up regularly and works. She’s not attached to good ideas and understands those good and bad ideas are produced in the same process of working.

Good ideas will come but commit to a routine. Write or sketch for an hour every morning before the work day or in the evening if you prefer it.

Seth Godin offers a powerful call to action in his book, The Practice: Shipping Creative Work. He distinguishes between creatives making art for the sake of art, like that screenplay sitting at the bottom of a drawer, and the creative professional that puts the effort towards building an audience.

Making a long-lasting career from your passions is possible. The path is simple, but not easy. Godin’s book makes the following points:

  • There is no pre-determined path to success as an artist
  • Art creates change and blasts new windows open. We need more of this.
  • To make the best possible art you need a feedback loop: share your work, receive feedback, make improvements
  • Join a cohort of others doing similar things
  • Being a creative professional is a decision to show up and do the work
  • If you treat your art as a hobby, it will never grow to be more than that
  • Creative blocks are the result of perfectionism

James Altucher swears by a simple practice of writing 10 ideas every day in his book Skip the Line.

Writing ideas helped him get out of a slump after losing all his money from a failed business. He would go to a coffee shop every morning and write a list of ideas like 10 ideas for a chapter in a book he read, 10 alternate endings, etc. He found it lifted his spirits and eventually started generating ideas and emailing them off to people that might want them. He emailed Jim Cramer, host of the show Mad Money, a list of 10 articles Cramer should write. Cramer wrote back saying “You should write these!”

That was the start of Altucher’s writing career and he’s gone on to write 20 books since then.

In 2021, artist Mike Winkelmann famously known as Beeple sold an NFT through an auction at Christie’s for $69 million. The piece, Everydays: The First 5000 Days was a collage of 5,000 consecutive days of art work shared through Beeple’s Instagram.

Beeple created and shared this artwork daily for over a decade before earning a dime from it.

Building a creative practice is simply a matter of consistent creation and sharing your work.

Expect that it will take years for any worldly results. And that’s why obsession matters.

It’s hard to show up consistently for years with no results for something you don’t care about. You have to hone your passion just as you do your practice.

While nothing is guaranteed, the journey is simple. Trust yourself and trust the process.

Originally published on Boundless Canvas on December 10, 2022.

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Hassan Karimi

UX/ product former architectural designer writing about building a creative practice in modern times