Radical Ways To Tame Chaos, Chase Passion And Embrace Discomfort

My experiments finding fulfillment through structured systems, a passion for life, and a willingness to face discomfort.
Radical Ways To Tame Chaos, Chase Passion And Embrace Discomfort

Being busy does not equate to being productive.

Fast responses, immediate action, or being dialed in on every decision does not make you a better business owner.

Grinding it out day after day, week after week for years upon years does not earn you any additional credibility.

These ideas are so glaringly obvious at this point they border on cliche. Still, even if we realize and embrace them as concepts, why do most of us tend to do the opposite in practice?

I have an hypothesis.

As humans, we are wired for survival. Our endless list of obligations have put most of us into a constant state of fight or flight, manifesting as anxiety. While its intensity may fluctuate, this anxiety exerts it’s influence over most of our decisions.

It has us incessantly checking our inboxes.

Or take meetings we know we don’t want to.

It causes analysis paralysis or its opposite — rash decisions.

It makes our tempers short.

So now that we’ve named it, how do we get rid of it?

Here’s the issue - we don’t — at least if you fall into the category of overachiever, like most entrepreneurs or business owners tend to be.

Our fundamental need to survive is what we draw upon to create, build, grow, experiment and take risks. To kill this primal instinct would deny us our full human experience.

It would cripple our ability to create.

The good news is that there are ways to keep it at bay and draw upon it as needed, versus letting it be the main driver in our lives.

It does require us to step outside our comfort zone, sometimes in some pretty drastic ways.

Below are a few ways that leaning into the extreme can help you find balance and fulfillment.

Building A Foundation

Most of my friends (and certainly my family) would consider me an extremely disciplined individual. I get up early, I invest in my physical and mental well being, I’m meticulous with my schedule and I prioritize balance.

But here’s a dirty little secret - none of this comes naturally.

Not too long ago (okay, maybe it was over 20 years ago), 8:30AM was considered extremely early. My days were unstructured, spent on Grand Theft Auto, band practice, and critical decisions like “What show or party are we going to tonight?’”.

During this period, I also owned a punk club. Aside from a few weekly hours of office work - booking bands, updating the website, and sending contracts - my work took place on nights and weekends. Money was tight, but I didn’t need much - at any given time I shared rent with 3 to 8 people and kept my expenses low.

Life was much simpler and while I was happy, it also lacked any semblance of structure, discipline or direction.

So what changed?

Earl 1.

Earl was a middle aged engineer turned business owner from Caldwell, New Jersey who would stop by the club most Friday evenings. He ran a software development company out of his house and had a small team of web developers, consultants, and other engineer types.

I can’t exactly recall where I met him or why he’d stop by (he never actually came to see any of the bands), and, if I’m honest, he was always a little annoying.

Still, he was a nice enough guy, and our shared computer science and tech background made for some interesting conversations.

Earl knew nothing about live music or clubs, but his wheels were always turning, and he was never shy about suggesting ways to improve the business—most of which I’d nod to and then immediately forget about.

At some point, he convinced me to use my free daytime hours to work for him part time. He offered to train me in .NET and web development while giving me the flexibility I needed for my business. I figured a bit of structure—and a $25/hour freelance rate—would probably benefit me, so I took the opportunity.

I don’t exactly remember how long I worked for Earl, and I’ve definitely forgotten anything I ever knew about .NET or Visual Basic. But what stuck with me was his relentless commitment to perfection and discipline. Whether it was checking out tickets, writing code, running a team meeting, handling client communication, or managing accounting—Earl had a process, usually dictated by Microsoft, for just about everything.

Earl’s systems for optimization went far beyond just client work—they shaped every aspect of his business and life, from how and when he ate to how he scheduled downtime. That same mindset carried into his client work and, as extreme as it sometimes felt, it clearly worked—his business was growing, and his team seemed to embrace it.

All this was a shock to someone like me who, at the time, was living the opposite of what Earl stood for. Still, I guess some part of his obsession with optimization and management resonated with me.

Fast forward almost a quarter century, and while I’m not naturally disciplined, I’ve learned to build systems that bring discipline into my life. They dictate when I wake up, how I structure my day, which projects I take on versus outsource, and even how I schedule downtime to maintain balance.

Lesson 1: In the absence of discipline we need to create systems.

Flipping Your Perspective

A large misconception is that discipline is rigid and boring. Nothing could be further from the truth. Establishing routine and predictability frees up significant cognitive bandwidth, allowing you to obsess over your craft, explore new ideas, try new things, and develop better mental models and worldviews.

A few years later things were humming along nicely - I had learned to incorporate and build upon some of the common sense time management principals I picked up from Earl.

I assembled a small management team — OK, a few friends I could trust with keys and a lot of cash — to oversee the club’s day-to-day operations. I had a few steady clients for my web development agency and I had recently launched a music merchandising startup with my partner Danny 2, another veteran of the music industry. I recently relocated from North Jersey to Asbury Park and had fully embraced beach life, surfing, Ashtanga yoga, and the dilapidated charm the city had to offer in the mid-aughts.

