Entrepreneurs, You Are Your Own Two Person Team

One of the biggest challenges when you run your own business or even when you’re the leader of a larger team, is that very often you have two roles or ways of being. Each role is different and vital, but because they function so differently if you start to mix the two you’ll likely find yourself paralyzed with doubt and uncertainty. Here’s the make up of your two person team.

Role #1 – The leader or CEO

The job of the leader is to figure out a clear and compelling vision. The leader might generate the vision from themselves or source it from the team. How you get there doesn’t matter. What matters is that you see something that you want to create and it’s clear, compelling and meaningful to you (and your team if you have one).

Once the vision is set, the leader stands for that vision, plans for that vision, and enrolls others into that vision.

As time passes they need to notice what is and isn’t working, uncover the breakdowns, and shift the plan.

Role #2 – The doer or executer

Even if you’re fully a CEO, some of the work you do will be as a doer or executer

The job of the executor is to do the best job they can, based on their current understanding of the strategy and requirements that have been set forth by the vision.

If they run into problems they need to note and report them. They might come up with creative solutions, ideas for trying new things, and even lead their own efforts inside the context of doing.

They can still have the being of a leader and be standing for something, but their focus in this role is on executing based on what has been decided by the leader or the group.

Two Person Team: Final Thoughts

The problem SO many CEOs, start-up founders, freelancers, small business owners, and coaches face is that they try to do both of these at the same time.

They decide to try a strategy of reaching out to potential clients who might want big projects to boost revenues.

They do a few phone calls, ask for referrals, and they get a couple of no’s. Because it’s hard to hear No’s they start to doubt the strategy. They think well maybe I should just go after some smaller clients instead, so they switch to that, maybe they get a few jobs, but there’s not enough money and they realize that isn’t working. So they think about the bigger job clients again.

Pretty soon they feel discouraged, trapped, and uncertain.
But if they were two people or if they better understood the two roles (Leader and Do-er), this wouldn’t happen.

The salesperson might tell the CEO that they were getting some no’s and the CEO might ask about the number of calls or what kind of response they had gotten. They probably would tell the salesperson to keep going until they made 25 or 50 calls so they have enough information to see if the strategy was or wasn’t working.

The salesperson would keep going because they had the support of the CEO who was standing for the vision and focused on the information and feedback needed to make a good call.

The CEO may start to think of other strategies but would trust the salesperson to do the best job they could and learn as they went along, knowing that it takes time to test out any strategy.

The challenge is that we are NOT two people.

The doubts of the salesperson can become the doubts of the CEO and vice versa.
The critical eye of the writer can become paralyzing to the writer.
The fears of the coach can undermine the trust of the marketing manager.

This is why if you’ve got a job where you have to be in both roles, YOU’VE GOT TO LEARN TO SEPARATE THEM!!!

You can do this by trading off days.

On Monday I’m just a salesperson for my company. I’m going to get on the phone, or on my email and try to make it rain.
Then on Tuesday morning I’ll sit down with myself and do my best work.

You can do this by having different spaces.

I do my writing in my living room chair and I DO NOT EDIT.
I do my editing at my desk where I do my other admin tasks.

You can even try different outfits or hats (physical or energetic).

When I put on my dress pants I’m the CEO of my company and I’m setting the strategy.
The rest of the time I’m a worker on my team and I’m focused on getting the day-to-day done.

And YES I’m fully aware the two will bleed into each other in certain places.

That’s ok. The key here is to do your best to notice where your head is at and ask if it’s where it needs to be.

To do anything well you need both the vision and the courage to execute that vision.
But you have to remember that courage sometimes means staying the course even when it’s hard. And sometimes it means taking a hard look at the strategy even when you don’t want to admit it isn’t working.


How To Be Free: The Three Types of Freedom

We all want a sense of freedom. The ability to do what we want, pursue our dreams and feel present to a life full of adventure and possibility.

But most of us have no idea what being really free actually means.

When I was a teenager being free meant doing what I wanted.

Freedom to stay out late, to date who I wanted to date, to keep my door closed, to drive faster than the speed limit, to skip the homework assignments I thought were stupid or that I just didn’t want to do.

For some people, freedom is just that. Not wearing a mask. Buying a fake vaccine card to get into a restaurant. Cheating on their partners and hitting on servers.

Sometimes their justifications are more complex but the desire to be free is the same. It seems juvenile because it is. It’s a juvenile idea of freedom dressed up in politics and business suits.

Most people who have developed some maturity and empathy see that this form of freedom is limited. The joy of doing what you want doesn’t last long and the pain you cause others isn’t worth it. But not all of us learn this.

When I got out of college and started paying my own way, freedom meant being able to live the kind of life I wanted.

It meant I could pay my bills, I could choose where to go to dinner, or where to go on vacation.

Part of why I started my own business was because I wanted more of this freedom. The freedom to choose when I worked and who I worked with. The freedom to change my location or to do list at will.

I sought the freedom of a particular kind of lifestyle, which while motivating also ended up feeling a bit empty.

But many people stay focused on this kind of freedom as long as their alive.

Part of the reason the great resignation has happened is that the corona virus destroyed the false trappings of this kind of freedom.

Without boozy brunches and business trips many of us started seeing that lifestyle freedom didn’t mean much unless we had constant freedom of movement and an endless supply of distractions.

Working a crappy job to pay for a decent vacation isn’t worth it. Sure losing the vacation made that become clear, but even when we could take the vacations it still isn’t worth it.

I came to realize how empty this kind of freedom was when I achieved more than most people do as a business owner. I consistently earn multiple six figures a year and live on a portion of that with ease. But I still wasn’t really enjoying life that much.

Which is how I stumbled on the third kind of freedom. What I call spiritual or energetic freedom.

It’s the freedom to be or become anyone I want. And I’m not talking about becoming an astronaut.

This isn’t about achieving some title or some state of mind. It’s about the ability to embody any energy the moment calls for. It’s about being able to be my darkness fully. It’s about being able to fully embody my sexuality and desire. It’s about being able to fully embody deep wisdom or deep foolishness.

This is the next level of freedom.

I touched this kind of freedom when I lived at a zen monastery for two years, but without the kind of lifestyle freedom, I craved.

It was only after achieving some of the lifestyle that I wanted that I was able to really see how meaningful energetic freedom really was.

Energetic freedom doesn’t depend on roles or status. It doesn’t depend on age or attractiveness. It’s the most generous kind of freedom, because it’s a freedom that allows you to respond moment to moment in whatever way serves the most.

And yet it’s a kind of freedom very few people talk about because it’s so hard to understand.

So many of the CEOs I’ve coached have achieved full lifestyle freedom but feel trapped in themselves.

So many celebrities live lives of glamour and wealth but seemed hemmed in by their own personalities and habitual ways of being.

At a time when so many of us still can’t go on vacation or return to our normal lives how are we supposed to continue to pursue freedom?

It’s time for us to pursue a freedom of being, a freedom that is accessible to everyone and helps improve the lives of everyone we meet. It’s a freedom that demands humility and practice, but rewards us with a flexibility of thinking and responding, unlike anything we’ve ever known.

If you’re ready for something new consider exploring what it would mean to let go of a fixed idea of who you are and embrace more of yourself not only to experience greater personal freedom and joy, but also so you can give more of what the world currently needs.

Which is people who are brave enough to stand up for something that comes from an authentic care for others and a willingness to not take things personally and instead do what most needs to be done.