My Whole Team QUIT! And How To Let Go

I’ve been thinking a lot about the choice to let go of something. Hope, people I care about, how I want things to be…


I recently took Facebook off of my phone and Ipad. I rarely go on to check it, just to post and share.

This didn’t feel that hard to let go. I notice an urge to go back and check it sometimes, but generally I just don’t, it’s that simple. If I can survive the urge I stay with letting go.


Recently my amazing assistant told me she wasn’t happy. At first, I tried to figure out a way to get her to stay but I don’t want someone to work for me if they aren’t happy. So we agreed to give it the weekend.

Over the weekend I stayed up SUPER LATE working really hard out of fear and panic. But I eventually saw what I was doing. I relaxed. I accepted. I let go.

So on Monday when my other assistant said she was quitting too it was fine. I felt some fear and I accepted it. I ended up talking to the last remaining member of my team on Wednesday of that week and we got clear it was time for him to move on as well.

I let them go. I was scared. I was sad. But it just felt like what wanted to happen. I relaxed and let go.


There are a few things in my life I continuously struggle to let go.

The need to try really hard.
Remembering my ex.
Dreaming about my future partner.

All of these feel impossible to let go of. Especially in the moment.

Pushing really hard is easy for me. Life has often felt like a bare knuckle boxing match and I just need to punch my way through.

Over and over I see myself doing this and I let go, but it comes back again and again.
I’ve sort of given up on the idea that this will ever go away completely.

Every time I feel resistance, I feel sadness. Part of me wants to reminisce, part of me wants to let go, part of me wants to feel grief.

Slowly I let go but there’s often pain. Even in the clarity of the path ahead.

Finally I often dream or fantasize about who I might be with next.
Having children.
Making love.
Laughing together.
The simple feeling of peace waking up next to someone.

Again and again, I try to let these go.

These are especially difficult because the fantasies often feel really good.
Sometimes they’re painful because it makes me feel even more lonely now.

But slowly I let them go.


Moment to moment these things seem like they never move at all.
At times I feel overwhelmed and hopeless.

But when I look back I see them slowly shift and melt.

I work less hard than I used to.
I go long stretches without thinking about my ex.
I forget about the fantasies and am just here in my life.

In these moments patience is the hardest thing for me to muster
I want to let go faster.
Which generally has me hold on harder.

But slowly, gently. I am learning to let go.


Stop Being A Simple Leader

In some ways, leadership is incredibly simple. Leadership is about guiding the future by using the tools of your past.

You decide what matters from a place deeper than your ego. Figure out how to make an impact on it. Use your wits, experience, and relationships to make that impact in a sensible and sustainable way. And then continue to develop yourself so you can lead more people and more projects with more skill and less effort.

And yet the true nuance of leadership is unsimple because it rests on who you’re being as a leader. It’s not some performance of the seven habits of highly effective people or the execution of a perfect morning routine and optimized schedule.

We all admire people with this kind of discipline, but the true leadership qualities we crave are so much deeper than that.


To be a leader is to inject leadership into your marrow. To stand for your leadership in the midst of your own terrible failure. To allow your heart to be shattered while holding to your belief in the possibility of people.

It goes beyond managing KPI’s (Key Performance Indicators) and quarterly goals. It’s about managing your own heart, the way you breathe in times of crisis, and how big you can expand your awareness.

It’s the reason so many great leaders were also highly spiritual. Because leadership demands more than just the tools and techniques.

It’s what makes leadership unsimple, but also powerful.


The Art of Leadership

Many people think about leadership as a process or a method.

If I input X then I can get my team to give me Y. And that might be true if the people you were leading were simply robots; easy to program and decode.

But the nature of leadership is that it’s messy humans leading messy humans. Humans who have deep-seated fears, hang-ups from the past, and dreams about the future.

So many leaders try their best to squeeze their teams into a box they want them to be in. They talk about leadership like a big chess game or a mass propaganda campaign. For a long time, that kind of leadership was effective, but the smarter and more powerful human beings have become, the less effective that style of leadership has become.

This is why I often talk to my clients about the art of leadership.

When you see leadership as an art you can begin to see the constraints of your team like the colors in your palette.

You can begin to see the uncertainty in the market place as the distortion your eyes create when it looks out on a landscape.

You can begin to see each challenge as an invitation to create art, inspiration, and possibility.

But this can only happen if you let go of the machine of leadership and the x=y mentality.

If you paint by numbers 1 may equal red, but if you paint as an artist 1 can be any color you want, so long as it invokes purpose, beauty, and serves the people you long to change.

Leadership as an art can be intimidating because what’s right gives way to what works and who’s in charge gives way to who’s committed.

But people are done being treated like machines. Especially the kind of smart, talented, caring individuals who you want to lead.

This is why when you take on the task of leading with art not only does your life get easier and more interesting, the people around you also become better at being who they already are.


How To Lead When Things Fail?

I’ve worked with executives in a range of fields, from the entertainment industry to advertising. I’ve seen a lot of incredible successes, but I’ve also seen my fair share of spectacular failures. And what I’ve noticed is that failure brings out the best and worst in leaders. It’s when the blaming and complaining starts, but it’s also when the best leaders do their best work.

While it would be easy to give you a list of 5 things great leaders do when they fail, the biggest difference actually comes down to one thing.

They own it.

They admit that they failed; they look failure in the eye; they come to terms with it; and they feel all the anger, frustration, sadness, hopelessness, and grief that comes along with it.

And they don’t just do this when things don’t work out. They actually start from here.

Before they begin the project and take the risk, they accept that failure is part of leading. They know the plans won’t always pan out and they come to terms with that.

What’s even more amazing is that they do this without losing any of their enthusiasm. They aren’t like some founders that are all hype and talk, whose egos are so fragile any mention of defeat will cause them to collapse. Rather, they look at failure right in the eye and smile.

It’s not that they know they’ll be successful—they know success is always a mix of skill and
luck—they simply choose to be responsible for leading if that happens. They choose to lead if the storm comes. They choose to lead no matter what.

It’s so simple and yet what so many leaders miss. Leadership isn’t really about leading when things go well. It’s about leading no matter how things go.