Intro: My coaching client, Laura, recently told me that she saved more money than she spent on my coaching because I helped her simplify and consolidate her tech stack. And now I want to do the same thing for you, too. I have put out a free tool called the Tools Audit. It will help you determine what tools you use, how much you're paying, and where you can consolidate and eliminate to simplify what your small business tech stack. You can go to streamlined.fm/tools to get your free tools audit today. That's streamlined.fm/tools.
Earlier this year, I spoke at Podfest 2026 and it was a blast. I gave a talk about not letting AI do your work for you. You can see Episode 515 to get a little bit more of that. I also got to spend time with my brother, who works at Disney World.
Now, for an extrovert like me, conferences are life-giving. I love meeting new people, having great conversations, and learning things that make my business and me better. I also love going to Disney World. My brother's worked there for like 15 years now. And, you know, I'm, I guess I'm a Disney adult, but whenever I go to a conference in Orlando, I bake in a couple of extra days to hang out with him at the parks. And I don't even necessarily need to do rides or shows or anything like that. If there's something new, I'll check it out. But I just like being in the parks.
Now, between the long conference days and the long Disney days, by the end of that week, I was beat. 40-year-old me definitely doesn't bounce back as well as 25-year-old me. I was excited to go home. But when I got to the airport at 3:30 for my 5:45 flight, it got delayed until 6 PM, then 7 PM, then 9 PM. We didn't end up taking off until after 10 PM. And I was super bummed at first, but there was nothing I could do about it. I realized that this was forced downtime for me. And that's what I want to talk about today.
Hey everybody, welcome to another episode of Streamlined Solopreneur. My name is Joe Casabona, and my mission is to help solopreneurs take time off in their business without feeling guilty or stressed that their business might crumble. I have done this successfully for several years, and this was a shining example of something that more solopreneurs need to do.
So like I said, I was stuck with nothing to do, and I realized that this was forced downtime for me. I was in the airport. I could not go anywhere else. My brother had left, and I wasn't going to call him back, especially if something miraculous happened and my flight suddenly got undelayed. And I was leaving the chaos of a long trip to go back home, where a different chaos awaited me. The chaos of a house with small children, 3 small children who were just getting over being sick. This made the airport a chaos buffer for me. I was forced to be in a place for 6 hours before taking off and going home
So I decided to make the most of it. I headed to a restaurant. I did some reading. I did some writing. And I actually ended up making friends with two other stranded travelers. While I didn't get home until 3 a.m. and I was extremely tired, I was actually grateful for that forced break. If I got word about a multiple-hour delay before I left for the airport, I would have ended up doing something more strenuous. Now that something more strenuous would have been staying at Magic Kingdom longer or doing something else.
But the point is that I was forced into this chaos buffer. Instead, I got a little bit of extra time to myself. And this is great because we have a lot going on right now. I, basically came back from a 2-week break. I had 1 week of work before going to Orlando for this conference, and now we're starting to enter a busy season at school, all while I'm trying to catch up on work. This forced chaos buffer was important to me because we all need downtime.
Something else I tested at the conference and in a poll I sent to my mailing list was the idea that I help solopreneurs take several weeks off throughout the year. I have done this successfully multiple times. In fact, I took 4 breaks of at least 1 week each in 2025, which was also my best fiscal year to date. In testing this line on people, I was shocked by the strong reaction that I got from them. They said things like, oh, I could never do that, or business owners don't take time off, or I just got a straight-up no.
There was a point in my lifetime where going on vacation meant actually taking a vacation. Because you couldn't bring your work with you, where being unreachable was a good thing. It's really a shame to me that the idea of not taking my laptop on a family vacation is met with people saying, oh, good for you, and not, why would you? Why would you take your laptop on a family vacation? Why would you want the temptation of working when you're supposed to be spending time with your loved ones? But I also completely understand this sentiment.
For a long time, I feel like I couldn't take time off either. And yes, I really do protect my vacation time. I understand that taking time off is better for you in the long run. It will make you a better worker because you're not constantly on. You're not constantly risking burnout. You're giving your brain a rest, just like you need to give your muscles a rest when you do a physical workout. There is research. My friend Cat Mulvihill shared this with me. So did Maegan Megginson when she came on my show to talk about sabbaticals. There is research that shows you that you see real big benefits when you take at least 2 weeks off.
