You're listening to Let's Talk Jobs, where we give you practical insights into jobs and careers. Today, we're talking about horror stories from our careers and what we've learned from that. Joining us is Troy Peterson and Jesse Ratner. How are you guys doing? What's up, Tim? Hey, Tim. I'm good.

Now, naturally, you guys have both had your own episodes, and make sure you guys click on the links to watch those. But between all of us, not to age us, we've got a fair amount of years of experience between us, right? I think I've been doing, I think, 24 years in industry.

How about you guys? Yeah, I'm at 25 years in tech, and then before that, I was in media for about four years after college. And I'm in about the same space, actually, as you would know, when I first, almost, first jobs in tech were with Troy. Actually, that was one of my first jobs in tech, and I think you were my manager for a minute.

And yes, I'm really excited to talk, and we certainly have decades of experience between us. Lots of horror stories, and looking forward to talking about it. Yeah, you know, the funny thing about horror stories is we've all got them, right? And it can range from small or big, and it's all relative to who we are as people and how we digest information and deal with it.

I think what we do with it and how we respond to it is really important. And I think early in our careers, mid and late, there's always something to take away from it. And so our goal is to share that with you guys who's listening and watching this podcast, and hopefully you can get something out of that.

So I'm going to kick us off, you guys, and you're probably going to laugh at me, because the first topic is dealing with mistakes. Have you guys ever sent a nasty email to someone and you forgot to take them off CC? I've never done that one, no, unfortunately, but I've definitely received mistake emails like that.

It's the worst, you guys. When you hit submit, you see the participants in the email quickly, and you feel this rush of heat and blood coming up the back of your neck, and that freakout starts to happen, right? It happened to me twice in my career. The first one was younger, maybe like, I think, two or three years into my job experience.

And then the other one happened like, I think, within the past three years. And I think how I dealt with it and how I process it was very different based on just how long I've been in the industry. The first one was really bad. I was on the agency side of the business.

So I was an account manager, right? So my whole job is to build relationships with customers and hopefully build credibility, trust, and gain more business. I had this one particular client who was really, really difficult, both verbally abusive to my team and typically, you give an inch, take a mile type of stuff, right?

That's interpretation from an agency side. And at that point, I really had it. I think I was maybe 27 years old. And so they had sent an email to the team, which was not a nice email. So I hit, so I did a reply all and I deleted them from the first draft of the email.

But then I didn't like the email, I closed it and I came back to it. The problem is when I came back to it and I redrafted it, I didn't take them off the chain. No. And I was literally, my choice of verbiage was like, "They're terrible," like, "I can't believe I have clients like this," and it was really bad and I hit send on that.

The blood rush happened. And my response to that besides, "Oh, crap," was sending an immediate follow-up email to just my internal team. I sent another email to the client and in some cases, almost overreacting on my part to the mistake. What I didn't do was pause, breathe, reread the email because I have more context around why I said that, but the reader does not and they may not read it the same way I read it.

And what ended up happening was my manager told me, "Hey, look, if you didn't respond, I don't think they would have said anything. But because you overly focused on it, now it's a thing and you've drawn all this attention to it. You could just let it lie." And it ended up taking me off the account because it damaged reputation of our – with the client.

It was really, really bad. Three years ago, I did another one and this one was about an individual. And similar things, we have gripes about people and they're annoying. And so I sent out an email and this time, similarly, accidentally CC'd them. My response this time around being older and having more gray hairs on my head was a lot different.

I did the pause. I drafted an email and then I – actually, before I hit the email, first, I erased everyone from the send. So that's the new thing. And whenever I send emails like that, I first remove everybody so there's no chance of accidentally something out. So I remove them all and I allowed myself about an hour or two to go back and forth and read it, put in draft mode, come back, shorten it, right, shorten, shorten it.

And then I sent the response back. And this time what I did was I went back to the individual and gave them context. Part of it was admitting my own mistakes. I was like, "Hey, man, that was embarrassing for me but here's what I meant to say." And I left it open-ended.

I said, "Hey, look, if you don't have a conversation, here's what it is. Here's what I truly meant and some of the truth behind what I'm trying to say." That was a very different response. So they came back saying, "Oh," they kind of laughed and like, "Thank you for calling yourself out." But then we got right to the heart of the issue of the concern, right?

And so that was that horror story. I'm glad I haven't had too many of those but I had another similar one through chat where I was talking about someone to somebody else and I was on the wrong window. And so the message I meant to send to someone else, I sent to them directly.

It was literally, "So-and-so is so annoying. I can't believe they said that." And actually, that was the midpoint of my career. And the way I dealt with that one is kind of like the medium of the two. I said, "Hey," I did a white lie. I was like, "Hey, man," oh, actually, first of all, he responded, "WTF," right?

