Why I needed to cry

Two days ago, I had a coaching session with Dave.

I shared some of my issues, specifically:

• I felt less inspired/excited than usual

• I felt more focused on business success than helping others learn/grow (my why)

• I really hadn't chosen a path forward for Gateway X

If you're new around here, after starting six companies over the last, roughly, four years, this year we took a pause to catch our breath and go deep on AI. 

At the same time, I've been thinking about the path forward. Should we keep starting companies? Invest in them? Buy them? Build? Do nothing?

I've found myself cycling on all of them, trying to get the answer right — but then also not actually taking the action needed to move one forward.

For example, I have a list of potential M&A targets sitting in my inbox; their CEOs’ names and ways to get in touch. 

And they just sit there, week after week. I'm a pretty high-agency person, so this was an immediate sign to me something was off.

To let myself off the hook, I'd say, "Well, I'm helping our portfolio and it’s not like I HAVE to do something." 

Or, another good one, “Why do we have to choose? Let’s do a few!” All the while, I'm sitting in indecision, not focused on my why and, as a result, feeling “blah.”

Dave and I were unpacking this bit by bit when it finally hit me:

"Oh, I need to mourn." Literally, I need to cry and feel sadness.

Over what, you ask?

The image in my head.

This is the big leagues of self-awareness! Externally, to both myself and others around me, I present an image of success and non-attachment. 

In other words, everything is going great AND whether it does or doesn't turn out that way, I'm good.

And, objectively, things ARE great. We've started six companies, four are still going and, this year, we'll do a combined >$30M in revenue with strong profit margins. 

We have amazing people, happy clients and everyone learns every day. I also think the whole thing is in the second inning and AI will be a game-changer for us.

Ok, Jesse. Then what's your problem?

Well, the mind (ego) is a tricky trickster. And it always finds ways to make you feel as though something is “not enough” or that something is wrong with the present. 

Even more dangerous is when it lurks underneath positivity (something that happens to me often).

What hit me during my session with Dave was, even though I had never said it out loud, I hoped (or probably even EXPECTED) that I'd be further along by this point. 

The negative part of me says, “Well, you've got GrowthAssistant growing, but it has AI threats. Aux has grown a ton YoY, but you haven't fully figured out staffing and the value prop. We're pivoting BG, and Unbloat is a mess.”

And then, the voices begin…

First, the Victim:

"This is hard." 

"How do I manage my time?" 

"Well, doing this in St. Louis is tough, if I still lived in San Francisco, it'd be better." 

"I’m trying to be a good father, husband AND entrepreneur.”

Then another voice, the Villain, starts to say,

"If ONLY I had spent more time up front planning each business."

Or, “Maybe I should have capitalized the businesses better."

Or, "What was I thinking with Unbloat?!"

Or, the biggie, "Maybe I'm not as talented as I think I am."

Then, of course, another voice, the Hero, shows up and says,

"Dude, you sold a company and have built several more."

Or, "Most people don't even have ONE successful company in their life — you're whining about several?!"

Or, of course, "Spiritual people don't worry about all this."

These thought patterns make up the "Drama Triangle.”

If this resonates (it should), it’s one of the most common human thought patterns and a telltale sign you are in a state of "threat" versus a state of "openness."

So, what's going on here?

There are many reasons we can get stuck in threat mode. Sometimes, there's a real or perceived external threat. Maybe a boss, a competitor or even a client. 

But as I do this work, I find it’s often an internal (or unseen) threat: feelings.

I tend to avoid sadness and disappointment. The reason why is a longer email for another day. But I don't like it.

And so in order to (subconsciously) avoid it, I'll cycle on things like I shared above, live in indecision or just plain old distract myself.

But there is another way: FEEL the sadness. Why?

Imagine your creativity or "aliveness" is a river flowing. A “sadness” boulder drops into it, blocking the flow. It is a blue boulder. I hate the color blue. 

So, instead of looking at the boulder and releasing it back into the water so it flows down the river, I cover it with wood, sticks and dirt. I effectively build a DAM in my own river to avoid the color I don't like.

Well, what happens then? I further block my creativity and aliveness because I avoid sadness. But by feeling it, I clear the blockage.

And, even more, there is wisdom in each emotion. In the case of sadness it’s, "What wants to be let go?" 

In my case, I want to let go of the attachment to where I thought we'd be after four years.

Another analogy to help this stick: say you are dating someone and, two years in, you thought you would be engaged and, instead, they dump you. 

That's sad, right? Maybe because you miss the person, but a big part of the mourning is letting go of the image in your head. 

In fact, if you try to date someone new before you've "let go," you will not be successful.

The same is true for me at this moment. It's time to let go of the image I had for where we'd be when I started four years ago.

The exercise Dave gave me was to pause and first be VERY honest with myself about all the expectations I had (eek, I've been pretending I have none!) and then write down the reality of where we are. 

And mourn. Cry, scream, feel the sadness of letting that attachment go. And then maybe tear up the expectations.

From there, start fresh and be amazed at what's here today. Then, I'll make my decision!

So, next time you find yourself cycling or being indecisive, ask this question:

"What feeling am I avoiding?"

Let me know what you find.

jesse

PS I record some of my conversations with my coach, Dave, in our podcast. Catch it on Spotify, YouTube, Apple and your favorite podcast apps.