Leadership: The Secret Existential Crisis Entrepreneurs Never Talk About

At some point in your journey as an entrepreneur, if you’re lucky, you’re going to face an existential crisis. It’s something few of us talk about but many of us have faced. But if you know it’s coming and you’re prepared, you can get through it with as little pain as possible.

You see . . .

When you start a business or side hustle your work is about two things
Doing great work and/or providing a valuable service or product
Finding customers and helping them understand the value of what you have to offer

These two things are not small, easy, or simple to figure out, but they are at least straightforward. Your work needs to be good and you need customers who see that…

But as you grow and get more customers, offer more complex services, and start to hire people to support you or do some of the work for you, your role begins to change.

You go from being a person who does great work to being a person who creates great work.

And this transition is challenging. Doing great work is simple, you sit down and do your best. Creating great work is more complicated, you are planning, leading, and assuring that great work is getting done.

The skills are different, the former is about keeping track and executing. The latter is about defining and communicating what is good, and then making sure “good” is happening.

I remember when I worked as a house manager at a music venue and the boss asked me to come downstairs. “What’s wrong with this picture?” I looked and everything looked fine to me. “It’s too bright in here,” she clapped back in my silence. “Oh?”

“How dark should it be?” She groaned and lowered the lights. “I can’t tell you everything, you’re just going to have to figure it out.”

I felt discouraged. What she was saying was somewhat helpful. Most places lower the lights at a certain time of night. It increases the vibe, encourages people to buy drinks, and makes it feel less harsh when you come in from the night. But it’s not something I had ever thought about before.

It was good she wanted to teach me, but this was the WORST way to do it. Instead of helping me learn and giving me some guidelines, she just got mad at me. What was OBVIOUS to her was NOT obvious to me.

This is essentially a failure in leadership and it’s something I see founders, entrepreneurs, and owners do ALL the time with new team members.

It all starts with What Can’t They Just!

Often when I listen to founders and entrepreneurs complain about their team members at some point they’ll say Why Can’t They Just . . .
Send me the updates I need
Answer this email
Make a decision on their own

The underlying assumption is that other people SHOULD think like you think. They should be capable, they should be leaders, and they should know what you know and act how you act.

But if your team simply duplicates your skill then
You need more skills
You’re not hiring the right people

The best people bring new ideas and talents to the table. The best people approach problems differently. The best people create things but not the way you will.

The hard thing for most leaders is that they don’t understand how to get good work out of people who are different from them.

So they expect what they would produce and then get upset when they don’t get it.

Next Level Leadership

This isn’t really leadership it’s cloning.
So if you want to be a better leader you’re going to have to let go of this strategy.

The question you should ask yourself is how do I get the best work out of the people I have?
NOT how do I get them to think like me?

The reason why this is so hard for most leaders is that it requires a shift in identity.

You start with the identity of I’M GREAT AT DOING THIS

And that shift in identity is hard.

It’s why so many founders end up writing code, getting on sales calls, or micro-managing people on their team.

They don’t trust what other people do and they are unwilling to let anyone else be better than they are.

So as you grow your business get ready for this.


It’s a key initiation as a leader. And a threshold you need to cross if you want to truly become a great leader.


Learning To Let Go

After two years living in the monastery I was restless, but I didn’t want to leave.

I loved living at the monastery. It changed me in so many ways. It also began to feel like a shirt shrunk in the wash, familiar but a bit too tight.

I struggled with the decision. I talked to a lot of people. I had many sleepless nights. Eventually I realized it was time to go.

The monastery was good for me, but I was ready to leave. I felt called to work outside this place I’d loved so much.

After I left, I watched too much TV. I ate too much junk food. I slept in a little too late. I noticed how loud the world was. I noticed how much harder it was to be quiet. And while all of these things were jarring they were mostly expected.

What I didn’t expect was the grief. I felt the loss of familiar sights and sounds. I didn’t wake up to a bell. I didn’t sit in the same room with the same people. The texture of my life had changed.

While the freedom was wonderful, the grief was palpable. It hung over me like a pregnant rain cloud, until eventually I couldn’t ignore it anymore. So I turned and looked at it, and what I found surprised me.

At the center of that grief was something really powerful: love.

At every other time in my life, the things I had left were things I didn’t want anymore. Things I despised or resented in some way. But the monastery was different.

I didn’t hate it. I loved it deeply. I loved it, yet it was the right time for me leave.

In your life you will leave many things behind: old business ideas, old websites, old partners, and old insights. Some of these things won’t serve you anymore, but you still love them, even when it’s time to let them go.

When this happens, you have to grieve. It may seem silly to grieve over a website or a partnership, but these things are a loss. When you create with passion, you get attached. You put yourself into that code, those words, and that part of your business and your life.

