When We Fail, We Win: 7-Figure Entrepreneurs Share Their Biggest Mistakes

I’m a 7-figure entrepreneur, but that doesn’t mean I’ve never made mistakes along the way. Quite the opposite!

In fact, I’ve made quite a few “what was I thinking?” and “why did I do that?” costly mistakes.

Like the time I spent thousands of dollars to plan and market a live event… only to cancel it three months out due to lack of interest. Ouch.

I learned then that it doesn’t matter how many hundreds of people say they’re “definitely” coming to your event — never pay or plan for anything until you’ve got a financial commitment from them first.

Pre-sell, then plan.

An ugly trend in online business

Why share one of the biggest mistakes I’ve made as a business owner with the entire Internet?

Because there’s an ugly trend in online business lately. All over my Facebook feed from the same people, it’s nonstop accomplishments, media mentions, and dozens of fancy photos. It doesn’t seem real.

And that’s because it’s not. What’s shared just isn’t the whole story — or even the everyday reality.

I know if I make mistakes or struggle to even get out of bed some days, it’s likely that other entrepreneurs experience the same thing. So why don’t more of us talk about it?

After all, we were all human beings long before any of us became entrepreneurs.

I call this “positivity-only propensity” an ugly trend because the experience of human entrepreneurship includes so much more than what happens when we’re feeling our best. It includes all the “bad” stuff too — our failures, mistakes, do-overs — and sharing the lessons we learned along the way.

That’s the stuff that fans and subscribers want to see. They want to know what real life is like after you’ve risen to the top. They want to see that the “human” part doesn’t change when your small business makes it “big.”

Most of all, it gives them hope.

So after years of witnessing this ugly trend — and feeling some serious pressure to follow the trend myself as I grew my own business to 7 figures and beyond — I finally had enough. I went on the hunt for other high-earning entrepreneurs who’d be willing to speak candidly about their biggest mistakes. I wasn’t surprised when many enthusiastically agreed to share.

In my research, I noticed some interesting recurring themes among the folks mentioned below — along with plenty of annoying validation of the very trend I’d set out to challenge.

Let’s dig in.

We’re overdoing the DIY!

When you start out in any online business, it usually starts as a team of ONE: you.

And you get used to it.

Overdoing the DIY and not recognizing when it’s time to bring on help was a recurring theme I found in chatting with other 7-figure earners in the blogosphere.

Michelle Schroeder-Gardner, for example, runs the $100k/month personal finance blog, Making Sense of Cents. When asked about her biggest mistake, she said, “For the longest time, I ran my business all on my own with very minimal outside help.”

Now, that might not sound like such a big mistake on the outset. Boo hoo; right? You make $100k a month but don’t need anyone else to help. What’s the problem?

But here’s the thing: Schroeder-Gardner travels full-time in an RV with her husband and two dogs — and that means having almost no help with her business made it extra difficult to fully enjoy the freedom on the open road… which is kind of the point of RVing. Who cares how much money you make if you don’t have time to enjoy it? That’s the problem.

Realizing she needed help was a game-changer for Schroeder-Gardner. Now she’s outsourcing daily tasks, and things are looking up. “Recently, I’ve been hiring out editing, replying to emails, and several things I used to do every morning,” she adds.

I asked her if she was glad she made the mistake, and she added, “Yes; I’m glad I made this mistake because I’ve become very good at what I do. Now I know the true value of outsourcing and how it can completely transform not just my business but my life!”

Talk about a lesson well learned.

Afraid of letting go? We’ve been there.

When my first blog (Proofread Anywhere) was just getting started back in 2014, I was a one-woman show much like Michelle Schroeder-Gardner.

You definitely do learn a lot more doing it all yourself, especially at first. All the ins and outs of WordPress, how to solve customer tech issues — I still have to pitch in on tech issues from time to time. I built the site from scratch, which means if there’s anyone who knows how all those pesky plugins fit together, it’s me!

Still, it was difficult to “let go” when I realized I had to give up the control if I wanted to continue growing — and if I wanted to gain back some of my freedom.

