What happens when an optimizer tries to embrace chaos?

For someone who thrived on structure and predictability, diving into the world of creativity was like stepping into a tornado.

My brain, wired for business goals and outcomes, struggled to adapt.

How do you balance the relentless pursuit of optimization with the limitless nature of creativity?

This is the journey I've embarked on, and it's been anything but straightforward.

To understand my struggle, let me take you back to where it all started.

Some background

For the past six years, I ran a 7 figure real estate investment firm, growing it from scratch.

My approach was simple: optimize everything. I standardized processes to ensure predictability and scalability.

For years, my brain was wired for business, driven solely by goals and outcomes.

It was pretty straightforward for an analytical brain like mine:

• I wanted to sell more houses, so I did more marketing.

• I wanted the renovations to go faster, so I always bought the same types of properties.

• I wanted predictable rehabs, so worked with the same contractors.

It was a relentless quest for optimization, always asking the same question: “How can I do to do more of what we do, without increasing the use of resources needed to scale?”

So, I doubled down on standardizing. I bought the same houses, in the same neighborhoods, used the same paint, the same cabinets, the same flooring, the same door knobs, the same everything.

I created a very strict buying sheet where I promised to buy any property within 10 days, sight unseen. The only requirement was that it checked out a list of 37 non-negotiable parameters.

This allowed me to have maximum leverage and scalability, because I would always buy these properties at the same price.

There was no room for questioning.

There was no room for error.

Everything was predictable, including the income I would make, because I would simply add a fixed markup before reselling it.

In fact, it even allowed me to sell these properties before I even bought them.

The way I saw it, I wasn't selling houses—I was selling a financial product, replicated 550+ times with a specific return, like high-value chocolate croissants.

The point of the story is that I enjoyed optimizing the win.

I’ve tried optimizing my creative journey, and it has not been as easy, because it creates a paradox.

My struggle with the pursuit of creativity.

Creativity thrives on the freedom to wander without a set destination.

This tension between structure and spontaneity is a struggle that I have been facing.

I find myself torn between writing about what interests me and writing to attract readers.

My business mind craves clear objectives, but my creative spirit needs space to explore.

It’s a constant push and pull.

Just as I once listened to business mentors at the start of my real estate journey, I've now turned to successful creatives for guidance.

Turns out, I was asking the wrong questions.

One specific podcast that featured Rick Rubin caught my attention and shifted my perspective.

He views creativity as a devotional practice, focused on the process, not the outcome. This radical shift taught me that true creativity thrives without fixed goals.

Creativity should be about the process and the growth that comes with it.

If you ask yourself if what you are working on it “worth it”, that means it’s reliant on an outcome. When you are trying to be creative, the goal should not be the outcome.

The outcome happens when you make the best thing you can make.

Because whatever happens after that.. happens. That part is 100% out of your control.

If you try to put any energy in that part that is out of your control, it’s really just a waste a time because it undermines your work.

When faced with a problem, I always try to figure out universal rules, the most basic common denominator. I’ve discussed a while back my approach to solving problems using first principle thinking. The experiment is the same here.

I believe that in business, like in the creative world, the same underlying fundamentals apply.

It boils down to trying your absolute best. And I have to admit, I had not been.

I’m sure that if you were to ask yourself the same question, I think you would admit that you haven’t either.

I’m not talking about pretending to try your best.

I’m not talking about trying your best 90% of the time.

I’m not talking about trying your best with excuses.

I talking about actually and genuinely doing your best.

All the time.

All day.

Every day.

—

This is the level of intensity that I am now striving for. Now, on to the practical and philosophical lessons I got out of this podcast.

4 lessons from Rick Rubin

1. Authenticity is Everything

"Each of us is here to play our part, not somebody else's part. And I think it's a big mistake that people see something successful outside of themselves and they want to have that. So they follow the path. They follow someone else's path that led to their success instead of following their own path to lead to your own success.”

R.R

So, here's the deal. Being yourself isn't just some feel-good advice. It’s a neurological must. Your brain’s reward system lights up like a Christmas tree when you are being authentic.

Think about it. Have you ever tried to mimic someone else's success only to feel like a fraud? I know I have.

Early in my real estate career, I followed the strategies of industry gurus, hoping to replicate their success. Sure, I saw some results, but something always felt off.

