November 25, 2025 | read online

You Hate Asking for Help (But You Should Do It Anyway)

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.

You need help, but you're not asking for it.

Maybe you need an introduction, some advice, or a favor from someone in your network. You know they'd probably say yes, but something stops you. You think: "I don't want to annoy them. They're busy enough."

So you struggle alone.

Today, I'll show you why this approach is completely backward — and how asking for help actually strengthens your relationships.

But first, I'll tell you about the time I asked many people for help... and what I learned from their shocking responses.

The time I asked everyone for help

When my book came out in 2022, I faced the reality that every author dreads: I needed to activate my entire network. Could someone buy a copy? Share on social? Have me on their podcast?

This made me cringe. I love doing favors for people, but I hate asking for anything in return. I just never want to be a burden.

But I had no choice. So I reached out to acquaintances, friends, and even a bunch of famous people. Almost everybody said yes, which was gratifying and humbling.

Then something stunning happened. A bunch of people said some version of this:

"Thank you for finally asking me for something. You've been so generous in the past, and you never gave me a chance to return the favor, and I've felt awkward about it."

I was blown away.

All this time, I thought that asking for help was the burden. It never occurred to me that not asking for help was the true imposition.

But wait, why would this be?

To answer that, let's go to an unexpected place — to leap back in time, to one of the strangest controversies of the 1800s.

When people hated birthday parties

Until the mid-1800s, most people didn't celebrate their birthday. In fact, most people didn't even know their birthday.

Then a bunch of things changed all at once:

States required that children attend school, so it was important to know how old kids were.
Industrialization led to more families having money.
An influx of German immigrants started opening bakeries.

So: People knew their birthdays, had money to spend, and had access to cake. Party time!

But this was very controversial.

Traditionalists worried: If we celebrate children just for being alive, we'll teach them to become selfish narcissists — which will destroy local communities.

Here's what that fear sounded like, from a 1913 article in Ladies Home Journal:

"The children's birthday party habit not only affects the moral nature of children in various ways, and sows dangerous seeds for the future in child character and habits, but it also threatens their happiness through the danger to health which such parties involve."

But despite the concerns, many families held birthday parties anyway.

Then a surprising thing happened...

What saved the birthday party

To learn how we embraced the birthday party, I called Russel Belk at York University. He's studied this history.

He said that, yes, people worried that birthday parties would destroy community. But as the parties became more widespread, the opposite proved true: Birthday parties actually brought communities closer together.

Here's why: "There's a lingering debt in the celebration of a birthday or the exchange of gifts, which keeps the group spirit alive," he told me.

That concept felt like a revelation to me. A lingering debt.

Consider it: When Sally invites Jimmy to her birthday party, Jimmy is in debt to Sally — which he can repay by inviting her to his birthday party. And when Jimmy gets Sally a present, Sally is in debt to Jimmy — which she can repay by giving him a present.

This isn't a financial debt, per se. It is a social debt. And it lingers until the next birthday rolls around.

That's the true genius of the birthday party: It's a self-reinforcing system that cycles annually, creating an endless loop of satisfying debt and repayment. And the kids love it!

The psychology of lingering debt

This is exactly what happens when we ask for help in our adult relationships too. We create a lingering social debt — and it triggers something deep inside of us.

In psychology, this is called the reciprocity principle. When someone does something for us, we feel psychologically obligated to return the favor.

It's not just politeness; it's a fundamental human drive that helps maintain social bonds. Reciprocating is satisfying, fulfilling and affirming.

Here's evidence: Think about your strongest relationships today...

You DON'T think: "I love that person because we leave each other alone."
You DO think: "That person would do anything for me, and I'd do anything for them."

This is what creates bonds. It is the exchange of time and energy, back and forth, over and over, forming a deeper connection each time.

This is what we want. This is what we love.

So... why do we also fear it?

Why we resist asking

I have four guesses, based on what makes me uncomfortable asking for help:

We overestimate the burden. We imagine that our request will be a huge inconvenience for someone, even if it's actually quite small.
We underestimate their willingness to help. Because we're terrible at predicting others' generosity.
We fear rejection. When we ask for help, it's almost like we're testing the strength of a relationship. We're afraid to be disappointed.
We've been conditioned to be "independent." Asking for help feels like a weakness… even though it's obviously not.

But psychology and history and my own personal experiences show otherwise.

People want to help. They need to help. They are uncomfortable not helping.

So the next time you hesitate to seek help, ask yourself this first:

Have I helped the person I'm asking?
If so, do they want to help me back?
Am I being unkind by not letting them return the favor?

Then ask. For your sake, and for theirs, ask. They'll be so happy you did.

That's how to do one thing better.

Final notes for today...

P.S. Want FREE FEEDBACK on your packaging from the branding powerhouse behind Supergoop!, Allbirds, and Casper? Just register here — I'm hosting a call with Emily Heyward of the branding agency Red Antler (who worked on all those brands I mentioned), and we'll be reviewing founders' packaging.

P.P.S. Do you have an event coming up? I've keynoted for major brands like Clorox, Pfizer, Google, and Crocs — as well as smaller brands and startups, both in-person and virtually. I help teams thrive in times of change, and would love to help yours. See me in action and get in touch.

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That's all for this week! See you next Tuesday.