How to Let Something Go, and Embrace Something New

Is it time?

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to level up — and build a career or company you love.

Today’s one thing: Letting go of something old.

That one thing, better: Creating the next old thing.

DALL-E 2. Prompt: "one-line drawing of someone struggling to carry a heavy object”

You’re considering something new. But there’s a problem:

You don’t want to leave the old thing you already have.

Why? Because moving on is scary! And also, you like the comfort of the old thing — even though, let’s be honest, it’s far from perfect.

Today, I’m going to give you a way to let go and embrace the new. And I’ll start by taking you inside my never-ending family drama, where old things are clung to fiercely. There is crying. There is screaming. There are… shoes.

Old comforts are hard to leave

My older son is eight. His name is Fenn. And like all kids his age, he goes through shoes quickly. They become too small or too stinky, and then it’s time for them to go.

That’s when the problem starts. Because Fenn haaaaaaates new shoes.

My wife and I buy them for him anyway, because what else can we do? Then he refuses to wear them. When we finally coax them onto his feet, he flails around. There are tears. He flings them away. He’s done this forever.

Fenn’s current old shoes, which need to be thrown away

Why won’t he wear the new shoes?

“They’re not comfortable,” he always says. “I like my old shoes.”

And every time, I tell him the same thing.

“Fenn,” I say, “I know you want your old shoes, but your old shoes used to be your new shoes. You once hated those shoes because they were new and uncomfortable. But then you started wearing them, and they became comfortable, and then they became your old shoes. And that’s exactly what will happen with these new shoes, because once you start wearing them, they will become your old shoes.”

This line of reasoning never works. I mean, he is 8 years old.

But it’s gotten me thinking: What am I really trying to tell Fenn, when I tell him that his old shoes used to be his new shoes?

Then I realized: I’m trying to teach him two things. And they are very relevant to you.

Lesson 1: Different isn’t inherently bad

We often cling to what we have, because we believe it is irreplaceable. We cannot imagine being as happy, satisfied, or comfortable with anything else — even if, weirdly, we are not always happy, satisfied or comfortable with what we have right now.

As the old saying goes: “The devil you know…”

But how about this: Let’s give the old thing its due. It really is irreplaceable. It provided you great joy or value at a time when you needed it. But what if its job isn’t to be with you forever — or at the very least, to not always play the exact same role in your life? What if its job is to set you up for what’s next? What if that is its irreplaceable purpose — to have helped you outgrow it?

Life is about cycles. We grow, we renew. We carry some things with us, and leave other things behind. And the greatest disservice we can do to ourselves is to stop — to bow out of the next cycle, simply because we lack the imagination or confidence that we can do better.

And the second lesson is this:

Lesson 2: Old isn’t inherently good

DALL-E 2. Prompt: “one-line drawing of someone throwing a colorful box in the air”

In most parts of our lives, we can keep old things and still gain new things. We can love our old friends, and also make new friends. Keep old t-shirts and buy some new ones.

But sometimes we must choose: It’s this old job or that new job. This old relationship or that new one. This is what Fenn faces with his shoes.

So let’s put it plainly: Although an old thing may be good, there is nothing inherently good about something old.

To be clear, many old things are wonderful! Old friends, old t-shirts, old habits — we should treasure and protect the ones that still give us joy. But oldness is not an inherently good quality. Oldness does not make something good by itself. Which means that oldness is not a reason by itself to hold on.

So it is important to consider: Are you holding onto something because it is good, or simply because it is old?

If Fenn were to debate this, he might tell me: “Old shoes have inherent value! They are more comfortable than the new shoes, because they’re softer and have formed to my feet.”

That’s fair. But let’s break it down like a logic puzzle.

Here are four questions to ask yourself, whenever you’re weighing old against new.

1. What are the core values of the old thing?

2. What are the core values of the new thing?

3. Can the old thing’s core values be replicated in the new thing?

4. Once the new thing has the same core values as the old thing, am I happier?

These answers might help you keep a wonderful, old thing. Or they might help you recognize the benefits of something new. Either result is great.

I’ll answer this for Fenn’s shoes: His old shoes’ core values are their comfort and familiarity. His new shoes’ core values are their smell (fresh!) and construction (strong!). Can the old thing’s core values be replicated in the new? Sure — just give it a few weeks, and his new shoes will also be comfortable and familiar. And once that happens, is he happier? Yes, because now he has comfortable, non-smelly shoes… and his parents will stop bugging him about it.

The choice is clear.

So, you ready?

If you’ve decided to embrace the new, but you’re still hesitant to do it, then consider this: You’ve already done it before.

You are not the product of static experiences. You are the product of change. You already built a career and life on top of changeable things. You already mastered new moments. You already identified new opportunities. You already stepped fearlessly through the changes that terrified others. This has all already happened. It is how you created the things you now find comfortable and familiar today.

And that’s evidence you can do it again.

In fact, Fenn has started to get it. While visiting family recently, another pair of his old shoes fell apart — and even he agreed, it was time for them to go. Here he is, slam-dunking them into his great-grandfather’s garbage can with all his might:


Sometimes old things break. That’s easier, in a way. It makes the choice for us.

But sometimes, we need to make the break ourselves.

That’s how to do one thing better.

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