Ever had an “oh sh*t!” moment in your business?

Here’s how to fix your mistakes and capitalize on them

When you’re building your online empire, slipups are bound to happen. You make a typo, send out a broken link, publicize the wrong date. 

Every entrepreneur knows that familiar feeling when you realize hundreds or thousands of people have seen something you never intended. 

Your heart sinks. You wish that time machines existed, if only to right this one wrong. While some suffer in silence, letting their anxiety run wild, others find themselves running down the hallway, muttering, “I did a bad thing. I did a bad thing.”

That’s what Tara Sota once did. As an inventor of a vaginal dilator, Tara had switched gears to help her business partner on a completely different product: custom golf cart mats. But she accidentally emailed 7,500 golf enthusiasts a link to the vaginal dilator website. Although Tara can look back and laugh about it now, she says it was, “by far, the biggest blunder (she’s) had.” 

Tara’s is one of many entrepreneur war stories we’ve gathered valuable lessons from. Recovering gracefully from your “oh sh*t!” moments doesn’t have to be as painful as it seems. 

Here are some creative ways to not only acknowledge your mistakes to your audience, but also use them to your advantage.

6 strategic ways to resolve silly mistakes

1. The “oops!” email

By far the most common way businesses apologize, email gives owners a chance to explain themselves and send the right information.

Most entrepreneurs agree that a simple apology can help humanize your brand. By admitting that you made a mistake, you’re showing your customers that you care.

Also, people are more likely to open the email if they see “oops” in the subject line. Entrepreneurs we interviewed reported open rates as high as 80% on their correction emails.

Scott Vogel of The Marketing Solution Institute and Be a Video Pro once conducted a postcard marketing campaign for his client, one of the top hotel brands in the world. The goal was to build an email list by driving offline traffic to an online offer. New subscribers, who were tracked demographically and psychographically, received an email certificate for a free steak dinner at the hotel’s high-end restaurant.

Everything was set when Scott had gone out of town to speak at a conference — or at least he’d thought it was. He soon discovered he had put the wrong date for the dinner: July 12 instead of July 11.

He replied quickly and explained, clarifying the marketing agency made the mistake, not the hotel. But perhaps the response went out too hastily. This time, the correction email had listed the wrong time.

“Holy crap and yikes!” he remembers.

So once again, he wrote a third email with the subject line, “Oops again” and admitted he was at fault. Interestingly, more people opened the two correction emails than the original email.

Ultimately, the steak dinner was successful. The campaign worked out profitably for the hotel, and the agency continued working with the hotel. Although Scott tries to block those email errors from his memory, he’s learned his lesson: “Always, always, always test everything. And then test again. That's why I love Kajabi's test email feature — no goofs.”

If you’re wondering what to say in a correction email aside, think about what sounds natural for your brand. Feel free to be lighthearted and show that you have something in common with the recipient.

Carina Glover is the founder of HerHeadquarters, a brand partnership app for women entrepreneurs. She introduces her oops message with lines like, “Don't you hate when that happens?” or in some cases, a more playful approach: “You know, I broke my streak. I was 60 days clean.”

2. Think on your toes, live

Maggie Giele, a business and marketing strategist, remembers filming her first live video. She was sitting on the floor of her living room with her phone propped up. Starting out with shaky hands, Maggie eventually settled in and found her groove. Ten minutes into the livestream, she realized the view behind her didn’t exactly convey a professional setting: a dining table full of empty beer bottles. She had thrown a party the night before.

“The moment I noticed the beer bottles, I had such an “OH F@!$" moment,” Maggie said. “My mind flew through the options of what I could say next. I decided to laugh at it. I said, ‘Well, I guess you all saw those bottles, too? Nope, I'm not an alcoholic, but we had a great time with some friends last night!’ And then I carried on.” 

Now Maggie uses that story to advise her clients. She tells them that things will go wrong on live video, and they’ll figure out a way to get through it.

“In scenarios like this, where it's personally embarrassing (I had a total fight-or-flight moment), there's not much you can do,” she said. You can either stammer through an awkward apology or laugh at yourself.

3. Meme it up

Sometimes, words escape you. You might feel so mortified by the mistake that only a meme can capture your message. A simple visual with a caption, if done right, can give your audience something to giggle about, inevitably cutting you some slack.

Liz Wilcox, an email marketing and launch strategy copywriter, presented at a virtual summit recently and offered a substantial freebie for new email subscribers. The event was a hit. In 48 hours, over 450 people had subscribed.

But Liz knew something was wrong when she started getting pinged with Facebook notifications and emails from subscribers. People weren’t getting their freebies. Meanwhile, her existing customers had become subscribed twice, which meant they were getting duplicate emails. Something had gone wrong with her email system. 

While any other type of business could easily explain a technical glitch, the mistake was especially painful for Liz, who had just taught hundreds of attendees about the very topic that had gone wrong.

