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Sanity Notes #021- Navigating loss from the right side of the road

Every challenge, every loss, can be viewed from one side of the road or another. Some honest thoughts from my own recent loss.

Matt Munson
Matt Munson
7 min read
Sanity Notes #021- Navigating loss from the right side of the road
Navigating loss from the right side of the road
Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.

Two weeks ago today, we lost my father-in-law. He lived on his sailboat in the marina a few blocks from our home. My wife had not heard from him in a few days and asked if I would stop by to check on him. I found him in his bed on his longer with us.

The feeling of loss has been massive for our family. He was our patriarch. He was a regular attendee at family dinners. He cooked the roast at Christmas. He played lovingly and patiently with our kids.

Whenever he came for dinner, he brought our kids' favorite flavored sparking water, which our two-year-old lovingly dubbed "Pappy Bubble Agua" (Pappy was the kids' name for him).

In the days after the loss, I found myself reeling.

I lost my stepfather seven years ago.

I lost my father six years ago.

Pappy's death marks my third loss of a father figure in the last decade.

A view from the right side of the road

The night before I discovered my father-in-law had passed, I attended a Hoffman graduate evening. (I have written separately about my attendance last year at the Hoffman Institute, a venerated personal development course with centers around the world.)

During that evening, the ten of us in attendance revisited one of the Hoffman tools known as "Left side vs. Right side of the road." The idea is that the left side of the road represents the way we show up when we are:

  • Caught up in our childhood patterns
  • Stuck in self-pity, fear, or anger
  • Responding to our circumstances on auto-pilot and without thoughtful choice

The right side of the road represents:

  • Viewing our life or situation from our grounded, wise place
  • Owning our culpability in creating our experiences of suffering
  • Embracing ways negative seasons or experiences may be serving us
  • Exploring how we might come with love, gratitude, and choice irrespective of our circumstances

There's more to it, but those are the broad strokes.

This next part is going to sound a little crazy.

That night at the Hoffman gathering, we were asked to do some journaling on how we might view a specific life challenge from the left side of the road vs. the right side of the road.

The prompt we were given was:

Imagine one of your family members has died. How might you experience that event from the right side of the road vs. the left side of road?

As I heard the prompt, I thought, "Maybe I'll use a different situation instead because no one in my family has died recently, nor is anyone sick." I thought about using a work prompt or a challenge with a friend. I ended up deciding to write about the prompt, as suggested, about the loss of a family member.

Twelve hours later, I found my father-in-law deceased on his boat.

A right side of the road exploration of loss

In my writing, I often share lessons I have learned in years past. Or I write about insights from a recent coaching session.

Today I want to do something different.

I want to share openly with you how I am trying my best in the midst of this painful loss to explore the whole situation from the right side of the road.

Perhaps you will join on this journey by selecting a current loss or challenge in your own life to explore.

Let me assure you I am spending plenty of time on the left side of the road.

There have been lots of moments where the darkness, the loss, the self-pity, the worry, and the pain all feel overwhelming.

I have a bunch of stories my dark side tells me. This loss fits nicely in the narratives of those stories. These stories, which I have carried for most of my life, include:

  • Everything good in my life will be taken away from me
  • Do not get too close to people because they will abandon you
  • No matter what you do, you are ultimately on your own
  • Do not relax in life; there is always pain just around the corner

In the days following Pappy's death, it has been tempting for me to sink into these familiar stories and let myself wallow there. And for stretches of the last two weeks, I have dong just that:

Wallow. Question. Flounder.

While I am doing my best to give myself grace when I realize I am sitting squarely on the left side of the road, I am determined not to take up residence there.

Now that I know about this practice, I aim to spend as much time as possible on the right side of the road.

The point is not to be 100% of the time on the right side of the road. I am no Buddha.

The aim is to have awareness that the right side of the road is there...available. We are not trapped on the left side: in our patterns, in our suffering, in our self-pity.

When we find ourselves dwelling on the left side, we can make a decision to shift.

Accepting myself with grace right where I am

In some of the moments these past two weeks, I have noted that I am on the left side of the road and elected to stay there. That is OK.

I have also repeatedly offered myself grace for being there.

These are the first two steps in finding the freedom that comes with moving to the right side of the road:

  1. Noting where I am
  2. Offering myself grace and acceptance right where I am

Looking at myself through the eyes of a friend, I can offer a grace that says:

Of course, you are on the left side! How could you not be? You are navigating a tremendous loss. You are doing your best to be a partner to a woman you love who just lost her father. To be a father to two children who just lost their grandfather. To navigate administrative details, host house guests, and manage the day to day tasks of adults life. It is ok you are on the left side.

But then a second message comes:

You don't have to stay there!

With that message, I can move to the right side of the road and begin to explore a new way of looking at this heartbreaking loss.

I can resource myself, care for myself, and invite my strength and my wise adult perspective. I can embrace and invite the grief without letting it engulf me. Even as the waves splash around me, I have a sandbar to stand on.  

In my coaching work, I often invite clients to explore new ways of looking at their challenges. Shifting our perspective can ease our pain, bring our creativity online, help us be happier humans, and empower us to be better leaders.

These weeks, I have been doing my best to provide myself the same gentle invitation I bring clients.

A big part of me is fucking angry that the universe has allowed me to lose another father figure. Allowed my wife to lose her dad and my kids to lose their only remaining grandfather.

But from the right side of the road, from a place of gratitude and wisdom, I can see:

  • I am deeply thankful for the years we had with Pappy. When I met him ten years ago, he was navigating health challenges that left him thinking he may only have a couple more years. He lived on to dance with his daughter at our wedding. He got to meet his granddaughter: to have her tiny arms wrap him in hugs and hear her musical laugh as he chased her around the backyard.
  • I am indebted to this man who raised the woman who is the great love of my life.
  • Our family has enjoyed a thousand moments together in these last ten years. I am grateful for each.
  • He modeled for our family a life of openness to people, small joys, and laughter. In his death, he reminds us these are the things that make a life worth living.

From the right side, I see I am well-resourced for navigating this loss. And that my wife and our kids are too. I can also accept loss of this kind as a part of life. It is OK. It is painful, but it is OK. Death, as part of life, is OK.

Why leaders need to talk about loss

Why am I writing so openly about my personal loss in my blog about leadership?

First, because I want to. Writing, for me, is a way of exploring, metabolizing, and learning from whatever I am navigating in life. I don't mind sharing that, and I don't mind modeling it for others who might find it helpful.

Second, because we are all navigating losses and challenges every day. Some are huge; some are small. Life is full of moments when we do not have everything we want or where something we love is under threat.

In my time as a CEO, I found myself navigating tremendous losses as a part of the journey, including:

  • The loss of loved ones
  • The loss of prized employees
  • The loss of two co-founders
  • The loss of numerous visions for the company as we iterated dramatically on our intended future
  • The loss of my own passion for the company's mission

Losses are part of life. Losses are part of leading. Losses are part of the journey.

The right side of the road metaphor is a powerful tool for helping us, as humans and leaders, reframe our losses and challenges.

We can move from victims to active creators of our experiences.

We can move from suffering to learning.

We can ground ourselves as we seek to care for and lead others.

Thank you for listening today! I hope my exploration of my current season of loss has shed some light on how you might explore loss in your own journey.

I appreciate that you are here. If you were forwarded this email and it resonates, you can subscribe here.

If you would like to learn more about how you might find your footing in whatever challenges are present in your own journey of leadership, please reach out. I would love to meet you.

With love from LA,


Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.
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