Matt in the Phillipines

The Guiding Hand of Life and Mentorship

This is a photo of me from early 2018, when I was backpacking the Philippines. I met many wonderful people, and learned a lot about who I was and who I didn’t want to be while on this trip. This woman helped me not become stranded in the middle of nowhere as I rode a bus through one of the islands.

When I look back at this photo, I remember how much I thought I knew at the time. And the reality of how little I did. Since the taking of this photo, it puts a smile on my face to consider how life and various mentors have held the mirror up for me to see what was once unseen. Privilege. Fear. Judgement. And the list goes on.

When you look back on photos of yourself, what comes to mind for you?

This reflection reminds me of the importance and natural occurrence of mentorship. It’s a reminder that through various points of inflection and process, evolution occurs.

As we walk through life, it’s as if life has one hand on our shoulder, and another pointing the way forward. Even during the times where it feels like life smacked us with a cinder block, there’s a message available.

I’ve experienced many of those moments.

Those moments can be the most telling about an opportunity to see and live anew.

The spousal separation

The pandemic

The bankrupted business

The health scare

The death or near death experience

Each offering moments to consider life and subsequent choices with fresh eyes. An inflection point that points towards new possibilities. Even if in the midst of it, everything but possibility is being felt.

When I look over my life, there have been countless accumulated moments comprising who I am today. Many of the experiences being catalysts for unlearning who I am not.

My life beyond late teens has offered countless moments of mentorship. When I listened to it. Challenging moments pushing me to the brink of total destruction, that I could not ignore.

Each offering a chance to consider the life I was choosing to unfold, given what was within my influence. Each moment offering the opportunity to continue following the same path, or not.

The choice was always mine to see and decide what comes next.

Some form of choice always exists.

Even when I told myself that is not true.

A choice was always available.

Even though I had choices, many times I would continue the same destructive path. Paths that have hurt myself and others along the way. It seems that at certain points, I was still not ready to see, feel, and acknowledge my own blindness.

I was not ready to let go of the identity that I clung to. This identity is often being fearfully attached to relationships with money, titles, and romance.

Aside from those moments there are many times where I did heed the message life was mirroring for me. Each time a new challenge or existing one became seemingly too much..

Life offered a moment of intervention followed by a falling apart of lies once believed.

As I began to unravel the story I had convinced myself of, new possibilities began to emerge.

Each time I stepped into the opportunity, more strength, courage, and compassion emerged.

It’s been only in the past few years that I began to see these moments as life being my mentor, guiding me forward.

I have seen and experienced things that I would not wish on anyone. And yet, for me to experience life as I do now, they were necessary catalysts.

These are events in life that offer each of us an opportunity to look in the mirror, and see what we have been avoiding. An opportunity to see what we may have before tried to distract ourselves from.

Currently, I am creating a custom snow-globe for a client that I have enjoyed working with for the past year. The message is simple. Like the snow being still, when the chaos falls away in our minds, our intelligence emerges.

The gift here is in seeing that chaos often proceeds order.

And in it’s in the small moments of stillness that our lives can alter course for ever. This can occur from those catalytic moments. Or, this can come from a direct source of mentorship.

A manager. A partner. A coach. An advisor. A close friend. Anyone that cares more about you than your constant approval.

These are the people that have had their actual hand on my shoulder, and the other hand pointing the way forward.

Back in 2012, my first manager when I was supporting Google comes to mind as one example. It was his trust in me that helped me get started down the path I’m still on to this day.

I had no managerial experience when he went to bat for me. He saw potential and commitment. And, he was even patient with me as I needed to do some growing up in my personal life.

That’s one big thing he did for me. That wasn’t the only thing.

I’ll never forget one of the first things he said to me when I was in my new role. I felt frustrated as I was recruiting my new team to launch a market.

His words hit me like a gust of wind, knocking me off balance.

“If you expect everyone to be like you, you won’t have a team worth anything.”

In that moment, I must have had my head cocked sideways like a dog who sees their owner making strange noises. The message took time to sink in. Though, it became clear over time.

Hire and surround yourself with incredible people that excel at many things I do not. Hire people that think differently than I do, and are willing to challenge me.

That same year, one of my new team members validated this lesson. After one of my first team meetings, he approached me and shared.

“Matt, it’s difficult to listen to you and believe you care when you are checking your emails while talking.”

Ouch. I had a lot to learn.

That man was on our team for four years. I’m grateful he was willing to step up and say it. It was a big lesson for me.

In 2015, a VP I reported to asked me about my childhood. We had wrapped up a quarterly business review out in San Francisco only moments ago. Again, I must have had my head sideways like that dog previously mentioned.

When I shared a bit with him, he offered that while I had a ton of talent, he could see the cracks in my projected confidence.

This one struck down to the core of me. It hurt. I felt defensive (a good sign to keep my mouth shut and sort it out within me first). This was a simple statement that served as a powerful intervention in my life. The mirror was being held up for me again.

At first, I didn’t want to take a hard look at what he said.

I initially rationalized his ‘error’ by pointing to our high performing team. Then I pointed towards how we were outperforming other teams. Then I pointed towards the rate of growth that had occurred in revenue.

Each rationalization was bogus. They were factual. And changed nothing about the truth of what he saw in me. My foundations were still fragile as a leader.

That was a true intervention moment for me, once I decided to hold the mirror up and consider what he was saying.

While there are many more moments, here’s what stands true.

Whether the moments of intervention and change occur as a natural result of being alive. Or, they come from an appointed person. Or someone you hire to guide you.

Each of the moments that will happen, offers us an opportunity to look in the mirror. The question becomes, will we look deeply into it.

It’s when we look in the mirror that we, and we alone, become conscious of what was once unseen. And it’s in seeing the once unseen, and owning it, that the opportunity for change occurs.

At this point, life has offered me many moments to heal and let go of my fragility. To grow more into who I am.

To allow false personas to come to my attention, see the holes in them, and then start the process of letting them go.

Many of the moments came from un-appointed mentors. Many more have come from those that I have sought out to be my mentors, because of a path they have walked before me.

The key here, for me, is to look and listen for the next opportunity to see what was previously unknown to me.

This mentorship has one hand on my shoulder, and another pointing the way forward. Even if the pointed hand is pointing me right back at myself to find the next answer.

As we bring this conversation to a close..

What’s emerging for you at this moment?

Where, in your life, are you seeing opportunities to hold the mirror up?

Is the natural flow of life holding this up for you, or an appointed person?

Will you lean into what is being offered?

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