Everyone wants a mentor, or someone to “pick their brain over coffee.”
Everyone wants to become an executive overnight.
But first, you need to carry the water. You need to put in your time.
Here’s what no one ever tells you early in your career: you actually have two jobs. The first job? Crushing your job. Your day-to-day to work. The things you were hired for. Your second job? Managing up and making the life of your manager or boss easier.
That’s what we talked about on this recent episode of our podcast, Seeking Wisdom.
You can subscribe on iTunes to listen on the go or catch the full transcript below right here on Medium.
Dave Gerhardt: Today on Seeking Wisdom, we’re going to talk about carrying the water.
David Cancel: Boom! I’m scared today. I’ve never seen Dave this fired up. Get ready people.
DG: I am fired up. I am fired up.
DC: Alright so we’re going to talk about carrying the water, and basically that’s an old saying that most of us know, which is for people when they’re getting started early in their career to actually spend time carrying the water of those above them, whether that’s mentors, whether that’s the people in their work place, whoever it is, and basically learning through the age old apprentice method. And the reason that this came up recently is that we always talk about the grind here, and I noticed something when talking to other founders and other people of a certain vintage, AKA old, that it seemed like a lot of people they were dealing with at work or their colleagues who were just out of school, fresh out of school, had a different set of expectations for how quickly their career would progress.
DG: Yeah. So when you mentioned this idea, when you mentioned this to me, I didn’t know what you meant by carrying the water at first, and then you explained it to me. I’m a big sports fan, and so the analogy for me was, a lot of times the rookies at training camp, on a hot 100-degree day, they have to carry the pads…
DC: Mhm.
DG: Of the veterans after practice. They have to carry their shit…
DC: Yep.
DG: And bring it into the locker room. And you said, “Yeah, it’s that.”
DC: And that’s true in sports…
DG: Yeah!
DC: In military and way long ago in the workplace as well.
DG: I don’t know, doing things for your parents, there’s just so many…
DC: Exactly
DG: There’s so many things and we’re going to talk about all of them because this is a topic that gets me fired up. But you basically were just saying early in your career, we talked about this back and forth, you kind of have two jobs. You kind of have, you have a job of, you have to do your work. You have to be good at your job, whatever, you’re a designer, you have to be an amazing designer, you have to create value for the company and value for your customers, but you also have a second job, which I don’t think a lot of people understand. And the second job is to make the rest of your team and your manager, your boss, look good and be successful. And it’s not just about looking good, but it’s putting them in a position where their life is now easier because they’ve hired you. And I think the biggest thing that people just forget is they completely forget that step, but it’s a hard thing to talk about because, we were just at lunch and we were talking about this, we also don’t want to come on here and say you are at the mercy of your boss, right?
DC: No, not at all.
And your job is to clean up their shit.
[2:55] Yeah, and I think it’s, because I think it’s true at both ends. So getting started, I think you should be focused on making the company and your boss, whoever that is, your manager, whoever it is, your team, look better, and give them the credit. But I also think on the other end, as you progress in your career and as you become a leader, that your job is to help those younger than you, those around you, look good, and not yourself. So I think it’s not just younger people, but I think it’s even as you become more experienced, your job should always be to make those around you shine.
Yeah, and I think the mindset is, if I’m an employee, it’s how can I do my job and also take as many things off the plate of the person who manages me?
Yeah, and I think it’s going back to your team idea there. It’s just like when you see a well-functioning team that everyone’s blown away by, it’s they’re all doing great things individually, but they’re also making sacrifices or assists, in basketball terms, they’re assisting other players. And those are the great times. There are great times with exceptions where there’s one dominating player, but usually that’s not the case. Usually that’s the exception, and usually the rule is a great team is everyone is contributing to bring the team forward.
Alright, so why… okay so I’m, for people listening, I’m 29, I graduated…
He’s a millennial.
I’m a millennial. I graduated in 2009 and started working.
The reason I mentioned he’s a millennial is it’s unusual for millennials to be as in touch with this subject as Dave is.
