UpSkill: The Leadership Marathon

In this blog I’ll introduce the UpSkill Leadership series. In each part of the series I’ll discuss one key leadership lesson. The first five will be based on my reflections on the 2022 Boston Marathon.

The Boston Marathon is one of the most famous marathons in the world. It’s historically held in Boston on the third Monday of April. The 2022 marathon was the 126th race. It is a 26-mile, or 42-kilometre race. It is the marathon that long-distance runners dream of running, a crown jewel of athletic achievement. 

That kind of journey is not for everyone, not even for every long-distance runner. The same is true for our leadership journey. To master leadership skills and perform at a high level is a marathon that requires us to step up to new and demanding standards.

We must perform at higher levels to lead in a modern business environment, to partner with modern organizations and to lead ourselves in a modern environment. The task is only for the fittest leaders, but it is a journey we all need to be on.

This kind of journey is for the courageous leader. The brave leader: The leader who is not afraid to try, to fail, to make mistakes, to step out of their comfort zone.

It is for those who believe it is possible to perform at a higher levels, and for those who are willing to subject themselves to the hard work – the long-distance work — it takes to perform at those higher levels.

If you are one of those leaders, here is the number one lesson the Boston Marathon can teach you: Leadership is a journey, a long, arduous but satisfying journey.

The competitors at the Boston Marathon are all marathon runners, but this is not their first race. They all prepared by running shorter races to build up to a level where they could compete in this environment. They ran other marathons and met qualifying standards to apply to this race.

Many of these elite runners ran in other marathons, the Olympics, or they competed in other sports.

A lot of work and effort went into qualifying.

We are entering a new leadership space that requires more from us, and we are going to need to step up our preparation to perform in this new environment.

The old ways of leading may no longer cut it in this new world order. We are entering a post-pandemic leadership space, a social justice leadership space, a mental health-focused leadership space.

Flex work, hybrid work, remote work.

A more scrutinized, demanding leadership space.

How can we take our leadership to the next level?

Did you ever think you would see the day when our entire world shuts down? Who could have prepared us for that?

What are the other unknown challenges ahead of us? Are we getting prepared for those?

This is not your first race.


All of your practice and experimentation has led you to this.

However, you will need new skills and a new mindset to succeed. New partnerships, new knowledge, new experiences. So much more will be required for you to prepare for this new business environment.

What does your preparation for leading in this environment look like?

Are you feeling like you’re prepared, or do you feel like you’re not sure where to begin?

If you’re feeling like you’ve already arrived at your destination in your career, in leadership, in life, I want to remind you of the first lesson.

What does your preparation for leading in this environment look like?

Leadership is a journey: we never arrive.

No matter how you feel ¬— underprepared, prepared, overprepared — preparation must continue.

On this journey, we must anticipate detours and roadblocks.

We will have issues with our own navigation, or maybe even the vehicle.

Like any journey, if you need to change your vehicle, change your vehicle.

The journey must not stop. You can take a pit stop to rest and recharge, but don’t set up shop. Keep moving and keep growing.

Leaders are learners, and only learning leaders will lead us tomorrow.

The experience you have had so far qualifies you to participate in a new leadership landscape. You must then compete to be able to lead in this new global leadership environment. In order to continue learning on this journey, leaders (like marathon runners) need a long-distance mindset.

We need a mindset that reminds us we are in this for the long haul. We are not looking for quick fixes or things that happen today, but don’t happen tomorrow. We’re looking for sustainable approaches to our learning development.

Today’s leader must have a marathon mindset that knows that this race is not done in the first 100 meters.

If you think about leaders as marathon runners, it’s important that you know that the journey requires sprints from time to time. We need a short-term approach that we can incorporate into our approach. We must have short-term strategies that are part of the process, and contribute to a long-term strategy.

Words, thoughts, decisions, actions and results follow our mindset. If you don’t like your words, thoughts, decisions, actions and results, check your mindset.

Your mindset is like an operating system. We hardly think about it or talk about it, but it runs all of our other applications. Sometimes you get notifications that your operating system must be updated. Sometimes we can check the option to automatically update.

If you are not mindful of updating, sometime down the road you will get an error message when trying to run a program. It will tell you your operating system needs to be updated. If we are not intentionally shifting our mindset then we will not be able to run.

I encourage you to check your mindset. Ensure you have automatic updates on Upskilling. Plan updates to your system.

Do you have an open, innovative mindset? Are you open to new ideas and perspectives? Are you open to making mistakes and trying again? Are you collaborative?

Do you have an equity mindset? Do you have an awareness of inequities and how you can contribute to the solutions?

Do you have a growth mindset? Do you have a belief that you can develop your abilities and do better? That you can change and grow and do whatever is necessary to meet new demands?

Do you have a marathoner’s mindset? Are you focused on your goals? Are you patient enough to endure the long journey to see the results your work produces?

You’re going to need these mindsets to engage at this new level of leadership, to engage in this long-distance journey. To design a process for yourself. To continuously Upskill and develop a mindset to inform your thoughts, words, decisions and your results. On this journey with its ups and down, think long-term. Keep learning, no matter where you are you are not at the destination in this uncertain world.