How Failure Can Feel Good

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:59If you have ever built something, have ever tried to build something, have ever put yourself out in any way, well, I can guess that at some point along the way, things sucked. You failed. It didn't work out the way that you wanted to. It was really frustrating, right? I mean, if that has never happened to you, then congratulations. You're the only one. For everybody else, the challenges are many. And I know that from personal experience. In fact, quite recently, I launched something. It did not work nearly the way that I wanted it to. And then I decided to do something, well, a little interesting, risky.

2:41I don't know. What I did was once I came to terms with it, once in fact, I discovered a really useful lesson and a way to reframe moments of major disappointment? Well, what I did was I shared it quite publicly with some of the people who, in one way or another, contributed to the failure. And today on Problem Solvers, I'm going to read you a version of what I wrote them, and I'm going to tell you what happened. And in the process, I hope that it helps you think about the good, the value, the insights that can come from your own disappointments and failures. And also, why maybe keeping them to yourself is not always the best thing.

3:30Coming up after the break. Welcome back to the show. I'm Jeff Fenster, and I believe experience is the most overrated prerequisite for being successful. After starting over a dozen companies, all in wildly different industries that have generated hundreds of millions of dollars, I've learned that while there are many paths to success, the formula stays about the same. Join me every Monday as I decode this formula to success with athletes like Drew Brees, entrepreneurs like Dan Fleischman, philanthropists like David Meltzer, marketers like Neil Patel, plus real estate moguls, industry influencers, A-list entertainers, or even the occasional animal whisperer like the real Tarzan.

4:07So if you want to hear what all these people have in common, then hit subscribe, get ready to take some life-changing action, and let me be the first to welcome you to the Jeff Fenster Show. All right, we're back. So today, it is just me and you talking. There's no guest. And I'm sharing this experience that I had and the lesson that I think you can take from it and that I still think about. This is going to happen in a couple different layers. The first is that I'm going to read to you my editor's letter in the January issue, the January, February, 2024 issue of Entrepreneur Magazine. On stands now, you can still get it.

4:43And the headline is, How Failure Can Feel Good. And well, let me just read it to you because you're going to learn very quickly about why things didn't work out quite as well as I wanted them to. Here we go. You want success. So why won't it just come easier? Haven't you put in the work, the time, the agony? I'll be honest, this subject is raw for me. My recent product launch flopped and I was crushed. Then I found something to pick myself back up. I want to give that to you today. Because here's the thing, you will fail at something this year. It is a certainty. Failure comes for all of us, but we will only be measured by how we respond.

5:30So here's my story. I spent all of 2023, building a newsletter about how to be more satisfied and successful at work. It is called One Thing Better, and you can get it by going to onethingbetter.email. That's a web address, onethingbetter.email. I grew it to 48 ,000 subscribers. Then in November, November of 2023, I launched a paid upgrade. After a week, 14 people paid. 14. To be clear, I adore those 14 people. They paid me because they trust me, and that is an honor. But if we are talking pure math here, 14 is less than 0.03 % of my subscribers. So as grateful as I was, I also felt a wash of panic and embarrassment.

6:22I mean, maybe I'd miscalculated. Maybe I'm just not good enough. What was going on? What was wrong? Then I thought of entrepreneurs like you. entrepreneurs like you who tell me their struggles and insecurities. I realized something. It has been a while, to be honest with you, since I had felt like a total failure. Because it had been a while since I ever launched something like that. It had been a while since I'd put myself out there in such a risky way. Which means that it had been a while since I could deeply, emotionally relate to what readers were saying and needing. That is when I thought of three words that changed this whole experience for me.

7:02And those three words were, this is useful. This failure, this failure had helped me relate more to the people that I serve. It gives me new ideas, new insights. It gives me a mission to do even better for them. I realized I was feeling, I was feeling what my readers often felt. And I needed to feel that because I can't be separate from my readers. If I am, separate from my readers, from my listeners, people like it, then what is even the point? What's the point? And so when you fail, whenever you fail, here's something that's worth asking yourself. What is this failure for? What is this failure for?