And I said, "Hey, man, I just want to share with you what I sent to someone else because you know what? I don't think that was an appropriate thing. I want you to know what I said because I'm trying to hold myself accountable." Total lie. But ironically enough, I was able to build upon that and use make lemonade out of the lemons and allowed me to start having more frank conversations with this person.

But I think they saw through it. I don't think they're that dumb, but that was my horrible mistake. I feel like if we were younger, Tim, you would respond with a meme this thin age, right? Or a GIF or something like that. Yeah. Yeah. I don't think us old fogeys have those skills to respond in that way today, but what about you, Jesse?

Have you had a nightmare like that? I've had a few. And, you know, I was thinking when you were telling the story, the second one, Tim, that sometimes fear is such a funny thing. Some of it is sort of like a biological response. You hear a loud noise and you're on the street and there's a backfire or something, you jump and you're like, "What the hell is that?" And some fears are more learned.

Like the fear of public speaking, I think is maybe it's a little bit of both, but you can unlearn it and become a good, confident public speaker, even though it's probably one of the scariest things for most people to do. And some things are cultural because of the culture you're in.

And, you know, in some cases, I think I've been on team cultures and corporate cultures even where I might have said to somebody, you know, in error, "Oh, you're so annoying." But the culture is a culture of forgiveness, of kindness, of understanding, and you could just talk about things.

And I actually was on the receiving end of one of those texts from a designer. He actually, I sat, I had a standing desk and I sat or I stood on one side and he stood on the other. And I think he didn't mean to send a text that basically said, "That guy, Jesse, is a real jerk." And I looked over at him and I'm like, "I don't think you meant that for me." And I didn't take it that badly, I just, he's a young guy.

He was also a guy who had been, he was very junior, but sort of like this was his first job out of design school. And after about a year, he started asking to get promoted. He was a junior designer. He started getting asked to be promoted to creative director every week.

Every week he'd come in and talk about how he needed to be, I was managing him and he said, "I need to be promoted or I'm going to leave." And then after a little while he left, so good for him, but I've been on a, not so much, I've sent a few nasty grams and had to clean up things afterwards.

But I think in terms of biggest mistakes or big mistakes, certainly I have one that really stands out and I was working at an agency where I had been in a sort of a managerial role, a lead role, but I was sort of under somebody that I couldn't move up.

And I was on this same account for a long time, it was a big account, we had Google as a client. And so we had, it had been years, right? I had done a two-year stint with one agency under the same manager and then another two-year stint with another agency under the same manager.

And we were very successful together, we worked pretty well together, we ended up starting an agency later on together. But at some point, and the agency had grown from like a very small size to many hundreds of people, we had weekly happy hours at this restaurant in San Francisco on the Embarcadero right under the Bay Bridge, it was beautiful.

And so we'd go over there with the Googlers and hang out and talk about business, talk about other stuff, it was very casual, we'd drink quite often, as you might imagine. And one night I was really chafing under this, there's a lot of things going on in my life, I was trying to buy a house, I had a young child, my wife and I have, still do, but our child was very young then.

And I had a couple drinks, let's say three or four, dark and stormies, and I went up to the boss above my manager, oh, and by the way, I had been moonlighting for a client that the agency subsequently gained as their client, which I then dropped. But I felt like, well, once the agency gained this client and I learned that they had been struggling a bit with the creative, and I thought to myself, well, this is a great opportunity for me, I could say, hey, I actually know this brand, in and out, I can help you, blah, blah, blah.

You know, and I've been thinking about it for months, like, how do I make my move, when's the right time, what's the right way to do it? Anyway, so this Friday happened, and like I said, I had a couple drinks, and I pulled the boss's boss aside, and I said, I can help you, here's why, I actually know this client and I've been working for them on the side, and he was like, wait a second, timeout, timeout, that's probably a conflict of interest, I need to talk to the partners, and soon after that I got pushed out of the agency.

