“You don’t have to be failure-proof. That’s not a thing.”
These wise words belong to my friend Kristen Kalp. I recite them frequently.
I recite these words anytime I happen upon those ‘income reports’ people share these days. How do YOU feel when you discover that someone who’s younger than you, less experienced than you, who’s been online half as long as you have is earning more in two months than you earn all year?
I usually alternate between
a) eating two bags of pizza rolls
b) telling myself that I’m somehow ‘above’ those marketing tactics (I’m not)
c) closing my laptop and asking my pets to give me pep talks
By now we know that comparison is the thief of joy. So in the spirit of transparency, vulnerability, and keeping ish real, I invited seven of my favorite internet people to join me in sharing some of their biggest failures – including but not limited to: an event that lead to $43,000 of debt, a course that only sold four seats, and what happens when your dream client/professional idol fires you after three weeks.
My failure:
Four years ago I re-launched my Post College Survival Kit ecourse. I called in every internet favor I had, running a huuuuuge blog crawl, featuring tons of big-name bloggers and creating a beautiful, free ebook that tied into the topic of the course. More than 11,000 people downloaded that free ebook and do you know how many people bought the course? 4. FOUR.
Why? Because I didn’t ask people to give me their email address in exchange for a beautifully designed, 62-page ebook. I didn’t want to create a sales funnel. I didn’t want to send more than one email reminding people the course was closing. So only four people bought it.
What I learned:
Just because you don’t like something doesn’t mean you can ignore it. There’s a reason people create sales funnels and email interested customers more than once. BECAUSE THAT ISH WORKS. If you created something you’re proud of and you know it will help people, you owe it to yourself and your customers to make it easy for them to buy it.
Hillary Weiss // copy writier + ghost writer + writer writer
My failure:
About 6 months into my business, I reeled in a huge dream client. Like had-been-following-her-for-years-and-bought-all-her-books massive. I couldn’t believe my luck. I couldn’t believe how much my palms were sweating when we spoke on the phone. I couldn’t believe she’d chosen me and believed in me enough to invite me onto her team.
I could have sworn I was too wet-behind-the-ears to take on the role. The writer who’d gone before me had 10 years under her belt, and I was still sitting in my underwear at 2 AM pounding out taglines. And it turned out… I was too wet-behind-the-ears.
I barely lasted 3 weeks on the team before I got the boot. I didn’t speak the lingo, I had too many questions, and I was too slow on projects. I fumbled the ball, once, twice, and I was gone. I can’t tell you how humiliating it is to both gain and lose a dream job in less than a month, because I screwed it up. No one was to blame but me.
What I learned:
After the overwhelming feelings of self-loathing subsided, I brushed myself off, and swore it wouldn’t happen again. I’d been given a golden opportunity too soon, and managed to screw it up, but it wasn’t the end of the world.
Mistakes meant I was learning, and I was ready to keep working, and keep honing my craft, and keep and putting great work out into the world. And if the chance ever came around again to prove myself? I’d be ready.
I also learned I couldn’t judge my self-worth by who I was working with. Ego was no longer allowed to enter my work.
Every single client I collaborate with deserves to have top notch experiences, and the highest quality deliverables, every time. So it became my primary focus – and help me build a business roster 200 clients strong and counting.
Kyla Roma // business coach + marketing strategist
My failure:
One of the first collaborations I worked on was based on the idea that we would pool our profits and expenses. I was less experienced, so we agreed to split everything 70% / 30%. I looked at her accounting from the past years and on paper, it looked great. She was making a great living that I would help expand. I would earn a starting salary for a year and then we’d renegotiate.
But as we got started and sales rolled in, she said that most of it didn’t count as part of our agreement because the sales were part of a separate online course. It turned out that the online course I didn’t get a cut of made up 75% of the revenue she’d made the year before, and if I’d been looking at her accounting without that, my decision would have been much different.
I realized I had agreed to give away 70% of every dollar I earned and I would need to leave or renegotiate. That simple agreement I’d made became complicated – fast.
What I learned:
You don’t know what you don’t know. I had never had to look through someone’s accounting before so I didn’t know what to look for, how important the different streams of revenue were, or to ask what other sources might be supporting the business.
As a new business owner, I was so excited to feel chosen by a collaborator and to have a business friend that I agreed to a contract put me at a disadvantage.
The whole situation helped me see that I needed to work on valuing myself and my skills. I learned that simple, percentage based agreements are usually only simple because they’re incomplete, and that being direct about what you need can be uncomfortable but it’s always worthwhile.
Kathleen Shannon // podcast host + personal branding expert
My failure:
Three or four years ago a blog buddy and creative colleague of mine suggested we put on a branding + online business workshop together. We put together a brand, an offering, and a modest marketing plan for our event. We launched with gusto and after only getting one sign-up we had to cancel the workshop that never was.
Why did this little workshop that never was fail? I’ve learned so much about marketing, launching with a blend of soft and hard sells, and leveraging an email list (I don’t even think I had a list back then) since then that I could point to a lot of tactical reasons why it failed. But to be completely honest: I think the project itself knew it wasn’t fully realized and the timing was all wrong.
What I learned:
Three years later I teamed up with that same blog-buddy-turned-business-bestie to launch what is now known as the Being Boss podcast.
