2024 Week 43 of 52 83% Hindsight

At the start of 2020 I wrote a piece '20x20 Vision ' reflecting on the previous decades of change, unaware that the world was about to hit a pandemic that would change us all.?2020 marked an exciting new decade, full of fresh starts and exciting new opportunities.

Now almost five years since, we all have the benefit of hindsight.

In many ways the chaos since has shaken the complacency away.

At the start of this year I wrote a piece about the complexities of creating change - and how making a commitment is the first step .

2024 has been, yet another, year of continued ongoing change, disruption, and evolution—reminding me of the core lesson in Ryan Holiday’s book from a decade ago The Obstacle is the Way : obstacles are not roadblocks, but part of the path forward.?

"When the going gets tough" ...

Challenges feel daunting in the moment, but often, when we look back, they seem like necessary steps in the journey—neither good nor bad, just part of a larger process. What feels tough today often reveals itself later as a turning point or an opportunity that wouldn’t have come any other way. Is this a year of transformation? Perhaps, but change is a constant. Hindsight is both clarity and potential failure.

"In hindsight, I slid into arrogance based upon past success." Read Hastings, Netflix founder

Ryan Holiday’s philosophy, drawn from Stoic thinking, teaches that it’s not the obstacle itself but how we respond to it that matters. Progress lies in reframing difficulty as opportunities to learn, adjust, and grow. Obstacles push us to act—whether by developing new skills, changing strategies, or sharpening our focus.

Instead of asking, "Why is this happening to me?" the better question becomes, "What can I do with this?" In hindsight, many struggles we thought would hold us back often become the source of our greatest strengths.

"The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition." Ryan Holiday

Growth, then, is rarely a smooth upward trajectory—it’s a process of evolution, marked by ups, downs, and moments that only make sense when looking back. Square Holes has seen these twists many times over the years, and in each case, the path wasn’t always clear. What seemed like setbacks—economic shifts, projects delayed, arseholes and misaligned strategies, values and expectations—turned out to be opportunities to refine our narrative, build resilience and innovate.

Holiday reminds us that the things we resist often contain the lessons we most need to learn. It’s about seeing clearly, without emotion clouding our vision, and taking action, even when things feel uncertain. By focusing on what is within our control—our effort, attitude, and response—we transform obstacles from burdens into stepping stones. This mindset shifts the narrative: we don’t 'survive' challenges, we evolve through them.

In business and in life, transformation is about embracing impermanence, staying curious, and trusting the journey. The work itself becomes the reward—whether it's building strategies, testing new ideas, or learning from failed attempts. When we view each obstacle not as an end but as part of the process, we find meaning and growth along the way. Often, what feels overwhelming now becomes, in hindsight, exactly what we needed to move forward.

An interesting life is rarely boring. Opportunity to be innately curious.

To keep the beginner's mind alive.

Have a good Friday and weekend!

Jason

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