Episode 105: How to Take a Sabbatical
Summary
Nick and Kai walk through how to take a real sabbatical as a freelancer, using Nick’s upcoming month in Japan as the working case. Nick booked the trip accidentally in March after finding enough airline miles for a round-trip business class ticket to Narita, and spent the following nine months managing client expectations. The episode covers the mechanics: how far in advance to tell clients, how to sequence billing before handing over the sabbatical work plan, and how a 15-hour time zone gap changes what “available” actually means.
Highlights
- Nick found the Japan ticket in March while drinking chartreuse and auditing his miles across ten accounts. The round-trip business class seat to Narita cost $42 in taxes with a fixed January travel window, and he booked it on the spot.
- Nick tells clients four months in advance: where he’s going, when he’ll be gone, and what level of availability to expect. That range runs from “Slack replies within 8 hours” to “I don’t exist, bye.”
- He won’t send the sabbatical strategy document until the client pays their next billing period. His reasoning: if billing isn’t locked in, the strategy may be irrelevant to the engagement entirely.
- Tests stay running while Nick is in Japan, so clients still get deliverable value during the gap. The strategy document covers that window specifically.
- With roughly 15 time zones between Chicago and Tokyo, Nick tells clients to convert the time before pinging him. If it’s 3 a.m. in Tokyo, he’s asleep.
- Kai is using the same pattern with a prospective client, disclosing a planned April/May move during initial calls so the campaign schedule doesn’t put a major launch the day before he goes off-grid.
- Both agree the urge to freak out is the main obstacle. Nick’s counter is nine months of lead time, which makes the logistics feel routine by the time the trip arrives.
Read the transcript
So, Nick, one thing I’ve always, always, always admired in you as a business owner. Is your ability to take sabbaticals from your work? And honestly, this is more me just asking you: like, how do you do it effectively? And Help educate me and help educate the listeners. So, I know you take a month off. I know you set the boundaries effectively. Walk me through what that’s like from your perspective and the client’s perspective and how that plays out in practice.
So while you listen to this, dear listener, I will be in Japan, recording this well ahead of time. And I had a brilliant idea. So basically, The short of this story is it begins like pretty much all of my stories. It involves chartreuse. And I was drinking chartreuse one night at my computer. This is not a joke. And I was poking around my like airline miles, because I have all of my airline miles in like 10 different places, right? There’s like United and Amex and American and Herfederf, right? So I’m like taking stock of all of it because I feel like they’re getting up to high numbers. And I’m like, well, maybe I can do something about this. This is like March of last year, right? And I find out that I can do one of three things. I can either book a one-way ticket to either Amsterdam or Charles de Gaulle in Paris, which doesn’t get me the other way back. Doesn’t matter.
You’re in Amsterdam.
Right. Or Paris. Or I can book a round trip ticket in first class to New York. I go to New York basically requiring no convincing. Like, I go to New York at least once or twice a year. I do enjoy it. And I basically buy all the menswear and leave. And then the third thing was I could fly a round trip business class to Narita, but it had to be at the beginning of January. And I looked at this and I’m like, fuck this. There’s one seat left. Conversion rate optimization. And got suckered into buying a international business class round trip ticket to Orda to Narita. Straight connection. No, you know, it was a nonstop flight. For $42. That’s quite expensive. It’s a lot of money. It’s a lot of it’s all taxes. I hate taxes. Who likes taxes? It’s all taxes. Oh my god. So I’m going to Japan. And I’m going to Japan accidentally right after my holiday break for a long time. Oops. I wasn’t deliberate about that. That was Chartreuse’s fault. So the first The first suggestion I have for you, dear listener, is throw caution to the wind and do something really stupid. And then try and sort out all the ramifications for it later. Always a good process.
It was similar for me in my day job. I think back specifically to One point when I just was like very, very burnt out. I had a bunch of miles. I booked a trip to Spain. I was like, where do I want to go? Spain. Spain sounds nice. I will go to Spain. I bought a ticket to Spain and I was like, I need to tell my boss that I’m going to Spain. And I was like, hey, boss, I’m going to Spain for three weeks. And he was like, okay. I did not expect him to say okay at that point. I did, I did not like the day job. And I went to Spain for three weeks and took a sabbatical and came back. I was like, man, that was recharging. I’m going to quit my day job in six months. I want freedom. And it worked well. And it very much was, I did the thing, okay. Now, let me figure out the ramifications of the thing. But that’s a little aside from the main point. So you’ve booked the ticket to Japan, you have the sabbatical planned out. How do you go about Setting expectations with clients, with colleagues, with people in your life around this travel time, just so things don’t get missed, expectations aren’t missed. How do you But yeah, how do you effectively communicate that you’re going to be gone? This is what’s going to happen, and this is what’s going to happen after that.