But there are people who will say, I can't take, I can't take time off. I don't want to take time off. Hustle is a badge of honor for them. Someone straight up said to me, I never ever want to go anywhere without my laptop. And I've got to tell you, that is so sad. It's such a sad sentiment to want to be attached to your laptop like that. I don't even want to leave the house with my phone some days. I want to be fully present in the life I'm trying to live.
But like I said, there was a time in there where I felt I couldn't take time off either. It was after I left my full-time job, which, by the way, when I was at my full-time jobs, I was very clear about taking actual time off. There were two times I can really remember where when I worked at the University of Scranton on my first day of vacation, my boss emailed me and said, Joe, if you have downtime and I just deleted that email. I cannot tell you what the rest of that email said because I'm like, I'm not going to have downtime. I am on vacation. Then there was a time when I was taking paternity leave at the agency I worked at where a project manager put something on my calendar during paternity. I messaged her, and I said, I don't exist, but I need you. No, no, I do not exist. I am logging off now. You can talk to me when I come back in a couple of weeks. I guarded that time ardently, viciously.
But when I started working for myself, like a lot of solopreneurs might feel, oh, things aren't that good in the business. If I take time off, it might fail. I might lose clients. No one is here to bring in the business. No one is here to actually do the work. And so you decide not to take time off. But I'm here to tell you, as a solopreneur who disappeared off the face of the earth for 4 full weeks last year, 4 separate instances, and I didn't disappear for a month, though I feel I can.
But there was a week in May, there was a week in Thanksgiving, and there were 2 weeks at the end of the year where I just disappeared off the face of the earth. You can do it. I built systems of automations with contractors and, most importantly, clear communication to give me the space I needed to take time off. After all, if I'm going to be chained to my desk, I might as well do it for a steady paycheck. Why would I want to work constantly for the uncertainty of money? I could fold up my business right now or not and get a full-time job and probably double my income. That may not be true anymore, but that certainly was like 2 years ago when I was stressed, and chained to my desk. I could have definitely folded up my business and gone to work for somebody else for way more money than I was making.
Why wouldn't I? Because I started my business for freedom. So how can you— maybe, maybe you're sitting here thinking, I don't want that. I want to hustle and make as much money as possible, and I don't care about personal relationships; my job is my most important thing. When I was a 25-year-old, I said that. Now I am 40, and there are a lot more things in my life that matter to me than work. There are a lot of things in my life that matter to me more than work. So maybe this episode isn't for you, and I'm sorry to have just wasted 10 or so minutes of your life, but maybe you're listening to this, and you're like, yes, I want this. I didn't start a business to be beholden to a different thing.
So how can you do the same thing? I want you to start simple by understanding the work that you do. Many solopreneurs are so busy doing client work. Or working on that next course or trying to create that next product, that it's hard to take stock of what's working and what isn't.
Instead of getting an idea of how the business is doing, we move from one task to another, and the stress builds up, and there's no relief in sight. This is what led to me having a panic attack in November of 2020. The time I had to work, I wasn't really focusing on how I was working. I just knew I needed to get as much work in as possible before my wife had to go to work and I had to watch the kids. And then I wasn't present with my kids because I was thinking about work, and the stress built up, and there was no relief in sight.
And that stress was not relieved until I took stock of what I was doing. So the first thing I recommend solopreneurs do in order to build a system that allows them to step away is to know what they're doing. Understand what you are doing. And this really means auditing two things in your business. Your time, and your tools.
So the first thing is to figure out where you're spending your time. I like to tell people to make a list of everything they do throughout the course of a week. This will give you an idea of where you're actually spending your time, and you can do it a few ways.
First is sit down with a notebook and write out a list. Spend 20 to 30 minutes thinking about all the tasks that you do. Or you can go back to your task manager and see the things that you check off your list or the recurring tasks. Just write down all the stuff that you have to do for your business in a week.
The other thing that you should do or could do is keep a notebook next to you and do some real-time documentation. As you move from task to task, write down what you do and how long the task takes you to do it. This will give you an idea of exactly how you're spending your time.
A more automated way to do this is to use a time tracker like Toggl. I like the combination of writing out a list of everything I do, and then also keeping a notebook next to me and writing down what I do, because this will also help me or show me what I think about what I do in a week, versus what I don't think of. Right? Because it's easy to be like, oh yeah, I just do these 5 things. And then as you write things down, you're like, oh right, I didn't realize I do that. Oh, right, I didn't realize I do that.
