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.


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.


Leaders Live On The Edge

The human species became so dominant because of our ability to live on the edge. We evolved by venturing out the safety of the forest onto the plains to hunt, gather, and live. Yet so many of the leaders I work with consistently fall into the trap of hiding in a nest of comfort or getting lost in a wilderness of overwork. If you want to be one of the world’s most exceptional leaders you must master the art of living on the edge between comfort and catastrophe.

Here’s how I help my clients find their true edge.

Knowing where you live:

If you:

  • Used to be passionate about your work, but now you’re mostly bored.
  • Find that your achievements impress others but don’t inspire you.
  • Think about quitting sometimes and you light up with excitement.
  • Notice yourself always complaining about your employees, your industry, your partners, and the market.
  • Feel like you’ve been coasting for a long time.

You’re living in a nest of comfortable success.

If this is you, then stop pretending that what you’re doing is hard. I know that this will be scary and maybe people around you will wonder why you’re shaking things up, but extraordinary leaders are meant to live on the edge. It’s where they thrive, grow, and create things that shape the world.

Stop protecting your success and start asking:

  • What would be possible if I challenged myself to create something truly extraordinary?
  • What would I have do to multiply my current success by ten?
  • What am I ignoring?
  • What do I secretly want to do, but am pretending it doesn’t matter that much?
  • Where am I holding back?
  • What is my impossible goal?

If you:

  • Notice that it never feels like enough.
  • Bury your head in work whenever things get hard.
  • Find yourself bragging about how busy you are and how hard you work.
  • Can’t remember the last time you took a day off.
  • Never ask for help.
  • Take pride in all the sacrifices you take, even if you don’t always need to take them.

You’re crawling through the wilderness of overwork.

If this is you . . . STOP being a flipping martyr! No one is watching and no one will benefit when you burn out in the prime of your life. The world needs leaders who lead and create, not tyrants bent on progress at all cost. (We’ve already got plenty of those.)

Instead SLOW DOWN and ask yourself:

  • What would I do if I could only work two days a week?
  • If I saw my adult kids/nieces/nephews doing what I’m doing now, how would I feel about it?
  • Why do I continue to remain in a situation that is so stressful?
  • What am I afraid would happen if I slowed down?
  • What am I holding onto that I need to let go of?
  • Who would I be if I lost it all?
  • Is what I’m building the legacy/impact project that I really want to leave to my children/the world?
  • What if I said ‘screw it’ and only did what I love to do?

Please don’t just read this post and think, hmm those are some good questions. Ask these questions. Live into them.

The cost of avoiding your edge is not small. Most people live in a place of stagnation. They grow only until they find a careful equilibrium called ‘success’ and then they wither.

The path of the extraordinary demands that you keep the hunger of curiosity alive. It demands that you look at your life with fresh eyes. Stop pretending that how you are is the way you have to be. Find your edge, wherever it is, and endeavour to live there with everything you’ve got.