Yeah, well, anyway. So I totally get, I understand this. And I think since then, right around that time, 2009-ish, why do you think this started to happen? Is it, you mentioned to me, it’s the Zuckerberg thing? It’s because everyone who graduates college now thinks they can start a company and be their own boss at 22?
Yeah, I think a number of things have happened in my opinion, and who knows if they’re true or not. But some things which may be correlated are all of a sudden you’re being brought up in an era where very young founders and celebrities, basically celebrities of all types, some of them being founders, are being celebrated by our culture, right? And that could be a singer or an actor, that could be Zuckerberg himself in technology, but all of a sudden you’re seeing examples, public examples, which we didn’t see in the past, of 22-year-olds, 20-year-olds, Justin Bieber, 16-yeah-olds, being phenomenally successful, and the media loves to focus in on those people because they are so exceptional, because that is actually so not normal that we begin to grow up in an environment where we may think those things are normal.
And part of the thing that often makes millennials great teammates is because they can figure… they think they can figure anything out. And that’s the mindset, right? I can figure anything out.
[6:00] Yep.
I can figure this out. Let me do it. I don’t have any experience, but let me do it. That is an amazing quality, but at the same time, it’s also, exactly what we’re talking about here, and it’s that mindset that I don’t have to carry the water.
Yep.
Because I’m a person just like you, and I can contribute.
What year did you start working?
I started working right after I graduated.
What year was that?
2009.
Okay. That’s important. So I ask that because I think Dave and most people that we’re probably talking about graduated 2009 or more recently. And the reason I think that’s important is the second reason I think this may be occurring more often than not, is that these people have come into a workforce where, in a workplace where there has been no downturn, right? In the last significant downturn that we had, economically, was 2009. Right? So if you came into the workforce after that, you’ve never seen an environment where things have been rough, right? You haven’t been through those rough times, and I think for the people who are self-aware like Dave is on this subject, they’ve probably seen some rough times, they’ve probably been through the trenches to some degree, and so they probably have some context.
Yeah, I think for me it was cuz I graduated 2009, and that was, 2008 was a shitty year. That was my senior in college and that was the weirdest I felt in my career, actually, even though I hadn’t done anything yet, was because everybody says you have to go to college so you can get a job. I know you have opinions on that, but…
Well that’s a separate thought.
But then when I graduated, they said “oh yeah, we’re looking for somebody with two to three years experience.” And I was like how the fuck do you get experience if you can’t get a job? So I took an internship…
Okay, talk about that.
Which was very humbling.
Talk about that. Important.
Yeah, so I didn’t know what I wanted to do. I know I wanted to be… I graduated with a marketing degree, which has absolutely noting to do with anything I’ve done in my career.
In marketing.
Yeah, I do marketing now, but it has nothing to do with anything I learned in college.
Okay.
And so I took this internship at an agency, a PR agency…
Yeah.
Because it was the only place that would hire me, and I thought I wanted to do business, and so I figured this would be a good way. Work with all these tech companies. And I think that actually had a lot to do with how I think now, is because of the agency model.
Yes!
When you’re 20, well I was 22; I don’t get to talk to clients.
Nope.
Right? So everything that I do has to go through somebody else. When I was an intern, emails that I’d write, if they were client facing, somebody would have to review them first.
Mhm.
And so I think that forced me to be say okay, damn, there is a clear ladder here.
Hierarchy.
Yeah. But once you can show that you can do it, and so it was kind of on me. If I don’t get to do any of this client-facing stuff, it was more of how can I make other people that get to do this, how can I make their lives easier?
Mhm.
So then I get to do it. So then it just became scheduling meetings for people. Doing all the other shit, like scheduling travel and putting stuff in Excel that nobody wanted to deal with.
[9:07] And were you paid well at this internship?
Ugh it was fucking terrible. I got ten dollars an hour. I was living in my parents’ house, which was in Worcester, which is 45 minutes away for Woburn, where this internship was.
