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Red flags, humility and other leadership lessons I’ve learned

Never, ever FaceTime with Liz after 6 p.m. It’ll start off innocently enough with inside jokes and sharing advice and swapping stories … and then she’ll get this look in her eye and ask something like:

“So, did 2021 turn out how you expected?”

I’m sorry, what? Weren’t we just talking about Shark Tank?

Before you know it, she’s propped up her MacBook against her iPhone to record a voice memo – and you’ve been ambushed into a content interview that requires deep reflection and introspection. 

And if you think I’m kidding …

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… this is exactly what happened to me last week. And that was the precise question she asked me. (Yes yes, I know … this is exactly why I hired her. Still, she’s sneaky.) 

Anyway, this time last year, I wasn’t really thinking about the future

Instead, I was standing in front of a whiteboard, marker in hand, asking myself “let’s break stuff!” boots-on-the-ground questions like:

“What is the right structure for a marketing team?”

This sounds glamorous until you realize the room I was building my business in wasn’t an office. In fact, I was operating out of what used to be my daughter Sawyer’s bedroom. 

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Back then, so much was happening so quickly. 

More than that, it felt like if I could imagine something, I could make it happen with little to no friction. Seriously, at the start of 2021, I was blinded by a waterfall of seemingly neverending yeses as I pushed forward into building a sustainable business.

As a result, I couldn’t put it all together. In hindsight, I see it was virtually impossible to look around and take stock of what my bigger picture really was. 

Today is a much different story.

Although I know a year from now I’ll have a fresh batch of “Oh, shit” lessons to share with you, I’m more future-oriented than I was last January. I also realize the lessons that I’m carrying with me into 2022 are quite basic in nature.

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I’m not joking, I’m about to share what I learned and I’m keenly aware that some of them are eye-rollers. To the point where I can already hear some of you saying:


“These are the lessons you needed to learn?”

“You didn’t already know these things?”

The answer is yes. Yes, on all counts. 

However, I’m willing to bet that, basic as these lessons may be, there are more than a few of you out there who will also benefit from this quick refresher course. When you spend most of your days making big decisions and solving increasingly complex problems, it becomes all too easy to forget the basics. 

Now, with that bit of “safe harbor” language out of the way …

Don’t ignore the red flags your gut is waving furiously

“Going with your gut” is a dangerous way to operate. 

On the one hand, being able to operate on instinct (without a lot of analysis paralysis) is critical to success in business, particularly when you’re in a leadership role. On the other hand, leading with your gut to the point of infallibility – where you leave no room to be wrong or to allow something (or someone) to surprise you – is highly problematic at best

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Of course, that’s easy to say, right?

Sometimes it’s hard to tell if what you’re feeling in a given moment is true instinct or something manufactured, rooted in fear or unspoken bias. This makes it easy to dismiss those feelings because, well… 

  • “Maybe I’m seeing something that isn’t there.”

  • “Maybe I’m imagining a problem that doesn’t exist.” 

I struggled with that a lot last year. 

Looking back, I can identify specific critical moments where I chose to overlook tangible facts and documented evidence that supported some of my worst, gut-based fears … because even though every internal red flag was waving inside of me with vigorous persistence, I turned a blind eye, unwilling to admit the truth.

As a result, I paid the price for it. What’s worse, others did, too.

I learned the hard way that people lie. Not just to others, but also to themselves. 

I learned the hard way that, for some, it’s second nature to throw on a sweatshirt that says “No Bureaucracy, No Bullshit” and call yourself ethos-driven when it’s easy, in the daylight … and then they’ll make choices that run counter to that ethos in the shadows when they think no one is looking. 

Undoubtedly, this will be a lesson I will continue to learn and re-learn, but one of the things I’m committed to in 2022 is not blinding myself to my gut just because the truth hurts sometimes. Especially since the cost of doing so is steep.

This is true not only from a business perspective; ultimately, you compromise your own character in doing so.

I came into 2021 with the goal of being the most humble person ever on the cover of Forbes magazine

Don’t worry, I am not blind to the overwhelming irony of that statement. That’s the point. I’m a deeply insecure person, which makes this even more of a painful, kick-in-the-pants lesson I had to learn and now own publicly.

