Why I'm Writing My Failure Resume

I first heard the term “failure resume” on Without Fail, a podcast with candid conversations with people who have done hard things: what worked, what didn’t and why. It’s hosted by Alex Blumberg of Gimlet and his guest was Nina Jacobson, a Hollywood producer with huge successes under her belt, as well as some notable failures.

It got me thinking about writing my own failure resume. Nina Jacobson owned hers, like a badge of glory that turned failure into the first step of something new. And that’s really what failure is. The opportunity to try again. This is something we all need to remember.

So, I want to do it. I want to write my failure resume right here. I want to unpack all the ways I’ve screwed up in life. Not to feel bad about errors I’ve made, but to see them for what they were. The last straw before the next step. The first step in a different direction.

Relationship Failures

How much time do you have? Like 27 min read or nah? Fine, I can condense it. I’ve had some wonderful relationships in my life. I’ve also made some poor choices. Some of those poor choices still reaped significant rewards, but the most important thing I’ve learned about evaluating past relationships is this:

If you always blame someone else for your past relationship failures, you will never have a successful relationship.

At some point, I decided that every failed relationship in my life was my fault.To be honest, it’s probably true. I chose to be with them. I chose to stay with them. I chose to accept certain things. I also acted irresponsibly. I moved too quickly. I waited too long. I couldn’t make up my mind. I kept thinking the grass was greener. It’s on me. Full. Stop.

So what would be the lowlights of my relationship failure resume? My failed marriage produced the two most beautiful things ever created so it’s hard to dwell on anything there. What I need to do is look at my own behavioral pattern to find consistent errors in my ways.

I moved too quickly.

Over and over again I had to teach myself this lesson. Like a block of cement discarded from an abandoned building, I never found the right fit. And I think it was because I pushed the turbo button on every relationship. And then I got myself in too deep. My fault. It wasn’t what I wanted. She wasn’t who I wanted. And I had to take the steps to undo it.

My promises of love were categorized as bullsh*t. My talk of the future now a sour package of lies. My excitement lost, mired in a swamp of disconnection and general ennui. All because I wanted it to go quickly. So I could get somewhere. But that was the problem. I didn’t need to get somewhere. I needed to be there. In the present. And I wasn’t.

I wanted people to be different than who they were.

I thought they’d change. They probably thought I would change. But neither of us were going to change. We may have the ability to grow as people, but it’s highly unlikely that our core behaviors and beliefs are going to change on a dime. And if we change just to please our partner, just wait — it won’t last. Because it’s not us.

In order to have a successful relationship, both parties have to be given the space to be uniquely themselves. Take it or leave it, but don’t sit around trying to change it.

I put myself in too many complicated situations.

I dated separated women. I dated married women. I dated people who were in a relationship. I dated people who were trying to get out of a relationship. I dated people who wanted a relationship when I didn’t. I dated people I knew weren’t right for me. I dated my friends. I dated different people at the same time.

All. My. Fault. Not theirs.

Work Failures

When it comes to the workplace, I suffer from premature evacuation. I get bored. I hate bosses. I hate being even mildly contained inside-the-box. I hate being told what to do. I hate being watched over. So, at all my jobs I did what I wanted to. And that was usually a good thing in terms of the actual work. I worked like a mad dog.

But in doing so, and bucking the rules along the way, I usually enraged my superiors. But I was someone that couldn’t get fired because I was always very good at my job and had a lot of friends at work. So they just waited. Waited for me to quit because they knew I would.

My biggest work failures all stem from the following issues:

I always thought I was smarter than everyone.

If this were true, I was working in the wrong places. If this were not true (the most likely answer), I was a pompous worker always telling my bosses how to run the office better. Bosses don’t usually like that sh*t. But the more they didn’t like it, the more I liked it. Because I thought I was smarter.

I had a reputation for always doing the right thing, but often that was in the face of an organization telling me to do it differently. I wouldn’t change this, but I should have realized sooner that the traditional work setup wasn’t going to work for me.

I didn’t value the traditional workplace trajectory. You stay there the longest, you rise to the top. It just never sat right with me. Because it bred complacency. But that didn’t mean I needed to sound constant alarms.

I liked being right too much.

I was a practicing trial attorney for ten years. I enjoyed arguing, but more than that, I liked being right. Too much. I would often grandstand in court, which I thought was funny at the time, showing up the other attorney for being unprepared or just nervous. But it didn’t help anything. It just made me look like a d*ck (even when it was kind of funny).

It’s like I had a chip on my shoulder for no reason. But it wasn’t a chip because I was insecure. It was a crappier chip, one that had to prove to everyone, including judges, that I was right. You might relate that to insecurity, but it wasn’t that. I used to be obsessed with being the best and that meant always being right. What an a**hole.

About premature evacuation.