Okay, so you’re commuting 45 minutes each way.
120 miles round trip every day.
There you go. Now I think I understand why Dave has some context to this. And I don’t think many people have gone through that.
But I don’t want to forget this thought. So the point of that story was to say that now, all the companies that people want to work at, there weren’t as many Drifts or startups, right, so the challenges that are now, if a startup is your first job, or all these tech companies, right? You think that work is ten people sitting around listening to rap on the Sonos and there’s a tap in the office… you think that that’s what work is.
Nope. No one’s work is that way.
How do we change that, though, because at the same time…
I love everyone’s opinion on how you change that. I don’t know because, and maybe the change has to come from someone like Dave. Because I feel like when I, if I’m to say that, then I’m the old man on the hill, who says, “back in my day, you had to work.”
Well it’s shitty, whoever says it, it’s shitty, because even if I say it, it comes off as I want people to… there’s rules, and you don’t, you’re not allowed to talk because you’re this role, and it’s not that at all.
Definitely not. But yeah, we have to have some context to understand that the kegerator, and the sitting around together having a good time, and doing outings, and doing all the fun stuff that we do as a team, as all of us do as teams, especially in startups and early technology companies, is not normal. It’s not normal at all. But when that’s been the only experience that you’ve had, it’s hard to have context, and I don’t know how…
You know what I think; I think the most underrated career advice is to join a big company when you get out of college.
I think it’s a really good idea. Gives you context. It gives you… you may like it, so it might be perfect for you, and if you don’t like it, then you have a reason, or kind of a mission behind your decision to either start a company or join a smaller company, and it gives you appreciation.
Yeah I think it depends on what you do. I can understand if you’re an engineer, it might be easier to go join a small company and you have a more focused role, but if you’re in sales or you’re in marketing, I didn’t appreciate this while I was doing it, but I worked at two big companies before Drift and two startups. So I’ve done two early stage companies and two big companies, and I think when you’re at a big company, at the time while you’re there, you hate it, and you say, “I want to be at a startup. This place…” But then when you get that first early stage job, you have subconsciously built in all this process, and not the bad type of process, but the way you communicate, the way you share your work, the way you work with others. I think that’s stuff that you can’t learn if you just go directly to an early stage company and so being in the constraints of a big company where you’re one of 150 marketers is actually a really good learning experience, but it’s just hard in that moment to think of it that way.
[12:20] Yeah, I think in our world, that we’re kind of in the B-to-B software, it’s kind of context for what is broken today, in order to fix it, and it’s great to have that kind of beginner’s mindset and to come in and not be weighed down by the way things work today, but it’s also super useful to have some context for what is actually broken? Do people care about what I’m building or proposing?
Yeah. So what… from where you are, tell me about the good things that can happen to somebody in their career if they carry the water.
So much. Let’s see. What are the good things? Well one you start to… it humbles you, right? So you need that humbling. And because the humbling is going to come no matter what…
I mean from your perspective, you’re more likely to invest in that person.
Oh definitely. Oh, so that perspective. Yes, I think…
For you as a CEO.
Yeah, people are always asking to get time with me or other people or whatever, I don’t want it to be about me, but they say, “Oh, I want a mentor, I want to talk to this person, I want to talk to that person” and, well the first thing you have to do is do stuff for them. People want to get, but they never want to give. So you have to start with giving, cuz you need to give what you want to get back, and so you go, work, apprentice, mentor, whatever the word is, go do… basically go create value for that person or set of people, and then they will give back to you, right? But to expect that they will give back to you without first creating value, it’s unlikely.
And this is what happens at companies. For example, I saw this at a company I used to work at. Day 1, new employee, emails the CMO, says, “Hey, can we get a coffee, I want to pick your brain?” 75 people on this team. $100,000,000 in revenue. He doesn’t want to sit down with you and have a coffee. You’ve been through the interview process. You’re here now. You don’t get to pull that card. It’s hard enough for other people to get meetings with this person.