Yeah, four months ahead of time, I tell them when I’m going to be gone, where I’m going to be going, and how available I’m going to be on the internet. And that ranges from I will be available, but it won’t really be during normal business hours because Japan to I will be available all the time and I’ll have Slack on my phone to I don’t exist bye. If your website breaks, I’m so sorry.
It’s a very elaborate A-B test. What happens if we take down the website? Will you still make money? We’ll find out.
And those don’t happen terribly often. And we’ve talked a lot about how to take vacation, but the sabbatical is like, what are the reasons for it? What are the outcomes of it? Because you want to make sure that it’s not just Nick D is taking a sabbatical because he’s a fucking weirdo. Is billing going to continue during the sabbatical? Is there going to be pro rating or refunds? Are you going to have to find another guy or gal to take over? These are all questions that a client is going to be thinking about, and you need to head them off months in advance, like far enough in advance that they’re like, oh, okay. And so like when I when I signed on a client in August, I already had the Japan thing done, right? Because March. And so they came in and they’re like, by the way, I will be in Japan at this time. And they’re like, okay. And this is after our first billing period is done. And then I tell them, okay, by the way, your next billing period is due. And they’re like, okay, great. You’ve been doing wonderful for us. You made $500,000 on Black Friday weekend. We love you. Okay, great. Here’s the billing link. Okay, great, we’ve paid. Here’s the strategy that’s going to take place while I’m in Japan. Like week after. Because you need to make sure that the time is actually going to be locked in. And you by doing that, you have to pay me, right? Like, I can’t. I’m not going to give you my Japan strategy until after that happens because maybe it’s irrelevant. Maybe. Maybe it would actually wave you off of the engagement. And that’s weird because people take vacation. So I sat down and I was like, and I already had this strategy prepared. It wasn’t like I was making it up. And they’re going to have tests running while I’m out, so they’re still getting value from me. But, like, yeah, no, I’m going to cease to exist for a minute. And it’s not because. I’ve turned off my phone. It’s because you’re in Florida. I’m in Japan. That means that when I’m waking up, you’re going to bed. Right? Like, or something like that. It’s very. Significant time zone difference. So by dint of that, we’re just not going to be hanging for a minute. If you want to ping me on Slack, eight hours later, I’ll probably reply. Um and setting those expectations very, very clearly. Knowing how time zones work helps a lot. The fact that I live in the city of Chicago, which everyone on earth thinks is in a different time zone than it is actually in has helped a lot on that. It’s helped me be very empathetic to differences in time zones, especially when there are 15 of them between you and the client. Because usually there’s one or two between me and a client. There’s two between me and the person I’m talking to right now. You know, there’s that. So you have to be very cognizant of that and be like, here’s how you convert to this time zone. So if there’s a fire and you convert to Tokyo and find out it’s 3 a. m. , maybe I’m asleep. I’m not going to answer it. I’m going to continue to human as best I can while I’m out there. So that’s a consideration that has to be put into place.
No, and I like it. I like how it centers around, as with everything on Make Money Online, communication, talking to the client, setting that expectation. I have to record this episode. I’m having a call with a potential client that I might start working with in the new year. And I’m looking at an extensive trip that might kind of be me moving somewhere in April, May. And so. I’ve started talking with them about it now and saying, Hey, heads up, if we end up working together, I’m going to be off the grid for about two weeks in April, May-ish because I might be moving someplace else. I’m scouting it out, figuring it out. But that’s something just to get out of the way now. And so they know, okay, so if we kick off in January, we’re going to renew three months later when April rolls around. Guy’s going to be updating us along the way, but there’s going to be a period where he’s off the grid. And so they’re coming into the engagement knowing: hey, there are these contingencies, there are these constraints around how we’re going to be able to operate. Around what’s going to get done and when, and so we’re going to be able to plan out the campaign and say, Well, hey, we really don’t want to launch a large part of this campaign, you know, the day before I suddenly leave. So, let’s make sure that we don’t do that. It all comes down to, I think, setting that expectation, setting that communication, and having the confidence in yourself to be able to take that sabbatical or take that break. Not enough freelancers or consultants give themselves the time in their business to take an actual honest-to-God vacation, and you deserve it. You owe it to yourself.
I mean, there’s that. Also, it shouldn’t feel abnormal. Like, I’ve gotten good enough at setting expectations around vacation time by now that, like, I just kind of spin up the machine and don’t freak out about it. I think there’s a temptation to freak out about it. Which, like, yes, you’re doing a lot of work before and after the thing to account for the fact that you were just gone for like four weeks. But that’s what’s necessary to actually take the vacation. Like, do it. That’s great. Now you know what’s happening. You also had nine months of heads up about it So the fact that I’ve like made that that air gap there and actually done it is very, very helpful. But yeah, I mean, that’s it. You owe this to yourself. You’re going to fight for it and you’re going to win. And your prize is going to be Japan. You win Japan. You have become the owner of Japan. You are Doctor Japan.