(upbeat music) - You're listening to Let's Talk Jobs, where we give you practical insights into jobs and careers. Today, we're talking about dealing with failure. We've all been there, we've all done that, we've experienced that in highs, and when the stakes are really huge, and we experienced at low levels as well.

It's always there as a part of growth. Jesse, you wanna lead us off, like share your failure story and how you dealt with it. - Sure, my failure story, and, you know, I wanna say that fear of failure, you know, is a real thing, like, and not that this is a surprise to anybody, but I think there's various levels of it.

And my fear of failure story comes into play. A few years ago, I was brought on a project for a startup. And at the time the startup, all they had was a pitch deck, and I was originally brought in just to help clean up their pitch deck. They didn't have a name, they didn't really have a refined positioning, they didn't really understand the market opportunity.

They were building a product, but they weren't sure about, obviously, product market fit. They hadn't raised any money, but maybe a little bit. So in those first few months, it was just working through some naming options, some streamlining of the positioning, some trying to make the deck look a little bit better.

So when they went and presented it in front of potential investors, they could get a little more traction. And I worked with them for months and months and months, and eventually we came up with a name, and we were building, I was brought on as a consultant, but I became more and more involved with them.

And originally the idea was to build this product that was, let's just say it was something like a CMS for 3D websites. So something that maybe no one had specifically done before, there were content management systems that have been created to build websites, but not specifically for 3D websites.

At the time, not necessarily 3D, but VR was becoming more of a, and AR was becoming more of a prominent technology. And so I was brought on at that point when the positioning had been a little bit more refined, we had gone through some pitch deck iterations to get something that was useful.

They had a couple more partners and other folks that they had brought on to fill out the team, and they started to raise some money. Not a ton of money, not, you know, series A money, let's call it, so less than 5 million. And all of a sudden, what had been a project around the CMS idea, which seemed like it had tremendous potential, you know, there's established businesses in the space that had been getting some real traction, like a business like, forget the spacing on the name, the e-commerce engine, stretch of the nest that, where you can spin up a website and then the business, and it'll come to me in a minute.

But in any case, so we had this business idea and we started building out the prototypes and getting that ready and all sorts of things like that. And the founders came to me and said, we want you to come on in a large capacity, we want you to be our first marketer.

And they said, we want you to be our CMO, but, you know, it was a CMO with a team of one. So, and I think that speaks to my sense of how scared I was of taking on a role where I didn't, while I had run a business before and taking it on clients where I was responsible for developing their marketing plans, their brand strategy, their content marketing plans, their digital marketing and all of that, I had never been brought in as a person with equity, a stake in the company with skin in the game.

And so it had a whole nother sort of level of engagement. And I was really afraid, I had no idea what I was doing. I wasn't sure it was the right job for me. And, you know, but the founder had enough, the two founders had enough confidence in, I guess the skills I had and the experience I had that they said, look, we want you to build a brand.

We want you to build out a marketing plan. We want you to help us bring this product to life, to market. We want you to help us find a product market fit. We want you to hire a team, all that stuff. And so I started to do that. And then we pivoted.

And what was a project to build this CMS became a project to launch an NFT, line of luxury NFT watches, which sounds like an amazing idea, like Rolex, but NFT Rolexes, which is kind of what it was. And the founder had all these connections to Italian design and had actually created then these digital watches.

They only existed virtually, right? And at the time, NFTs was this booming market. And there was lots of hype around it. And people like Snoop Dogg were buying NFTs and they were selling for millions and millions of dollars. And so we pivoted and we started getting ready to go to market with this limited edition of luxury watches.

And I had hired a team. We had a team of amazing designers and writers and a PR person. And I hired a social media expert and paid media specialist. And some other had worked with some publications to get PR articles placed and found ways to get the CEO in front of influencers who could interview him and get him some traction online.

And we started making waves and developing a brand and building all the assets we needed to go to market. And then I started seeding the message in the market. So we bought a lot of paid media and spent a lot of money on paid media, probably too much. And in any event, we had a rather large following and it came to launch the campaign.

And it's sort of like, this kind of market is based on exclusivity. It's you have a limited number of things that you bring to the market. People think they're valuable because they're exclusive. It drives up the price and they're NFT. So they're not physical things there. You could like bring them into your virtual world and put an NFT watch on your, in your virtual world.

So it's, and there was a lot of sort of hype around it. And what I found in developing the marketing efforts to bring it to life was I had to work with various influencers on Instagram and other places which would often be like these sort of side deals where you pay somebody $200 to tweet out like one message and another person would charge $20,000 for a tweet.

Like I literally had this spreadsheet with all the various influencers from the couple hundred dollars ones to the ones that were charging hundreds of thousands of dollars a tweet. And that was in this world, that's how you cultivated your brand. And we launched and the site didn't work. And it was the, while the products were on OpenSea which was the NFT site, we sold six out of 50.