“So here I am talking about email marketing and they’ve just learned all these fantastic things — and my ConvertKit was on the fritz,” she said.

So Liz made this meme as she recreated her email sequence from scratch:

The meme helped Liz explain the mistake in her own offbeat way. 

“It was actually kind of on brand for me because I always tell people I'm only semiprofessional here,” she said jokingly. 

For other entrepreneurs going through an oops moment, she says, “Just have fun with it and don't overthink it. People will see your vulnerability and your humanity. And it's going to make them actually love you even more.”

4. Give a discount … and make yourself the butt of the joke

Drizly, known as the "Amazon for liquor,” is an alcohol e-commerce platform operating in over 100 markets across the United States and Canada. In a recent email malfunction, Drizly butchered its personalization attempts in multiple places. 

The subject line read: “I can’t wait to drink {alcohol} delivered by {company}!!!” 

And the email started, “Let’s get this party started, {name}”

It gets worse. In the body of the email, where Drizly intended to list personalized product recommendations, subscribers got dummy text “Lorem Ipsum” text with prices listed as $XX.XX. Oh the horror. 

Here’s the email that Drizly sent afterward:

In this case, Drizly went above and beyond the simple apology email. 

Who could read their oops email and not chuckle? The “lol, wtf was that” subject line worked well for the alcohol brand and its customers. And for an extra bit of good will, they offered a perk with one last self-deprecating jab in the promo code: LOREMIPSUM.

5. Make a contest out of it

If your budget doesn’t have room for discounts or perks that can benefit all of your customers, you can still engage them with a sweepstakes contest.  

When the San Francisco chapter of the American Marketing Association made a typo in an email, they followed up with the subject line, “Oops … Catch our typo for a chance to win (2) tickets to our SUMMER PARTAY!”

The email read:

We made a boo-boo, and we are willing to pay for it. 

We misspelled a word in yesterday’s email and now we have to live in shame forever (or at least until this weekend).

The first two spelling enthusiasts that email us at info@*****.org and tell us what the mistake was will get two complimentary tickets to our AMA SF Summer Partay on July 31st.

But even if you don’t win, you can still attend this fun event. Get your tickets here.

See how short and simple your followup email can be? Notice how AMA used the last line to promote their event one last time without being pushy.

6. Celebrate your slipup with social media and experiential events

Billboard typos are glaringly obvious — perhaps more so than email typos. A phone services company, Visible, discovered that the hard way when they launched a series of billboards across Denver, CO offering “unlimited massages, minutes, and data.” 

Massages, not messages — a mistake that sends chills down every proofreader’s spine.

Initially, the typo attracted some good-natured Twitter trolling and some LMFAOs.

Amid the social chatter, including a tweet from a local CBS anchor, Visible decided to seize the moment and keep the jokes coming. According to Chief Marketer, the phone services company followed up with social quips like, ”oh cram (instead of crap) we messed up,” and “Hey we are a phone service that we think you are going to really knead (instead of need).”

Responding to a tweet with harsh hashtags targeting the copywriter, Visible used the thread as a recruiting opportunity.

Topping all corporate responses ever made to address a typo, Visible kept their word on the free massages. The phone services company held a one-day event in Denver offering free massages, no strings attached. To sweeten the deal, they offered free kombucha, eye masks, and essential oil bracelets. And of course, a place to charge your phone during the massage.

The wisdom of failure

Every blunder comes with a painful aftermath. But if you allow yourself some time to reflect on the situation, you’ll end up a savvier, more resilient entrepreneur. Here are a couple of lessons our brave entrepreneurs shared:

Don’t work while exhausted

HerHeadquarters founder Carina Glover once sent an email to a potential investor, referring to her company as “HerHeadache.” At the time, she’d been trying to work through a horrible headache. Carina immediately caught the mistake in the split second her email was going out. A moment later, she received a notification that the investor had opened the message.

“That just crushed me a little more,” she remembers.

But Carina thought quickly and explained in her apology email, “I'm a great founder and I work hard, even through headaches.”

She realized that trying to proofread her own work while exhausted had been working against her. You could easily make the mistake of relying on your memory instead of reading the line in front of you. 

“My perspective has always been ‘No excuses. I get it done,’” Carina said. “But that also doesn't mean I have to neglect myself. Now I take breaks when I need it.”

Forgive yourself 

When Jenn Robbins accidentally sent out a Frankenstein email with bits and pieces of three different emails stitched together, she initially worried about the impression it would leave on prospective clients. Jenn is a copywriter who specializes in funnels and she imagined prospects thinking, “She can’t even schedule her own emails correctly.” 

But in the end, a quick apology email did the trick. She forgave herself and moved on.

After all, failures are inherent in entrepreneurship.

Albert Einstein once said, “Anyone who has never made a mistake has never tried anything new.”
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