26: The Biggest Mistakes We've Made + Some Book Recommendations

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This is a podcast episode titled, 26: The Biggest Mistakes We've Made + Some Book Recommendations. The summary for this episode is: If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. --- A little impromptu episode of Seeking Wisdom to head into the weekend on the biggest mistake we've each made in our careers + some book recommendations if you need something new to read. Join the community of Seeking Wisdom listeners at seekingwisdom.io and on Twitter @seekingwisdomio. Make sure you subscribe to Seeking Wisdom on your favorite podcast app so you never miss a new episode. Follow David (twitter.com/dcancel) and Dave (twitter.com/davegerhardt) on Twitter.

Dave: Today on seeking wisdom, we're going to each talk about the biggest mistake we've made in our careers.

Speaker 2: Shout it out.

Dave: All right. Do you want to go first?

Speaker 2: Why don't you go first?

Dave: You want me to go first?

Speaker 2: Let's flip it.

Dave: All right, I was thinking about this. We just did it little impromptu. We said, let's just talk about something different, talk about something that we screwed up. So my thing is more of a... I kind of ruined a relationship at work. So I was working for...

Speaker 2: What was her name?

Dave: That's funny. I was working for somebody and I was on one team, in one part of the company. And after being there for a year, I decided I didn't want to be on that team anymore. And I made a connection with somebody else at the company and they said, hey, you can come work for us. I just took the job. I didn't tell my boss. And this was the second job I had. I think I was 24. So not that I know what I'm doing...

Speaker 2: You need some humbling.

Dave: Not that I know what I'm doing now. So anyway, the thing that I fucked up is, I didn't tell her face to face. I just called her, because she had been out, and I called her and I said, I want to give you a heads up on something. And you know, here's how this is going down.

Speaker 2: Don't you know that work and relationships are just like any other relationship?

Dave: It's crazy.

Speaker 2: This is like doing the...

Dave: Crazy.

Speaker 2: Facebook message or text breakup, man.

Dave: Totally. I would be rip shit if somebody did that to me. And you know, looking back, good thing I did it because I learned a lot from it, obviously. But that's just like a good example of common sense and relationships that you don't think about. I have a good relationship with this person today and so it's all good.

Speaker 2: So you've turned it around.

Dave: Yeah, it's all good.

Speaker 2: How did you turn it around?

Dave: Pretty shortly after I made that call. I realized that wasn't the right way to handle it.

Speaker 2: How did you realize, on your own?

Dave: No, it was pretty instantly. Her reaction was less than stellar and just thinking about, you know...

Speaker 2: Did she call you a punk?

Dave: No she didn't call me a punk. She actually handled it pretty well. But it was pretty obvious from the tone, that it caught her off guard. And that was actually the hardest part. It would've been easier to get screamed at, I think. But it's when you clearly just catch somebody completely off guard. She thought I was just calling her to check in or something and I was just like, I'm leaving your team. I'm going to do something else. So yeah, that was hard for sure.

Speaker 2: That's brutal.

Dave: I think it happened because I knew what I was doing was wrong and it's easier to just pick up the phone and try to have gotten that done. But now thinking about progression since then and going through that. It's like there's a right way and a wrong way to do things and you have to fuck up like that in order to understand how to handle it appropriately.

Speaker 2: That's a great one. I don't know if I have that level. crosstalk

Dave: Actually talk about this for a minute though.

Speaker 2: Yeah.

Dave: What do you think the best way to have handled that would have been?

Speaker 2: Just like any other relationship. So I think the fuck up was that... And people do this all the time, where they treat, they think there's like a business version of you and there's a personal version of you. And then they do things at work that they would never do to other people that they're friends with. And there isn't, there's just relationships, that's it.

Dave: crosstalk that was a transactional thing by the way.

Speaker 2: Yeah, you went transactional on someone. And if you did that to anyone in your life, family, friends, girlfriend, boyfriend, whatever, you would know instantly. Well, one you would probably have never done it because you would know immediately. And so you just treated that person as like a transaction and didn't think about the long- term relationship. So that's the big issue there. I don't know if I have anything that level. I think mine is more... I don't know if I've ever made a mistake. Let me think about this, made a mistake.

Dave: All these people listening that have worked with you are probably like, I could tell you something right now.

Speaker 2: So many. Actually, that's probably the hardest part. I have so many mistakes you know, more time, more mistakes.

Dave: Hit us with one.

Speaker 2: Mine is more of a meta mistake.

Dave: Yah, that's cool.