We’ve sold out two events that we call “boss vacations” (in New Orleans and Miami) and decided to take the vibe of our offline events online in our Being Boss Clubhouse. Our podcast has had over 1.25 million downloads and everything about it feels like a dream.
What I learned is that you have to keep working through the failed projects and know that it’s not the end of your entire creative career or a statement on your worth as a creative professional. Those very projects might even come back around even bigger and better than you could’ve imagined!
My failure:
I created a real-life summer camp for 125 entrepreneurial peeps in the Pocono Mountains of Pennsylvania in 2014, and when all was said and done I had lost about $43,000. (You know, nothing major, just more than my salary from the teaching job I’d left a few years before.)
What I learned:
Sometimes, your best and worst moments will be linked. The actual days at camp were some of the best of my life, and there’s nothing like seeing a dream you’ve had (sunrise ferris wheel in the middle of the mountains? YES!?) come to life. Just because something costs you financially doesn’t mean it doesn’t pay dividends in joy, purpose, meaning, and the full-on pursuit of being alive. (Also: you don’t have to be failure-proof. That’s not a thing.)
My failure:
I started two software companies before my current one. Both crashed and burned hard: one, an eco-ad network, had zero customers and the other, customer service software for car dealerships, had one client – for exactly one month. Both companies were started with very smart cofounders too, who did and have gone on to do very amazing things.
What went wrong? In both cases we thought it was a good idea to work in secret for 6-7 months on our product before letting anyone know about it.
What I learned:
A lot of marketing happens during the product creation phase. You have to let people know what you’re building, why, and why they should care. Give them behind the scenes info, which lets them feel a little bit of ownership in what you’re making. You can also do useful things like pre-sell/pre-order, find beta testers, find people to get testimonials from, etc.
Start talking to the people who would benefit from what you’re making before you’re ready to sell to them.
My failure:
Chocolate & Zucchini was well established when Pinterest started to become popular in 2011, so I was in a prime position to join the platform as an early adopter with lots of quality content.
But I completely ignored it. It didn’t speak to me as a user, and I shrugged it off. By the time I realized other food bloggers were getting tons of traction from it, the platform was super crowded, and my window of opportunity had closed.
What I learned:
Life happens. 2011 is the year I got pregnant with my first son, and I entered a four-year blur of exhaustion and overwhelm until my second son went into daycare. It was hard enough to keep up with my blog and other freelance opportunities then, I wasn’t in a place of growth for my business (but I was for my family!). It’s fine to miss a boat every now and then; there will be plenty more boats!
My failure:
Years ago, I dreamed up a spicy new program to bring more bliss into women’s lives. In a ten-day giveaway called The Bliss Scandal, I gave away way too much money in chocolates, champagne, books, and vibrators (oh yes I did). I had a blast, and thousands of women got scandalously blissed. But when I offered the deluxe Bliss Conspiracy coaching package at the end…it TANKED.
What I learned:
People will pay more to fix a painful problem than to feel happier. This makes me crazy. Why do we wait until it’s horrible? Why? (Because humans.)
It’s a key thing to understand about your clients. It’s not enough to know what they need— you have to figure out what they THINK they need, give them that, and ALSO give them the deeper thing that will truly help. You’re basically pulling off a benevolent covert op.
But I want to hear from you, brave souls. Are you willing to share one of your professional failures with us? You can even post anonymously if you’d like!
P.S. What you’re really seeing when you see “success” + Surprise! Absolutely no one has it all figured out
Thanks for including me, Sarah! I’ve never been so pleased to have my shortcomings highlighted 😉
Thank you for sharing these experiences, Sarah (and thanks to the honesty of the people who also shared, many of whom whose work I admire!). Like many people who have been around on the internet for quite a while, I’ve been too early to the party and moved on, ignored a service because it didn’t speak to me, and missed capturing massive traffic to my business site because I wasn’t paying attention to Google Analytics! At the same time, I pursued other (usually offline) opportunities that had their own benefits! This is a nice reminder that it’s important to take the long view and those “missed” opportunities probably just weren’t *my* opportunities and that’s okay too! As long as we learn from whatever it is we do invest time in, it’s worth it. 🙂
I recently wrote an article about my failure as an entrepreneur. Thanks for sharing all these stories!
https://mom.me/kids/33715-my-husband-gave-me-15000-start-business-and-i-failed/
I’m so surprised there aren’t more comments on this. I have “failed” so many times!
I was among the top of my high school class and killed myself taking difficult classes and juggling leadership roles in different clubs. I still didn’t get into my first choice college. I got into a choice further down the list and ending up growing more than I think I would have at the first school.
I nearly failed calculus 2 during my first semester of college as an engineering major. I got C’s in most of my math and science classes. It stung my pride, but I stayed with it and ended up with an engineering degree.
I applied for over a hundred internships and paid research opportunities and was rejected from every single one – after freshman, sophomore, and junior years of college. Now I’m in a leadership development program with an international company where the goal is to get me and the others in my cohort into board-level positions as quickly as possible. I’m moving to Switzerland in 3 weeks for the next stage of this job.
I was the slowest runner on my high school track team (no tryouts, no cuts). I loved running though, so I joined the club running team (also no tryouts/cuts) in college where I was also one of the slowest. To date, I’ve run 3 marathons and 7 half marathons.
Literally everything good in my life has come after a period of feeling uncertain and deflated in that realm. It’s SOO important to talk about this!!!