297: How to Create a Failure Resume
8 Dec 2025 · 28 min
Jenny Blake explains how to build a failure resume: a list of setbacks that taught you something. She shares her own rejections from college, leaving seminary, and a failed meditation app to show how perceived failures become stepping stones during career changes.
Chapters
When the holidays start to feel a bit repetitive, reach for a Sprite Winter Spiced Cranberry and put your twist on tradition. A bold cranberry and Winter spice Flavor Fusion Sprite Winter Spice Cranberry is a refreshing way to shake things up this sipping season, and only for a limited time. Sprite Obey your thirst. Of course people are gonna ask for your resume. They're gonna see what you've done, and it feels nerve wracking to feel like you make a mistake. If you have an interim pivot that isn't really where you want to end up, or you end up on some toxic team or work culture and you need to leave again quickly. It stings when that kind of stuff happens, but for me, at the end of the day, the biggest failure is not trying. So I encourage you to determine what your values are around risk and failure and really understand at this current pivot point that you might be at or pivot in progress, what failures are acceptable to you and which ones are not. What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot Podcast and author of the only move that matters is your next one.
For show notes from this episode, visit pivotmethod.com podcast if Change is the only constant, then let's get better at it. Here we go.
Hello friends. Welcome back. Today I'm building on Last week's episode 296 Top three do's and don'ts when leaving a corporate job. As I was reflecting, what else could I add? What else am I missing? It occurred to me that it would also be a good idea to create a failure resume. Whether you're leaving a job, you're in the midst of transition, or at any point in your career, these have a long history over the last few years. This also came to mind after I recorded freetime episode 112 on My Three Biggest Business Regrets and 114 failure is the frame, not the picture. That's an image that I saw that reminded me not to gauge failure too soon. I'm really intentional about when I use the word failure, and eternal optimist that I am, I don't use it very much. If you've read Pivot recently, you know that the entire chapter 11 is called flip. What will move you into action? I open with this message that was tacked to a tree at a temple called Wat Umung in Thailand. It's a 700 year old temple and this sign the monks wrote Handwritten signs that were taped or tacked to trees all around the property. This one made me laugh so much it said, cut yourself some slack. Remember, 100 years from now, all new people As I open chapter 11, I say that it is impossible to talk about pivoting without addressing the fear of failure. We all have it. It's normal, I write. I'm an optimistic realist. As a business and career coach, I don't insult my clients by pretending their fears are not real or that they can move past them with simple affirmations and positive thinking. I have experienced years of wading knee deep in my own doubts. So when they tell me their fears, I reply with, yep, those things might happen. And then I follow up with but will that stop you? What would you need to do to feel more confident moving forward in spite of these fears?
I'll share a little bit more before I move on to the failure resume, because I think this can be a helpful reminder for all of us. Are those worst case scenarios going to stop you when you think about failure? If something were to go haywire or it doesn't work out, would that stop you from making the move at all? And if so, that's okay. It's a signal that you might need to develop a game plan that allows you to sidestep that analysis paralysis, or the feeling of potential catastrophe if you make the wrong move. Who can pivot in that context? A lot of us do have a sense when it's time to leave our comfort zone, but there is a blurrier line between when weaving through that stretch zone without tipping into the panic zone. You might remember that comes from the riskometer diagram that I share early in the book, that we each have a different tolerance for risk and a different tolerance for, quote, failure. We have a comfort zone, a stagnation zone below that where we're actively bored, uncomfortable, disengaged, and even the boredom feels like it's killing you slowly. When you move out of the comfort zone, you're in your stretch zone. But if you try to pivot too far, too sharply from where you are now, that's where you tip into the panic zone. Compare and despair analysis paralysis. Any next move is so big that it just has you frozen in place. Coming back to the definition of failure. This is a relative term. Your definition of failure may not be the same as somebody else's. A common gremlin that pivoters experience is what? What if I'm not cut out for this? To that I ask, what is your definition of failure? Because it's different for everybody. And I don't mean this in a Pollyanna rhetorical sense or as some loaded question where you go, there's no such thing as failure because the fear is real. But what does it mean to you, and what does it mean in the context of your current pivot? In some cases, failure is very real. If you lose a job or a critical income source or you're cashing in all your remaining savings, that might be your finances telling you, this path has failed. Please pivot. Please choose another one. In other cases, sometimes reflecting on this question of how do you define failure? Reveals a strawman that can be dismantled through further inquiry. I remember when my husband Michael was doing a project on Instagram and it involved publishing memes that he would write every day. Life of a Lebanese Artist. I'll link to that episode where we talked about it in the show notes. And it was so interesting because in the beginning he had so much fun creating these memes, this intersection of Lebanese culture. Life of an