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Why Solopreneur Vacations Feel Impossible and How to Fix That · The Life-First Solopreneur

• 0:00
  Carly Ries: Can you actually take a vacation as a solopreneur? Many of you go solo for the unlimited time off, so why does taking time off feel impossible? In this episode, Joe and I break down the vacation anxiety every solopreneur knows. What if a client leaves? What if something breaks while I'm gone?
• 0:15
  Our take, if your business can't survive you taking a week off, that's a design flaw, not a workload problem. Cover why prep should start four to six weeks out, not four to six days. What vacation ready really means, the hybrid vacation debate, and the step everyone forgets, your reentry plan. So tune in, and then go take that vacation. You're listening to The Aspiring Solopreneur, the podcast for those in pursuit of a life first business.
• 0:42
  I'm Carly Ries, and my cohost, Joe Rando, and I spend every episode with solopreneurs who are proving there's a better way to run a one person business and experts who are helping make it happen. We like to say life first, then business. So let's get right to it. Okay. So every Monday, we have a meetup within our community.
• 1:04
  It's for people to get together, either ask questions about their business, or just have a a sense of, belonging when you're working alone all the time. It's nice to meet up with people and be like, oh, let's just talk about our plans. And two of our community members who we see all the time, they're so engaged, we love them, they were saying, we're taking June off. one of them was genuinely just going on vacation, and I was like, you know, I'm gonna take the month of June off. This sounds like a good time.
• 1:33
  I'm solopreneur. I can do what I want. The other one was taking the vacation because she was burned out. And she genuinely, genuinely needs to take June off to regain her pride, like, just herself, and refocus when she comes back with clarity and motivation. And it got me thinking, taking time off as a solopreneur can be very daunting.
• 1:58
  You think when you go off into solopreneurship and go off on your own, you're like, I can take vacation whenever I want. I have unlimited PTO days because I set my PTO days. But I know I'm guilty of this, and Joe, you are also guilty of this. Even when I'm on vacation, I wanna just check-in a little bit. We're both good at disconnecting, but you like, even when you're in Europe, I'm like, Joe, put your phone away.
• 2:22
  You're in Europe on a bike trip.
• 2:25
  Joe Rando: But, you know, the other thing is it's not necessarily for a lot of solopreneurs PTO. It's UPTO, unpaid time off. Right?
• 2:33
  Carly Ries: So glad you said that. Yeah. I think PTO rolls off the tongue, but you nailed it. Yeah. You don't get paid when you take time off.
• 2:40
  Unless you have systems in place to help you get paid and have that passive income going. But a lot of solopreneurs we talk to, they haven't set those systems up yet, and they equate their time for money, which we try to get people away from, but just the reality is. I think the reason why solopreneur vacations feel impossible is what we've talked about, the ownership trap, and it's very applicable here. When you leave, it feels like the business leaves too. And I think a lot of solopreneurs just have a fear set in of like, what if while I'm gone my clients will leave?
• 3:17
  What if I miss an email and an opportunity is missed to sign a new client? What if since I'm not working that week on my vacation, I may get less money this month. Or if something breaks with a client, nobody's there to pick up the pieces. All of these things run through people's heads, and I think it's because of the ownership trap. But my question is for people that go through all those fears and have anxiety around it, how many times do those fears actually come true?
• 3:46
  I think it's easy to get anxious when you're leaving. But I want people to think about this. If your business can't survive you taking a week off, that is a design flaw, not a workload problem. And we talked about, next week we're publishing the manifesto episode. But a lot of people, a lot of times the issues that they run into is a design problem with their business, and this is no exception. I think before people take a vacation, they should do, a readiness audit. Because I think most solopreneurs try to prepare for vacation, the week before, and then it's too late. They think that that's the time that they'd be like, okay, I just need to double my hours or do this.
• 4:31
  Joe Rando: Something tells me that you do this a lot earlier than than a week.
• 4:36
  Carly Ries: I try to do this a lot earlier, but even still, like, I think back to when I was pregnant and I was gonna go on maternity, I thought I was way ahead, but then I unfortunately had to leave about two weeks prior than what I thought. And there were still two weeks of things that I could have squeezed into that preparation doc that I didn't quite make there, but you were a champ and figured it out.
• 4:58
  Joe Rando: All worked out.
• 5:00
  Carly Ries: But I think what vacation ready actually looks like is client expectations are already managed, not just during vacation prep. Your basic automations are in place year round. Your systems are set up, and you have a clear open close signal for your business. And you set that up ahead of time. Now if I leave tomorrow for ten days, what would actually break?