By letting it go you are losing a part of who you are, so you have to grieve. You have to feel the loss. You have to give yourself permission to feel it. Otherwise you end up being stuck, not ready to move onto the next thing because you’ve never let go of the past.

We see this all the time in big companies. The auto industry didn’t want to let go of the old way of making cars. Yahoo didn’t want to let go of the old way of doing searches. Cab companies don’t want to let go of the old way of giving rides.

It’s natural to not want to let go. To hold onto to the good old days where things felt safe and secure. But it’s a mistake.

Instead you have to grieve; you have to feel the loss and learn to let go.

How do you do this?

While I’m not an expert on professional grief here are the 4 ways I deal with grief in my business and my life.

1. Notice. Just notice when you’re feeling grief. Notice when you’re wishing it could be like it was. Notice when your thinking in the way you used to with the same parameters and rules. Notice if you go back to living in that old world.

When you notice what’s happening you can feel it, you can deal with it, you can compensate for it.

2. Turn toward it. Sometimes we avoid grief by wallowing; other times we run from it. We try to push past the grief to get to the new thing too fast. We grab at any straw we can find and don’t give ourselves enough time for the new thing to arise. To let the new way of being come to us.

Watch when happens. It means you’re not ready. It means you’re not grieving. It means you’re trying to avoid this uncomfortable feeling of letting go.

If you find yourself in that place, slow down, let yourself grieve, accept that you’re having a hard time.

These first two you can do anytime anywhere. They are practices that you carry into your day-to-day life.

3. Be grateful. At the center of grief is love. Take some time everyday to remember things about the past you were grateful for. Think how nice everyone you worked with used to be.

Appreciate and honor what came before. Love it with all your heart while also knowing that it is gone and that you can love it without trying to get it back.

4. Set intentions. Last think about the things about the past that you got a lot out of. What experiences, what kinds of relationships, what kind of work did you most enjoy. Get down to the core of each of these powerful place and if you can draw out what’s essential in each.

Then set an intention to find a way to bring these experiences back in new ways. If you used to enjoy having lunch with a partner, think of other ways you could create that connection with someone in your life. If you used to enjoy working with your hands think about a hobby or skill you could learn that would help you get that feeling back.

While we can’t live in the past, we can learn from what it gave us and bring it with us moving forward.Tweet: While we can’t live in the past, we can learn from what it gave us and bring it with us moving forward. @mindfitmove http://ctt.ec/m5UdM+

There are some things about the monastery I could never bring back. The feel of the place, the smell of the incense. These subtle things that will forever live in that time of my life.

But I can bring with me the things that really matter. The compassion I felt for others. The deep investigation of my life and in the lives of others around me. And my willingness to accept whatever comes my way.

I’ll always grieve my time at the monastery but that doesn’t mean that I can’t have a wonderful life as I live now. As I live I know I’ll have to do this again, to love and let go, over and over.

But with each life I feel so grateful, for my heart simply grows and my ability to move into a new way of being increases in capacity.


How To Let Go Of Suffering

Several thousand years ago a guy named Shakyamuni was sick of the cushy life his father had created for him. He realized that life was more than soft pillows and fine food. So one night he snuck out of his palace, abandoning his wife and child, to discover what life was really about.

For a while he sat with a group of hardcore monks. They starved themselves, ate feces, stood for hours, and engaged in all forms of self harm in order to free the mind for the body. Shakyamuni was a devoted follower. He did what they did. Ate what they ate and generally beat the crap out of himself.

He gained understanding but he didn’t find what he was looking for. So he quit. Walked away from his friends who all called him a failure and a traitor. He ate some rice, got some rest, and then wandered off to sit under a tree. He simply decided he would sit there until he found enlightenment. And so he did. One morning as the sun rose in the east, he obtained his goalless goal. Finally at peace with himself he got up and went out to teach the world what he learned.

On the most basic level the Buddha taught that in life there is suffering and that suffering is caused by our desire for things we want, aversion towards things we don’t want, and ignorance of the way things actually are.

The good news is that we don’t have to just accept it; we can change it.

I’m not a Buddhist scholar nor have I claimed to master any of what the Buddha taught, but recently a client and dear friend asked me about how we do this. He asked me to share my strategy to stop being attached to my desires, my aversion and ill will, and my ignorance.

So here is my imperfect method and approach to following the Buddha’s teaching.

How to let go of desire

People tend to think that if they satisfy their desires, then they will be happier. They think, if my kids behave a certain way, then I’ll be happy. If I don’t lose my patience, then I’ll be happy. If I can do something really new and interesting, then I’ll be happy.