7:47Really emphasize the for. What purpose can it serve? I'm building off of this insight that I had a moment ago where the failure was useful. You have to know how it's useful. What is this failure for? Our failures, they get all twisted up with self-doubt and rumination. Were all those hours of work wasted? If I was this far off the mark, then am I fighting a losing battle? And that uncertainty, it sits inside you like a dead weight holding you down. It is painful because we are people of action. We want to keep moving and failure feels like the end of action. It feels like nothingness. But what if that weight that you are carrying around, that weight of failure, what if it is for something?

8:34What if it's actually a key designed for a specific keyhole? What if this painful stillness is not the end of action, but merely a reorientation and your failure is the tool you needed to complete your mission? Some founder friends have told me when they heard this story, I told them about the 14 people who subscribed, they said, you didn't actually fail at all because launches are hard, they told me. People need time to decide. And 14 is actually pretty fine for a new product. And it's grown since. I'll tell you more about that later. I acknowledge all this. I do. But it just goes to show, right?

9:10Failure is a matter of perspective. And I needed to fix mine. So should I be sharing this with you, this very thing, this thing about my failure. Some might argue no. They would say, it is embarrassing. You shouldn't reveal bad numbers. But here's why I did. And I'm doing it again right now. Because, well, I recently interviewed a leadership expert named Jacob Morgan. He's the author of a book called Leading with Vulnerability. And he says that we have vulnerability all wrong. Actually, you just heard him on the podcast a few weeks ago. He says, we've come to lionize it at work, assuming that vulnerability builds trust.

9:52But Jacob surveyed 14 ,000 employees and found something far more complex. Purely being vulnerable at work can cause you far more harm than good, he told me. Instead, leaders should just lead with it, lead with the vulnerability, admit weakness, and then follow it with a plan. Vulnerability creates connection, but you must also demonstrate competence, Jacob says. And this is the final lesson that I draw from this experience. Simply telling you right now that I have failed, that is unlikely to inspire you. Because what are you going to do with it? You just feel bad. So instead, I'm telling you my plan.

10:34I am using this failure. I am experimenting with my pitch. I'm interviewing my subscribers. I am working to build something that is valuable to 14 people and then 140 people and then 1 ,400 people, then more. Because that's what we do when we fail, right? People of action, we don't just sit around inactive. No, we figure it out. We try every key on every door, even when the doors stay locked. We keep trying even when it's hard. You know what? Especially when it's hard. This sounds cliche. I know all of it's so cliche, but that's because hard is hard is hard and everyone's experienced it and the best of us put it to use and live to tell the tale.

11:14So, okay, now it's back to me talking to you. That was my column and the column actually came out of something similar but longer that I had written for my newsletter. Honestly, here's the timetable here. So I launched that product in November. Originally, it was more of a second newsletter each week that was paid. And then there was going to be a monthly Zoom call. But very quickly, I heard from people who did subscribe that they weren't actually really interested in another newsletter. They love the newsletter. It comes once a week. They don't need a second newsletter each week, which was great because writing a second newsletter was exhausting me.

11:57Instead, they were really, really interested in connecting with each other. They found that the kind of person who reads my newsletter is like them and is going through some kind of work transition like them. And they were interested in connecting with me and people like them. And so it has evolved into this really interesting community offering where we now hold two calls a month and we do workshops and we have really interesting conversations and then people connect offline, starting a LinkedIn private group. Anyway, that's the product. So 14 people subscribed and I felt this wash of panic and embarrassment that day.

12:38And then I came to that realization that it was useful. The way that I found it useful, the way I came to that realization was that I had gone onto LinkedIn and I found a post about failure and I just really connected with it. And I thought to myself, boy, I really needed to hear this today. And then I stopped myself and I said, wait a second. I really needed to hear this today. That is literally word for word what people often write me when they read my work, where I'm helping them with failures or challenges or whatever. They say, I really needed to hear this today. And I realized, wow, that was when I realized, oh my gosh, I haven't had the hard experiences of my readers in quite some time.