Artist, New York City. He was having so much fun and he was imagining creating them for a friend that lived in Lebanon. But then as he started to learn more about Instagram's metrics and what's the correct time of day to post and how many times a day should you post? And then he would analyze which ones were getting a lot of likes right away, which ones weren't. It's so slowly started to drain the fun out of the process. And now instead of gauging success of any given post or meme based on did it make him laugh? Did it make his friends laugh? Was he proud of it? He started gauging posts as a failure if they didn't get enough likes or get enough likes quickly enough. And honestly, a lot of that vibe killed the momentum of the whole project. So really think about how do you define failure? Does your definition of failure focus only on quantitative or financial consequences, or does it include qualitative measures too? I often say that even if no one was listening to this podcast, though, thank you that you are here right now with me, even if no one was listening, there are still so many benefits that I couldn't even call that a failure. Let's say the listenership. Let's say you all ran away, I did something that just sent you running for the hills, and all of a sudden my listenership dropped down to zero. People. Probably most people would look at the project and say, all right, jb, that failed. You know, your listeners ran for the hills or nobody likes it. Nobody's sharing it. Even if it were getting one star reviews, you could look at that and say it failed. However, if I would look back on seven plus years and 300 episodes, I could see how much I learned, I could see how many friendships I created, I could see the ways that I challenged myself, the ways that I grew, the the ways that it helped me launch a second show, free time and actually redefine and reframe that quote failure into all the many successes and riches of abundance, of learning and experience that it really did deliver and that it still continues to so again, thank you for being here. So when I think about failure beyond not being able to pay my bills or getting to zero financially, that's obviously a sign that I'm overdue to pivot something in my business. Some of my qualitative failure categories include not giving something my best effort or over committing to the point where I deliver sloppy work. I talk in free time about some of my mortifying business moments of things falling through the cracks for clients, big clients, big stakes, big money, and dropping the ball. Those are just horrible. And they always lead me to invent new systems to prevent that kind of failure in the future. Another qualitative failure could be failing to act in my own best interest, steamrolling my own needs to please others, gain approval, protect the status quo. Dishonesty. Any situation where I act without integrity that conflicts with my values, I feel that one right in the pit of my belly. I hate that feeling so much that I don't even tell white lies. I mean, maybe they slip through every now and then, even unaware to me, but I hate it. I won't cancel plans and say I'm sick if I'm not. I just want to be truthful and above board because I can't stand the sick feeling in my stomach of being dishonest. Something like not trying something new based on an irrational fear sometimes. I have been known to negotiate against myself with corporate clients and proposals for things like licensing contracts where I'll start out at what I think is a fair market rate based on the value I'm delivering, and then I'll go, oh, that sounds too high. And I'm basically negotiating with myself before I ever hit send on the proposal, or not trying something new because maybe I discount myself from the jump. That's gonna be too hard, that's not gonna work, as opposed to an actual strong instinct that might indicate that something isn't for me. These failures happen. They happen all the time. They happen for all of us, but they're very different than quantitative failures or some kind of failure not to get just the right most perfect next move on the great resume in the sky, as I call it. And it's hard with LinkedIn being as ubiquitous as it is, we know that if you are a pivoter looking for another job in a corporate environment, of course people are going to ask for your resume, they're going to see what you've done and it feels nerve wracking to feel like you make a mistake if you have an interim pivot that isn't really where you want to end up, or you end up on some toxic team or work culture and you need to leave again quickly. It stings when that kind of stuff happens. But for me, at the end of the day, the biggest failure is not trying to if you read pivot, you know I say that we don't have fomo, we have font fear of not trying. So I encourage you to determine what your values are around risk and failure and really understand at this current pivot point that you might be at or pivot in progress, what failures are acceptable to you and which ones are not. So someone asked me a question I share in the book is a year from now, how would you feel if nothing had changed? And that was one of the driving inquiries that got me to go all in on my own business back in 2011. Because I knew that I would really regret not trying at all. I was blogging at that time. I had been blogging for several years. I knew that a year from now, if nothing changed, I would start to feel like a fraud. Because all the blogging and personal development posts that I was writing wouldn't be true if I wasn't taking risks and living in into my own values of going big. My dad taught me a little saying at that time, you can't cross the Grand Canyon in two small leaps. I love that that's true. And also sometimes I'm all about the tiny steps and the tiny trail that you can build. You don't always have to take a big leap. That's what the pivot method is all about, is narrowing things down to small experiments when you can't know the full picture, because that is most often the case.