I met Alan Nash at a yoga workshop organized by my local Ashtanga co-op. Besides being an accomplished Ashtangi, he held dual PhDs in Computer Science and Mathematics. We quickly became friends. At the time, I was practicing yoga six days a week and working through the Intermediate Series on my own. He offered to take my friend and I under his wing to help complete our training. We’d meet at a studio in Red Bank where he snuck us into one of his weekly classes. While he taught a led class, he had us practice individually on the side and guided us through the more advanced asanas.

After class, we helped clean up and then headed to his nearby apartment to drink tea and dissect passages from Patanjali’s Yoga Sutras, the Hatha Yoga Pradipika, and more obscure writings from yogis like Theos Bernard—one of his personal heroes.

I asked Alan how he managed to develop one of the most advanced physical yoga practices I’ve ever witnessed while earning two PhDs in challenging fields. His answer was deceptively simple.

When he was deeply engaged in yoga, he’d stand on his head for up to six hours each day. Once he became a PhD student, he gradually shifted that same practice into his research and studies.

It was all about balance (and maybe a touch of discipline).

By intentionally creating space to experiment and explore his interests, he became hyper successful in both fields.

Sadly, our time with Alan was cut short. About a year after we met, he was tragically struck by a car while riding his bike in Southern California. I may have never gotten to say goodbye, but his curiosity for life and kindness will always hold a special place in my heart.

Lesson 2: Learn to balance a consistent routine with relentless curiosity.

Finding Beauty In Discomfort

I heavily romanticize the period between 2009 and 2015 when I travelled to Nicaragua 2 to 3 times per year. I lost track of how many trips I’ve taken there over the years - probably close to 20. It was a special time, marked by nature’s raw brutality paired with the beauty of its people and places.

It was also the first time I had experimented with slower, less deliberate travel. I’d often spend as much as 6 weeks abroad at a time, showing up with little more than a carry on backpack, $1000 cash in small denominations, my well worn copy of Lonely Planet Nicaragua and a loose itinerary of where I wanted to go.

I first heard about Playa Maderas from college friends who ‘discovered’ it a few years prior while backpacking in Central and South America. Located about 9km north of San Juan del Sur and roughly an hour from the Costa Rican border, this beach—overlooked by the iconic ‘shark fin’ rock—had become a favorite for surfers and travelers seeking a quiet place to settle in.

By the time I arrived, Playa Maderas teemed with all the energy of a vibrant yet under-discovered gem poised to explode. Still, other than a $8/night hostel on the beach and a makeshift taco stand run out of the back of a Toyota Hilux there wasn’t much to do other than surf, eat, and slug Toñas.

Electricity hadn’t yet reached Playa Maderas, and any internet access was limited to about an hour in the evening when my surf camp fired up diesel-powered generators to provide a bit of light. Honestly, most of us were so exhausted from a day of surfing, hiking, and running through the jungle with machetes that our schedules quickly shifted to a diurnal rhythm.

Nights were oppressively hot and muggy, leaving our straw mattresses drenched with sweat. Days were sweltering and breezy, but as soon as the wind stopped, the flies swarmed.

Calling it uncomfortable would be an understatement. Yet, the common sentiment among most long-term expats I met was, ‘You should have been here 10 years ago,’ often followed by bragging about how much more ‘authentic’ and ‘challenging’ it was back then.

Still, during those early years, Playa Maderas offered the perfect dose of discomfort when contrasted with a very comfortable life back home. It felt as though life’s guardrails had completely rusted away, forcing me to rethink my priorities, perspectives, and what I really wanted out of the life I was creating.

Coming home was always tough — everything felt overly busy and alien compared to the slower, simpler rhythm I had grown used to. Living off the grid and being mostly disconnected from phones and emails wasn’t just refreshing — it was a big reason I kept going back.

Sadly, like many special places we encounter on our travels, word eventually got out. Over the years, that humble taco shack evolved into a bustling restaurant, soon joined by several other establishments along the beach.

Surf camps turned into boutique hotels, and for a while, the hills above the beach resembled one giant construction site. As accommodations and amenities increased, so did the crowds in the surf lineup. Influencers and bloggers arrived, eager to document and share the secret.

It was over.

In my mind’s eye, I revisit a fictitious moment - I’m watching the sunset from Tacos Locos, sipping disinterestedly on a Toña with limón. A smiling surfer coming out of the water makes eye contact an nods casually at me. I respond, “You should have been here ten years ago.”

Lesson 3: Lean into discomfort and let it realign your priorities.

At the end of the day, being busy isn’t the same as being productive, and I like to think we can all do a little better. True happiness and success come from building your own framework.

For me, establishing systems to bring order, balancing routine with curiosity to keep evolving, and leaning into discomfort to strip away the excess have allowed me to better align my daily actions with my core values and focus on what truly drives fulfillment, rather than just filling my schedule.


[1] I definitely may have altered his real name.
[2] We sold that company in 2020 but Danny and I remain partners to this day in several other business ventures including FRESH markets and Cowerks.

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