[14:22] Totally. And when I was… back before Drift I was at Hubspot and actually that would happen. I knew when we were bringing in new classes of MBAs, because it would happen every single time. So I knew when the new class was starting because I would get all of these emails. So every MBA that would start, their first day, the first thing they would do is to send emails to everyone on the executive team and say, “Hey, can we go to lunch?” So first day, you’re getting all these emails and they say, “Hey, do you have time? Can we set up a meeting for Tuesday to chat?” And I’d say, one, “Who is this?” Two, I would always reply the same thing; I would be the ass and say, “No.” And then some of them, a small percentage of them would reply back and say, “Why can’t we meet?” And I’d say, “You need to do something here first.” Do something here first, so that not only that you create value, but so that we all have context, or I have context to even understand what are we talking about? Because you haven’t been here for more than 30 seconds, you haven’t contributed to the team or the company, but yet you want to have a meeting. I don’t know what we’re going to talk about. And so, most of the time, they would always want to talk about, when I did do it at the beginning, just nonsense, right? They just want to meet for the sake of meeting.
They want to talk about your career.
Yeah.
That’s why we do this podcast now, so you don’t have to… people don’t have to meet with you now. You just listen.
Exactly, and I can point it back and say, “go do that, because every time I would meet with them, I would be say we already talked about doing this. Have you done it yet?” “No I haven’t done it yet.” “Well that’s your fuckin problem.”
Whereas…
What are we going to talk about?
So this is just a self-awareness thing, whereas the right way to approach that would’ve been, I want to meet with this guy, but I don’t have my card to play yet…
Yeah.
But I’m on his team, I’m going to bust my ass, I’m going to do a good job, I’m going to make sure he knows who I am, maybe make a couple things in his life easier…
Yeah. Right. And those people, guess what? You go out and you pull those people closer to you, because they’re exceptional. So the people who would come in and crush it, man I’d be running to meet with them. Not only me, but anyone else would say wow, that person is creating so much value that I want to be a part of them. I want to help…
Well you take the opposite mindset; you say, “Man I want to try to get my hands on that person early in their career. “
Yeah.
Versus them just coming to you saying, “help”…
Exactly.
Tell me a story.
So totally underrated. Carry the water first, push, and then people will, because it’s so not normal, you will stand out and people will pull themselves to you. So you will create a pull versus trying to push yourself onto them.
[17:00] So that’s some career advice today.
Yeah!
From us.
So what would you tell people… other millennials like yourself, who haven’t carried the water yet? Why would it be beneficial?
I just…
How do they do it?
So the beneficial part is you just notice that people take good care of you, right? That’s the number one thing. That’s why you should do it. Because if you can take little things off of that person’s plate, then their life is easier and it’s more likely to trickle down to you. But it also just shows self-awareness, and I think that can be applied to a lot of other things other than the day-to-day job. They understand, oh this guy obviously gets how things work, I trust him working on x because he’s going to think about it the right way. As far as how to apply that in your job, I think just remember that you have two jobs. You have the job that was in the job description on the website that you applied for and got, or whatever, didn’t apply for, but the role, you have to do that well. And so that’s check number one. You don’t get to earn the right to do all this other fun stuff and hang out with execs if you’re not crushing your job. But once you’ve done that, it’s just, you need to think about opportunities where you can take things off of people’s plates. So whether it’s just that you’re in slack for example, and somebody mentions your CMO and they say, “Bob should go do this.” You know that… if you have self-awareness, you know that that’s not something that that person needs to spend their time on, just grab that. Just say I got it, I’ll do it.
Yep.
It’s a lot of just doing stuff and then telling someone that you did it. Say, “Hey FYI I booked this thing for you. Don’t worry about it. Here’s all the information. Got it covered.”
Huge.