I never thought humility was going to be a problem area for me. I thought my previous experiences and trauma would gatekeep me from ever acting from a place that wasn’t rooted in being humble. 

What I see now is how that early stream of effortless yeses inflated my ego about what we were doing. Yes, we were all working extremely hard and our wins were sincerely earned. But still, everything came so easily.

Too easily.

You see, keeping a 50% profit margin isn’t hard when you only have three people to account for. And growing and doing what we were doing based on pre-existing relationships isn’t really running a business. It’s working with your friends.

So, there was this lift that happened at the beginning of the year that created this sense of touchlessness – and everything we did, people were responding to.

That’s when I started saying asinine things out loud like:

"Oh my God, I don't understand why people think this is hard!"

In reality, we were still playing in a blissfully ignorant sandbox. We hadn't actually stepped into the arena where you learn what it takes to run a real business.

Then I had to fire what amounted to a third of our small staff at the time… and after that, every rock I kicked over for a good long while released ugly, messy, painful problems instead of anything that even remotely resembled a win. 

Here’s the thing, though. As I’ve talked about before, leadership (of a company or a team) is supposed to be hard. If it’s not, don’t take that as a sign of success; it’s not. It’s a very loud warning siren signaling you’ve got dangerously large blind spots you need to address before it’s too late. 

More importantly, every single time I came up against one of these challenges, where I was put to the test against our own ethos, the right people drew closer. More than that, I grew in my confidence with my own decision-making and my instincts. 

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As I come to the end of this year, yes, I am more confident. And I still have to work just as hard to continue to make sound decisions and keep my ego checked at the door.

I need to continue to learn and be open to learning. I need to always work hard to pull the right people in. Also, while we’re doing incredibly well and have an impressive track record, fuck-ups will continue to happen. I will be wrong. I will make mistakes.

To others of you out there who may be struggling in this way with humility, trust me when I say this is something you need to address now instead of later. 

We all fall down.

This is a feature (not a bug) of running a business and being a leader. But if you lack humility in business, your falls are going to hurt a hell of a lot worse.

I also relearned how resilient a vision can be

Look, most lessons we learn are ones we learn the hard way … and that includes the two I’ve already shared. But there is one “basic” lesson I learned in 2021 that brought so much brightness and joy and lightness to my heart, especially during some of the darker times:

A vision when pure and carried with true conviction is an incredibly resilient thing, even in the hands of imperfect, fallible human beings. 

Through every twist and turn, the vision I’ve carried with me since that snowy day in 2018 is still here. It’s expanded, it’s more in focus and polished … but its foundational elements remain. In all of this time – and over the last year, in particular – I’ve realized something.

Beyond people having feelings about what you say, how you do business, how you show up in the world, everything has bumps and bruises. As a human, you're going to go through situations that are tough and hard, and a business and a vision are going to endure those very same trials. 

  • You're going to have people who use your vision and your ethos as a weapon. 

  • You're going to have people who use it as a reason to hate you or to hate the thing that was created. 

  • You're going to experience injuries that are self-inflicted and could have been avoided.

  • You're going to rough up your vision; it's not going to stay pristine. 

  • Your vision won’t be a shining star that never has to defend itself, fight for its place to live or brace itself for impact.

But think about a diamond. A diamond isn’t created under serene, calm conditions. Diamonds are only created under an intense amount of pressure and brutality, and that process takes billions of years. 

Visions follow the same path 

Throughout the last year, there were moments where I was afraid the sacred vision I guarded within me might get lost. That, despite my best intentions and efforts, it would succumb to my failures as a leader or become corrupted through circumstance.

But time and again, I was wrong. Time and again, it proved its resilience.

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The funny thing is, I never once thought while standing at that whiteboard this time last year that a vision required resiliency. 

But as I look back, I see it. I honestly don’t know how I didn’t.

More than that, I’m so proud and elated by the fact that this vision – which was once solely contained within me – is now so much bigger. It lives outside of me, shared and living and breathing through every single member of our team. As a result of every test it faced, it’s more fortified than ever. 

Of course, once more with feeling, future failures are a guaranteed certainty. I also can’t wait to look back and reflect on all the boneheaded mistakes I will undoubtedly make this year. I know, however, our vision will continue to endure.

As long we remain committed (and accountable) to each other, we will bring it to life.