This Is Not My Usual Newsletter. I Hope You Read It Anyway.

I don't know what to do now.

I have heard some version of that phrase more times this year than I can count. From executives at the peak of their careers. From people who have achieved everything they set out to achieve and found themselves standing in the middle of it, wondering what comes next.

From young adults just starting, staring at a world that feels overwhelming and full of possibility in equal measure.

I know that feeling intimately.

As I navigate life and the many roles I fulfil- husband, dad, coach, strategist, colleague, friend- I have the opportunity to talk to and engage with so many interesting people wrestling with this question in one form or another.

This edition of Leadership on the Edge is a personal one. It departs from my usual format to share something that I hope will be valuable as you navigate your own journey, or as you help someone close to you navigate theirs.

The Hourglass

It is helpful to think of life and meaning like an hourglass, shaped around a journey from things being all about me to things greater than myself. The pinch point in the middle centres around getting clear about why I exist.

I am neither an existentialist, atheist, nor religious, though I do believe that satisfaction comes from pursuing something meaningful and impactful. The definition of meaningful and impactful will shift as you move through life.

Here is the model:

20s — hot mess

30s — focused on what you are: accountant, lawyer, salesperson

40s — focused on who you are: a leader, a parent, a spouse

50s — focused on why you are: what is the essence of me

60s — focused on who have I impacted

70s — focused on what am I leaving

80s — back to a hot mess?

What is interesting is the shape of that journey. The early decades are intensely self-focused. The later decades turn outward. And right in the middle, at the pinch point of the hourglass, sits the hardest question of all.

Why?

I have the great fortune of interacting with people in a meaningful way who are either in or approaching each one of these stages. Let me share what I have observed and experienced at each one.

The Hot Mess (20s)

Hot mess is meant to be funny, not a clinical diagnosis. And I distinctly remember being one in my 20s.

Completely self-centred, focused on the near term, and entirely convinced of my own invincibility.

I was fortunate to have parents who provided opportunity and enough rope to experiment, but who also intervened at just the right moment.

One intervention in particular set the trajectory of everything that followed. I was selling pots and pans door to door and making the most money I had ever made. Living at home with no expenses, it did not take much to feel rich. When I was offered a career move with the company, I was ready to abandon university without a second thought.

My Mom sat me down and asked me to fast-forward ten years. She asked what I saw.

I stayed in university.

That single question from someone who loved me enough to ask it changed everything. I have never forgotten it.

What Am I? (30s)

My 30s were a battle for career identity. What is the best application of my natural skills?

I started in a technical role: dark, air-conditioned rooms, lots of blinking lights, very few people. That environment didn't match my skills, and I struggled. Until I found work that emphasized human interaction. Then things started to click.

The 30s are about finding where your natural abilities meet the world's demand for them. Once you feel solid ground under your feet, you can start to ask a deeper question.

Who am I?

Who Am I? (40s)

The nuanced difference between what and who is this: what is extrinsically assigned and valued, and who is an intrinsic decision.

In my 40s, it became important to me to be a trusted and valued partner to Shan, a role model for my kids, and a reliable leader for the people who worked with me. Later in that decade, I became a community sports coach, sharing what I loved about sport with young people.

Any of those qualities of who could be attached to almost any what. But without a what I felt satisfied by, I could not get to who. The foundation had to be solid before I built the next floor.

Why Am I? (50s)

Why slapped me in the face pretty hard.

It was the dream scenario. Chief Revenue Officer of a California-based software company. Huge equity package, great pay, and sixty months to exit. I was pursued, sold the story, and bought it hook, line, and sinker. There was a twitch at the back of my mind. I ignored it.

Seven months later, I was fired the same week I turned 50.

Boom.

I had spent years chasing titles, money, and illusions of responsibility. Despite some success, I was never entirely satisfied. That moment put a very fine point on it.

It was also the best thing that has ever happened to me because it forced me to get clear about why.