So then that person doesn’t have to think. And especially, unless you’re at a huge company, there’s usually the story that we’re telling today applies to execs, it’s not usually the director of sales at a big company, it’s more about people whose schedules are already nuts and already have enough stuff going on and any sliver that you can make their life a little bit easier as it relates to work, whether it’s you see some bullshit, stopping it before it gets to them. It’s almost like you see a fight with your sibling, you could either let your parents find out so everybody gets in trouble, or you can deal with it yourself.
So I think the one takeaway, the one thing I would tell people if they’re early in their career and they have kind of a goal of “hey, I want to be the CMO some day, I want to be the CEO, I want to be…” whoever you want to be, or “I want to start a company some day,” whatever your goal is, to go and find out, to go find the person closest to you who has already done that and has been successful at doing that, and then go and figure out how you can carry the water for her, for him, and then learn from that person by doing so.
[19:56] And realize how long it took that person to get there, right? You and I were talking about, you shared a story, you said one time… you started a bunch of companies and manage hundreds of people, you said one time somebody basically jumped five different steps to become an exec before they were 30.
Oh yeah, totally. I think this is something that people don’t see is…
It takes time.
It takes a long time, so some people might come out of school and say, “I’m 22, I’m 23, I’m 24, or whatever… how can I be VP of whatever or the CMO in a year?” And when someone is that far out or that far from being self-aware, it’s really hard to kind of coach them, but you can use examples and say, the best case scenario or the phenom or the person who has blown you away, that you’ve seen or either work with you or has worked around you, who has been the Kobe of their era, it took them, whatever, eight years or ten years to be…
And that was the best person you’ve ever seen.
Yeah, and I’ve only seen one. So maybe you can be faster than that person. Probably not. Probably most of us cannot be the Kobe of our position or of our generation.
But the thing is it doesn’t come down to if you’re 24 or 25, that next step isn’t about the work that you’ve done in the 365 days of that year.
Exactly.
It’s the experience that you have to, that just compounds over time. Right? And a lot of times, you can do an amazing job, but time, you just need time, cuz you need to see more things happen, there’s going to be ups and downs. You need to go through all that. It’s not like you just crush it in one year and because nobody has seen results like that, that you just get to be this role.
Yeah, you need time to make mistakes and to learn from them. And you’re going to make lots of them. I’m reading this fantastic book by the founder of Sam Adams, Jim Koch, I don’t know if I’m saying his last night right, fantastic book. I think we’re going to do a podcast in the future about this. Great book. He started this beer, he started this microbrewery industry, he started Sam Adams, which most of us know as a great beer company, and one thing that he always said that he always remembered that his dad told him, and he came from the longest line of American brewers in history, right? His dad was a brewer, his grandfather, his great-grandfather, but his dad told him one thing that he always remembered, he said, “you need time to be able to make mistakes. You’re going to start out and you’re going to make $100 mistakes in business, then you’re going to make $1,000 mistakes, maybe you might even make it one day to make $100,000 mistakes,” and he said “if you’re really, really, really, lucky, and part of the very, very few percentage of people who get this far, you will some day make million dollar mistakes.” And he always thought about that because he did make all of those mistakes, including making one multimillion-dollar mistake that could’ve sunk his company. But you will need time in order to make all those levels of mistakes and it’s one thing to learn from a $100 mistake, but guess what, a $10,000 mistake is coming up, and a $100,000 mistake is coming up, and that just is a matter of time. You cannot rush that.
[23:14] That’s a good place to end. I was hoping you’d mention that new book.
Oh yeah. Everyone has to go out and read that. We’re going to do an episode on that soon.
Cool. Alright, that’s a good place for us.
Go carry water!
Go carry the water. And then once you’re done carrying the water, help us, and go to seekingwisdom.io and catch up on all the previous episodes. We talk about a bunch of things that we’ve mentioned in the past before, they’re all on the website.
Come on, stop hiding! Show us some love! Five star review, come on. Hook up an uncle.
We’ll take a five star review and you’re in the spirit and you’ve been liking what we’re doing.
Hook up Uncle DC. Five stars.
We’ll talk to you next week.
See ya!