Failure is not uncertainty. Trying something new, trying something that doesn't work, doing something imperfectly, making the wrong decision, getting rejected. These are all part of the process. And as I shared in that free time episode from It's a site called VisualizeValue.com, failure is the frame, not the picture. So you can't judge something as a failure if it's too soon. Yet your story is not done. It's not done being written. If we're watching a movie about somebody in their hero's journey, we actually can zoom out and see the perspective that that rejection or that moment of seeming failure is actually a stepping stone to success.
So where does the failure resume come in? This is where we reflect on what are the moments that could be gauged as a failure but that were critical stepping stones to your success, that taught you incredibly valuable lessons where you learn something that you will never forget and that you probably couldn't have learned any other way but the hard way. I don't know who originated I tried to do some initial digging on who first talked about the failure resume. I did see an article with Dan Pink where he talks about a failure resume. I'll put that in the show notes. And there are even conferences that have been on my radar for many years. One of them is called failcon it, a conference for startup founders to learn from and prepare for failure so they can iterate and grow fast. I'll put that in the show notes as well. In a New York Times essay called do youo Keep a Failure Resume? Here's where you should start. They cite Melanie Stefan, who may be the originator. She's a lecturer at Edinburgh Medical School, and she called on academics to publish their own failure resumes, eventually publishing her own, and I'm pretty sure this went viral at the time. On it, she listed graduate programs she didn't get into, degrees she didn't finish or pursue harsh feedback from an old boss, and even the rejections she got after auditioning for several orchestras. Let's say you are leaving a corporate job. As I talked about in episode 296. I think you should take a moment to take stock not just of your successes and your wins. As I shared in that episode. What were some of your failures? Write them down while they're fresh so you can capture internal failures during your tenure at that company. And then also, of course, zoom out and think about your entire failure resume of your whole life. That can be an interesting exercise too. And why not keep this with you as you keep building on your success resume, the shiny one, the one that Everybody sees your LinkedIn profile, your failure resume can be a cathartic exercise. And by the way, if you are interviewing for jobs in the future, they may very well ask you, when's the time something didn't go right? When's what's a mistake that you made. What's a project you wish you could have done differently? And you will have a very handy list that you've already thought through.
We'll be right back just after this.
With Venmo Stash. A taco in one hand and ordering a ride in the other means you're stacking cash back. Nice. Get up to 5% cash back with Venmo Stash on your favorite brands when you pay with your Venmo debit card. From takeout to ride shares, entertainment and more. Pick a bundle with your go tos and start earning cash back at those brands. Earn more cash when you do more with Stash. Venmo Stash terms and exclusions apply. Max $100 cash back per month. See terms@venmo me stashterms in Walmart Soon Louisville Time was ticking away. Only a few nights left till the big holiday, but last minute gifters had no need to worry. Walmart Express Delivery got their gifts in a hurry. From Nintendo to Nespresso and Lego flowers, they could check off their lists in as fast as an hour. All of who Newville, East, west, south and north could order gifts up until 5pm on December 24th. So this holiday just do as the who's do with gift delivery this fast. They all gassed from Walmart. Who knew subject to availability terms and fees applied.