Though I would not change much about my path, it has given me experience and wisdom; it would have been valuable to have been more patient at each stage. I realize now that my early impatience probably left a lot of value on the table. In my hurry to get somewhere, I likely missed detours that could have extracted value for myself and everyone around me.

What I have realized is that what gives me energy is leveraging my creativity to unlock the performance of the people, teams, and businesses in my sphere of influence.

That is so energizing to type. I am not finished with the work, but I am so much clearer than I was just a few years ago when I started this journey.

Who Have I Impacted? (60s)

I can feel the tractor beam of the next existential question beginning to pull.

The executives I work with who are entering this stage are philosophizing about similar things.

"I have been there and done that. A little bit more is not energizing. What energizes me now is impacting the people around me who are in the early stages."

The energy shift is not about what they can achieve as individuals. It is about the abundance that the system they have created can provide, whether that is a company, a team, a family unit, or a community. The focus has moved from me to things greater than me.

What Am I Leaving? (70s)

Inevitably, legacy emerges as a theme.

This is the stage I have the least direct experience of. Whether it arrives through retirement or through staring down your own mortality, eventually chapters need to close. The hope, as my Dad has always said, is that you leave it better than you found it.

There is a need to be remembered and valued across the what, who, and why roles you developed through your 30s, 40s, and 50s. All of that work was not in vain. It becomes the thing you leave behind.

Hot Mess Again (80s)

This is still meant to be funny.

My parents are either in or approaching this stage, and they joke that life now revolves around medical appointments.

But watching them, I see something else too.

A lightness. A freedom from the pressure of having to become something. They already are what they are going to be. They are leaning into their interests and investing in relationships with the family. There is a quiet peace in that I find genuinely inspiring.

Maybe the second hot mess is not so different from the first. Less invincibility, more acceptance. Both are a kind of freedom.

What to Do With This

If you have made it this far, thank you. As with most of my work, I like to make it practical. Here is what I would suggest, regardless of the decade.

Do an energy audit.

If you are not clear about what gives you energy or what you naturally excel at, that is the work. Go deeper than "I am good at sales." You need to understand what tools you use to be good at it and why those tools feel natural rather than effortful.

For me, I did not realize until recently that creativity is not optional; it is a requirement. I am not an artist, but I love building a good 2x2 matrix or finding a new way to explain a complex concept. That is my creative outlet, and it is what fuels me.

Some great assessments are CliftonStrengths, PrinciplesYou or DISC. There is also a great exercise from a colleague to help uncover your SuperPower that was very impactful. If you want more information on any of these, you know how to reach me.

Get curious, not frustrated.

Jim Collins has a great new book recommended to me by my Dad, What to Make of a Life: Cliffs, Fog, Fire and the Self-Knowledge Imperative. I have just started it, and in classic Jim Collins style, he has created an empirical model for a very ethereal concept.

The idea that there are cliffs and fog in every career and life, and that there are likely multiple acts for everyone, is one worth sitting with. Knowing what you are encoded for helps you navigate the fog rather than panic in it.

Be patient and experiment.

Shan will tell you that patience is my greatest strength, NOT.

Impatience, which often leads to anxiety, triggers the same hormonal cascade as physical danger: adrenaline, cortisol, a narrowing of focus as the brain's emotional centre takes over. Curiosity, creativity, and expansive thinking fade in favour of immediate resolution.

Unless you are face to face with a bear, nothing good comes from that state.

The universe sends messages constantly. We have to be in the right state to receive them. And once we receive them, we need the confidence to act on them, even imperfectly.

Writing this is one of those experiments. Creativity gives me energy. Putting ideas into the world without fear of judgement is how I honour that. This newsletter is part of my why.

Maybe it is part of yours too.

The week I was fired, I made one decision. I let go of the lifelong ambition of a CEO title, a big company, a big compensation package. I chose to find more satisfying ways to add value to the world instead.

It has been the best career decision I have ever made.

If you are standing in the middle of your own "I don't know what to do now" moment, I want you to know something.

That feeling is not the end of something. It is the pinch point of the hourglass. And everything that comes after it is shaped by what you discover there.