But satisfying desires never makes you happy, at least not for very long. Yes, it will feel good for a little bit, but ultimately it won’t solve the problem of suffering.

The first step to letting go of your attachment to desires is to notice whenever you’re telling yourself a story about how satisfying a desire will solve your problems. This seems simple but can be quite challenging. You were raised on these stories. You are told these stories daily. “Buy this and you will feel happy” is a the core of 90% of our advertising.

This story isn’t true, but in order for you to see that, you must first notice when you’re telling this story to yourself.

Next, you have to stop believing this story. Look into your desires and see how empty they really are. Do you really think your children’s obedience will solve all of your problems? Do you really think getting that hot girl will totally change your life?

The final step is to actively seek out ways to dispel the myth of the satisfying desire. Practice letting go of the things you want when you don’t get them. Develop an appreciation for difficult circumstances. Instead of seeking your desires try instead to notice how things are right now and find satisfaction in that.

With each of these tiny actions you can demonstrate to yourself that when you see the story of desire as false, you begin to realize that you can be joyous and happy even when your desires aren’t met.

How to let go of aversions or ill will

Aversions are simple, negative desires. They are things you don’t want to have happen or things you don’t want to get.

Ill will is simply aversion personified. People kill other people, because they want to control them. They want them to behave in a certain way, because they think if only the whole world acted in the way they wanted their suffering would end.

Things happen whether you want them to or not, people almost never behave the way you want, and even when they do the results are unsatisfying.

Destroying everything and everyone you don’t like won’t change your suffering. Instead you have to learn to see your aversion and ill will for what it is.

The first step is to acknowledge when you’re feeling averse. Whenever you feel angry, irritable, frustrated, or judgemental simply acknowledge what’s going on. There’s nothing wrong with feeling averse. There’s nothing wrong with having ill will. The only problem is when you think that other people are to blame for those feelings.

Next you must accept that no amount of destruction will solve your suffering. You could never destroy enough behaviors, circumstances, laws, or ways of thinking to satisfy you.

Suffering has nothing to do with creating exactly what you want, and it has nothing to do with destroying what you don’t like. Suffering is simply caused by our attachment to this idea that the world we see should match the image in our minds. But it never does.

The final step is to actively lean into your aversions. Try to love your enemies. Try to appreciate things you don’t like. Notice your irritations without reacting. Don’t give into the story, the energy. Just notice what you want to destroy and instead let it be.

How to let go of ignorance

Ignorance is hard to let go of, because you’re often not aware that you’re holding onto it.

The first step of letting go of ignorance is to have wise friends. Friends who will talk to you and tell you when you’re being a dumbass. Friends who are trying in their own way to find a path out of these stories to something more meaningful. They may not notice your minor ignorances but at least they’ll notice your blatant ones. So find some people who are wise or at least trying to be wise. Find some people of practice and spend time with them.

Next you need to acknowledge your own ignorance whenever you see it. To stop trying to create a world in which suffering won’t happen. This is the world you were born into. Nothing in your vast knowledge can free you from it. Nothing you will learn can give you a way out. Instead you have to accept that you don’t know what’s going on. You have to ask yourself the hard questions again and again. You have to live the questions without getting attached to your answers.

Finally and most importantly you have to be willing to see “the truth”. You have to experience what it means to see your desire arise, to not act on it, not grasp it, and to watch it fade away. You have to experience what it means to see your aversions, your ill will arise, not act on it, to not grasp it, and to watch it fade away.

The ignorance the Buddha talked about is the ignorance of how things really are. You want to believe that if you get what you want and destroy what you don’t like, then you’ll be happy forever. It’s what you’ve been taught your whole life. Our whole economy is based on this idea. Our government is based on these principles.

But it’s not the truth. The truth is that satisfying desire and destroying annoyances won’t make you happy. If you want to be happy you have to let go of these things. You have to step into a space that is large enough to hold both what you want and what you don’t want. You have to let go of your attachments even to ideas of who you think you are. You have to sit and become willing to see life for yourself.

I know this isn’t the kind of truth you want. Because this kind of truth doesn’t come from a top ten tip list. It’s the kind of truth you only get to, by sitting quietly and seeing with your own eyes. What’s really there.

To truly let go of ignorance you have to see what’s real. Which you can do in small ways every day or maybe one day in a very big way if you decide that what you will do.

Final Thoughts

I struggle everyday to let go of my desire and my aversion and I fail A LOT!! I get grumpy, I get horny, I want something sweeter to eat. I want there to not be a line at the store. I want to believe that if I just change one thing everything else will get better.

So I do my imperfect practice, I make my numerous mistakes, and I just keep trying to see what is real.

