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.
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You want to do something, but you assume you can't.
Maybe you want to reach out to someone, ask for a favor, or pursue an opportunity. But you tell yourself: "They won't be interested." "I'm not qualified." "That's not for me."
So you don't even try.
But here's the problem: You're accepting a barrier without testing whether it's real.
Today, I'll share a story that changed how I think about this — and I hope it emboldens you to get what you really want.
The celebrity and the security guard
This past summer, I was backstage at a conference talking to another speaker. He's a large celebrity whose name you know.
Nearby, there were two people: the celebrity's assistant, and an event security guard.
While we spoke, I noticed a small crowd gathering. About 20 attendees had been let backstage for some reason, and they were all looking at the celebrity.
The security guard noticed this too, so he asked the celebrity's assistant: "What should I do if those people approach?"
Her response was one of the most remarkable, nuanced things I've ever heard.
She said: "If they ask you for permission to approach him, say no. But if they just walk directly up to him, don't stop them."
This made sense. She didn't want these people bothering the celebrity — but if they reached him, she didn't want to cause a scene.
In other words: The security guard was now functioning as a scarecrow. He was there for deterrence. But if anyone actually tried, they could walk right past him.
The scarecrow principle
I've thought about this moment a lot, because it perfectly illustrates something we all do:
When we see or feel a barrier, we stop. But we rarely test whether it's an actual barrier… or just the appearance of a barrier.
Think about the assumptions you might make, as you stop in front of barriers:
"They won't want to hear from me." Have you tested this? Or are you assuming that person is too busy, too important, or too uninterested without actually finding out?
"I'm not qualified." Says who? The job posting that lists 'preferred' qualifications? The person who hasn't even seen your application yet?
"That's not for me." Based on what evidence? Have you tried and been rejected? Have you tested whether you like it? Have you challenged your assumptions?
In most cases, you don't actually know if you'll be stopped or rejected. The only person saying "no" to you is… well, you.
The solution is very simple.
Whenever you see a barrier to what you want, just ask yourself:
Do I really know if this is a barrier? Or does it just look like one?
And if it simply looks like a barrier, you can ask two follow-up questions:
- What's the worst that can happen if I try?
- What's the best that can happen if I try?
It's a simple assessment of cost and benefit.
Here's often the worst that can happen: Someone says no, or they say nothing at all. Maybe you feel a little embarrassed.
And here's the best that can happen: You have an incredible experience. You fulfill a desire. Maybe you even change your life.
If that's the case, the potential reward definitely outweighs the risk.
Also, the worst isn't the worst!
Even if the "worst" happens, it can still be a positive experience.
In 2012, for example, my wife and I experienced a similar situation to the one I described above — but back then, we were the people looking at the celebrity.
We'd gone to see Crosby, Stills, & Nash, one of my wife's favorite groups. As we arrived at the venue, we saw David Crosby walking out of his tour bus. A security guard was nearby.
My wife hesitated for a moment — should she approach Crosby? It was intimidating, but this might be her only chance to meet him.
She decided to go for it. And the "worst" happened: The security guard stepped in, Crosby totally ignored her, and my wife had to quickly turn away.
I snapped this photo of the moment:
She didn't get to meet Crosby, but we had an experience we still laugh about, and a story we've been telling friends ever since. It was totally worth testing the barrier.
So, what happened backstage?
Now let's return to the other celebrity moment — the one I witnessed this past summer.
A celebrity was backstage. A crowd had gathered. And a security guard was given instructions: Say no if they ask permission, but don't stop anyone from approaching.
What do you think happened? Did anyone get to meet the celebrity?
Here's the answer:
Only one person approached. It was a teenager. The celebrity was kind and generous, and they had a nice conversation.
Everyone else watched from a distance.
Take this to heart: So many barriers in our lives are scarecrows. They may look and feel real, but they have no actual power over us.
The only real barrier is our willingness to test them.
The next time you want something but assume you can't have it, remember that teenager. He got what he wanted — not because he was special, but because he was unafraid.
See what happens.
That's how to do one thing better.
Finally, simple bookkeeping that works!
I hate bookkeeping.
For years I let transactions pile up, panic-categorized before taxes, and paid my accountant extra to clean up the mess.
Then I tried Kick.
What surprised me most: I actually set it up the same day. Connected my accounts, answered a few questions, and it just started working. No tutorials. SO simple.
Now it just runs. Transactions are categorized automatically. Real accountants review everything. When my CPA asks for my books, they're clean. First try.
Honestly, this saved me at least 20 hours last year.
If you run a business, freelance, or do contract work, Kick has a wild tax-season offer: Sign up before March 1st and they'll do all your 2025 bookkeeping for free, plus 25% off 2026 — a deal worth over $2,000.
Use code JASON25 here: https://refer.kick.co/jason25
I don't usually promote tools, but this one genuinely fixed a problem I'd been avoiding for years. If you've been putting off your bookkeeping, this is your excuse to finally deal with it.
Final notes for today...
P.S. Remember that newsletter I wrote about regrets? I asked you all to share your regrets with me, then wrote a newsletter about the trends I'd seen. Well, fun update: We published it in the current (January) issue of Entrepreneur. So if you were one of the people who sent me an anonymous regret, you can now find your words on newsstands everywhere. :)
P.P.S. Want to create more short-form video? It's one of my goals in 2026 — and I got some really great advice about it on my podcast.
P.P.P.S. Send this newsletter to someone who needs it! Forward to them, or just send this link to today's edition.
P.P.P.P.S. Want my help in a 1:1 call? I'm on Intro, where people book my time for quick consulting calls. Let's talk!
That's all for this week! See you next Tuesday.
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