You know, I was on a really good path, I was on a good path, had a strong, well, at least, I would have probably continued in that sort of corporate agency path, and it completely changed the trajectory of my career, and I've been a consultant ever since, and in some ways it's been really good, you know, I took a risk, but it wasn't well thought out, and I think I was going to be stuck in a role that I didn't feel satisfied with, if I didn't somehow make a move, and I might have made the wrong move at the wrong time, but the result was it opened a bunch of doors, because I had to, then I had to hustle, I lost my job, I got another job right away, I had a good, you know, good resume, having worked at a big brand, or at an agency for a big brand, and some of the things, and, you know, other doors open, and I, you know, I can, some of the other things I think we'll talk about in terms of fear of, you know, fear of fear itself, fear of failure, those kind of things, came to the forefront as I then moved down the road in my journey, but yeah, it wasn't a mistake, probably, you know, the timing, not so good, the inebriation part probably not so helpful in my decision-making at the time, and I think I, you know, I held that inside for a long time, and I saw the guy at the boss's boss, I hadn't seen him, yeah, I hadn't talked to him, like, I was somewhat of a friend, I mean, he'd kind of been to my house, and I'd been to his house, and, you know, we knew each other quite well, worked close together, the boss's boss, that is, and then I didn't see him for like seven years, you know, I got pushed out, I remember that last day, he walked me to the door and like that was it, and I saw him like about six months ago, it had been like seven years, and I was getting a test for CPAP machine, I took a sleep disorder test, and I go to leave from the from picking up the instructions, and the elevator door opens, this is a hospital, you know, upstairs, and the door opens, and there he is, and he walks out, and we shake hands and sit, I sit down for him, with him for a few minutes, and it was weird, because I still was kind of looking for him to acknowledge what had happened, and he didn't, and he texted me or I texted him or something, we had like a very short text communication, and then nothing really, you know, we're not really friends anymore, but yeah, really, it really was a probably not such a good move on my part, sorry about that, but it happens, right, and then you move on, because you have to, and I'm gonna put myself on mute for a second, so Troy can maybe share about a couple of things, but that's probably the biggest mistake that wasn't a mistake, but was a mistake type experience.

Yeah, I kind of actually wonder, you know, we always have stuff to bring to the table, and I wonder if you hadn't brought up the fact that you're moonlighting, and you're just like, hey, I have some insights, or maybe I know this company, and maybe this nugget would help you, do you think that would change it, because now you're, again, you're trying to position yourself in a company, and I think this happens all the time, right, like we have connections, relationships, and some stuff might better position us, right, is there a way that could have played out differently, do you think, or just in general, just having a relationship was gonna doom you by whatever information you're about to disclose?

I think I definitely could have positioned it better, I didn't need to, you know, talk about how I came by that experience, I just could convey that I had a, you know, a deep appreciation, it actually was LinkedIn, oddly enough, that was the client that I knew about, that had worked for, on the side, and yeah, I could have positioned it as I had this experience, I understand the brand, I know their voice, I know their goals, I know their, you know, the core value props, and I think I could help, and leave it at that, I didn't necessarily need to go on how I came by that information, experience, and the problem was that I was a little bit drunk, and you don't think straight, and if there's any lesson I could take away from that is, you know, don't get drunk and ask questions that could change the trajectory of your career, you might not, you might not know where you're going the next day, and it's risky, it's highly risky, and it's probably one reason why, especially in agency life, and you're probably familiar with this, Tim, it's often the case that you're smoothing with clients, and there's alcohol involved, or other things, and you know, sometimes it doesn't always go in a straight line, and I think that's life, right, and in some ways fear is that accelerant, you know, it can accelerate us down a path that maybe we are trying not to face, and so maybe this was a point in my life where I was sort of admitted at crossroads for a long time, and I was sort of stuck in a role, I had all this experience, I had led large teams, like the designer who told me I was a jerk, and things like that, and had a bunch of success, and when then I was later able to go out on my own, just, just enumerating the things that I had done often got me into the door when I started my agency for conversations with potential clients, and even now I think, I still, you know, I didn't lose all that experience, it just, I don't necessarily lead with that story when I'm in an interview, but yeah, but to your point, I think, I think framing it certainly is important, when you're in a situation where you're about to make a mistake, maybe step back and write down a script for yourself, this is what I think I ought to communicate, you know, and maybe sleep on it, you know, or show it to a trusted person, your spouse or friend, colleague, yeah.

That's interesting to hear you guys tell these stories, I feel like there's almost like two layers of learning, there's the sort of short-term, and I think it's really important to short-term sort of react in a way that is productive, but then there's also like the longer term, like in terms of, you know, how do you deal with mistakes, you, whether you realize it or not, when you make mistakes, you're learning, and even if you can't articulate what the learning is, the next time I think you're faced with a situation that rings familiar, I think you're going to be better suited to respond to it appropriately.

So like, you know, my example is much more tactical, but it was an important thing for me to learn about how to take responsibility for it. In the short term, I had started working for a software as a service company, my first job that was like fully digital related is sort of around the 2000 time, 2010 timeframe, and I was in charge of the CRM or slash email marketing at the time, and in one of the first big email sends that we were, that I was responsible for, went out with the big call to action, we forgot to put the link in for it.

So it was like, I don't remember exactly what it was, but it was like, you know, sign up here. And there was no, it went nowhere. It was dead. It was dead link. And dead for the context that it was kind of a nightmare job for me in a lot of ways.

We might get into this later, but my boss was the temporary CEO because my other boss had been removed and he hated email. He like just didn't like the whole practice of it. But we also knew that email marketing and a lot of marketers know this, like it's one of the, to your own, owned lists are one of the most high ROI tactics going and that still stands today, I believe.

