Asking for help is a superpower

The weight many leaders carry

My mother recently sent me an article about an elk who lived for two years with a tire around his neck. He lived in the wild, going about all the things he needed to do to survive, held back by a heavy black tire snug around his neck.

We might imagine there arrived a day where that tire felt a part of him, where foraging or resting without the tire would have felt more foreign than life with the tire.

As a coach, I meet leaders every week who are leading, working, and living with a heavy tire around their own neck.

In the earliest years of my own time as a founder and CEO, the weight around my own neck was substantial. Like all startups do, our company went through some wild ups and downs. There were false starts, mistakes, money wasted, wrong hires, market shifts, and more. Looking at those years with the clarity of hindsight, I can see the most painful part was not the actual setbacks but the story I told myself about those setbacks.

If we made a wrong hire, the story would come raging into my mind that I was messing up, that I would never have what it takes, that I was leading my team astray, that I was setting all of us up for failure.

Rather than moving through the failure, bringing the team together to learn from it collectively, and turning my attention to the next opportunity or challenge, I might ruminate for days at a time.

The self-flagellation felt like a necessary penance for my mistakes. I owed it to the team, to our investors, or to my family to ensure that any missteps were coupled with tremendous suffering. How else could I ensure I was sorry and would not let it happen again?

In my life, this kind of self-incrimination was modeled for me by the man I looked up to most: my dad.

My dad was an entrepreneur for most of my childhood and early adulthood. I perceived him as wildly successful. We lived in nice homes in our small, Michigan town. We took frequent vacations, and my fall purchases of back-to-school outfits from J. Crew were the envy of my friends.

My dad seemed by all accounts quite the success. But behind the scenes, unknown even to me at the time, the truth was not quite so bright.

My dad had his own entrepreneurial journey going on, and it was as marked by setbacks and pain it was with success.

My dad was from a generation of leaders who were taught suffering was to happen in silence. Particularly for men, the model of masculinity was the American cowboy, Rambo, and Reagan. When my dad’s company faced substantial financial setbacks, he suffered them alone.

To ease his loneliness and pain, my dad turned to alcohol and later prescription painkillers. The abuse escalated until the brilliant, creative, determined leader he had once been was no more. My dad self-medicated his way through obstacles until the self-medication became the obstacle. Eventually, his addiction took his life.

With the right support, my dad may have saved not only his business but far more importantly his life. Instead, he lost it all.

It does not have to be this way

Turning back to my own time as CEO, I can see that my self-flagellation was a subconscious attempt to punish myself for the ways I felt I was letting others down. The irony is the hours or days I spent wrapped in those stories kept me from being present, and helpful, to the people I most wanted to do right by.

The stories were also deeply isolating.

The shame and self-doubt I felt kept me from letting others in. Other founders, good friends, my co-founders, even my romantic partner. When I was wrapped in my negative thoughts, I pushed everyone away. In doing so, I separated myself from the very support I needed most.

Every leader reaches a point in their journey where the realization comes: ‘What got me here is not going to get me where I need to go.’

For me, that point was mid-way through my time as co-founder and CEO of my last business. During a short, but deeply painful time in my life, I went through multiple severe losses: of a child, of a marriage, of a father, and of a step-father. In the midst of such personal loss, our business was struggling.

That season of my life began a deep exploration of this question: Might there be another way?

Might there be another way of living?

Might there be another way of leading?

The way of leading that is waiting for us all

With the support of my coach, therapist, and a few close friends whom I began choosing to let into what was really going on for me, I began a multi-year exploration of what this new way might look like for me.

The result was a complete shift in how I understood my life, my relationships, and my work.

Since moving from CEO to coach, I have been privileged to walk alongside dozens of leaders as they step into and through their own transformation.

What I found in my own journey, and what I have since seen confirmed in the journeys of these other leaders, is that a new way is not only possible but necessary. And it is right here waiting for each of us.

The world is hungry for a model of leadership that invites both the humanity of the leaders and the humanity of their teams into the organization.

At Sanity Labs, we hold that the role of the CEO is as follows:

1. To hold the vision
2. To recruit and retain the team necessary for executing that vision
3. To resource that team with capital, clarity, and care

These accountabilities have at their heart a theme of clear-eyed seeing, of groundedness, and of connection.

When we stew in our own inadequacy out of a false belief that there exists out there, somewhere, a leader who could step in and get this job right, we short-circuit connection, clarity, and groundedness.

The old way just does not work anymore

The old way, the way of being our own harshest critic and most grueling task-master may have worked in the past. It may have guaranteed straight A’s in school. But this is not school. This is leadership. This is organization building. This is the bringing together, inspiring, and caring for a collection of human beings: a group gathered together to achieve a shared mission.

The opportunity at hand is to view leadership, and even entrepreneurship itself, through a new lens: as a vehicle for connection instead of isolation, and as a craft that supports, rather than endangers, our humanity and that of our teams.

I speak with leaders every week who feel utterly alone in the deepest parts of their experience. In our conversations, these hidden parts come pouring forth: the fears, the self-doubt, the anxiety, the depression, and burnout, the feeling of self-imprisonment, the loneliness. The feeling they may be leading not only themselves astray but also their co-founders, their teams, their investors, or their customers. The feeling it all rests on their shoulders, and that the weight has become too much to bear alone.

You are not alone

If these experiences resonate for you, fret not. You do not have to walk alone.

You do not have to carry the full weight of your organizations’ success or failure on your own shoulders.

You do not have to hide.

It is ok to ask for and receive support.

It is ok to desire and seek out real partnership. From your co-founders, from your board, from your team, from your partners and customers, and from your friends and family.

More than possible, it just might be necessary. An organization led by a leader stuck in her own loneliness and self-doubts will always struggle to find its real potential. When we fail to approach our own work with honesty and openness, we model such hiding behavior for our teams. The result is an entire organization lacking in the kind of support and collaboration necessary to foster real creativity and innovation.

An invitation

If you are experiencing in your own journey a sense that what got you here will not get you where you need to go, welcome!

I waited the majority of my entrepreneurial career to realize the new way. But you need not wait. The new way is here and available here to you now.

There is no need to change everything today. That is not how we tend to change as humans or as leaders.

As you experiment, what may unfurl is your own vision of leadership. Not any right way prescribed, or practiced, by some mythical leader someplace else. But your way. The way you would like to, and perhaps even must lead: at this time, in this organization, in this market.

No one has done before precisely that which you are endeavoring to do today. Every human endeavor, including your unique company or organization, takes place in its own unique conditions led by its own unique leader.

Therefore let’s explore and find your way.

Welcome, my friend, to your own journey of leadership. Go gently forward. I am so happy you are here.

-Matt