You could say I went into it kicking and screaming; I was terrified something would go wrong if I didn’t do it all myself.

Anton Kraly, CEO of Dropship Lifestyle, had a similar experience. He felt like he needed to carry all the customer service on his own plate — despite being spread thin over the other aspects of his business. All the while, the need for more help with the customer service side of his business continued to grow.

Finally, Kraly decided to get the help he needed: “Outsourcing customer service was something I held off on doing for far too long in my eCommerce business. I thought that no one knew my customers better than me and that outsourcing this would destroy my business… I couldn’t have been more wrong.”

Making the switch to remove himself from the day-to-day customer service experience helped Kraly dive into more important areas of business growth and gave him more everyday flexibility.

It’s not just about time

It’s not just time we gain back when we bring on help to manage our businesses.

We also reclaim mental energy — and mental energy is exactly what we need to continue scaling up. If we’re using the best part of our days to complete the miscellaneous small tasks in the business, we’ll have less mental energy to conjure up new stuff. And the new stuff? That’s growth!

In the case of Proofread Anywhere, if I’d continued to “man the ship” all by myself, I never would’ve had the mental energy to dream up new products and ideas that would continue to grow my business into the multi 7-figure zone. Thanks to the team I’ve [slowly!] put in place, I get to focus on our company‘s big ideas and goals.

Being everyone’s tech support just isn’t the best use of my brain!

Sometimes we undervalue ourselves

Kyle Brost started out mowing lawns, importing goods from Mexico, and commercial carpet cleaning. He’s now an author, speaker, and corporate strategy consultant who’s learned an excellent lesson on valuing our own work.

“As a brand-new business owner, I once walked into a sales meeting and handed a quote to the decision maker that was 60% of the market rate for my services. The owner said, ‘I don’t want you to charge me so little that you can’t do a good job.’ I never got their business,” Brost said.

This mistake taught Brost a lesson about undervaluing his services. “Through that mistake, I learned that value can matter a lot more than pricing. I’ve never undervalued myself or my teams since.”

Valuing ourselves carries over into offer pricing as well. In pricing my online courses at Proofread Anywhere — which teach people skills they can use to make money — value played a major role.

I receive emails on a regular basis from people upset that my courses cost a “small fortune” in their book. I explain many of my students earn back their course fee in the first few months of work after completing the course — and they go on earning infinitely after that.

When you invest in something that can help you earn money on an ongoing basis, that isn’t a cost; it’s an investment.

It’s about what your product can do for the customer and how much that’s worth to them. In effect, I’ve found that most people will pay $500 for access to a course that will help them earn a lot more than $500 over the course of their working lives.

The biggest mistake is being afraid of sharing your mistakes

Being afraid to outsource was a clear recurring theme among the 7-figure earners I spoke with, and it’s been a theme in my own business.

Undervaluing ourselves and our products came up often as well.

Yet a big handful of 7-figure entrepreneurs who wrote in to share about their “mistakes” sent in vague, fluffy answers that frankly, stank of veiled self-promotion.

It was icky.

Which made me think… what if the biggest mistake a 7-figure business owner can make is being afraid of sharing mistakes?

Maybe you think other people knowing you made mistakes would damage your credibility.

Maybe you think it’ll cost you sales.

Maybe you think you’ll get less media attention if you really come clean on exactly how you screwed up your last product launch.

Here’s the thing: Mistakes don’t damage your credibility; they validate your success and make you relatable. Your mistakes tell others “I made this mistake, but I’m still here. I’m not perfect, but I did it. So can you!”

If you’ve reached the fabled 7-figure mark in your business, other people want to know about your mistakes! The media will want to interview you on what you learned by screwing up your last launch. There are enough people yammering on a hour-by-hour basis about their accolades; it’s way more interesting to learn about what NOT to do.

Not being afraid to share your mistakes also indicates you’re a genuine and caring human — you may be at Step 581, but you haven’t forgotten what it was like to be at Step 1, so you use the valuable lessons you learned from making mistakes to teach others.