So, you know, we weren't going to stop doing email, but the fact that this went out on my watch and I was reporting to a CEO that hated email. And I was, I was devastated because like, you know, the very concept that I could make a mistake in front of, you know, thousands of people, you know, it was, it was, it was kind of devastating to me.

I took it really hard. But in the moment, I also, I was able to at least like quickly take responsibility. And I knew that this, the news, the acting CEO was sort of a very matter of fact guy. So like we quickly built sort of the mitigation plan, which was, you know, we're going to re we're going to send another email, apologize and, and include the link.

Which it was very embarrassing, but you know, we, I approached him, I said, I'm really sorry we made this mistake and had a verbal conversation with him. I think it was the other thing that, you know, I think we've all had moments in our careers where we follow up with a, with an email, we maybe send another follow up email.

It's like this is it swingers, the movie where the guy keeps, you know, leaving voicemails for the girl he likes, and it just makes makes things worse, right? It's like, it's better if you can just have like a quick conversation and attack the problem in the moment. Yeah, I think having a mitigation plan, or immediately building one as response to it is really, really important.

You know, I think in that moment, especially with stakeholders who are watching your response to that, and how you're going to fix it in the plan, that's important to maintaining and building on credibility, because your point, mistakes happen. The difference is the person who is proactive and takes initiative.

The brand you're building for yourself is one of responsibility, right? As opposed to, oh, you know what, I can't trust this person anymore, because they make a mistake, they just go off the rails, and they just lose their marbles. And I think you're, I've had a few emails go out as well, from like a nurture blast or whatnot that had broken links or a website, since that's my domain, and we published wrong information and analysts are seeing it right away.

And there's varying degrees of how apologetic you should be, right? Because again, if you're too apologetic, sometimes you're going to blow something out of proportion. And so being like, as we think about this way, like we've also received stuff before as well, right? And under construction, or hey, here's an updated link or whatever, that doesn't scream, I made a mistake.

It just tactically tells me as a consumer, oh, here's another link, I'll just do this one here. That feels less like a mistake. But then again, you're totally right. There's sometimes where you just need to call it out. And sometimes that actually helps build credibility and relationships with your customers.

But yeah, that's a great story. I have a sort of related, I wasn't responsible necessarily for this, but I worked on a team that sent out an email that had a broken link. And we followed up with the email with just a very short subject line, oops, and it was the best performing email of the whole year, just an engaging subject line.

I hate the fact that people actually, I think we've all received now purposeful mistakes for that reason, right? It's the digital marketing sometimes, marketing in general, I think we often end up doing some things that feels a little uncomfortable, right? It's a little cringy. I mean, I wouldn't necessarily call it clickbait because it was going to a friendly list, but a little bit odd.

No, I mean, I'm saying that what's cringy to me is the people that do it on purpose to get clicks. Oops, we made a mistake and then draws attention to it. I think responding to a genuine mistake is authentic, right? And then there's a difference, although sometimes the reader can't tell the difference.

Yeah. Yeah. But things like emails, your internal stakeholders, they think in terms of metrics, right? And so having a mitigation plan and then doing something like, "Hey, here are the total amount of sends and here's the amount of opens," because maybe the open rate, because you caught it so quickly, was really, really small.

And so the impact of the mistake may not be that huge, right? If you don't provide context to people, then they just assume the worst. So I think control the narrative as often as you can, and data is your best friend. Yeah. Yeah. Our CEO at the time was huge into data, so I remember him showing him the, we showed him the open rate, the click rate, and also the, yeah, I think even more important, the unsubscribe rate.

Yes. And it was definitely within the normal range for any email. It wasn't like a, yeah, it didn't, we didn't spur a huge loss in subscribers to the newsletter. And I think for digital, it's an easy, well, not easy, but you can clean up a mistake. If you put out something that has bad message, typo, whatever, missing link, you can update it, send out a note, or if it's a webpage, you just update it.

I recently took a picture, this is a sort of a humorous aside, but I think it's relevant. So this is a, in downtown, in North Beach, in San Francisco, there's an area of town that has a number of strip clubs, and these strip clubs often have these big neon signs out front.

And so there's two of them. I took a picture of next to each other that used the apostrophe, and one used it correctly, and one used it incorrectly. One was Big Al's, A-L apostrophe S. The other was Roaring 20's, two, zero, apostrophe S. The damn grocer's apostrophe. Well, you know which business went out of, which strip club went out of business, Roaring 20's.

Now they met, I mean, it's sort of a humorous example, and they were around for decades, but you know, and they didn't feel the need to change it, I guess, or didn't know. They just made this giant sign with the grocer's apostrophe and left it up there for decades.

And yeah, the beauty of digital, so quite different than brick and mortar. Hey guys, thanks again for watching and listening. Next week, we'll be talking about dealing with difficult managers. So make sure you hit like, subscribe and the notification bell so you don't miss an episode.