To kick things off. Maybe this will inspire you. I'll share a couple of items on my failure resume. One of them is that when I was applying to college out of high school, I had won this prestigious California Journalist of the Year award and I even made it to the top four finalists in the country. That was a big success. Where the failure came in is I then proceeded to get rejected by almost every university I applied to out of college. All my stretch schools rejected, even the Northwestern Medill School of Journalism, which where I was sure I was gonna end up, or Columbia rejected, Northwestern rejected. And I thought at the time I was the top four journalists in the country of my graduating class. And this was back in 2001 and they still didn't want me. Now I was not a good standardized test taker, so I have a feeling that played a role in it. And you just don't know the roll of the dice, how it's gonna end up. It was very interesting to just get rejection after rejection and I know that that's so many people's experience. It's always a gamble figuring out where you're going to get into school. That failure led me to accept to Go to school at ucla, which I was very grateful to get in. It's a fantastic, incredible school with great academics. But I hadn't planned on staying in California. I grew up in California. I really was craving the east coast, where I live now. As I finally scratched that itch. I just hadn't been looking at California. I didn't want to go to school in norcal. That's where I grew up. It wasn't really on my radar. I kind of applied to the UC system just as a backup again. Even, you know, some of the schools, ucla, Berkeley, they're all really highly ranked. I'm so grateful I ended up at ucla. I loved my experience there. It was fun to go to school in the sun and be part of these different scenes of movie premieres in Westwood and fun clubs in Hollywood. I don't know, I only did it for a few years. I even met a mentor, a professor, who got me my first job at the startup company. That is what inspired me to launch Life After College and everything that came after that in my career to this day. So if it weren't for that failure to get in, everywhere I had applied, everywhere I wanted to go, who knows how my life would have turned out. And I might have been more tied to journalism because if I got into a journalism program, maybe I would have felt worse or given myself fewer options about what to pursue, because I ended up doing communications and political science. When I was in undergraduate, I almost minored in computer science, but I ended up working at that startup instead. Another failure as it relates to education. I mean, I don't. Again, I don't really use this word, but on paper it looks like that you might remember from an earlier episode. I'll put it in the show notes that I recorded called Put yourself in the path of pivot. In 2018, I enrolled at Union Theological Seminary. I was really interested in studying interreligious engagement and the intersection of faith and work. The faith and spirituality that we can infuse in our work that draws us to the type of work we're doing and that so many of us crave in terms of making an impact and also being a messenger for something greater than ourselves. I didn't grow up very religious at all and in fact had parents of two different religions. So my life was always questioning by default, religion. What does it mean? What is it for? So I enrolled at Union Theological Seminary. I made it through a semester and a half, and then I went on leave. My business started picking up and I just couldn't Juggle. I had just gotten married at City hall during my first semester. And in fact, our Intro to Bible, the Bible 101 class, was fascinating. The teacher surprised me, Michael, who was sitting in with me, and she had us read the Beatitudes in front of the whole class because it was the night before we were getting married the following day. So there were some really special moments like that. But we had bought a house, we got married, we were moving. I was juggling my business full time while attending school full time. I did a semester and a half. And then as my business started picking up in that middle of the second semester, I just couldn't do it anymore. I was going to have to travel for speaking gigs, momentum that I had been trying to build for 10 years. And if I were to travel and take those gigs, really lucrative ones that I needed, I needed to just stay afloat and pay for the household. I would have had to miss so many classes, they would have given me a drop anyway, so I went on leave. I genuinely thought, maybe I can come back if I can just get my business humming. And then the pandemic hit and it was out of the question. And Union even emailed me and said, we're taking you off leave now. You can't stay on leave anymore. So there is a part of me that feels unfinished about that and that my attempt to get a master's degree in interreligious engagement just didn't work. It was a semester and a half and I spent actually a lot of money on the course credits and everything. And kind of this feeling that I didn't finish something. And it's rare in my life that I start something and don't finish it. My mom always taught us when we were playing sports as a kid, you gotta finish out the season, that she would never let us quit anything mid season. You could only quit the next year, but you can't quit when it's hard in the middle of a season. So with union, I feel a little bit that I canceled failed in the middle of a season.