It wasn't until I embraced my unique approach that I truly hit my stride. I created my niche instead of just following a formula.

The same goes for my writing. I started by imitating the style and tone of seem popular writers. But it didn’t feel right.

Why not be yourself when everyone else is taken?

Plus, when you are true to yourself, your brain releases dopamine, which enhances our mood and motivation. Authenticity is a neurological imperative.

So, take a moment to reflect: are you living your truth?

Are you showing up as your authentic self in your work and life? If not, what’s holding you back?

2. The Best Work Divides the Audience

“The best art divides the audience. If everyone likes it, you probably haven’t gone far enough”.

R.R

Great work divides opinions.

Bold, risky work evokes strong emotions and stands out. If everyone likes it, you're playing it too safe.

Think of your favorite movies. They didn’t aim to please everyone, and neither should you. So, take those creative risks. If you’re not pissing someone off, you’re not doing it right.

Whatever you create, a rather large number of people are probably going to end up hating it. And that's good news.

It means you’ve broken the rules, pushed the limits, and ventured into risky territory. Your art isn’t safe, and that’s exactly what makes it great—playing it safe never created anything memorable.

Don't aim to please everyone. Take bold, creative risks, and accept the inevitable backlash.

I recently lost close to 4% of my newsletter subscribers after posting about why watching sports is a waste of time. 🙄 Thanks Rick.

3. Let Go of Control

"Giving up some of the feeling of control and looking at them all and seeing some of them are going to have more life than others." (talking about ideas)

R.R.

Control freaks, listen up (me). Too much control chokes creativity.

Csikszentmihalyi’s concept of 'flow' tells us that true creativity happens when we let go and immerse ourselves in the process.

Rick Rubin's thoughts really resonate with me here. He talks about coming up with a lot of ideas, planting many seeds, and then observing what happens.

It's not so much about us deciding which idea will succeed; some ideas just naturally take on a life of their own. They gain momentum and find their way into the world, while others, no matter how much effort you put in, just don’t go anywhere.

Rubin suggests letting go of some control and paying attention to the clues around you.

Some ideas will show more promise and reveal pieces of the puzzle. It's less about forcing things to happen and more about being observant and responsive to the signals life gives you.

4. Keep Experimenting

You know, I never know. It's always like everything's an experiment. And then you're experimenting, you're experimenting, you're experimenting. And at some point, you step back and like, whoa, that thing is good. You know, that one is better than all the other, all the other experiments up until now. And that's, that's all it is.

Thomas Edison wasn’t kidding when he talked about his 10,000 failed attempts.

Experimentation is the playground of creativity. Every failure is just another step towards success.

When I tried optimizing creativity the way I did in business, it flopped. But each failure taught me something new. So,

• Keep experimenting

• Learn

• Tweak

• Repeat

I've learned that failure isn't the enemy—it's a crucial part of the process.

Remember, the goal isn’t to avoid failure but to fail forward. Each experiment, each failure, brings you closer to finding that one idea that will soar.

So, embrace the experimentation. Dive into it with curiosity and enthusiasm.

Don’t be afraid to try new things, even if they seem crazy at first. Often, the most innovative and successful ideas come from the willingness to explore the unknown.

Final Thoughts

Rick reminded me that creativity is not just an end product, but about the process and the growth that comes with it.

In fact, he argues that the audience should come last.

Bridging the gap between business and creativity has shown me that each has unique demands and rewards. Moving from optimizing real estate to navigating the unpredictable world of creativity has been a challenging journey.

In business, clear goals and ruthless efficiency were my best friends.

But creativity? It thrives on chaos, on wandering without a set destination.

Rick Rubin taught me a few hard truths:

• Being authentic

• Taking bold risks

• Letting go of control

• Experiment, experiment, Experiment.

It’s not just about the end game—it’s about falling in love with the process, putting in the work, and giving it your all without getting focused on the outcome.

So here’s my challenge to you: Are you truly giving yourself the freedom to be creative?

Are you putting your heart into the process without obsessing over the result?

Keep pushing boundaries, keep exploring, and most importantly, keep creating. That’s where the real magic lies.

Did you see this recent post?

I did a thorough analysis of Rockefeller’s 38 letters to his son and broke it down in this thread. It’s packed with powerful lessons that can transform your approach to business, but I made sure it was bite-sized.

You can read the full post here.

Strategizingly yours,

Ben