Episode 29:How To Prep Your Clients For Your Travel
It’s one thing to be totally awesome at traveling. It’s another thing to travel a lot. But how do you preserve your client relationships while traveling?
Summary
Nick and Kai walk through the practical realities of maintaining client work while traveling: how to set expectations before you leave, what work actually survives the trip, and why the fear of everything falling apart is mostly unfounded. The episode covers communication cadence, time zone negotiation, inbox delegation, and the hard lesson that productivity drops more than you expect.
Highlights
- Nick’s pre-trip routine runs in three beats: a Basecamp post four months out, a heads-up two weeks before, and a final check-in three days before departure. When he lands back in Chicago, he asks each client how things went and whether they can get on a call.
- Both Nick and Kai cap billable work at two to three hours a day while traveling, and both default to writing tasks rather than anything requiring sustained technical focus. Kai puts it plainly: he cannot fix a CSS issue on day four of a trip.
- Kai’s first major work-travel experiment, two months hopping between Philly, Phoenix, and San Diego to dodge allergy season, produced none of what he planned: no client onboarding, no book progress, no podcast appearances. Productivity dropped more than 50 percent, not less, because the city pulls attention.
- Nick held his Copenhagen clients to Central European hours, told them every email would get a one-day turnaround, and did not negotiate around it. He applies that same time zone transparency even for a one-hour difference like a New York trip.
- Kai came back from one trip to 130 emails, 15 of them actually actionable, because he did not hand inbox keys to his assistant before leaving. His proposed fix for next time: have her star things, ping him once a day in Slack for urgent items, and send a holding reply for everything else.
- Nick flagged that Kai’s assistant-delegation problem partly comes from a single inbox mixing direct client email with emails sent from client domain addresses. His fix: a second inbox (kai davis@ instead of kai@) with no autoresponder, so the two streams stay separate.
- Kai’s bigger point on fear: for consultants already doing remote work, clients barely notice a time zone shift. The computer box still works from Stockholm. Nobody has ever done more than note he was less responsive, and that was the end of it.
Read the transcript
So, how do you pitch travel to clients, Nick?
We did an episode on taking vacation before, but there’s also like The kind of travel where I’m going to a conference and I’m still on call. So, one thing I do, and this is a lot of kind of tactical things, but I plan all my travel four months in advance. And then I post to Basecamp when I’m going to be traveling and where I’m going to be going and how they should be expecting me. About two weeks beforehand, I give them a heads up, and then about Three days beforehand, I give them another heads up and ask the schedule call and check in one last time before I leave. When I land back in Chicago, I. Ask the client how things have been going and if we can get on a call to talk further. And that allows me to kind of get back in the swing of things. And I do this for all of my clients. I’ve already put together like reminders to schedule these follow ups and make sure that people are okay with it. Because when you’re traveling, and I think this is kind of the broader consideration, you have very little executive function. You have very little free time to actually afford to billable work, even when you’re Traveling. And like, if you’re traveling and you’re just going to a co-working space all the time, like that seems a little bit disingenuous. You can be going out, you have that luxury, but you’re missing out on like maybe museums, parks, boutiques, a lot of things that are dope in a city. So I really cut my work time to like two or three hours a day max. And it’s usually spent in coffee shops so I can also have awesome coffee while I’m doing my work. And I limit it really to like writing stuff. So it’s a little bit different. And I’ve structured the activities that I do in my job such that I know exactly what I’m going to be doing while I’m traveling, even when it’s for a really big trip. How do you do it?
I communicate beforehand that I’m going to be traveling and let them know the different types of travel. I try to block out as many. Kai needs his full attention on this, sort of infrastructure things ahead of the trip as I can, even if it means pulling a late night or two just to get them out of the way. And I’m coming to the realization, I have come around to the realization, that I am a useless bag of flesh when I am traveling. And to actually accomplish most work is a difficult thing. Again, preloading infrastructure-related things, focusing on what I’m good at while I need to be mobile or might be shifting location, which is writing, which is creating text, which is responding to email, which is some human interaction things. I could do coaching calls perfectly while I’m on the road. I can’t really do hardcore client work while I’m on the road. So, figuring out what my strengths are, figuring out what your strengths are, dear listener. Optimizing for those strengths. You might be like, sweet, I’m on vacation. Like, I’m going to code for four hours a night because that’s how I come down from wandering around the city all day. Good for you. Do that. For me, if somebody was like, Kai, can you fix the CSS issue on day four of your trip? I’d be like, what? No help. And does not compute. Select all, display none. We’re done. We fixed it. And. And so, by figuring out what I’m good at in these different contexts, it’s allowed me to get better at it. I’m by no means good or great at it. And by no means will you be good or great at it until you’re actually in the thick of it on your first trip. So. Beforehand, if you’re planning your first, like, hey, I’m traveling and I have clients and I’m doing this working type thing. Like, expect the unexpected, expect to learn as you go forward. And be okay with the fact that you’re going to come back knowing a lot more than you went into it with. And it’s been that way on every single one of my recent trips over the last three or four years. I’ve learned more about where I suck and fall down. And more about where I’m really, really good. And so the next trip rolls around, and I’m like, cool, let me optimize a little more for that. And it just gets better with time. If something does drop, I found that more communication earlier is better than not. And so, like, A. Always try to communicate more than possible. If a deadline slips, if a thing happens, reach out to the client, be like, I did not expect this, I’m so sorry, this is the new timeline. They’ll appreciate it. If you fall on that or fail on that and you don’t have that proactive communication, as soon as you’re back in the office, reach out and be like, hey, sorry, communication thing. This is where we are. This is my plan moving forward. This is what I propose. Let them know that you see the situation and you’re in control of that. Don’t not communicate. Don’t avoid it. Be forward and be direct and figure out if something does slip how you could make it work.
Absolutely. I think that overall, you need to convey the impression that things are normal and that this is normal and that you will have your shit together when you’re gone. And I think that’s insanely important to be keeping in mind as you’re going through and doing this. I also want to note: you will screw up your first five trips. You will screw up something major. And you have to recognize that. And maybe I’m wrong about that. Kai might push back and say, well, it’s actually only three. But the first time you travel when you’re doing billable client work You’re going to underestimate what your body is doing to you, and you’re not going to know how to actually respond to it effectively. So that’s actually going to be really, really difficult for you. And you just need to recognize that the only way to do it is the only way out is through. And you have to practice at it.
So, my first, we told this on a previous episode, but I think it’s good to recount. My first real experience doing a major work while travel thing was last summer when I took two months out of Oregon to avoid allergy season and hit up Philly. Phoenix and then San Diego across those two months. And my intention was to do all the client work, onboard new client, continue marketing myself, appear on OnePlus podcast a week, and finish my book. None of that happened. Not a single bit of that happened because it’s incredibly stressful to be city hopping like that and expect to be able to output the same amount of work. I thought. I’m going to be in a new location with no distractions like friends or obligations or things around me. I’ll be able to focus more. Entire opposite. I want to go out and see things. I’m figuring out where the whole foods is. I’m. Buying food, I’m dealing with, oh, I’m seven time zones over from where I expect to be. Productivity drops by 50 plus percent. It does not in any way increase.
Yeah. Yeah. I think that’s an interesting point, which is that you’re just going to be less productive. You don’t have to be unproductive. But you always have to be thinking about what you’re doing. You’re not off your job when you’re doing this. Unless you are, in which case, great, bully on you. That’s a choice that you have to make beforehand and let your clients know. Because if you promise work and then don’t do it, that is your own fucking fault. Yes. That is horrible.
Yes. Completely agreed. Yeah. Yeah. And so it comes down to communication and it comes down to expectation setting. And without those two, I think you can’t really travel and have effective client work happen. Yeah, my big punt on this past trip was I was not as assertive as I needed to be when I met up with some friends who were purely on vacation about I need to carve out two to three hours a day to do CHI related things. And it ended up getting shifted to the evening and then butted up against evening events. And so that was a big lesson learned for me that I need to clearly communicate to my travel partners. There is work that needs to be done. It is minimal work that needs to be done, but it’s going to eat up some amount of time and such from noon to three. I’m going to be in that cafe over there while you’re doing something, and then we’ll meet up afterwards. If you don’t see me by 3:30, please come rescue me from the cafe. I have fallen into a pit of work. And if I had done that, I think it would have Lessened my anxiety around client-related communication around the trip. It would have helped me manage my inbox better. I came back to 130 actionable emails. And yeah, I mean, it all comes down to communication and setting the expectations for yourself. For your travel partners and for your clients.
Tell them what time zone you’re going to be in and convey to them that no, you are not actually taking on the original business hours of your home time zone. I, you know, when we went to Stockholm and Copenhagen, I was like, well, I’m going to be working nine to five Central European Standard Time. They’re like, okay, so what is that Central Time? And then I told them, and they’re like, oh, wow, that’s seven hours off. I’m like, yes. We’re not getting on any meetings during that time. When you’re emailing me, there’s probably going to be a one-day turnaround on everything. And you have to be okay with that because that’s when the sun rises and sets in Copenhagen, and I’m not changing my entire life around you. And that’s a choice. That’s another choice you have to make. But you have to recognize that and set the expectations properly. And this goes for a time zone difference of even one hour, right? Like I tell people this. So that they’re not burned at 4 p. m. when I’m in New York, right? Mm-hmm. Mm-hmm.
Yeah, completely agreed. Completely agreed. As somebody who has employed contractors and had them go on vacation both while doing work and not doing work, I have like a tiny glimmering of the other side of the table. Communication is important. As the person who’s paying somebody money, I really don’t give a fig if there’s like a super high important deadline. I should have communicated that earlier and we should have finished it ahead of time or planned for it. 90% of things I really don’t give a fig about. And so if you get back and you’re like, oh, I got back from vacation, it’s taking me a week to catch up. I’ll be like, cool. Let’s schedule our call and figure out what things look like moving forward. And yeah, 90% of the things as the person Paying money for a consultant or paying money for a contractor, 90% of the things really don’t matter, but the 10% that are left are very, very important. Clearly communicate that you’re going somewhere, clearly communicate that. You’re traveling and you’re in a different time zone, clearly communicate what the high priority things are going to be and what the I’ll get to it when I get back things are going to be. Because they’re business people who travel also, they realize that, like, yes, there’s a 10% category of Will focus on and a 90% category of, oh, it’s not that important, and I’ll get to it later. They know that. Right, right.
