3 Strategies to Help You Run Multiple Businesses (Without Losing Your Mind)

If you’re a multipod with an entrepreneurial streak, chances are you have more than one money-making venture (whether it’s multiple businesses, or multiple streams of income within one business). In my case, my current project slate looks like this:

• A freelance writing business
• My site where I write about (and do workshops/books about) productivity and business for creative freelancers
• Editing my first novel
• Running a Kickstarter funding a line of planners for freelancers
• Working (when I can!) on my next nonfiction book and on other nonfiction writing endeavors

Whew.

As a bona-fide productivity nerd, I’m all about helping everybody get and stay organized. But for people like you and me, with multiple huge projects running at any given time, it’s even more crucial. With this many projects going on at once, I can’t afford to waste time, or I’d be dropping balls and losing money left and right. So, what do I do to avoid wasting time?

Three time management strategies to squeeze the most out of your day:

1. Timeboxing

This isn’t about making units of time compete with each other in a physical battle. Rather, it’s about setting aside chunks of time or specific days to each project. One set up might look like:

• 9 AM to noon is for Creative Project A
• Noon to 3 is for Project B
• 3 to 5 is for Project C

But you can also set it up so that you’re working on Project A on Mondays and Wednesdays, Tuesdays and Thursdays are for Project B, and Fridays are for Project C.

There are multiple ways to apply this. I actually do timeboxing both by day and by work category, like so:

• Mondays and Fridays are for my internal business work. Things like writing my own blog posts, pitching new clients, recording any video posts for the week, planning my marketing strategy, processing the bulk of my email, and so on.
• Tuesdays through Thursdays are typically dedicated to client work, though lately I’ve been switching it up a little and taking Wednesday afternoons to work on my business or creative side projects.
• Mornings are by far my most productive time of day when it comes to straight up creating. So any writing is usually done in the morning and I like to have most of my writing done by 1 PM or so. (If you want to figure out what time of day is most productive for you, check out the Productivity Heatmap from Productive Flourishing.)
• Afternoons are for things that require slightly less creativity. I usually do all of my “pre-work” for articles (research, outlining, reaching out to potential sources) in the afternoons (read more about how this speeds up my writing process), will poke around in Facebook groups to see if I can help anyone, or edit something I wrote the day before.
• Late afternoon (4-6 or so) is for tying up any loose ends, checking email and replying to anything that needs an urgent response, and doing light admin work.

This is a little off right now because you can’t exactly take days off when you’re running a Kickstarter, but for 95% of the time, that’s what my work week and work days look like. You’ll notice I didn’t just pick times and days at random—I created this schedule based on what makes me the most efficient and frees me up to create the most. My clients’ schedules play a part in this, too, as a lot of them have meetings on Mondays and Fridays, so they don’t want or need me to be immediately available to them on those days.

You might not want something so structured, and that’s totally fine. But I’ve discovered that this really helps me, because it soothes that part of my brain that’s always freaking out about how I’ll never get to work on project A.

2. Endcapping

Whether you’re running a business or working at a day job, chances are you have one or two projects that are close to your heart but not really generating any money yet. I’m guessing you’ve had a few days where your internal conversation has gone like so:

“Okay, up and ready to work. I want to work on my novel/play/fun project…but I know I probably should work on this project first, because it’s going to generate income. I’ll work on my fun project after lunch.” (several hours pass) “It’s after lunch…I can work on my novel now, but I should probably answer client emails…” (6 PM rolls around) “Ugh, I’m so tired. I’ll work on my novel tomorrow. I need to eat dinner or I’m going to Hulk out.”

I had this exact problem when I was doing NaNoWriMo last year and I’ve ran into it repeatedly while editing that same novel. What’s worked best for me is a technique I call endcapping, where I put the project at the beginning and the end of the day, doing 30-60 minutes on it each time. I usually do 60 minutes in the morning and 30 minutes in the evening. This is what let me finish NaNo with around 65,000 words, on top of a full freelance writing workload (although the weekend writing sessions certainly helped!).

The thing is, as a freelancer, I’m never going to half-ass my client work or blow it off. But I will blow off my own projects or put them dead last, even though those same projects are what keep me creatively fueled.

In some sort of weird magical math, I’ve discovered that if I put my work very first, even though it feels selfish, I go into my work day with much more energy and focus, feeling like I’ve already accomplished something (and feeling extra jazzed because it was my baby project that I love working on). As a bonus, I’ve noticed I’ll often get started earlier when I know I’m starting with my project, because I’m looking forward to working on it that much. Ending the work day with another 30 or so minutes does the same thing; it gives you a buffer between your work-work and the rest of your life, and it lets you wrap up your workday with a smile on your face.

3. Layering

If you examine your day carefully, you’ll probably find that there are several packets of “lost time.” Things like the time you spend in your car alone, or on the bus, or walking the dog, or cleaning the house. These times are ripe for “layering,” which is what I call it when you’re taking advantage of time that would otherwise be lost by stacking something on top of it. My favorite example is podcasts (because they work great whether you’re cooking, cleaning, or walking the dog), but you can also read or listen to audiobooks.

Of course, if you’re doing something like riding the bus, you can bring along a notebook to write or brainstorm in, or type up things in Evernote (so they’ll be easily accessible from your computer later). Or use the Skillshare app to sync videos offline and watch them then. When I had a day job, I used to use my bus time to type up posts in Evernote on my phone, then edit them on my lunch break and schedule them once I got home. But if you’re walking the dog or driving, that’s a little less feasible!

I recommend leaving some empty space in your day—it’s good for your brain. You don’t want to pack everysingleminute with reading or listening, or your ideas won’t have any room to percolate and come together. But this is a great way to find more time in your day to get inspiration, actionable tips, or ideas, and it’s helped me to keep up on industry news and events without having to spend my peak creative hours reading about it.

Your Turn

So there’s my three favorite ways to get more done in less time. Have you tried any of these in running more than one business project? If not, which one are you going to try out to see how it works for you? I’d love to hear about it in the comments.