what I learned from my worst leadership mistake


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.

Stop waiting to feel inspired (or motivated)


(Here’s an excerpt from my book, Your Most Courageous Self: the definitive guide to unparalleled bad-assery. Your Courageous Life email subscribers will get access to the audio of the introduction. Sign up, here: YourCourageousLife.com/begin).

Good gravy, the number of times someone has told me that don’t follow through with things, because they get excited but…then they lose their motivation or inspiration.

It stops feeling pleasurable and fun, so they stop moving forward.

Where are people learning the idea that the things you want in life, the things that are most important to you, are always going to be endless journeys of inspiration? Where are people picking up the line that motivation is easy, or that people who succeed in doing things always feel motivated?

Hard truth: You won’t always feel inspired. You won’t always feel motivated.

You’ve got to get out of the delusional thinking that motivation and inspiration will always be present on the way to the life that you really want. (I pose these thoughts not to put anyone down, but rather to really get people to look and see that the start-stop-start-stop stuff perpetuates more suffering, and keeps them from the life they really want).

No one who is improving her marriage feels “inspired” by tough conversations that so easily turn into arguments. But what’s the alternative? Not having the conversations, which equals nothing changing.

No one who builds her own business always feels “motivated” to finish what she starts. But she sits her arse down in the chair and gets the work done, because the bigger picture of what she’s trying to create is more important to her than the smaller picture of a day, week, or month where she feels less motivated.

No one who decides that they want to start expressing a creative desire—painting, dance, or something else—always feels “motivated” to do it. In fact, you’ll often feel inadequate, wonder why you’re doing what you’re doing, or commit something to paper and later think, “I wasted time.” But those moments aren’t the whole picture. Something within you has to know that all of these efforts, even if they were shitty first drafts or rough sketches or flailing in dance class, are all going into the whole: the whole that is you, living more joyfully and fully alive.

Fear and Fun

Usually, we lose motivation and inspiration when we’re either afraid (fear throws down “I will zap you of inspiration!” to get you to stop) or when you haven’t had any fun and you’ve made the thing you’re trying to create into a (ugh) chore.

I’ve seen so many people do this with their businesses. They stop having fun because they’ve convinced themselves that they have to spend all day sitting in front of a computer watching Facebook ads results, if they want to succeed in business. They stop tapping into the craft of coaching and get hung up in the business of coaching, and then even the business of coaching is something they can turn into drudgery.

Yes, you’re going to have to spend some time doing the boring stuff. The grunt work. It’s not always fun (though you can make it more fun, the less you complain), but it’s necessary.

Sometimes, the stuff you “gotta do” even downright sucks. You’ll ask yourself, “Is this worth it?”

Well, it also sucks to live a life where you keep ending up right back at the same place, over and over. That’s what happens when people continually buy into fear and don’t step forward into their Most Courageous Self.

If you stop thinking that motivation and inspiration must be a prerequisite at all times for you to be happy, you’ll unhook yourself from the start-stop-start-stop cycle.

When people never find their way through, and their answer to discomfort is to quit, or to change locations, or to leave that relationship for someone else, or to otherwise move around the external variables in search of happiness and endless fun, they always end up right back at the same place–at some point, the job or the relationship or the whatever? It stops being fun, inspiring, motivating.

Instead of seeing the loss of inspiration or motivation as an automatic sign that something is wrong, see it as a sign that there’s a skill-set that you might need to learn–a skill-set for finding the magic in the mundane, recognizing your triggers for losing motivation and where you set yourself up for that, tapping into the bigger picture of what you’re creating so that a few rough weeks or months don’t sway you.

There is magic to be found everywhere, even in the mundane (if that’s what you choose, and it absolutely has to be a mindset and a choice).

There are more easeful ways to find your way through that don’t involve that exhausting hustle-push-pull-gritted-teeth stuff. Learn how to find and create those ways, before you quit anything else.

your most courageous self awaits


I’ve been working on something, behind the scenes…a book. The title came to me in a flash, one day, and I wrote it down on a post-it note that would live on my computer for several months.

Your Most Courageous Self: the definitive guide to unparalleled bad-assery.

I didn’t want to write a new program that does a deep-dive into living with courage (I’ve already created that) and my vision for Your Most Courageous Self was clear: Kindle format, on Amazon, intended to be the inspirational launch point for releasing a person’s Most Courageous Self from the leash of “have to,” obligation, work-work-work-hustle-work, worry, over-thinking it, self-doubt, and…not having fun.

Your Most Courageous Self is a side of you that believes, wholeheartedly, in having fun and living a fully-alive life. She’s the inner bad-ass that’s sick of being on a leash. She wants to go, do, experience. She’s sick of caring what anyone thinks or trying to figure out all the steps, in advance, or any other joy-killer.

Get a free copy

Want a free copy, before it’s released on Amazon? Head to YourCourageousLife.com/begin and become a YCL subscriber (already a subscriber? Fabulous! You’ll automatically receive everything).

Then, check your email on October 3rd. That’s when I’ll be sending out the download link to the Kindle and PDF versions, and…

– The audiobook
– Worksheets and other Most Courageous Self downloadable resources
– Information about how to participate in the Most Courageous Self challenge (#MCSchallenge) on Instagram.com/katecourageous or Facebook.com/YourCourageousLife. Not only is participating in the challenge a way to push yourself to take action and connect with other like-minded people who are interested in living more courageous lives, you’ll also have opportunities to enter for a free gift card giveaway.

Want to listen to the introduction?
Here it is: