Episode 8:“Getting the Heck Out of Dodge”
Nick went on vacation. What happens before you go on vacation? What happens after you return? How do you manage client expectations? What happens if a client oversteps their boundaries?
Summary
Nick and Kai talk through the logistics and fear of taking vacations as solo consultants. Nick is days from a three-week trip to Australia, New Zealand, and Hawaii, his longest ever, structured across all three of his vacation types back to back. Both admit the fear of client fallout during time off is mostly self-imposed, with no actual client behavior to back it up.
Highlights
- Nick has three defined vacation tiers written into client contracts: a working vacation (on-call, eight hours a day at a desk), a conference vacation (reachable but slower due to time zone gap), and AFK, meaning completely unreachable. He is running all three consecutively on this one trip.
- Nick gives clients a minimum of four months’ notice for all vacation dates and posts the schedule on Basecamp. His assistant emails each client during the vacation to ask what they need.
- Kai has not taken a true AFK vacation in over two years out of fear of losing clients. He also notes that not one client has ever signaled this would actually be a problem.
- In 2015, Kai took a six-week allergy-season trip through Philadelphia, Arizona, and San Diego while serving five clients and trying to write the first draft of his book, The Traffic Manual. Two of three Airbnbs had bad DSL. Figuring out where to work, dealing with unreliable internet, and navigating new cities ate the mental bandwidth he planned to put toward creative output. He came back burned out.
- Nick has never done good creative work on vacation. Taking in a new environment saps executive function, and you can’t make the large, complicated decisions your clients hired you to make.
- Kai plans Burning Man at end of August as his first true AFK vacation, with six and a half months of run-up to prepare clients. There is no internet in Black Rock City.
Read the transcript
Here’s our actionable business takeaway for everyone who fast-forwarded to the end of this podcast episode to get the takeaway. I tan easily. Monday is my birthday.
You’re right. Happy birthday.
Thank you so much. Thank you. I’m very pleased. I can’t believe I survived this long. And that is an official holiday in all of the contracts with all of my clients, which is wonderful. And then I fly out of the country. you know I’m around the weekend going to other birthday parties because my birthday is really a season. It’s a six-month duration. Six months. The whole first half of every year is my birthday. Today is my birthday. Happy birthday. I should go someplace and like see if I could like get like sparklers and little chocolate cakes for like free and see what happens if I’m just like it’s my birthday and Aaron is like Nick it’s March 14th like It’s not your poor room. It’s not your birthday.
Have I ever told you my six-person birthday strategy? No. So, my philosophy is: if I’m eating dinner out with a group of friends at a restaurant and there are at least six of us at the table, it is automatically someone’s birthday. And I will just choose somebody at random and go to the host staff and be like, It’s Nick’s birthday. We want this to be a bit of a surprise. Can you bring out a piece of cake or a nice dessert and sing happy birthday to him? And they’ll be like, oh, sure, we’d love to. And then one of the friends at the table gets trolled by the entire wait staff singing, Happy Birthday, and presenting them with a piece of cake. And they’re faced with that awkward decision of like, Do I say it’s not my birthday, or do I just roll with it? And it is wonderful.
The best way to roll with that is with like fine dining, if you’re ever doing like double dates or something, because they always ask you, Are you celebrating a special occasion of some kind? And then I say, It’s Mark’s birthday. Day, and then I go with my friends Finch, Mark, and Aaron, and we’re all sitting around, we’re having a good time. Then they hand you the menu at the end, and it says, Happy birthday, Mark printed at the top of all the menus, and it has to be this Keepsake that you’re like framing and putting on your wall somewhere because how often do you go to fine dining? Like, yeah, that’s that’s my grand troll, steal that one, folks.
That is beautiful. That is beautiful. But that’s its thing, yes. How do we go back to the main topic here? Vacations.