Yeah, you’re making sure you’re fulfilling your professional commitments. That’s really what it is. You’re honoring that. Admitting your limitations, being a clear communicator with somebody, making sure that they have the right expectations, not leaving them in the lurch when something matters. And that’s really what it comes down to, I feel.
One thing I did, another thing I did poorly on this trip, was I did not delegate my inbox over to my assistant like I originally had planned on doing. I’m still behind you on full delegation there. And I wish I had handed her the keys and said, stuff’s going to come in, star it, and ping me in Slack for the important things once a day. Everything else either decide this does not need a response, or, hey, I’m going to send a short response of, hey, Kai’s currently out of the country. I’ve let him know about this, but he’ll be getting back to you once he returns on Kai’s return date plus one week. I wish I had done that because again, 130 emails in my inbox. 15 of them are actually very, very actionable. The remainder 115 were Slowly actionable.
So, yeah, I wish I had done that. Set a really great autoresponder. Yeah, that’s an autoresponder.
Yeah. I can’t use autoresponders because I’m often emailing on behalf of clients using an at client domain email address. And so, because it all funnels into a singular inbox. If I set an autoresponder, it’s that autoresponder for everybody. And so I don’t want the Kai’s jovial autoresponder tone or the instructions to contact. Kai’s assistant at Kai’s business address to go to somebody emailing me where I’m presenting as being part of a client’s team.
So here’s one part where I feel like you’re screwing up a little bit. That seems to me like an opportunity to create a second separate inbox for those types of emails, and you have everything forward in there, and you don’t set an autoresponder for that one. Then all the things that are actual client communications that are direct, then you have those go into your normal inbox. You need to build a sock puppet, basically. Like you just need to go over here and Yeah, just and it can even be something as simple as Kai Davis at instead of Kai at.
Yeah, you’re absolutely right. Yeah.
Or office at, or, you know. Outreach at.
Yeah, no, I love the Kai Davis at versus the Kai app.
Yeah, it’s such a like small thing, but you just create a whole separate email inbox. And I know then you’re checking it. Second separate email involved.
Ferks turned fourth in box.
Great, then it’s easy for you. You’re fine. In box what?
Hitbox error. But no, that’s a good tip. And so, I mean, email is a big thing, but email is also something that I think people acknowledge will slip off the table. I’ve had somebody follow up with me. Three times over Twitter and twice over email about a document. It’s not a high priority thing, but they just wanted to make sure that it was on my radar and I was paying attention to it. And it was much appreciated because it let me know, like, okay, this is something that is time-sensitive or relevant to them. I will prioritize that a bit higher in my email follow-up than random cold outreach from somebody who wants to guest post on my site.
Absolutely. Yeah, I think there’s a lot to making sure you’re kind of keeping the wheels going. Lean on your assistant if you got one. We gave a whole episode about having one and make sure that they’re keeping everything humming along. The only person, the only two people who get my phone number when I’m gone are my assistant and my partner. And that’s it.
Yeah, exactly the same for me. If disaster happens that they need to reach me, they could reach me.
Absolutely. So, what else? I feel like that’s kind of a small episode in comparison to the big travel one, but it’s that’s just you know, set the expectations, be a good communicator, make sure you and just Recognize you’re underestimating the ability you have to maintain your executive function while you’re traveling.
And so, talking a bit about the fear, I think the number one thing I struggled with, and the number one thing that somebody listening to this episode would struggle with, who Has it done a lot of traveling while working as a consultant? Is what if everything fucks up? Or how do I Deal with this. And I think we’ve been saying it throughout the episode. Your clients are going to understand if you’re doing remote work already, there’s really no difference between doing remote work from Eugene, Oregon, and doing remote work from Stockholm, Sweden. To the client, there’s a time zone shift, but it’s still okay, great. Kai talks to me through the computer box like magic, and things happen. It sort of ends there. So, unless you do a ton of local work, which is ancillary to the type of businesses that Nick and I both run, so sorry. It really won’t affect your clients as much as you fear it will. I was always afraid that it would just completely, completely make things go pear-shaped. And the truth is, it never really has. Somebody might be like, oh, you weren’t as responsive. And I’m like, oh, I’m so sorry. I’ll make sure next time. And that’s about where it stops. It’s not As big of a negative thing, or as big of a thing to be afraid of. Rather, I think it’s an opportunity to take advantage of the lifestyle that you’ve built for yourself. With this type of business and use it to your advantage. Don’t stay stuck in the same spot because your business has put you there. Instead, say, I have built this business that lets me go anywhere I want. It’s time to buy that ticket and fly somewhere new.
Yeah, yeah. Get out of town.