As an entrepreneur, it took me some time to embrace failure. I remember not so long ago talking with a friend about how I had failed at something and her rush to reassure me: “You didn’t fail!” She went on to tell me a number of reasons why it wasn’t a failure. Like failure was somehow a black mark I couldn’t possibly bear.
But these days, I hold failure close. I study it. Learn from it. Embrace its teachings and try to do things differently the next time. Because isn’t failure our greatest teacher? Can we even recognize our best moments without our worst?
This week, I’m sharing five lessons I’ve learned on my long, winding road of failures. Because, after all, I can’t make it to nearly thirteen years in business without some big and small snafus along the way.
1. When it doesn’t work, know when to redirect or quit.
This is probably the hardest lesson to master, because when does one actually know when something is never going to work or might eventually work with enough time and effort?
I’ve learned this lesson a lot of times over, but perhaps the greatest lesson was when I started my business back in 2009. Back then, I dreamed of being a freelance travel writer, but it became clear quickly that such a path was going to be difficult financially. When I made almost no money my first few years in business, and after significant fruitless efforts (working hours a day alongside a full-time job with nothing but exposure to show for it), I started paying attention to what might work instead. As a result of my travel writing efforts, I got an opportunity with a publisher, redirected my efforts into the world of nonfiction books . . . and here I am today.
For a fantastic read on when to keep at it or when to quit, read Seth Godin’s The Dip.
2. Be willing to go all out for your dreams.
Now nearly thirteen years in, I’ve also seen the power of how hard work pays off, but only after time and follow-through. A great example of this, again, is my business. It took me years to find a business model that was sustainable and fulfilling and hit the six-figure mark. It also took me years to realize that the way I was running my business was not personally sustainable . . . like, for example, working at 10 p.m. on a Saturday when I was seven months pregnant.
Or when a client had a major business disruption that ended a contract early, only a couple of months before my second child was born, causing me to effectively lose 60 percent of my revenue overnight.
Or when medical bills started stacking up when my kids were tiny, causing our already-tight budget to be stretched even thinner, and the medical hardships taxed both my spirit and finances. A clear answer could have been a j-o-b with benefits. But I believed in the long-term ROI of sticking with my business—both for financial and personal reasons—and stuck with it.
Or when we had some truly terrible (and truly wonderful) experiences in Thailand that could have derailed our dreams of living abroad entirely, but instead we redirected our energy and tried again. Thank goodness we tried again.
I could have easily called it quits many times along the way, but the fire within me to be my own boss, do life my own way, and leave my mark on this world was too strong to squelch. Today, I’m living my dream running a location independent business in Portugal. Yes, it was worth doubling down. So worth it.
3. Sometimes you have to dust yourself off, get back on that horse, and ride.
Years ago, I launched a retreat focused on helping leaders make the transition from success to influence. It was a several-day event focused on vision-building and strategy development for people who felt something within them they couldn’t quite pinpoint—a desire to make an impact on the world. They’d made it to a height of success in their fields and were looking around asking: “Now what?”
Conceptually, strategically, and tactically, it was strong. I booked a beautiful resort in California and put down a fat deposit. I began marketing, hopeful that my idea would resonate. And then . . . crickets. Nada. Nil. Not one person signed up.
Eventually, I had to pay the hotel another chunk of change to cancel the reservation, go to the team who had invested their time and energy into supporting my idea, and let my network know it wasn’t happening anymore.
This was a tail-between-legs moment if I’d ever had one.
I’d had a big idea and I’d gone all in. I’d traveled to multiple US states to find the right location. I’d taken time away from my family and business to plan this new thing I believed in. I’d put money on the line. I’d involved people I respect to help make it happen. I’d told everyone I was doing this thing . . . and then not too long after, I just . . . wasn’t?
But as hard as pulling the plug on my idea was, it also made me stronger. I learned about marketing. I learned that vision isn’t everything—you need to be able to clearly communicate that vision and pull people into your ideas. I learned that I had more agency over the direction of my business than I previously thought—I didn’t need to wait for others to create opportunities for me. I could create opportunities for myself.
I got back on the horse and rode on, building the business I have today. And yes, I successfully launched a multiday event years later.
There are many more lessons I could detail from my many failures. A lifetime of them. And I know I’ll continue taking big risks and learning big lessons along the way.
How about you? What is one failure you’ve experienced and what lesson did you learn? Share with me in the comments. I love learning from you.
Stacy, I remember a conversation on this topic with you a few years ago. It was a good and honest chat!
Whatever you call it and however you view it (Failure. Opportunity. Teaching moment. Time to pivot. Retrospect. Foreshadowing), all that really matters is that we sit with that moment/event long enough to recognize that we made a decision that landed us in that space and that we can (and must) make another one, and another one, and another one.
As Helen always said, “You make a decision, and then you make another. That’s living.”
You’ve made some spectacular decisions along the way, and you’ve definitely learned how to sit in the moment, absorb the implications, and make the next decision. Hats off to you! JW
Jennifer, I love everything about this comment but especially this line: “all that really matters is that we sit with that moment/event long enough to recognize that we made a decision that landed us in that space and that we can (and must) make another one, and another one, and another one.” This may make it onto a sticky note that lives on my monitor someday. 🙂 Thank you for your continued mentorship and friendship on my journey. I’m grateful for you!