I’m leaving. Yeah. So the secret here, guys. We already went pretty far afield on this one. I’m going to Australia and then I’m going to New Zealand and then I’m going to Hawaii. I actually have three types of vacation that I take with clients, and I like make this contractually enforceable. And the first part, the part that’s in Australia, is what’s called a working vacation, where I am On call eight hours a day, working in a co-working space or a client’s office or someplace, and it’s like any day draft. Go in, answer email, do work, do my writing, go home, I record podcasts, et cetera, et cetera. The other is the week after that in New Zealand, I’m going to a conference. And so I’m not working, I’m not at a desk. But if something happens, you can ping me on Slack, I will reply to it. You can email me, I will reply to it. I might take a little bit longer because I’m 17 time zones away from you now, but that’s not off the table. And then the third kind of vacation is the harshest mistress of all. It is AFK vacation, and AFK stands for Away from Keyboard. I cease to exist. Is your website on fire? I’m very sorry. With that cackle. I’m very sorry, and Kai is cackling behind me. It’s a product I’m going to be able to do. We’re both on the beach together because we take all of our vacations together. BFFs for life. Yeah. So, and I’m doing all three of those in one trip, which is highly, highly uncommon. That is not something that I normally do. I’m also out for three weeks, which is. The longest I’ve ever taken on vacation in my entire life. I’m also going to Australia, which is 15 time zones away, and expected to continue being present for clients. And Draft’s opening hours are 9 a. m. to 5 p. m. every day. And after 5 p. m. , if you email me something, all bets are off. So there’s a lot of challenges in all of that in terms of how I Manage my time, how I set up expectations, how I lead up to a vacation, and how I come back from the vacation and deal with stuff. And I’m not good at this at all. Are you good at this, Kai?
It’s the area I struggle with the most. I think I’m okay at and I think we definitely should dive into each of those three areas. The area I’m the best with is the upfront communication to the client. A thing is going to happen. I am going to be outside of Eugene, Oregon for a period of time. This is what to expect. But I really struggle with the during the vacation. Like, Having those boundaries in place, keeping those boundaries in place, not breaking those boundaries myself, and feeling okay with it and dealing with the uncertainty of it. It’s I’d say I’m probably like a seam Inusan scale at this. Yeah, I’m I’d say I’m a B minus, so uh I win.
Which is great.
We’re grading on.
But in another more accurate sense, we both lose. We should be A pluses at this. We’re not. I’m. Sound very poised and comfortable on this wonderful podcast because I’m hanging out with a good friend of mine and having a really great conversation. But I’m freaking the fuck out all the time about this vacation. I could not Leading up to a vacation and immediately after a vacation are always the two hardest times of the year for me. And I spent four weeks decompressing for my holiday break and compressing for my trip to Australia. And it shouldn’t have to be this way. It sucks. It completely sucks. Like, I deal with a lot of stress on it. And with many of my vacations, actually, a lot of clients lose enthusiasm in a project, and then one of them parts ways. And You know, if you’ve known me well enough and you’ve been listening to enough of these episodes of the podcast, you know, probably in the back of the head, I’m like, great fuck them, God, table flip, whatever. But in another sense, like maybe I actually liked working with them before I went on vacation and feel really sad that I couldn’t have salvaged that relationship. And I’m cringing for that this time, man. Like, I’m not taking any other major vacations for the rest of the year, but we’re coming off the holidays, and it’s like the fallow period, and the market sucks. And I’m just like. I’m waiting for the other shoe. And I’m doing this while trying to build more business. I’m aggressively hiring new clients right now. Not because I’m panicked or desperate, but because I hired an assistant and it’s finally hitting well and I have a lot of discretionary time. And I want to take advantage of that. And have more bandwidth for it. So I’m like trying to do two things at the same time, which are hire a bunch of clients and retain my existing clients. And actually, there’s a third thing, which is leave. And leaving is a practice. So, what are the things that you do, I’ll go into the things I do, before you go on vacation?
Before I go on vacation, I freak out and panic for probably six weeks or so. Communicate to a client what the expectations are in terms of Communication with me, what work is going to get done, work might be getting done slower. What, like, okay, we might have a list of six things we want to tackle in the coming month. What’s the number one priority? Like, what can we push forward? What needs to happen now? And how do we negotiate and balance the two? So, good communication, I think, is a key there. Just so. Like, if there’s one thing that absolutely must happen, we’ll get that thing done and the other things might slip. And have that conversation with a client just to make sure While I’m on vacation, their needs are still being met. I haven’t yet done this, but on my next big vacation, I will be like opening that conversation with a client and saying, listen, this is going to impact our working relationship for a multi-week period. Do we want to hit pause and like you just don’t get billed for a month and we don’t do any work for a month? Do we want to continue work, but no, it’s going to be a little less this month and we’ll make up for it in the coming months? How do we Negotiate and reach that compromise there. And at the same time, set those boundaries in place so the client knows: like, hey, I’m on vacation, which means I’m going to be distracted, or I’m spending time on personal development or something else. So, this is what you could expect from me.
Setting those expectations is super, super important. I actually take vacation with four months’ notice minimum for all of my clients, and then I post a list of vacation dates. on Basecamp, and then I give people a heads up around vacation. And one thing that I’m actually trying while I’m out is my assistant is emailing all of my clients while I’m on vacation and being like, hey, Do you need anything right now? Let me know. And I know we have, you know, the assistant hasn’t talked with a lot of people, so we’re going to set it up well. But, like, That is going to be super important for ensuring that we have the right expectations set. Describing what the type of vacation is. Having three types of vacation is really weird, and I don’t know if I’m overcomplicating the process or not. And I worry about that a lot. Asking a couple of weeks beforehand, are you okay? What do you need? How can we get this set up effectively? I’m atrocious at that, but I think it’s super valuable. So that’s free advice for everybody listening to this. Do what I’m not doing. But, you know, I think that would be super helpful. Yeah, I think that’s pretty much everything. Overall, just like coping with fear and scheduling yourself out and not doing any giant initiatives right before you leave, because leaving is a giant initiative pretty much all the time.
One personal case study story I could share is I so I have terrible grass seed allergies. And Trivia fact for the audience, Oregon, specifically Lynn County, the county one county above Lane County where I live, is the grass seed, number one grass seed producer in the world. So This makes Oregon uninhabitable for me for six weeks every year. So I take a six-week vacation every year where I’m doing that. Hey, I’m working, but I’m going to be remote. Connecting with your previous statement about not doing any huge initiatives, this past year, 2015, during the six-week stretch, I visited Philadelphia for a conference, went to Arizona for four weeks, then went to San Diego for two weeks. So I was visiting multiple states, living in multiple houses, multiple Airbnbs. And I decided I was going to try to write the first draft of my book, The Traffic Manual, while I did this, while working with five clients, while doing multiple podcasts. And it just, it burnt me out. I came back from this vacation and I talked to my mom and I’m like, I can’t ever do something like that again. It was way too much. I thought. Being out of my normal environment would free me up for creative capacity, but I didn’t realize the cognitive load it puts on you or it puts on me. To be traveling that much and be doing client fulfillment work since I couldn’t hit pause on all the client engagements and I didn’t want to hit pause on all the client engagements for that six-week period. What’s harder? Since, like, you show up in a new city and you’re like, what’s the coffee shop I work at? Where’s the whole foods I buy stuff at? How do I know that they have good internet? Two out of the three places I stayed had terrible Terrible DSL quality internet. And suddenly I’m trying to Skype with clients and it just doesn’t work anymore. So there are all these contingencies I didn’t factor in, and what was supposed to be a semi-restorative Walkabout for me ended up being a very stressful process because I didn’t think about all these contingencies and issues. And on top of it, I overloaded myself with what I wanted to accomplish when really I should have set the expectation within myself of. Hey, I’m going on vacation here. It’s going to be work to be on vacation. I need to like aggressively shunt things forward to July, August, and September instead of putting more stuff on my plate for
While I’m traveling, I’ve never had good creative work happen while I was on vacation because I’m spending too much time taking in my environment and it just saps all of your executive function. You don’t have the ability to make Large, complicated, thorny decisions while you’re out of your environment. It’s so weird because I feel like I’m simultaneously like a total homebody. Like, I love Chicago and I love hanging out here, and it’s so familiar. I’ve lived in the same five blocks. Radius for eight years. But I also love traveling, and balancing those two is a mind fuck, man. It is so hard. It is, I’m very grateful I get the opportunity to travel. I’m sure a lot of people are listening to this. Like, boo-hoo! He went to Japan three months ago. He’s going to. Melbourne in a week. And it’s 86 in Melbourne right now. And it’s 32 here, which is actually pretty warm. Like, there’s definitely this weird, like, um, cognitive dissonance you get where it’s like, oh yeah, I can. I’m going on a writer’s retreat, you know. I’m going to my cabin in the woods and banging out the great American novel. Fuck no, you aren’t. You have to figure out how to forage when you’re in your cabin in the woods, and you don’t know how to do that. You’re eating out probably twice a day, every day. So, you don’t know how to you aren’t cooking for yourself, so you don’t have agency on that. So, you’re probably feeding yourself a god-awful diet. You’re probably going out every night because there’s booze in that town, and why not? You know, what does the booze taste like in this side of the world? I want to know. And then you have a drink, and then you are not as focused the next day. Just a million like worlds of hurt on this that just like make it so so hard. So so hard to like Write a book. Do serious business strategy. Think at a really critical level that’s necessary to To further the businesses of your clients in the same way. Like, why did they hire you? They hired you because you’re brilliant and you’re capable of doing this really well. Well, what happens when you get to be a little less brilliant? I’m sure I’m going to be de-jet lagging horribly when I’m in Melbourne. Right? Like, I’m not going to have any energy. It takes 25 hours to fly there from Chicago.
I could not do that. I would. Stopped six times along the way. I flew to Spain a couple years ago, and that was 14 hours from Oregon, and I was dead for the first three days.
You can’t stop because you’re over the Pacific Ocean for the entire flight. I’m stopping once in LA for two hours. And like taking as many sleeping pills as, you know, not lethally possible. I’m just hoping I can sit upright and sleep. Oh, please don’t die.
We can’t record Make Money Online without you. No brain damage for Nick D. But yeah, it’s a challenge. And to circle back to that idea about how do you prime a client for the expectation of I’m not going to be operating at 100% during this vacation or slightly afterwards. Well, I think it comes back to communication. It comes back to like literally saying that, like, and also communicating up to them that Hey, I’m a human just like you. I’m going to take a vacation and it’s going to make me a better person. Since, do you really want to be working with a consultant who never takes a vacation? Is that the type of people person you want to be hiring for your business? Most clients will say, like, oh, no, that’s not. Okay, how do we negotiate around this and set expectations and set deliverables? So we’re balancing expectations on both sides. And likewise, As a business owner, do you want a client whose expectation is you will never take a vacation? You are mine. You belong to me. That sounds like a terrible relationship to have. Yeah, exactly.
Like there’s on the one hand, you’re completely right. On the other hand, the consultant who’s being hired is typically a contract And you might be on a monthly retainer with them, and so paying them. And that’s what happens with my coaching clients, that’s what happens with my revised clients. It’s what’s going to happen with like bigger clients like Dashboard and Foundation when I run into giant stuff like that. Draft my first Foundation client took seven and a half months. When I said on the webpage it would take six months because I was on vacation for the holidays. And I was in Japan for a part of it. And so, like. They have to be amenable to that. And doing that communication is absolutely critical. And you’re just, it sucks because you’re working twice as hard doing two pretty mutually competing activities. You’re delivering the work and then you’re talking about the prospects. Of delivering the work later. And that’s just tremendously difficult for me at least. Like, I’m too up in my head figuring stuff out for my clients all the time. Yeah.
I think that this connects to the previous episode as well in terms of onboarding clients, telling people, like, I take vacation, like, you do this very well in your welcome packet. Telling people, like, I take vacations and this is what to expect. If the client’s like, well, that doesn’t work for me. Okay, great, let’s not work together then. And like, it’s a position of privilege and power to be able to say that. I think it’s also necessary. Since if you say to a client, like, hey, by the way, I have a vacation coming up in a month. This is what that’s going to look like. This is how it’s going to impact our work together. This is how we could route around that impact. And if they’re like, that’s unacceptable, you’re like, you’re right. Is we can’t work together. Thank you. Goodbye. Hang up on Skype. Or they’re like, hey, that sounds great. Let’s ride around it.
I love when clients get the welcome packet and they think, oh, okay, Nick D is going to take this amount of vacation. And I’m. Very, very clear in spelling out all three kinds of vacation and how much I take each one. And then I actually do it. And they’re like, and they like freak out about it. And I’m like, well, what did you think you were getting yourself into here? I wasn’t kidding when I said I’m not going to be answering email. And it’s very hard, which is why I stress the importance of setting up expectations and blame myself largely for not setting them properly.
And I don’t know if I already said this in the episode. I think we said it in the pre-episode. I haven’t taken a true AFK vacation in over two years because I’m afraid of the fallout from losing a client from that, a client being angry about it. And so Every vacation I’ve taken has been those middle ground around from emergency or traveling and on-call vacations. And I know it’s burning me out to have not had a true AFK vacation. It’s scary. And part of me is still in the for even though I’m so many years removed from having a day job, is still in the I need to ask my boss for permission to take time off. Oh shit, I have seven bosses right now. Ooh, this seems complicated and scary. I better not do it. When the truth is, I’ve set up, or if I’m doing it right, I’ve set up each of these client relationships to be us talking to each other as partners and equals. So just like my clients frequently say like, oh, you know, I’m taking two weeks off, so we need to skip the next call. I have that same privilege and ability to say, like, oh, by the way, like, I have, as I notified you a month ago, I have an upcoming vacation. I’m not going to be available. We need to reschedule that call. But there’s still that fear inside of, like, well, what happens if they say no? And the truth is, if they say no, well, I’m sorry you’re saying no. How, like, let’s use communication here. How do we work around this? How do we make sure that everything is being met? And is it really going to impact your business if I’m away for two weeks, if the objectives are still being met? Are we thinking in terms of hours, or are we thinking in terms of output and value? Let’s get back on the output and value train. That’s the one we need to be taking.
Yeah, you’re exactly right. And yeah, I mean, you’re right about having seven bosses. In many ways, it feels like you’re hiring bosses whenever you have a client. But you know what, man? This is a sign you have to do it. And you can’t just go halfway. You have to leave your laptop at home. You have to delete all of the apps that you’d use for work off of your phone. Only personal Slack rooms, no work Slack rooms, not even your own. Like you have to do it. You have to do it. Do it in June when Oregon is going to turn into a hellscape for you. I’m serious. That gives you five months to set this up. You have to do it for one week. If any client fires you for taking an AFK vacation for one week, And you have set up the expectations properly that you will be gone, and here’s what you can do while you’re out and everything. And maybe even have your assistant check in that Wednesday and do all of these things. And they still fire you, fuck them. Entirely.
