I started my first business in 2014 (massage therapy) and my second in 2016 (virtual assistant), and the road between and thereafter has been paved with side hustles, part-time jobs, and plans for passive income. My tiny empire isn’t done growing.

Why have multiple businesses?

There are a number of reasons to have multiple businesses. In my case, what started out as a side hustle alongside my first business turned into something I’m WAY passionate about. I want to keep growing because I love entrepreneurship and I want to find ways to diversify my family’s income streams, including creating passive streams of income that require minimal maintenance on my part.

The Real Truth About Multiple Businesses

It’s really hard sometimes. As I write this, I’m bouncing back from a hellish week in which I contemplated closing my first business down entirely.

After two amazing months in which I felt like I was completely on top of operating two businesses, my older business brought in almost NO income at all this month.

Blame it on the bad weather here in PA or my husband being absent for training and the toll it took on my routine, blame it on bad luck or the tides of entrepreneur life. WHY it didn’t bring in income matters, but I didn’t really care. I just wanted to close up shop.

It kills me that after 2 years, I still have months where I wonder WTF I was thinking when I opened this business, and whether or not keeping it while running a second business is worth feeling that stressed. People kept asking me if it would be better for my sanity and my second business if I ditched it entirely.

I made the decision to keep it. For lots of reasons. BUT…

I am telling you this story so that you know that running multiple businesses is insane sometimes. If you don’t want to put literal sweat and tears into entrepreneurship, stick to one business. You’re still going to have a good snot-dripping “what am I doing with my life” cry once in awhile, but you’ll have less of them if you aren’t multiplying it by more than one enterprise.

Tips for Running Multiple Businesses

So you’re feeling adventurous or you want more money or you’re just passionate about a lot of things and LIKE having different projects. Whatever your ‘why’ is, welcome to having multiple businesses. Here are my best tips for running multiple businesses without ending up in a blubbering heap on the bathroom floor in yesterday’s pajamas:

#1. Only Start One Business at a Time

If you’re saying, “That should be common sense,” right now, you’d be surprised at how many excitable, multi-passionate, and just plain brilliant entrepreneurs have difficulty holding themselves back from chasing ALLLLLLLLLL the dreams. Take it easy. There’s time to go after every one of them, and I’ve been there – it feels like you need all those great ideas to come to fruition NOW.

Save yourself the pain and crazy and wait. Do one thing at a time. See how one business does, then build onto it, expand it, or start something totally different. Doing everything at once will lead to burnout, confusion, and each business’ inability to thrive as its own thing. I’m biting my tongue as I write this because I struggle with it more than anything, but you have to be patient. Juggling multiple businesses is a long-term commitment that needs a carefully crafted game plan. Speaking of which…


Write one. FOR EVERY BUSINESS. With Details. Update frequently. If you hate business plans, use my favorite creative business plan here.

Biz Plan: Write one. FOR EVERY BUSINESS. With Details. Update frequently. #business #girlboss Click To Tweet

#3. Delegate Like It’s Your Other Job

I’m a virtual assistant, so people laughed at me when I said I needed an assistant. I let them laugh and I hired two assistants and it CHANGED my life. At least, my business life. Even though I do social media and blogging for a living, having someone handle MY social media and backend blog stuff, and having them do the admin stuff for my other business really cut back on my stress. It allowed me to focus on my clients, which is exactly what I preach in my VA biz.

Shameless self-promo: If you need a VA, I’d love for you to check out my company. My team really loves what we do, and we strive to match our clients’ passion and enthusiasm for their business, and I’d be happy to chat about your business and how we can help you delegate.

And now that that’s out of the way…remember that a VA isn’t the ONLY way to delegate. Sometimes your husband can help or your mom or a friend or your kid who might be more tech savvy than you. The important thing is to ask for help when you feel overwhelmed.

#4. Take Breaks

Daily, weekly, and vacations.

Take breaks during the day, preferably every 90 minutes or so. Let your brain rest.

Take days off during the week. I’d love to have 2 every week, but sometimes right now it’s just one. STICK TO IT. If you have one day off, stay strong and don’t work, answer emails/calls, or plan your tasks for the next day. There is nothing so important that it can’t wait until tomorrow when you’re on your day off.

Take vacations a couple times a year, even if it’s just a long weekend or a mini staycation. You need time completely away from work to recharge and prevent burnout.

#5. Know that Your Focus Will Shift…A LOT

You can run several businesses, but you can’t give them all one hundred percent, one hundred percent of the time. It just doesn’t work like that. Know that when you plan a launch or campaign or new product, one business is going to take priority for awhile while the other just coasts. Unless you have A LOT of help, your focus, priority, and motivation will fluctuate. Embrace it as a positive – it keeps things interesting.

Also know that sometimes we try to make money doing things that don’t work out. A business that doesn’t work out isn’t a failure, it’s a learning experience that you can use to make future projects better.

#6. Know When to Move On

Some businesses are forever, some aren’t. I know that I’m going to let my first business go someday because it isn’t physically possible for me to keep up for another 5 or 10 years and because, as my husband and I try to have a family, I’d rather work from home.

I know that I want to create passive income, and that related projects are going to take more of my time.

You have to weigh all your options and priorities and know when something has come to completion and it’s time to move on. That point is going to be different for everyone, and it may never come, but be aware that it CAN happen. If it does, let it go. It’s OK.

Running multiple businesses is so rewarding, challenging, and fun, but you have to have realistic expectations going into it. It’s stressful sometimes and your focus will shift back and forth. Asking for help and having a plan are two must-have elements of running more than one business. Finally, know that not all businesses are forever, and it’s OK to cut ties when that time comes.

Do you have multiple businesses? Tell me your best tip for juggling all your projects in the comments!