Middle Aged Men on Skateboards

Recently, I found myself arriving at an office building with my skateboard tucked under my arm, only to be greeted by one of my peers with a disapproving look and the question, "How old are you?". As a 45-year-old software entrepreneur, I have become familiar with the stigma of doing things outside of the norm. Yet, 10 minutes later as I observed the same person who questioned my choice of transportation complain about their long walk from their car due to limited parking, I couldn't help but feel a sense of satisfaction knowing that my unconventional approach had saved me both time and frustration.

As a niche software entrepreneur, I am no stranger to the discomfort of operating outside of many societal norms. The endurance coaching profession itself also exists beyond the bell curve of conventional expectations, but I want to explore how embracing the unconventional, inside our industry, can help us stand out in a crowded field.

In this blog post, we will delve into the importance of breaking free from societal (and industry) constraints to better serve our clients and achieve success in our businesses.

Challenging Societal and Cultural Norms

Society often dictates what is considered "acceptable" or "normal" for certain age groups or demographics.

Let’s use skateboarding (surf skating) as a bit of a silly yet simple example of the impact societal and cultural norms can have on our behavior and our ability be successful.

Middle-aged men typically don’t ride skateboards and if they do face judgment due to the perception that they are "too old" to be engaging in such activities. These age-specific norms and expectations can be limiting and prevent people from pursuing their passions or exploring unconventional methods that could benefit their lives.

For me, skateboarding is a simple and easy form of transportation and an absolute gamechanger for improving my surfing skills. Surfing is a very difficult sport to make progression, and most surfers never make it past “intermediate” level. I have aspirations to be much much better than that, and thanks to my surf coach who introduced me to surf skating I’ve been progressing exponentially faster than I would otherwise.

When I ride my board around, I always feel a little embarrassed and to be honest, like a bit of a dick. I feel a lot of resistance, but I have goals, so I push through that discomfort and just do it anyway. F**k it, I don’t care what they think I tell myself.

How Societal Norms Limit Our Potential

By adhering to societal norms, we may inadvertently limit our potential and the potential of those around us. As coaches, you should strive to break free from these constraints to unlock the true capabilities of your business. Exploring unconventional methods or adopting practices that may be considered "outside the norm" can lead to personal growth, improved performance, and overall satisfaction in your business life.

Many coaches hold down “normal” jobs while coaching on the side. I love this approach, but I also worry that it might be the adherence to societal and cultural norms that is holding many part time coaches back from taking their coaching business to the next level.

The Mental Benefits of Challenging the Status Quo

By challenging societal and cultural norms and embracing unconventional practices, we open ourselves up to personal growth and self-discovery. Stepping outside of our comfort zones can help build mental resilience and foster a growth mindset, which is crucial for achieving success in endurance sports, business, relationships and life in general.

Endurance Coaching: A Profession Outside the Norm

The Unique Challenges and Rewards of Being an Endurance Coach

As endurance coaches, you work in a profession that already defies societal norms. You guide and support individuals as they push their physical and mental limits in pursuit of their goals. This unique position allows you to embrace the unconventional and encourages you in turn to encourage your clients to do the same. By doing so, you not only help them achieve their objectives but also create a more rewarding coaching experience for yourself.

However, even the endurance coaching profession has it’s own cultural norms which are difficult to recognize from the inside.

It’s easy to get complacent and succumb to cultural norms inside the industry which also limits our potential.

Constraints Within Endurance Coaching

Within the endurance coaching community, there are norms and expectations that can limit our potential for growth and success. One such area is marketing and sales.

Coaches value the respect of each other, which on one hand is great, but on the other hand can hold them back. Coaches don’t want to be seen by their peers as being too much of a salesman or a marketer.

For some reason, investing in sales, advertising and marketing isn’t a cultural norm for endurance coaches. This is the biggest gap coaches have to bridge when taking their coaching from a hobby or lifestyle to a valuable and healthy business.

I’ve lost count of the times I’ve seen coaches avoid any sort of sales or marketing strategies in their businesses and say things like “I just rely on word of mouth” or “my results speak for themselves”.

Well the problem is, results DO NOT speak for themselves, they are representative of your abilities but they certainly do not speak or promote themselves in any way shape, or form.

Reluctance to engage in sales in marketing strategies is the number one reason why most coaching businesses never progress beyond just “earning enough to get by”.

By stepping outside of the traditional methods and exploring innovative ways to promote our services and connect with potential clients, you can set yourself apart from the competition and grow our businesses beyond the bell curve.


As a 40 something surfer, skateboarder and software entrepreneur, I have come to appreciate the value of breaking free from some societal and cultural norms to embrace the unconventional in both my personal life and my business. By challenging the status quo and avoiding being limited by expectations, we can unlock our potential and help our clients achieve success beyond the bell curve. So, the next time you see a middle-aged man on a skateboard or an endurance coach experimenting with unique training or marketing or sales methods, remember that embracing the unconventional can lead to extraordinary results.

And don’t forget marketing is not the same thing as advertising and there is a multitude of ways to integrate marketing and sales into your business to create win win relationships between you, your business and your customers.

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