Yeah, it was a problem. I left a startup because I wasn’t getting paid on time. It’s like I had no idea how startups worked. I also thought I knew better than the founder, who already had successfully exited a company with a nice payout. So I quit a high paying, cushy job where I had total control of hiring and building because of ego. Stupid ego. I gave up my stock options. The company sold for more than $10 million five years later.

I always had another stream of income and I think that made me more IDGAF at work. I knew I could quit and part of me likes that I can dismiss the bullsh*t and just leave, but there is the other part that knows how it looks. It doesn’t look good. It’s like I take my football and go home. But at home, I don’t have a job anymore.

Life Failures

When I think about my life failures and my failure resume in general, it’s really about acknowledgment and finding the pot of gold at the end of the rainbow.

“Failure is simply the opportunity to begin again, this time more intelligently.” — Henry Ford

All of our lives are full of failure. To think otherwise is to hide inside a bubble of self-involvement. Even if we are successful in one area of our lives, it’s likely we are neglecting another one because of that success. Failure is a stepping stone. So, I guess I’ve stepped on a lot of stones.

And failure in life doesn’t have to be rock bottom. Just because my failure wasn’t a tragedy doesn’t mean it wasn’t a failure. We all fail in our own ways and at varying levels. It’s about how we accept it and move on from it that matters the most.


I put this under life failures because growing up I told myself I would never get divorced. My mom got divorced twice before she passed away. My dad got divorced twice, and it should have been three times before he passed away. I just didn’t want to be like that.

But my parents were amazing people. So why was I resisting being like them? It’s because we look at divorce as a failure. And I really, really did at the time. I stayed in the marriage too long because I didn’t want to feel like I failed. But the true failure, for myself and for my children, would have been to stay in a marriage that was not going to work.


I don’t have any qualms saying I am an exceptional parent. I’ve devoted my life to being the best father I can be, but I still fail at parenting all the time. Because it’s impossible to be perfect as a parent. I’m sure I fail, in some way, daily as a parent. If you think you don’t, you might not be trying hard enough.

I remember I once yelled at my daughter out of frustration because she wet her bed. She was maybe 6. This very moment is still ingrained in my head and I will never forgive myself for it. Something this little. I let my emotions get the best of me all because I didn’t want something to happen. But it didn’t help. It hurt her. And it still hurts me.

I’ve given in too quickly on punishments because I just don’t like doling them out. It actually hurts me to take something away from my kids. Some people say that I should toughen up, or “man up,” or teach them a lesson. But I am teaching my kids a lesson and it’s not about being a doormat. It’s about love. Not tough love. Just love. But all discipline in parenting is wrought with failure

Extended Family

I’ve had so much death in my family. It’s actually made it hard for me to continue to engage in it.

Watching My Family Die Made Me an Expert in Death

I’ve failed many of my relatives by not keeping in touch as much as I should have. Or by ignoring them because they were annoying. I didn’t call enough. I didn’t visit enough. And now I regret it.

It’s reasonable considering what I went through with my parents, but it’s still not a proud moment. I was holding both of my parents’ hands when they died. But I wasn’t there when my grandmother died. I should have been. The night after she died I got too drunk and crashed my car. Then I flew out to go to her funeral the next morning. I still hate myself for this.

Much of my extended family was super annoying at holidays and overly invasive. They wanted a relationship that served them. But they were old and I wasn’t looking at it from their point of view. I missed their later years. I didn’t even go to many of their funerals. I had just had it with death. But that’s not an excuse. I failed my extended family.

The Point of a Failure Resume

For most people, it’s done in the context of business. Kind of like a mea culpa to jumpstart their next project and to let everyone know they are fallible. But I haven’t seen them much for life. Maybe it makes us feel too bad to write out our biggest failures in life.

But, why? We are ruminating about those same failures all the time. Our lack of acceptance of our biggest failures is what is holding us back from stronger relationships, better jobs, and closer ties. So why is it that a business failure resume is a sign of strength and a life failure resume is a sign of weakness?

It’s not a sign of weakness. It’s just being vulnerable. A not-so-subtle acknowledgment that life is f*cking hard sometimes. A lot of the time. And maybe if we categorize our biggest pain points from our past, we can finally start to move on from them.

When you sit down and look at your failures, you can see the line to your next step forward. Even if it’s a really long line. Even if you aren’t there yet. I’m definitely not.

I’ve learned a lot about relationships from my failures, but I am still ignoring love. I’ve learned a lot about my expectations in the workplace, but I still leave careers in the dust for the same reasons. I’ve learned a lot about life, but I’m still not trying hard enough.

The point of a failure resume is to hold yourself accountable. And to see where you’ve lost. Because we can only win again when we are able to move on from our losses. I, for one, am ready to move on. Are you?