Now again, I'm not too hard on myself about these because any failure, any decision involves trade offs and involves other things that I was optimizing for. I'm really proud of what I did with my business once I went on leave and I needed that momentum heading into what would become a big pause button during the pandemic. One more failure that I'll share from my failure resume. Launching a social meditation app with friends. We were launching this in 2013 and 2014. I had two co founders. We were pretty early on. This is before Headspace was a thing. We wanted to create a meditation app that was fun, sticky and social. And I spent at the time 15 grand that I didn't have on development and two years just digging in, giving the nitty gritty of interface design, how it was going to work, how it was going to flow, piloting it, inviting my community, talking about it publicly. Two years. So it was more time I dedicated than just the money and also the kind of angst and agita and thinking about it. There's a lot of brain cycles that go into any project. At the end of that two years, we just realized this was too hard. And my $15,000 lesson learned of a failed meditation app was how I never ever want to be in the app building business. In a way, this lesson saved me from many more headaches in the future. Because building an app is so challenging. You have to design the ui, but then there's all these bugs. And as soon as you fix all those bugs, large and small in the software, well, oh, the Android and Apple operating systems upgrade and now you need to pay the developers again to fix, fix all the new bugs because of the systems upgrade. Oh, and now the design is out of date. Oh, and there's all these customer service questions to take care of. And it's just so intricate on this one to many thing that is not in my zone of genius at all from the design or the development side. I was kind of bringing community and communications to it. So while I believed in the mission, oh my goodness, I'm not good at being in a really intricate project like that and supporting it. You know me, I like to work solo by myself. I don't like working on big intricate things that require a big team to keep up with. And then as we were toward the tail end of that project, we saw Headspace get funded, venture backed, funding for who even knows, gazillions of dollars. I don't want to tell you the wrong number. And their momentum and they kind of took off and then they do what Reid Hoffman calls blitzscaling, where they spend so much money on ads that they become part of the public conscious and get that winner take all effect. There was no way we were going to be able to compete with Headspace and keep up with them. No possible way. So that was one where you got to take a page out of Kenny Rogers song lyrics in the Gambler. You gotta know when to hold them, know when to fold them, know when to walk away, know when to run. That's my terrible karaoke. In this case, I'm running. And I'm still running away from building an app ever again. I'm so grateful to the co founders that I was working with and the team, the delightfully tiny team we had assembled. I really enjoyed all the ideas we had. I'm proud of the progress we did make. And I still have my running shoes on of never to take on a project of that level of intricacy and complexity again if I can help it, without a very, very compelling reason, an exception to everything I just described. If you want to hear more of what I would consider missed opportunities, you can also check out the Free time episode that I'll put in the show notes on my three biggest business regrets in over a decade of business building. But I share them kind of with a smile and a nod because it's all part of the process and there are things that I did that I'm really proud of, even at the same time as these failures I shared and the regrets. So there are always two sides of a coin. And there's a quote from Robert Kiyosaki that I love as well, that sometimes it's not even heads or tails. There's the side of the coin as well, a neutral place where you see both. So if you know coins, at least in the States, they've got that thick edge, kind of small, but it's there where on either side you're just looking holistically and compassionately, I would add. So I encourage you to keep a failure resume if you don't already have one. And really, our brains tend to learn more when things are not going well, when they're going wrong. I learned this from the episode with Susan David on emotional agility. That's on the Pivot podcast. I'll put it in the show notes that actually, when things are going really well, we're not learning. We're just coasting. We're flying. We don't have any need to pay extra attention. But it's when we fail. It's when we have regrets. That's when we zoom in. That's when we analyze. That's when we learn. And it's how we learn. So let's all celebrate our failures today. You have permission to try something big and fail. And you have permission to keep going. Thank you so much for being here listening, everybody. I'm so grateful for you. Onward we go. Have a beautiful rest of your day.
Thanks so much for listening to this episode of the Pivot podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to and the latest tools I'm geeking out on. Sign up@pivotmethod.com pivotlist get show notes from this episode@pivotmethod.com.
And connect with me on Twitter @jennyblake.
Remember, build first, then your courage will follow. Hasn't it always.
Hey Ryan Reynolds here for Mint Mobile. You know one of the perks about having four kids that you know about is actually getting a direct line to the big man up north. And this year he wants you to know the best gift that you can give someone is the gift of Mint Mobile's Unlimited Wireless for $15 a month. Now you don't even need to wrap it. Give it a try@mintmobile.com Switch upfront payment.
Of $45 for three month plan equivalent to $15 per month required new customer offer for first three months only. Speed slow after 35 gigabytes if network's busy. Taxes and fees extra. See mintmobile.com.
More from Jenny
215: Stay Relevant, Sense What's Next, and Solve Difficult Problems with Stephen Shapiro
12: Belly of the Pivot Beast: On Bouncing Back from Zero with Adam Chaloeicheep
218: We've Gone Over-Bored (Part 2) with Michael Karsouny (Listen at Your Own Risk!)