• 5:24
  But instead just, if I leave tomorrow, it's so good to know my systems are set up. I think people dread going on vacation because they think of that week before or the week after, and it stresses them out. So get to a place where the week before and the week after are just part of your system. And you know who I think is really good at this is George. Don't you think?
• 5:44
  Joe Rando: George B. Thomas? Yeah. He does it. I mean, he's not quite a solopreneur in the sense that well, no. I guess he is actually. I mean, he's got some family members that are employees now.
• 5:58
  Carly Ries: Or their contractors?
• 6:00
  Joe Rando: Yeah. They're family members, but it's the contractor that kinda keeps him running when he's gone. Geroge is a HubSpot expert, so, you know, he can pick up the slack on almost everything. And, you know, you don't get quite the same level of service maybe when you have multiple people there, but it all works out, and emergencies get handled by having that.
• 6:22
  Carly Ries: The process.
• 6:22
  Joe Rando: An Interesting model. Yeah.
• 6:24
  Carly Ries: And George and Jorge contract with LifeStarr. They're on our contractor team, if that's a way to say that. But George, not notoriously, what's the good way of notoriously? Reputably?
• 6:40
  Joe Rando: Notably.
• 6:41
  Carly Ries: Notably. Thank you. Loves his cruises. He loves going on cruises. And I know that when he's about to go on one, it doesn't seem like he's stressed out at all.
• 6:49
  He's just seems like he has his ducks in a row, and he stops. I always look at him as like, oh, you know how to take vacation correctly. So if you're trying to think about how to build this pre vacation runway, I think the timeline starts like four to six weeks out. Not four to six days. And I think with clients, you have to focus on client communication.
• 7:11
  You set expectations before you go. Not the night before you say, hey, in a month I am going to London, let's say, is a random example. And these are the things I'm going to get down for you after. I am not gonna be responding to anything while I'm gone. In the case of an emergency, You can text me.
• 7:35
  I cannot guarantee that I'll respond right away because I'm in a different time zone. But it has to be an emergency. And this needs to be in your scope of work at the beginning From the beginning of your relationship. Just as you're designing your business, you need to be able to factor in these vacations as well, and what that looks like, and get it in writing so people understand that you respect your boundaries. I think in terms of project sequencing, you need to push or pull deadlines intentionally and let your client know. I think you need to decide if you are truly going dark or if you are scheduling time ahead, like, hey, you can either reach me by emergency or I'll be available from one to two eastern on the Monday that I'm gone. if that gives you peace of mind to know that you're still kinda keeping some tabs on your business, you can do that. But if you wanna check out completely, do it. Just get everything set up ahead of time. Set the away message on everything, on your social media, on email. Just make sure people know.
• 8:40
  Communicate that.
• 8:42
  Joe Rando: You know, I set up my vacation six months in advance, at least. I plan them in. I'm gone here, and it's just completely clear to everybody that I work with. And, it just makes it easier because I like to plan vacations. there are some people like, oh, let's do this. And it's like, great. But if you try to do that as a solopreneur and you don't have a completely automated business, like you said, it's not gonna go well. You have to plan early. I will pull in another thing, because you said you know, talk about a week. And sure. If you're, basically functioning at some level of time for money. Right? it might not just be time for money directly, but even if you're on something like some kind of a retainer, you know, selling a product that, has a fixed price. If you're going away, you're probably gonna have to make that up somehow to people if you're not available so that makes longer than a week vacations a little tricky. let's say you wanted to go to Australia. And, I don't know, I go to Australia for a week. I think you did that.
• 9:54
  Carly Ries: Right. I just did that.
• 9:55
  Joe Rando: Do You recommend it?
• 9:59
  Carly Ries: No!
• 9:59
  Joe Rando: Yeah, I Wouldn't think so.
• 10:01
  Carly Ries: I loved it. I had the best time, but it was just I mean, it was the timing. Yeah. Go for two weeks.
• 10:09
  Joe Rando: Three. I would say. I won't go till I can pull a month off. But the point being that, my daughter, does something that really impresses the heck out of me. And, she works for a major educational university as a data scientist. And she's like, have laptop, we'll travel.
• 10:32
  So she takes vacations, but works. So she had a conference to go to in Europe and then just said, you know what? I'm gonna go hang out in Berlin. I've got some friends there.
• 10:45
  She for two weeks after the conference, hung out in Berlin. You know, they didn't care because she works remotely. And she had her laptop, and she just cranks out the work during the day. And, so there is something to be said about a kind of hybrid vacation where maybe you bring your laptop and you don't let everything go completely, but you kind of tone down and have a great experience and not have to give up on the business completely. I mean, I'm a big fan of, shut it down completely, you know, two weeks of just not even thinking about it, but it's not real for some people.
