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We start online businesses, in part, because we want to throw out the rule book. We’re sick of policies, dress codes, and memos. We’re tired of someone who isn’t even on the front lines, most of the time, dictating how we’re supposed to be doing things on a daily basis.

We start working for ourselves because we want to shake up the limitations, and in my own business life, I’ve been no exception.

My wish has been to be human.
My wish has been to be real.

These are wishes that we cast when we’re thinking about how great it’s all going to be when not only have a positive impact on others, but when we’re also able to sail our own ship. Policy books and dress codes feel neither human nor real.

We’re not usually thinking, when we’re wishing to be human or real, about the parts of humanity or realness that are messy and imperfect and a total flub.

And that, my friends, is how I arrived at my worst leadership mistake.

My worst leadership mistake (yours, too?)

Super simple: not setting up appropriate boundaries.

For years, I had been aware that my worst leadership mistake was not setting up appropriate boundaries, and I’d kinda-sorta, mayyyybe in the back of my mind thought that I should do more about that. Over and over, the opportunity presented itself, and over and over, I would kind of flub my way through asserting boundaries and then I’d analyze the situation and what I could have done differently and think, “I’ll do better, next time.”

This is a legitimate way to learn, and sometimes the only way that we can. In my case, the next best step would have been to take action on what I’d learned in terms that were distinctly uncomfortable, for me: buttoning up contracts, being clearer about policy and procedure, etc.

But ugh, setting up boundaries and getting all legal? That so didn’t jive with the free spirit, “now I get to do it my way” stuff that I was enjoying behind the scenes.

I wanted to have fun, and to me, setting boundaries wasn’t, like, fun.

Also, if I was getting honest? I was afraid to set boundaries. Sure, there were some places where it was no problem, but in others, I struggled with wanting to be liked and caring what others think. These are very human things to struggle with, and these places aren’t necessarily where I lived, emotionally, 100% of the time.

Nonetheless, whenever a boundary most needed to be asserted, these fears were behind why I didn’t assert them.

the price of fear

The price of fear is that we want sovereignty, but we fear making the hard decisions, and then the fear ends up being our master more than the old boss and his dress code and policy manual ever did.

The price of fear is that we can hide out from dealing with it for as long as we want, but it will always keep on coming back, upping the ante and raising the stakes.

That’s exactly what happened, with me. My worst leadership mistake was public. Someone had been communicating with me in ways that were disrespectful for awhile, and I was trying to address them but without actually stating very directly, the necessary boundary: “The way that you’re talking to me (and others in our community) doesn’t feel good, and I need you to communicate respectfully.”

I would walk right up to that line, and say every other thing except that sentence.

So of course, things amplified from there. It was big and messy and stressful, and most of all, sad, because once that tipping point was reached it was basically impossible to go back and untangle for the other person, “Here’s why this snowballed. I actually don’t dislike you or wish anything negative for you, whatsoever. I think that I’m being misunderstood. I bet you are feeling misunderstood by me, too. Let’s work it out.”

You know–the human, real stuff that I’d been wishing for.

boundaries are courageous

My more playful side has needed to reconcile this fact: boundaries are not fun, but they are courageous.

Boundaries “are like drawing a line in the sand, and saying, ‘Beyond here I will not go and you cannot come.’ ” –Iyanla VanZant.

Boundaries let people know where they stand because you’ve defined where you stand.

Boundaries let bullies know that you won’t kowtow to them.

Boundaries let people know that you’ve considered all aspects of a situation.

Boundaries are a kindness, the neutral third party that can be turned to when there’s disagreement in a relationship.

boundaries as values

I’ve come to see boundaries as being less about rules, and more about sharing values.

The value is that respectful communication is a necessary part of loving interactions, so my boundary is that communication must be respectful.

The value is that we will practice behaviors that are healthy for every member of this community, so the boundary is that if you disrespect members of this community, you can’t stay in it.

The value is professionalism, so the boundary is that if we don’t agree on what ‘professionalism’ looks like, then we shouldn’t work together.

learning from my worst leadership mistake

Want to learn from my worst leadership mistake? Super-simple:

1.) Ask yourself what situations you’d be most afraid of, in your own business, as they pertain to leadership.

2.) Ask yourself why you’re afraid. (“If that happened, what would I be afraid of? And then what would I be afraid of? And then what else would I be afraid of?”).

3.) Ask yourself how you’re setting up the conditions for that leadership mistake to happen, right now, through avoiding dealing with the problem.

When you’re willing to look at it with clarity and love, you’re empowered to change the stakes. Raise your vibration. Up the ante in the game. Play to your own courageous edge.