Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to achieve a breakthrough at work — and build a career or company you love.
A reader (hi, Natalie!) recently emailed me, saying this newsletter from last year inspired her to take a bold risk at work — and it paid off. So I wanted to reshare it today, to inspire other bold moves.
You’re being cautious.
You want something, but you’re scared. You keep telling yourself: I must be careful. I can’t ruin what I already have.
Like, maybe…
- You have a new job opportunity, but you’re hesitating — afraid you’ll lose the security you fought hard to build.
- You want more from someone (a favor? a partnership? a relationship?), but don’t want to risk your friendly connection.
- You want to create content (writing, videos, whatever), but you’re afraid it won’t be perfect and you’ll embarrass yourself.
Today, I want to help you move forward — and to do this, I’m going to teach you the Messy Couch Principle. It’s a new way to assess your problem, and then find the confidence to act boldly.
It’s time to stop hesitating, and to see what’s on the other side of action.
But first, let’s talk about that couch.
A very clean couch
When I was a kid, I’d often visit my grandma in her retirement community. She liked nice things, so her living room was full of stuff I couldn’t touch — glass vases, works of art, and so on.
The centerpiece was a fancy couch, which, like many people of her generation, she had wrapped in plastic. That way, no visitors (especially children!) could spill something or scuff it up.
I can’t find a picture of her actual couch, but it looked sorta like this one from Reddit:

As a kid, this couch intrigued me. It was funny and shiny, and made noises when I sat.
But as an adult, this couch has become a puzzle. Here’s what I wonder:
A fancy couch covered in plastic isn’t a fancy couch anymore. It’s just a crappy plastic couch. And what’s the point of that?
My grandma isn’t here to answer that question, but I think we should all ask ourselves. Because we all do versions of this too.
You have ambitions and ideas wrapped in plastic. People wrapped in plastic. Career plans wrapped in plastic. These are the things you talk about, or think about, but do not actually act upon, for fear of changing them in some way.
The plastic is preserving something’s potential at the expense of its actual, realistic value.
What happens if we remove the plastic?
Well, let’s think about the couch.
Imagine that my grandma removed the plastic. What’s the worst that could have happened? Let’s see…
- Her friends might have sat on it, and maybe spilled wine.
- Her grandchildren might have climbed around and scuffed it up.
- The cleaners might have need to be called.
In the meantime, the couch would have felt softer without that plastic. More comfortable, too. Every day, she could have sat there and enjoyed her fancy couch in all its splendor — until yes, over the course of many years, she might need a new one.
Was that worth the trade-off of a couch forever encased in plastic? I do not think so.
This is the premise of the Messy Couch Principle. It is a simple way to evaluate risk, and it goes like this:
Are we happier with the safe and sanitized version of our life, or with the messiness that comes with taking action?
Here’s a good way to assess it for yourself.
The Messy Couch Test
You know what you’ve preserved in plastic. It is the job you’ve held for years, or the idea you’ve never tested, or the person you’ve never gotten truly personal with.
Now ask yourself these two questions:
- If I act, what’s the worst that can happen?
- If I don’t act, what am I left with?
That’s it. That’s the whole exercise.
I’m not asking you to consider the best-case scenario — because, well, we aren’t motivated by best-case scenarios. They might not happen! We know that!
Instead, we are motivated by fear of loss. Decades of research has confirmed loss-aversion theory: Our human brains are programmed to protect against loss more than to seek gain.
The Messy Couch Principle forces you to ask: Which bad option actually contains less loss?
The answer might surprise you.
I have many messy couches
Here’s a big one from me: When I was 28, I was living with my long-time girlfriend in Boston. It was a good relationship, but I knew it wasn’t the “right” one — and yet, I was afraid to break it off. So it went on for years.
Then I got a job offer in New York, which would provide the career advancement I craved — but my girlfriend didn’t want to move.
I almost turned the job down, so that I could preserve that OK relationship.
Then I basically asked…
- If I leave, what’s the worst that can happen? Answer: We break up, and I spend a while awkwardly dating and building a new life in New York.
- If I stay, what am I left with? Answer: I remain in Boston, where there were fewer career opportunities for me, and I stay in an imperfect relationship.
The choice became clear: I moved to New York, stumbled through a lot of mistakes, and developed the awesome life I have now.
Of course, things don’t always work out.
For example, I once became friendly with a very famous person. Then I asked them for a favor, they thought I was taking advantage of them, and we haven’t spoken since.
That was a bummer, but my Messy Couch questions helped put it into perspective:
- I asked for help, and what terrible thing happened? Answer: I lost the relationship.
- If I didn’t ask for help, what would have happened? Answer: I guess we’d still be friendly, but always at a distance. We’d never reach a more meaningful level together.
In retrospect, it was worth the chance.
Let’s take off the plastic.
The plastic is fear. We wrap so much of our life in fear.
When we take the plastic off, life can get messy. Some of what we feared might come true.
But that’s often worth the trade-off. The things we protect too much are the things we never truly experience. A couch is meant to be sat on, and a life is meant to be lived.
So take the plastic off.
That’s how to do one thing better.
This is my favorite AI writing tool

For the past year, I’ve been using Poppy to speed up my tasks — and it’s magic.
It works unlike any other AI tool you’ve seen, so here’s the basics:
- It looks like a digital white board
- You place any source material you want (files, websites, YouTube videos, etc), and then link them to a chatbot.
- That chatbot is now informed by what you gave it — so that you can use it for customized projects.
This makes it the simplest, clearest, most customizable AI tool I’ve found.
For example, see that board above? I built that to speed up one of my most boring tasks.
Whenever Entrepreneur publishes a list of top franchise brands, we publish a press release to announce it — and it always includes a quote from me. I spent years writing those things myself. Now I have Poppy do it. I created a new board, and trained it on lots of examples of past press releases. Now it understands my voice, and produces great quotes from me in seconds.
