A Little Bit Messy, a Lot of Fun: Why We Need to Stop Taking Ourselves So Seriously

Some conversations follow the outline perfectly.

The questions are answered in order. The transitions are smooth. Nobody forgets what they were saying halfway through a sentence. Everyone sounds polished, prepared and incredibly wise.

And then there are the conversations where you laugh, wander completely off topic, forget the question you were going to ask and somehow end up exactly where you needed to be.

Honestly, those are often my favorites.

My conversation with BrookeLynn on The Seed was one of those conversations.

It was fun. It was real. And it reminded me of something I think a lot of us need to hear:

We can take what we’re building seriously without taking ourselves seriously all the time.

When Did We Decide We Had to Have It All Together?

I don’t know exactly when it happens.

Maybe it’s when we start a business.

Maybe it’s when we become parents.

Maybe it’s when people start looking to us for answers.

Or maybe it’s somewhere around the time we realize other people are watching what we’re doing.

Suddenly, we think we need to know.

We need the answer.

We need the plan.

We need the perfect website, perfect Instagram post, perfect elevator pitch and perfect response when someone casually asks, “So, how’s business?”

Fine.

Everything is fiiiiine.

Meanwhile, there are 27 tabs open on our computer, three ideas written on random pieces of paper, something we were supposed to respond to yesterday and at least one thing happening in our personal lives that was definitely NOT included in this week’s time-blocking exercise.

Welcome to being human.

Polished Doesn’t Always Equal Connected

I spent a lot of years thinking I had to get things right before I put them out into the world.

And I still fight that instinct.

I want to prepare. I want things to make sense. I want the experience I create for someone else to be good.

There is nothing wrong with that.

But there is a difference between caring about the quality of what we create and believing we have to appear perfect while creating it.

Those aren’t the same thing.

Some of the best connections I’ve made haven’t happened because I said exactly the right thing.

They happened because something went sideways.

Someone told the truth.

We laughed.

A conversation went somewhere completely unexpected.

And suddenly, we weren’t two people trying to impress each other anymore.

We were just two humans talking.

That’s where connection happens.

Fun Doesn’t Make You Less Ambitious

This is a big one.

Somewhere along the way, we started associating success with seriousness.

Serious people have serious businesses.

Serious leaders have serious conversations.

Serious entrepreneurs wake up at 5:00 a.m., drink green things, journal for 47 minutes and apparently never lose their car keys.

I’m kidding.

Sort of.

But I think we need to give ourselves permission to have more fun while we’re building the things that matter to us.

You can be incredibly ambitious and laugh a lot.

You can be a strong leader and be ridiculous sometimes.

You can want to change the world and still send your friend the completely inappropriate meme.

You can have big goals and enjoy your life before you accomplish them.

That last one might be the most important.

Because if we’re always waiting for the next milestone before we allow ourselves to enjoy what we’re building, we’re going to miss a whole lot of our lives.

The Messy Parts Usually Make the Best Stories

Think about your favorite stories.

Are they really about the days when everything went exactly according to plan?

Probably not.

They’re about the vacation where everything went wrong.

The event where someone forgot something.

The dinner that burned.

The meeting that took a completely unexpected turn.

The thing that felt mildly disastrous in the moment and became hilarious six months later.

The messy parts become the stories.

And maybe we don’t need to rush quite so quickly to clean all of them up.

This doesn’t mean we stop planning.

Trust me. I’m still making the list.

I’m still preparing.

I’m still trying to figure out what comes next.

That’s part of who I am.

But I’m also learning that not every moment needs to be managed.

Sometimes the conversation can wander.

Sometimes you can change your mind.

Sometimes you can laugh at yourself.

Sometimes the plan can fall apart and something better can happen because of it.

Maybe This Is Part of Growth Too

We talk a lot about growth like it’s something measurable.

Revenue.

Followers.

Members.

Opportunities.

Miles.

Goals checked off the list.

But maybe growth is also being able to sit inside an imperfect moment without immediately trying to fix it.

Maybe it’s becoming comfortable enough with who you are that you don’t need every person in the room to think you have it all together.

Maybe it’s laughing when you would have once been embarrassed.

Maybe it’s realizing that your personality isn’t something you have to tone down in order to be taken seriously.

And maybe it’s understanding that joy isn’t the reward we get when the work is finished.

Joy gets to be part of the work.

A Little Bit Messy, a Lot of Fun

I am still going to make the plan.

I’m still going to prepare my questions.

I’m still going to think about what comes next and probably overthink something that did not require nearly that much thought.

Again…human.

But conversations like the one I had with BrookeLynn remind me why I love doing The Seed.

It’s not because every conversation is perfect.

It’s because they’re not.

People laugh.

Stories come out that weren’t planned.

We learn something about each other.

And sometimes, somewhere in the middle of all of that, we learn something about ourselves too.

So here’s what I’m working on:

Taking the work seriously.

Taking the people seriously.

Taking the opportunities seriously.

But taking myself?

Maybe just a little less seriously.

Because we’re allowed to build big things, want big things and work really freaking hard for them—and still have a lot of fun along the way.

Listen to the Conversation

Listen to my full conversation with BrookeLynn on The Seed for more laughter, stories and a reminder that life doesn’t have to look perfectly put together to be pretty damn good.

And then ask yourself:

When was the last time you were having so much fun that you forgot whether you looked polished doing it?