Entirely. And you’re absolutely right on that. I think in this case, It looks like I’m going to Burning Man for the first time this year, and that’s end of August. That’s very AFK vacation. That is a huge AFK vacation. Okay. Yeah, and that’s going to be like the two-week AFK vacation. And that gives me six and a half months run-up to be like. Hey, I’m going to be literally AFK. There is no internet in Black Rock City. There is zero internet. Ah, I will not be able to talk with you. Let’s get any issues out of the way now. And by the way, I will be completely unavailable for those two weeks and probably the week following that as I decompress from the burn. If that’s going to be an issue, let’s get the issues out of the way now. But you’re absolutely right. Like, that has to be the AFK vacation. And even the six-week walkabout in June. That’s a perfect time to field test this for a week and say, like, you know, there’s a conference I’m going to there. I’m going to be AFK for this one week period, but I’ll be traveling and on-call for the rest of it.
Yeah, yeah. I mean, well, now you have an opportunity to figure this out. And I look forward to checking in with you in about nine months and seeing how that actually goes. Like, seriously. Oh, yes.
And I think it’ll go well. Like, none of my clients have ever given a sign that it would be an issue. And I think this is a recurring theme through all of our episodes. A lot of the issues and fear we experience as consultants are entirely internal. It’s our monkey mind saying, like, you should be afraid right now. When the truth is, there’s no outward signal. We’re afraid of the expectation of a client being mad or a client firing us. Well, until the client actually says, if this happens, I’m going to fire you. Why are we living in fear of that?
Yeah, I don’t know. Like, a lot of this is just put on us, right? Like, it’s something that you impose on yourself. Honestly, it’s a sign that you care, right? Like. Can you imagine if we didn’t care about our work and like were just really cavalier about it? Like, it’s a good sign that we’re running good businesses, that we’re freaking out about vacation.
No, absolutely. And yeah, you’re absolutely right. It shows that we care and communication and notifying the clients in the onboarding process and a welcome packet months ahead of the vacation. Like it shows that we care about them. It shows that they are important to us, and because they’re important to us, we want to let them know that this thing is coming up. Let’s make sure that everybody’s needs are met. Just like you communicate to a business partner or a romantic partner or your family, your client is or should be somebody who’s important to you and deserving of that communication and care. Yeah, yeah, absolutely.
Absolutely. So let’s care more. I think that’s the takeaway. That’s the only takeaway is care more and prep your clients and set good expectations.
For sure. If your client gets mad because of a vacation, well, part of it is their attitude and their mentality. And are they just, is this a sign that they aren’t a good client and they’ve gone feral? Or is it because you didn’t take the time to properly prime them and properly set expectations about that? And if so, well, maybe you lose a client through this experiment, but you also. at a cost, have gained the knowledge that you need a better process for priming the client and setting the expectation and having that communication happen. And then great. You’ve learned and you’re able to implement a better system, and your business is healthier for the pain, for the growth you went through.
Yeah, yeah, absolutely. I mean, This is another example of you do something, you try it, you see if it works, if it doesn’t work in some way. Was it you, was it them, what can you change, what worked, what didn’t. Try again. There are other clients. You have not lost your final client.
No, no. And yeah, that should be another episode in and of itself. The abundance versus scarcity when it comes to clients.
Yeah. Oh, for sure. For sure.
Anything else we should touch on when it comes to taking vacations? No, I’m leaving. You’re recording this from Chicago International.
God, it would be a lot louder if I were recording it in O’Hare. That would be grim. The blue line boards at gate 12. ORD Airplane Emoji M-E-L.
Tweet. Well, have a wonderful, beautiful, amazing vacation, my friend. I will. I’m scheduled to. On the calendar. Have a wonderful vacation. And I guess by the time our listeners. Here, this episode, you will be back from vacation. So, welcome back, and I hope it was an amazing vacation. Thank you.
You know, I got a huge tan, and now everyone thinks I’m weird because I’m the only one with a tan in Chicago. I really, you know, it was really great. I tan easily. So That’s another thing you’ll learn about me. Day two and Nover, Nick has. Nick looks like a hot dog. Nick is fried. Here’s our. Here’s our actionable business takeaway for everyone who fast-forwarded to the end of this podcast episode to get the takeaway. I tan easily.
And with that advice, we hope you make money online. Never not make money online.