3 Strategies to Help You Run Multiple Businesses (Without Losing Your Mind)
Photo courtesy of dinesh rao.

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

Written by Emilie

Topics: Productivity

Editor’s note: this is a guest post by Michelle Nickolaisen.

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


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.

jo_authorbioMichelle Nickolaisen is the creator of the Freelancer Planner, as well as being a freelance writer and business owner based in Austin, TX. When she’s not working on one of her many projects, she’s typically hunting for some new sci-fi on Netflix or reading about creativity. Find her on Twitter, Instagram, and Facebook.


  1. Nela says:

    Ha, I just realized I already do all of it one way or another! :)

    Although I’m a night owl, my most productive hours are in the morning and I do my writing and design in the mornings. Afternoons are for admin, email, writing proposals and socializing online.

    I tried making a fixed schedule for client work and my own work, but I’m still struggling with that.

    And yep, I totally work on my own projects first… It really does fuel me up, though sometimes it’s so hard to stop and work on client projects! I hate breaking my flow :/

    • Michelle says:

      High fives for already being a productivity guru, Nela!

      I hear you on the flow, and I don’t love it either, but after a while I got used to it and found that it was definitely worth the…slight disappointment? that comes with breaking your flow on your work vs. feeling frustrated b/c it’s so hard to make time for your work. Others might have different results, though.

      • Jennifer says:

        Yeah, right there with ya. My primary client is my three-year-old and she is Very. Demanding. So if I have fifteen minutes to myself, I’ve gotta take it and run with it, even though it means I have to stop way before I want to.
        The flow can be forced, and isn’t gone forever once broken. It’s not perfect and it takes practice and repetition, but for some phases in life, you either force the flow, or never work on your “heart work.”

  2. This post means a lot to me, Michelle! You pretty much addressed all of the problems I had as a freelancer. While freelancing I could never manage my time well and ended up doing LESS work on my creative projects than when I had a 9-5. I finally got around to writing some scripts when I tasked myself to write them first thing in the morning. However, this got interrupted as I had clients in Europe who needed freelance projects delivered earlier in the day. It just never seemed to stop. Something always had to be done, and I wasn’t even making that much money!

    Soon I’m taking a job in China where I’ll have one job that starts later in the day and I hope to employ these strategies!

  3. Crystal says:

    Thank you for posting it.this website is seriously quenching my thirst!

  4. Charlie says:

    Thanks so much for the link, Michelle. And great post!

  5. Gawd, this is awesome! Endcapping?? Are you kidding me? So freaking smart! Perfect way to start AND end the day with heart and soul. Love it!

    AND you’re an Austinite. Sheesh, we may be soulmates. Ha!

    Thanks for the great info, Michelle!

  6. Yaiza says:

    I have in one way or another done two of the three, but I had never heard of end capping one! and I am going to try it for sure. I think that leaving your fun work towards the end ( and consequentially abandoning dream projects over the paying the bills ones) has to do a lot with that guilt we feel about having all these interests and not being happy with just one hat like the specialist do. It had made me feel somewhat irresponsible in the pass and so I overcompensate by being obsessively responsible with clients ( like you I also do freelance writing, have a blog, and have some books I’m writing on ice, among many other things!).
    On top of all the things I am doing and a the one that I still want to do I have an adorable 10 month old baby that takes most of my time, so the one technique I’ve adopted lately is working in bits of time.
    I use to wait until I felt i had a good chuck of time to concentrate and start some good work. Now when you have a baby a “chunk” of free time is like a fairy, a beautiful mythological creature that you keep wishing was real. So now I work whenever I get a bit of time here and there and leave tings on standby for the next set of minutes I can string together. It seems like it will take forever but at the end of the week I have put together hours and hours of work.
    This bits of time technique I usually combine with the layering (for example I use the afternoon stroller/walks to think about articles and I record the ideas on my phone) and the scheduling ( usually by day of the week works best i my case).

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