Speaker 2: Which has been, I've made the same mistake in different ways. And I think the meta mistake is that, it took me a while to trust my own instincts and to trust myself and to be myself. And for too long I listened to conventional wisdom. And you know how we feel about that or how I feel about it now today. But there was a day where I listened to it and there was no role models for anything for an alternative path. Whether that was spending a lot of my energy, trying to focus on your weak areas and try to bring those up and be well- rounded. And then don't just lean on your strengths, just focus that. You know, I heard that a lot. And so I'd spent years trying to get better at all these things that I'm not good at naturally. And then I woke up one day and realized that I was wasting my time and I should really be thinking about how to surround myself and get in positions that I could be around other people who are amazing at their superpower. But that sounds so obvious now, but it took years. I listened to conventional wisdom on that stuff or conventional wisdom, the path that you should take early on in your career. You just listen to all of these things that make no sense or conventional wisdom on how you should hire people. And we've talked about hiring and our views on hiring. All those things are based on, for me, having done it the other way. Following conventional wisdom and learning that those don't play to my strengths. I don't think they actually work, anyway outside of myself and I need to stop playing someone else's playbook. And so that's my meta mistake. And it took me years, in different ways, whether it was hiring, whether it was my own personal development, whether it was the way to manage people or teams like all that stuff. Every aspect of what I did was kind of too ruled by conventional wisdom.

Dave: But I think the lesson from both of these, we'll do a quick one on this and we'll leave it today. I think a lesson on both of these kind of goes back to, putting in the work and figuring out over time, who you are, what you're good at, what you want to focus on, learning how to interact with other people like my situation. But it just all comes from experience and putting in the work.

Speaker 2: Absolutely. I want to share one thing, surprising Dave here, with the community. We just launched our Seeking Wisdom on medium. So we moved all of that stuff over to medium. And so we're out getting like- minded individuals to contribute to that publication. It's seekingwisdom. io And one area that I'd really liked to focus on, and we're just starting now is an area called The Book Club. And so these are like us writing reviews or giving feedback on books that have made an impact on us. And if anyone out there listening wants to write or has feedback on a particular book that has had a big impact on them, we'd love for you to submit that to seeking wisdom and add that as part of that publication. And we're good at marketing and we'll get lots of people to read it. And lots of people to kind of share your ideas.

Dave: Yeah, we want to turn the Seeking Wisdom community into something that is actually two way. So right now is one way it's a podcast and the audience has been growing and that's amazing. We appreciate that. We have so many people that write in with amazing ideas and we want to cultivate all that stuff, or maybe curate is a better word and have it on seekingwisdom. io, medium publication. So if you're writing on medium, or even if you're not, go write something, send it to us and we'll add you as a writer to this publication. So you can start sharing some of your stuff right there.

Speaker 2: Awesome. Let's let's grow this community together.

Dave: Speaking of book club, what's one book you're reading right now?

Speaker 2: Holy cow.

Dave: I know you never read one book, but give me one. Look in your list.

Speaker 2: I'm going to look at my list. You know, I've been taking screenshots of, finishing up or rereading sections of From Impossible and Inevitable. So I've been reading that. I've been reading another book called Algorithms to Live By.

Dave: Oh boy.

Speaker 2: crosstalk If you could only see Dave's face. It's amazing. These are like algorithms for your life.

Dave: You just read Bill Walsh, The Score Takes Care of Itself, right?

Speaker 2: Just read that. Dave does not want to talk about this algorithm book. It's amazing. It's called the computers, Algorithms to Live By: The Computer Science of Human Decisions.

Dave: There you go.

Speaker 2: So, I'm reading that. I'm also reading, right, not too many books, Producing Ideas. Another book I'm going through right now. And let's see, I'm going to give you one more. I'm going to hit you one more. One book, one more.

Dave: I've never seen a list this long.

Speaker 2: The list is so long. Dave is scared of the list.

Dave: That's why you need algorithms.

Speaker 2: That's right. And I was rereading, which Dave actually just read, although I just finished it, which is called Marketing: A Love story: How to Matter to Your Customers, phenomenal book by our home girl, Bernadette. We're going to have her on this show.

Dave: We are going to have her on the show.

Speaker 2: She's our homie from Australia.

Dave: We got to get some time zone stuff figured out.

Speaker 2: Can someone teach us about time zones? Anyway, that's what I'm reading. What about you, Dave? What are you reading?

Dave: I set a goal of, I'm trying to go back and read all of the copywriting classics.

Speaker 2: Okay. There we go.

Dave: All of the David Ogilvy types. I read Ogilvy on Advertising, which was amazing. Then I read Scientific Advertising, which is from 1924. Some science from 1924 and I found myself nodding at all the stuff this guy was saying. His name's Claude Hopkins. It's a hundred pages. It's like five bucks. Get it. And now I'm reading, the next ad book I'm reading, is called The Boron Letters. It's from a guy Gary Halbert that he wrote...

Speaker 2: More science.

Dave: More science, letters to his son that he wrote while he was in jail. This stuff is insane.

Speaker 2: DG is getting deep.

Dave: I'm getting deep, no algorithms out of me.

Speaker 2: Algorithms'.

Dave: seekingwisdom. io, go write something, read what everybody else has written and we'll catch you on the another episode.

Speaker 2: See ya.


If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. --- A little impromptu episode of Seeking Wisdom to head into the weekend on the biggest mistake we've each made in our careers + some book recommendations if you need something new to read. Join the community of Seeking Wisdom listeners at seekingwisdom.io and on Twitter @seekingwisdomio. Make sure you subscribe to Seeking Wisdom on your favorite podcast app so you never miss a new episode. Follow David (twitter.com/dcancel) and Dave (twitter.com/davegerhardt) on Twitter.