How to Take a Break While Still Running Your Video Business. EP #317 - Den Lennie
8 Dec 2025 · 13 min
Den Lennie talks with Ryan and Caleb about taking extended breaks without tanking your video business. Delegate shoots to trusted people, systemize your workflows so nothing depends on you, and keep marketing running through scheduled posts and outreach. Use travel projects like shooting in Italy as positioning material.
Chapters
As a videographer, have you ever wondered or gotten freaked out at the prospect of taking a couple of weeks off to go on holiday and worrying about what will happen to your business during that? Well, one of my clients recently just decided to take a month off from his business and go and do some shooting in Europe. And we had a big discussion about how you can prepare yourself for that and what that would look like for your business. So I want to give you a bit of an insight today and show you a clip from our, our VBA elite mastermind and how we actually work as a group to support one of our members who's about to make a big decision in his business and take some time out and how he's going.
To prepare for that.
Check it out.
We're just talking about, you know, taking time out the business and leaving the business and that the anxiety that can be around that, you know, you know, happening and how you manage that. Given that, you know, to be here for a couple of weeks, is there anything you want us to support you on or help you just kind of work through, given that, you know, you're going to be sort of in a different time zone?
How are you handling, like, the prospect of going away? And, you know, we all do it and we leave our business alone for a couple of weeks, we shit ourselves a little bit.
Oh yeah, it's pretty scary, that's for sure.
Jay is going to be on deck doing like the bookings, et cetera. And then I've got a friend on the coast here who shoots photo and video, so he's going to be taking on as much of my work as possible. And then there's another photographer who will do the photo only jobs.
What's really interesting about this, and we're actually talking about this in the call last night with the guys over in Ireland, is that.
We get so used to running our businesses ourselves that we actually think that nobody else can do it. Like, you know, we get into our heads that no one can service the clients the way we do, et cetera. And then you flip that on the other side with the worry of if I get somebody else to do this, they might like them better, they might do a side deal and cut me a deal. There's all of these, like, things going in your head, right? Whether you admit to it or not, that's what's really going on. But what you might find, Ryan, is that, you know, a business that's transitioning into a proper business away from being reliant on the business owner which is the goal of this whole thing, right, is to sort of step back and not be the, the person that the calls come to and the person that does the work. And it's like unpeeling an onion, right? It's a layer by layer thing. This is a kind of forced opportunity which I think has been put in your way that, you know, I want you to go and enjoy yourself. Like go and have the best time. Like, you know, you're getting to go to Europe on somebody else's ticket, do a little bit of work and have a bit of downtime. I would say that it's probably, if you listen to books, get, get some cool books to listen to and just, you know, use the time to absorb some, some different perspectives, but also just breathe the air, eat the food, drink the wine, like, you know, enjoy the experience because it will all be here when you come back. And Jay's very capable and, you know, you can say to her if she's got any challenges at all, she can always ring me, you know, and just like if a decision needs to be made that you just, you're worried about, you're not awake or something, some kind of emergency, just you call me or any one of us here. But it's actually a great opportunity to battle, test how robust your business actually is. And I think you'll probably be surprised in the shortest time we've been working together, you've gone from working at home solo from your kitchen table to moving into your second office, having almost a full time editor and in a position to. If you compare this to what it would mean like a year ago if you'd taken this month off, it would have been just shut down time. Or you might not have gone.
Oh yeah, definitely. If I'd taken a month off last year would have, I would have just had to stop everything and then try and rebuild that momentum when I got back. But luckily I've got good people around me who I can rely on to, you know, do the edits, do the shooting, do the bits and pieces. So I think you're right. It'll be, you know.
A bit of an eye opener when I get back. I think, I think I'll either get back and go, oh, that worked out pretty well, I'll book my next holiday or.
Time to put my head down, ass up.
I mean, Caleb, you've done this a couple of times, right? You've done it. You pretty much had a month off last year for military work. You've had a good two or three week breaks Each baby that was born, plus you like to enjoy your other commitments to the church and to hunting and all these. What, what advice could you share with Ryan, who's kind of probably doing this the first time, like leaving the baby at home and going away for three weeks. Aren't you running away for three weeks? A month. A month, yeah.
Yeah.
And it's worked.
Varying degrees of, well over the multiple times I've done it.
But the one thing that meant that it was possible for me in the first place was knowing that the, the production workflow was all systemized so there was nothing that was left in my head that people didn't know how to do.
The only challenge that I find with going away now is the sales side of things because I'm not as actively.
Out there and.
I suppose, yeah, looking for those sales that can take a dip. But even so, I just make sure, like, it sounds like you've got everything in place that I would be, you know, having in place. You just, you need people that are going to do the work and someone who's going to take the bookings. Um, so, so long as all of that is really systemized and there's a good, good way of doing it. Good process then. Yeah. I found that's been the, been the winning ticket for me.
Whenever I take time off, stuff always happens because I'm pretty consistent in doing stuff all the time. When you take a week off, there isn't actually a lag in the week that you take off or the month that you take off. It's the month after and the month after that. If you don't maintain some sort of consistent outbound.