Meditation is key to letting go of suffering, but starting a practice can be intimidating. If you’d like to learn how, I have a free 5 min a day meditation course you can sign up for here.


Never Forgetting and Letting Go

Never Forget

I don’t think I will ever forget waking up in the morning and hearing about what was going on in New York. I was living in DC at the time and the fear and sadness were palpable.

Some of my friends drove out of the city to be safe, while the rest of us hunkered down and dealt with all the crazy rumors that were flying about: A fire at the state department, bombs on the national mall, and so much more.

I remember walking out onto the back roof of our house and watching the smoke rising from the pentagon in the distance. It’s a day not many of us Americans will forget anytime soon. However, that doesn’t mean we need to hold on.

To Honor

I used to think that in order to honor a memory of an important day or of a lost loved one, that I had to take their memory and hold it tight to my chest. Moreover, if I owned items associated with them, I could never get rid of them. So, I would force myself to be sad to honor them.

But I started to realize that torturing myself wasn’t really honoring anyone or anything. I discovered that the only reason I was doing it was to combat the fear that I would lose some piece of that moment or that person that I cherished so much. I was afraid that if I let it go, I would forget.

But what I found was that when I let them go, the people and moments became more alive. Instead of forcing myself to remember and be sad, memories naturally arose in my mind.

Some of these memories were sad, but others were happy or funny. And best of all they were memories that I could see, appreciate, and let go without feeling like a jerk.

To Let Go

So while I think it’s good and important for us all to remember this day with compassion in our hearts. I think it’s just as important to let go. Let go of the anger, let go of the sadness, let go of the outrage, and let go of the tragedy.

Know that as long as you have faculties that you will remember, and also know that as you remember and you let go, your life and compassion becomes the gift that honors everything that was lost on this day.

Being here with love is the best memorial you could offer.


Photo Credits

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What Mindfulness, Oral Sex, Massage, and Haircuts Have In Common

What Mindfulness, Oral Sex, Massage, and Haircuts Have In Common

The other day I had the pleasure of getting a really great massage. The body worker was skillful and I was in need of a little self-care. But while the physical sensations of the massage were great, I realized there was something even more enjoyable about the experience. Specifically the opportunity for total and complete surrender.

The Danger of Control

Control is one thing many of us strive for in life. And it’s understandable; the ability to control seems to offer the shortest and easiest path to getting what we want.

But while control is attractive, it’s also deceptive. Not only does control often rob others of their freedom. It can also rob us our ability and willingness to surrender.

You see while control gives you more ways to pursue happiness, it also puts the responsibility for that happiness squarely on your shoulders. It makes you believe that you and you alone can and must create a world that meets your needs.

The truth is that nobody can find true and lasting happiness by themselves. Not because we depend on others to make us happy, but because we need the kindness and engagement of others to live full and complete lives.

However, when we try to control everything, we lose sight of this simple truth. We get caught up in the constant struggle to stay in charge, until it feels like we are guard duty twenty-four hours a day. And that’s why it’s so important to let go from time to time.

The Relief

You see what I realized on the massage table was that deep surrender is a huge relief. A relief I felt so deeply during my massage that I was almost moved to tears. As I sat there naked and vulnerable letting my body be manipulated, I was reminded that I didn’t have to rely on myself. I was reminded that it’s not only essential to ask for help, but also to I surrender when it’s offered.

What makes surrender so powerful is that it requires us to express deep faith not only in the person or situation we’re in. But also in our own ability to trust, love, and accept.

It’s so easy to think that life is a big hunt where we must stalk and kill our prey in order to eat. Instead, I’ve found it’s wiser and more conducive to happiness, to see life as a flow of giving. Instead of having to hunt to get what you want, all you need to do is stay on the path so that the blessings of life don’t have to find you and give you what you need.

Seek Out Surrender

So my challenge for you this week is to seek out healthy situations of surrender. Get a massage, spend time with a lover, get your hair cut, or pamper yourself at the spa. No matter what the act or occasion please take a chance, trust someone, and let go of the need to control. Even if it isn’t exactly how you’d like, your willingness to surrender can give you so much more than what you think you want. It can give you what you deeply need.


A Final Note on Surrender:

Before I go, I wanted to make a brief note about surrendering safely. Surrender more than anything else demands deep trust by the parties involved. And while you shouldn’t withhold trust forever, you also shouldn’t give it without some due diligence or caution.

Our desire to trust and surrender has been used by many false prophets, religious cults, and snake oil salesmen to ply what they want from the bodies and minds of their willing victims. So please let your own intuition and better sense guide you as you engage in this practice. And if something feels off or wrong at all please seek wise counsel from an outside source who can help you stay safe and happy.