• 11:23
  And at least something like that can maybe extend the vacation a little bit without having to give up, or to engage a 100%, but just keep the business kinda cranking along. I know that maybe you don't agree, Carly, but I've seen her do this.
• 11:41
  Carly Ries: I agree, but I also think some people design their businesses just to run that way. Like, that's their business, where they travel from everywhere. So it's not a vacation lens. It's an I travel full time and I work.
• 11:52
  Joe Rando: Right. This is my life. So, yeah, we've known a bunch of solopreneurs that just live wherever they want to whenever they want to, which I am jealous of. I would have loved to have been able to do that when I was young and single.
• 12:06
  Carly Ries: It's so funny you say that because, you and my dad are the exact same age. And when my husband and I were hitting the road in an RV for the first time, I was mid twenties. I obviously didn't need my parents' approval, but just I like my parents. I love my parents, and I wanted their approval with this. And I was like, so here's the thing.
• 12:26
  We are going to and at the time, he was my boyfriend. I was like, we're gonna travel around the country and work full time. I'm gonna leave my job, but I will have another one lined up. And I was so nervous, because he was always the guy that was like, never have a job without another one lined up.
• 12:40
  Joe Rando: Blah blah blah blah blah blah.
• 12:42
  Carly Ries: 401 k, everything. And so I made a PowerPoint presentation and took him to a restaurant. I was like, that way he can't really get mad because there are people around. And he was like, if I had that ability and the technology existed when I was in my mid twenties, I would have done that in a heartbeat. And so it was the opposite.
• 13:01
  But yeah, that's the thing. Now people have the option to do that given the technology we have. So if that's your thing, do it.
• 13:08
  Joe Rando: Absolutely.
• 13:10
  Carly Ries: I think the other thing that people forget about is they they think they prep so hard. like the lead up to the vacation is planned, the vacation itself and what will happen is planned, but they forget about their reentry plan. And that is a big part of the plan. And that could be part of or one of the most draining parts of plan. Coming back to the amount, even if you have all your systems in place, let's say you come back to a bunch of emails. Now that , it's a vacation killer.
• 13:41
  You're on this high on vacation and then you come back and you're just slammed.
• 13:45
  Joe Rando: Guilty.
• 13:46
  Carly Ries: Yeah. Right?
• 13:46
  Joe Rando: Guilty.
• 13:47
  Carly Ries: So I think try to design your first day back before you leave. Block it as a transition day. Maybe even still tell clients that you're gone that day. So you give yourself a day to play catch up work when people think you're still away. And that way you can come back refreshed once you're all caught up without people trying to interrupt you or distract you.
• 14:09
  And have a short reentry list waiting, like three to five items that you know you need to tackle. And like I said, give yourself a buffer day so you can process everything that came in. also just, if you need two days to do that, and you tell people two days, one day to just recover from the trip and another day to get caught up, that's fine. You're a solopreneur and you are allowed to do that. Again, you have unlimited days off.
• 14:34
  It's just the pay factor that you may not have unlimited of. But I don't know. Joe, anything you'd add to any of that?
• 14:43
  Joe Rando: No. I totally agree. I think that was a great point about the reentry because I've had a lot of vacations where I come back, and I'm just like, oh, you know, everything's great. And then I get back in the office and sit down. Within half a day, I'm like, oh, all of that relaxation is gone. And planning that in and is a really good idea. I like that.
• 15:05
  Carly Ries: Well, and I have a challenge for our listeners. it's summer and people are wanting to take those vacations, so just ask yourself, what is the one thing that would need to be true for you to take a full week off in the next six months? And is that one thing currently in your business? And if not, can you build it over the next six months so You can actually enjoy your vacation.
• 15:26
  So that is my challenge, and that's all I have for today. Take that vacation. Listeners, thank you so much for tuning in. If you think this is the best episode you've ever heard in your entire life, and now you're gonna go take time off,
• 15:39
  Joe Rando: Or not the worst.
• 15:42
  Carly Ries: Thank you. That's a better way. If this isn't the worst episode you've ever heard,
• 15:46
  Joe Rando: I'm stealing from Jay Schwedelson.
• 15:47
  Carly Ries: Exactly. Leave that five star review. We would so appreciate it. It helps us spread the word to other solopreneurs leading a life first business. Share this episode with a friend or another solopreneur that you think would find it helpful, and subscribe to our show on your favorite podcast platform, including YouTube.
• 16:05
  And we'll see you next time on The Aspiring Solopreneur. You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs.
• 16:30
  Be sure to join in on the conversations at community.lifestarr.com