Communication, then that's when things slow down. So what my advice, Ryan and I mean, Tom's got a team, obviously. Thomas, obviously. So it's a bit different, but some ways yes. Some ways no.
Is like just allocate some time during your trip to just do a few bits. Like if you can knock out three posts a week on LinkedIn.
Do that.
The real danger is that you stop doing any kind of marketing and what we have to do is suspend any skepticism that it won't work for you and actually deploy the effort into just fucking doing it anyway. Because that's like when I said the other day on the weekly goals, it's like I came out the gym at 6 o' clock on 6, 7 o' clock on Monday morning having left, you know, 190 kilogram, you know, sumo squat. And last week I did 130 kilogram deadlift and I'm like. I'm like, fucking. Like, I only got there because I'm consistent. Like there's no other fucking. The reason for it is that I go five times a week. Two stretching, three weights every single week since the beginning of January. I'm averaging 15 to 20 sessions a month. Not really changing my diet too much. I'm just being consistent. And this is the beauty of it, right? You don't have to be amazing at this marketing thing. You just have to be consistent. And where I see I'm in a very fortunate position, I get to see everyone's numbers and everyone's position, everyone's journey. And those people that I see growing consistently are doing things consistently. And it's actually all there is to it. And it's just that we as creatives complicate the fuck out of shit by going, oh, but I don't think this and I don't think that, and I don't think they'll like this. And we let our egos get in the way of what is factually correct, which is if you post stuff three times a week consistently for a long enough time and you reach out to 10 or 20 people a day for a long enough time, it will turn into gold. It's just hard work work and it's boring. And you know what? Just got to suck it up because, like.
That'S where the opportunities come from. You know, you are actually going overseas to shoot an event. So, like, you're out of office. Should probably say, hey, guys, I'm actually out shooting a project in Italy for the next four weeks.
In my absence. I'll be checking emails periodically in my absence. Please go straight to Jay. She will be able to help you. There's two things that happen there, right? One is massive positioning. It's like, he's going to Italy. You could even say, I'm off. I'm actually shooting in Lake Como because that's like, everyone knows that's where George Clooney lives, right? So their first thought is going to be, well, I said, are you going to see George Clooney? Right? So there's an association with the fact that you're going to Lake Como and you're not telling them exactly what you're shooting. I'm shooting a project in Lake Como and I'm out for the next month. Massive curiosity. All of your clients are going to be like, what the fuck are you doing in Lake Como? And then you don't, you know, you're just not available. But you're then training your Market that Jay is the person to connect with. And then you'll come back and they won't want to talk to you because they'll be used to talking to Jay and she's awesome. And so you're actually going to create an environment where your clients are going to disconnect from your teat. Right. And like, be on solids without you. And that is awesome. But add to that, shooting a project in Lake Como has massive sex appeal. It's like, what are you doing in Lake Como? It's like, oh, look, I can't say too much about it at the moment, but I'll feel you when I get back.
Like, just create the curiosity, keep them guessing.
And be like, look, I've got a project I'm shooting in Lake Como and Milan.
My email will be periodic. In the meantime, urgent inquiries, please. Such and such. I'll get you inquiry when I get back. It just puts a really strong message that a. What are most media doing filming in Italy?
And you're obviously going to take your drone and stuff and shoot some nice shots and be like, you know, shoot some architecture, shoot some properties, and they're going to be like, fuck you. There's going to be a lot of questions and curiosity will be spiked. And you can use that curiosity to huge effect by not actually telling people what you're doing.
And you just position yourself as an international business.
Yeah, that sounds good. That's what I was going to put on my email signature. All my email out of office. Yeah. When I leave.
Very cool.
Should be good. But yeah, scary though.
Yeah.
But you know what? You're only ever a phone call away and you can still do your marketing, you still post stuff and schedule it, you can still do outreach, you can still do all of those things. And in many ways, when you are not actually working out there, you're going to be like, you'll be happy to spend an hour working on your business sitting in an Italian cafe, you know, because the environment is so different. Like the perspective you have, the kind of the big picture thinking you have when you're actually doing that and your business is still operating is phenomenal.
Yeah, I'll be still posting regularly and I think Jay will be doing posts as well. And I'm gonna be doing uploads into Dropbox, like, of everything that I shoot in that day kind of thing, which then can be turned into reels and stuff back here to be then posted. Hey, this is what we did and, you know, this is what we saw in Italy today. This is you know, whatever it may be.
So.
That in itself is is you doing front end marketing.
So if you found these interesting and useful, there's a couple of things you can do next. One is you can our free community the Scale youe Video Business Community, or go and watch our free training. Both are linked below. And let's work together to build your video business.
You've been listening to the Video Business Accelerator podcast with your host, Dan Lenny. If you are a video business owner who is tired of going it alone and would benefit from mentorship, support and weekly accountability, then mouse over to www.videobusinessexcel accelerator.com to learn more about how the Accelerator program can help you today. Don't forget to subscribe and rate the show over on itunes, and we'd really appreciate you taking a few minutes to leave a review.
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