And so the fear of failure kind of like manifested itself in that the project really didn't do so well. And they didn't lose all their money but they lost a lot of it. And now they pivoted to another opportunity in the same related space design and VR and that kind of world.

But my fear of failure kind of was, oh, I can't do this. In fact, I did do it. Like I did hire a team. I did build a brand. I did bring the project to market. You know, I did all the digital media stuff. I did the PR stuff.

And I think some of it is related to what we talked about earlier in terms of imposter syndrome is the imposter syndrome was like dragging me along saying I couldn't do it. And even if I was doing it, I'd be exposed as a fraud 'cause I've never really been a CMO or whatever I was, you know, lead marketer.

And I was afraid that if I failed like I'd let the investors down or let the founders down and all this. And in some ways we failed, but I think it's very, you know, it's a very common thing in the startup market especially in one that's so volatile. And so, yes, I had a definite fear of failure and a little bit of imposter syndrome thrown in.

And it all kind of didn't materialize in the way I thought it would. And, you know, even though I was compensated fairly for my time there, the equity ended up, you know, never being worth anything. And though I still have quite a bit of equity, you know, it doesn't amount to anything unless something significant changes.

It was a really good experience though. It was a really good experience because I went through it despite all my fears. I learned a lot about marketing, a lot about bringing a team together, building a brand which I had sort of done before, but not in a way that I had such an ownership stake in the business.

And so some of those things like the fears, the fears that we bring to our job are a little bit of a reality check. Like, oh yeah, you might never have done this before. But reality, in the sense of maybe it's not, it's not an experience of something that's happened in my past, but it's something I'm gonna do now.

And it's sort of, I have to take that leap in order to learn. I think that's something that as creatives and as marketers, we're sort of like the original humans out there on the Savannah with, you know, in a way, I think it's a little bit like, you're leaping into the unknown.

You may, you know, the earliest, I'm getting philosophical here, but like the earliest people, and they're picking up whatever they're picking up to go up and get food. And they don't really know because there's no stories, there's no Facebook, there's no, you know, New York Times to tell them or Amazon to tell them how to do these things, but they're leaping out into the future to try and, you know, capture the bison or whatever.

And we're kind of trying to do that in a way, despite the fears. And I think it's somewhat heroic to take on those things that we don't think we can do. We think we're gonna fail and do it anyway. And I think that's kind of the lesson I would, you know, take from that.

Get properly prepared, you know, do all your research, lean into other people for things you may feel you're not strong at, but, you know, take the leap. - How about you, Troy? Is there a similar story for you in how you dealt with failure? - I've actually got two totally different stories and I'll keep them short, but I just want to react to Jesse's thing about sort of failure.

I think failure, I think for most people, will define your career path more than success because you, by going through these moments and having these, you learn a lot about what situations you don't want, you know, moving forward in terms of how you make choices and the paths you take.

You learn an awful lot through failure and stress and anxiety and all the things that go with it. The biggest, so I have a job failure and then I have a project failure. Job failure was a failure because I felt like I was the perfect fit for the perfect job.

It was a technology that I loved. It was a software as a service company, but it was a company that I loved the story. It was, had elements of my job that I had great experience with. I fit the profile. I felt better than any other candidate I could possibly imagine.

But my first week on the job, the company fired the head of products, they fired the CEO. And basically it was the beginning of three years of just weirdness, unease, insecurity for me. Like I never really do. I reported at one point to the new CEO. I reported at one point to the head of sales who didn't want a marketing report.

At one point, I wasn't sure who I was reporting to. And there's just so many forces working against me, even though I still look back and I'm still, I still, to this day, I feel like, I should have done things differently. For one, I should have been more confident in my abilities and maybe I couldn't get out of my own head and couldn't get past my insecurity to where I was just focused on action.

I could have been more, I could have had more action. I did some good things, some good work that I'm proud of and I don't wanna go into details, but by and large, I was stuck in my head and I couldn't, I simply wanted to, I was focused on survival rather than doing the work.

So my takeaway there is, it's advice to myself and anybody else out there, but try to focus on, try to focus on the work, not necessarily the environmental forces that you don't control and feel proud of, try to feel proud of what you do rather than proud of your standing based on what you think other people think of you.

Anyway, so that was my job failure. Project failure was, as a freelance writer, this was probably about two years ago, I was hired by a healthcare startup to write a hello world post, basically sort of announcing that they've arrived, they've got a sort of an early solution, they have a couple of rounds of funding and really tell the story of the opportunity that they saw.

And as storytellers, we always like to focus on personal bits of narrative, but this particular startup was co-founded by a husband and wife, which that's always kind of an interesting story too. Sometimes those work, sometimes they don't. They both had, he had a technical background and she had a sort of a pharmaceutical background.