13:17And I've taken a lot of risks in my career, but just not a big hard one lately. And that was when I realized this is useful. And once I realized that, I thought, is there some way to process this? I often think best when I'm writing or when I'm speaking, it's just kind of putting words to air, putting words to paper, just taking abstract things and trying to nail them down into something coherent that helps me think through things. So I just started writing. I just started writing the thing that ultimately became that column that I read you. I wrote it pretty fast. I think probably within an hour or two, I had it done.

13:55Then I obsessed over it for many days. I showed it to my wife. I showed it to some friends. I fussed and fussed and reworked. And eventually I decided to send it out. I actually sent it out just days after the flop of the launch. And I was pretty nervous hitting send. And I got to tell you something. The response was literally unlike anything that I have ever published in my career. So many emails came in. I mean, dozens in the first hour. People thanking me. People telling me why they didn't subscribe and what would make them subscribe. People subscribing. There was a wave of subscriptions. I went from 14 subscribers to 50 something that day.

14:45It was wild. And I really, I really linger on the way in which people wanted to help and the way in which people felt helped in that moment. You know, when I published that thing, that newsletter, a lot of people, I mean, I didn't ask people to do this. A lot of people, they wrote and they gave me advice on what about my initial launch pitch worked for them or didn't work for them or why they were thinking about it or where their hesitation was. They were trying to use themselves as a case study for how I could win people over. It was a really generous thing to do. I read through everything. I saved all those emails.

15:27I thought a lot about them. And then I was also so grateful. I mean, I'm grateful for the 14 people who originally subscribed. Those are the people who had the most faith in me. It is incredible. It should never be overlooked. But also just a tremendous, I felt a tremendous thanks to the people who saw me open myself up there and said, that is something that I need to support. That is something I need to be a part of. And as I process it now, I think it really does come back to that thing that Jacob Morgan was saying about leading with vulnerability. I didn't just say I failed. I gave people a way to help themselves through my own experience.

16:09I showed them that I was marching forward, that this wasn't something that was holding me back. That's what it means to really share, to really show the hard stuff. Because look, we're all going to go through that. The reason that you have made it this far in this episode is because you have gone through something like this. You relate to it. And here's the thing. Everybody does. Everybody relates to that stuff. Everybody relates to whatever the challenges that you are going through right now. They do. Maybe not the very specific, hyper specific, whatever it is that you're going through, but the broad strokes of it, the challenges, the anxieties, the this didn't work out, the I thought it would be better, the things that color in the shape of this experience for you, people know what that's like.

16:58I assure you, they know. And when you're open about it, and you lead with it, and you show them where you're going, and you still want to help them, they will follow you because they want to be a part of that journey. That's what I learned. And as a result, I'm building something pretty great. These days, there are about 100-something members. We're a couple months in. I've really refined the product, but there's still a lot more to do. And every day, I'm talking to those members, and I'm creating things for them. And it's just an absolute blast. You got to get through those hard early days. I'm sure a year from now, I'll think of this time right now is part of those hard early days.

17:43But you know, it's a lot better than that first day, that first day of disappointment. And that's the most we can do, right? Every day, just a little bit better. And that's our episode. I would love to hear what you think, and maybe even about a problem that you solved. You can find me at my website, jasonfeifer.com. J-A-S-O-N-F-E-I-F-E-R.com. Also, I have some more useful stuff for you. I write a newsletter about how to future-proof yourself and become more adaptable and optimistic. I would love for you to sign up. It is at jasonpfeiffer.bulletin.com. Also, check out my other podcast. It's called Build for Tomorrow.

18:22In each episode, I take on some belief that we have that holds us back from progress and show you why it is not as bad as you think. Problem Solvers is a production of Entrepreneur Media and comes out every Monday morning, so make sure you're subscribed so you don't miss an episode. Thanks to Deepa Shah for production. My name is Jason Pfeiffer. See you next week.