Imagine waking up with an oppressive sense of guilt — not because you’ve done something wrong, but because you’re not working. Sound familiar? You’re not alone.

Success in the startup world can often feel like a relentless pursuit that demands your energy, time, and commitment around the clock. This constant strive to do more often brings an unwelcome guest — guilt when not working. But what if we told you that this guilt, the self-imposed pressure, could lead you down the path of burnout, quitting, and, inevitably, failure?

Simon Sinek, the acclaimed motivational speaker and author, famously coined the term “Infinite Game.” He suggests that too many business leaders have their eyes fixed on the finite game — a game with set rules, known players, and an end point. However, in the world of startups and entrepreneurship, we’re playing an infinite game — a game where the rules are changeable, the players are numerous, and the game itself is ongoing. Winning isn’t the goal here, but rather staying in the game.

This notion parallels legendary investor Charlie Munger's principle of “Inversion Thinking” — start by considering what you want to avoid and work your way backward. If you wish to avoid burnout, quitting, and failure, you must rethink how you perceive not working and understand its long-term value.

The Inherent Guilt

For both the entrepreneur trying to build a team around a product, and the freelancer trying to maximize their billable time, the guilt of not working can be particularly heavy. This guilt often stems from an urge to constantly innovate, to solve the puzzle of simultaneously promoting services, operating the business, and developing the product.

I experienced the same guilt.

During my college years, life threw me a curveball. The birth of my young family’s first child coincided with the ‘07/’08 financial crisis, which resulted in a total loss of financial security. The loss of status and shifted circumstances removed support networks. The pressure to succeed was immense, with no room for failure. I found myself unemployed, possessing negligible marketable skills, and shouldering the responsibility of providing for my family.

In the face of these challenges, I knew I needed to control my time, experiences, and path. Relying on a conventional, entry-level job at that point seemed unfeasible and risky to long-term prospects. I had played around with freelancing in college and decided to go all in.

If I was awake, I was working. 100+ hour weeks. For five years.

But… it took 3 months to get my feet under me and another 15 months for things to stabilize.

I believed that working continuously was the only way to continue to successfully provide. Despite burnout. Despite exhaustion. In a very real way, I knew I didn’t have the option for failure. My defense against failure was an unrelenting drive for more — clients, contracts, jobs, gigs, growth, opportunity, whatever.

It wasn’t until I realized that I was missing the major milestones of our second kiddo that the balance was way off. Together, we took steps to recalibrate and prove that it was possible to work less and still progress.

Of course, more than a decade later, I still feel a deep need to keep pushing but I’ve learned channel this in healthier ways.

Remember, this isn’t a sprint, it’s a marathon. It’s not about rushing towards an imaginary finish line but maintaining a steady pace that allows for growth, learning, and the occasional pit stop.

Reframing the Notion of ‘Not Working’

But how do you transition from feeling guilty when you’re not working to accepting the necessity of breaks?

The answer lies in shifting your mindset towards the concept of “not losing.” I found the answer in the precious moments I was missing with my family. I began to understand that racing toward an imaginary finish line was costing me irreplaceable moments and experiences.

The epiphany here was realizing that not losing was not about working every waking moment, but about balancing work and personal life to ensure that you don’t lose out on either.

You’ll often find that the most fruitful ideas don’t come when you’re knee-deep in work, but rather during those “idle” times. Those moments when you’re reading a book, going for a jog, or even taking a shower. The brain needs this downtime to process information, generate new ideas, and spur creativity.

However, over time, I came to understand the importance of redefining my relationship with work, and how crucial it was to ‘not lose’ on all fronts.

The Importance of Rest

Through my journey of 100+ hour weeks, the impacts of neglecting rest became very evident. The long hours led to burnout, reduced productivity, and a disconnect from personal life.

Sinek and Munger both advocate for the idea of maintaining your momentum in the game. A crucial aspect of this is ensuring that you’re in the best mental and physical state to continue the journey. That’s how I learned to value rest, to schedule it as diligently as I would a meeting, and to see it not as wasted time, but as an investment in my future productivity and creativity.

Even for early-career programmers, this principle applies. You’re learning to navigate the complexities of coding, productivity, and professional growth. Remember, growth doesn’t equate to constant action. Rather, it’s a balance of learning, working, and resting.

Balance: The Key to Longevity

Those interested in the convergence of technology and finance understand that balance is vital. Much like a diversified investment portfolio, balancing periods of intense work with moments of rest can yield the best results.

In the infinite game of startups, the goal isn’t to out-do everyone else, but to build resilience, agility, and longevity. By reframing how we perceive the concept of “not working” and understanding the value of rest, we can foster a healthier mindset, promoting long-term success.

If you’re feeling guilty for not working, remember — it’s not about winning or losing, it’s about staying in the game. Embrace the break and shift your perspective. Let’s play the infinite game together.

I’ve been known to be a bit of a hermit on social media, but I’m slowly becoming more active. Feel free to follow me on Twitter as I start sharing more about my journey.