And another really important thing as you do this exercise, is write down everything, even the distractions. This is an honest look at how you're spending your time in your day. Sitting at our desk for 8 hours almost never yields 8 hours of work. So write down everything that you do while you're sitting at your desk, everything in inside of your working hours. This will give you a good idea of how you're spending your time and further how to optimize how you spend your time, because maybe you're like, oh, well, I'm doing a bunch of things that I don't actually have to do.
The second part of it is understanding if your tools are helping you or hurting you. You should also determine what tools you're using, how much they cost, and if they're actually useful. In Episode 514, I talked about why gear and tools actually matter a lot. If you're spending your day fighting your tech stack or using something overly complicated, it wastes more time than it saves. Not to mention, it probably wastes some money too.
When you audit your tools, you should do this: Make a list of all the tools you use and how much you pay for those tools annually. So if you're paying monthly, you know, multiply the monthly cost by 12. You know how Math works. Make a list of all the tools you use and how much you pay for them annually. For each tool, answer 4 questions: Do you need it? Do you use it? Do you like it? And how would you rank it on a scale of 1 to 10, where 10 is the best?
Armed with this list, you can determine a few things. What are the tools that you don't use and are therefore wasting money on? What are the tools that you really need, and which tools can you completely eliminate? And like 1 and 3 sound similar, but like there's a tool, you know, there could be a tool that I use a couple times a year, and maybe the way I'm wasting money on it is by paying for it annually instead of monthly and going month to month.
This is what I do with Microsoft Office or Microsoft 365. I need it a couple of times a year. It doesn't make sense for me to keep paying for it monthly, and it doesn't make sense for me to pay for it annually. So I saved some money there.
What tools can you eliminate? I realized, you know, that I don't use Adobe Creative Cloud at all, and I was paying a ton of money for that. And so I eliminated it. This tools audit, coupled with how you're spending your time, allows you to get a complete view of the day-to-day operations of your business. And if you are wondering, you know, like, I, like, how helpful are these questions? Or how do I organize this information? Uh, I want you to check out my free Tools Audit Template. It'll have everything I just outlined in a Notion database. It'll ask you a couple of questions, but it also has a list of like 50 of the most common tools that solopreneurs use. And so you can just check the ones off the list instead of having to compile that list yourself. So you can get that over at streamlined.fm/tools. That's a free Tools Audit Template over at streamlined.fm/tools.
Now, armed with all of this information, you can eliminate wasteful tools and tasks. You can use the tools that you actually use to automate tasks instead of performing them yourself. A really good example of this is like, I don't email my editor when I have a new podcast episode. I marked it, I mark it in Notion as ready to edit, and he gets an email. And then you can also delegate tasks to a VA or a contractor like I do with my editor, or when the episode is ready for scheduling, my VA.
This audit allows you to understand the problem so you can fix the problem. From there, it's up to you to optimize and trust that you can step away for a week without your business crumbling, because you will be able to when you set up this system. You are only doing the things that you need to do. There are tools running in the background to keep things moving.
And so that third crucial piece of communication is saying to your clients, hey, I'm going to be away starting on May 1st. And having the broader picture, you know, in March, hey, I shouldn't take on any new projects because I'm not going to be able to work on them in May, or I won't be able to work on them the first week in May. And so you can mold your schedule instead of just letting your, letting your work dictate your schedule.
That's what I did. And I couldn't be, I honestly could not be happier. I started my business for freedom. When I quit my job at that web design agency, they said, what can we do to make you stay? I said, I will not miss my daughter's first steps because I was working late for you.
I started my business for freedom, and that's what I've given myself. I want to help as many solopreneurs as possible break free as well. You shouldn't have to wait until you're stranded at an airport to get the downtime that you deserve.
Thanks so much for listening to this episode of Streamlined Solopreneur. Again, head over to streamlined.fm/tools to get your free Tools Audit Template. Let me know what you think of this. Do you take time off? Are you one of the people who say, I never want to ever go anywhere without my laptop ever? Write in at streamlinedfeedback.com and let me know.
Thanks so much for listening. And until next time, I hope you find some space in your week.