And there's a great story about how they met and sort of how they both ended up at this point. It's like, oh, this is fantastic. I mean, I have this really nice, sort of powerful personal anecdotes as the jumping off point to really tell their story. But then like I spent probably an hour and a half talking with the woman and she shared all of this, but then after the briefing found out he didn't want to share any of the personal stuff.

He wanted to be focused on just the business opportunity. And there was elements of a story there, but I knew it just, I'd lost a lot of power and just a really, really moving story. So I felt a little defeated the whole way through, but my mission at that point is like, I just, I wanted to write something and get it to them.

And I did, and then what I wrote, I thought was actually pretty good. They never actually used it. They never actually told the whole world story. They just kind of like continued down their path. I don't know if they're actually gonna launch ever, but my takeaway from that was like, I was hired to do something.

A certain point I realized it wasn't going well. And so I kind of wanted to just bail fast, just to get something done, do what I said I was gonna do, get it to them, call it a day and move on. So that, I think, throughout your career, the listeners, you'll come across different circumstances that you might recognize at a certain point they're probably not winnable.

And I think it's important to just, rather than try to save some of those, sometimes it's better just to cut your losses and move on. - Yeah, I love the last part, 'cause failure is always gonna happen, right? The question is, what now? I had an experience even just past work with some members of my team where something happened, it was unplanned for, unexpected, and there was a small window of which many people could see this mistake on a website.

And obviously they were freaked out about it, and rightfully so. I mean, that's healthy, actually, I mean, you care. But so my first question to them was, I was like, okay, cool, what did you expect to happen? What happened? And what are we gonna do now? Are we just gonna let it go?

Are we gonna course correct it? Are we gonna observe and measure? And I think when you're dealing with failure, the best thing you can do is be objective about it and strip away all emotion. And that's actually the hardest part, but the emotion does cloud your judgment and makes you react too quickly, makes you make the wrong decision sometimes because you're making an emotional call or a reactive decision, right?

So for me, and this is easier said than done, and of course, if the stakes are higher, your need to rapidly get to a conclusion is more paramount. But my first guide is always like, I'm just gonna be objective about it and figure out what my ideal outcome is and document really quickly.

And I remember earlier in my career, and there's an older video we talked about, which is like, I had a harsh manager and how do I deal with failure under that purview or deal with, and harsh feedback is all kind of tied to that. What I did not do enough of during those points of failures was give myself room to breathe and think.

And so I immediately internalized all the failures, assumed everything was true, and I became reactive. I was in fix-it Felix mode on everything, just trying to fix, fix, fix, fix, fix. In some instances, that actually hurt me a lot more than it helped. I think in those points of failures, I wish, what I would have done is, if the failure come from a source of truth that was incorrect, maybe you're in a position where maybe things aren't failures and someone else is forcing the narrative on you, maybe by circumstance, politics, or whatever it is, going to the individual and asking the pointed questions to get down to the nugget of truth becomes really, really important, right?

The easiest open question is, what does that mean to you? And if you can ask that three times in sequence, you'll get down to the truth, right? If it's not an objective failure, if someone has a impression or whatever, it's like, cool, I understand your impression, what does that impression mean to you?

They'll explain it. Oh, interesting, you just mentioned something, like, what does that mean to you? They'll explain it again. Okay, well, if that what you just said were to be different, how would that look like? And then they'll say, well, that's how you'll uncover the truth nugget behind everything, right?

And that's how you deal with harsh feedback. I deal with failure the same way. Things are objectively failures, or they're subjective. And in the world of web, when things are objective, it's the, it's sitting down and figuring out, like, what's the core structure of my mind? I like what you said, Troy, about letting some things fail.

And I'll give you guys an example. And those who work with me right now, I'm gonna out myself 'cause you're about to hear my strategy. With web, we're a service organization, and we serve many masters. Product marketing, comms, support, executive team, you name it. And the larger the organization, the more requests you're gonna come in.

And when you don't have resources to execute on it, you become restrained, right? Now, either quality is gonna dip, or your SLAs are not gonna be met. Sometimes, to get people to learn or adopt your processes, your SLAs, you almost have to allow things to fall through intentionally so they experience the failure.

Like, using failure as a tool to illustrate a pressure point, right? You don't do it on the big ones where everyone's gonna be at political risk, but you surgically pick the right ones that illustrate a point where the stakes aren't super high. And so, I actually use failure as a tool, frequently, with either individuals.

And of course, these aren't all necessary failures, but failure here is defined as an outcome that doesn't meet your expectation, right? And so, maybe that's a deadline that can't be met. And so, that happens all the time. And again, there's always gonna be scales to failure. But I like what you guys are all saying, essentially.

It's like, strip yourself away from the emotions of it, diagnose and break it down, figure out if there's gonna be actually a plan to fix it, or do you just let it go, right? And sometimes, because you're sitting so close to it, the failure feels a lot, like a bigger deal than it actually is.