This blog post was originally written by Andrea Henry for Henry Business Law

My last post in this series was about how I found out that I made more money in my business every time I took a break from it. Some of you wrote to say that only worked for me because I have a team so I wanted to break down how solopreneurs can take breaks and make more money too.

FYI when I took a month off last summer my team was me and my assistant who couldn’t provide legal services to clients, so I know it can be done.

1      Systematize and Automate

One of the best things you can do for your business (and your ability to leave it) is to map out your client journey from the time someone shows an interest in working with you or buying from you all the way through onboarding, providing deliverables and to when their journey with you ends (at least for now).

Once you understand all the points on the client journey, your next step is to create systems for all those points and automate as many of them as you can. There are platforms such as Dubsado, HoneyBook and ClickUp that help you to do this. Even if you don’t want to invest in these, it’s $FREE.99 to create workflows, manuals and templates that sit in a systems folder to be used over and over again.

The more that you can automate, the more your business can function without you. If you can trigger the entire onboarding sequence with one click, you free up so much of your time and you make it easier for people to help you.

2.     Your team doesn’t need to be permanent

Those people that can help you? They don’t need to be full-time employees. Once you have systems in place, you can hire freelancers on a short-term basis to flip the switch to start the automations and manage client concerns or tech issues that come up. If you’re fortunate enough to have a friend who is also a business owner and whose judgment you trust, this person can be invaluable in providing a backup while you’re away, particularly when it comes to dealing with clients. I’m lucky enough to have a business buddy and we’re on call for each other’s business on an emergency basis if one of us goes away or if we get injured or sick. If you refuse to have anyone else involved in your business, you will never be able to leave it – voluntarily or involuntarily – without it falling apart.

3.     Plan ahead

I remember being a student in Paris, seeing a return flight to NY for the next day for $200 and booking that fare immediately.

*Be right back. Just reminiscing about a life before children and responsibilities….*

Spontaneous travel is amazing but if you’re a business owner, and you want to not work while you’re away, you need to plan your breaks well in advance.

One of the best bits of advice I ever got was to plan your year around your breaks because if you wait until things slow down, you’ll never go!

Do you have fixed-length programs? Maybe schedule your break right after one is complete. Do you have seasonality in your business? Take a look at your revenue and activities on a month-by-month basis to see when your business tends to be busiest and then avoid those months.

Once you’ve decided when you’re going, let you clients know. Mention it on calls, put it in your newsletter, be open about it on social media. Your communications should clearly state when you’re off and what your clients or customers should do while you’re away. You should also pre-record videos you need for social media, plan your posts and emails etc.

(If you had a team that could keep all parts of your business going while you’re off you wouldn’t need to do this. Just saying.)

4.     Take Microbreaks

When you haven’t taken a ton of time away from your business before, taking a whole month can be a great test of your systems and team but it can also be overwhelming and anxiety inducing (ask me how I know).

Instead, work your way up to longer stretches away by first taking a few days at a time, then a week, then 2 weeks before you take the plunge and take a whole month or more off.

Every time you go, take note of what worked and where there were gaps in your planning, refine and try again.

5.     Leverage your Intellectual Property

There are only two ways I know of to make money while you’re away:

(1)   have a team that continues providing services and/or selling to your clients/customers

(2)   have assets that make money for you

As I’ve made clear, I think you should have both but let’s be real, having a team can be tough to achieve in the early days of entrepreneurship. So, if you’re a solopreneur, having assets that continue to bring in money for you while you’re not working is key.

I remember the feeling when I first woke up to a sale of an e-commerce product that came in overnight. While I was sleeping in my bed. And that I didn’t have to do anything else with.

That feeling. Honestly? Better than sex.


If you have real estate that you can rent out, that is amazing! But you don’t need to own real property to be able to leverage assets. Your content, your videos, your knowledge can all be harnessed to create streams of revenue that will continue to fatten your bank account while you’re away. Whether that’s through creating an online course or licensing your content, your intellectual property is the path to money and time freedom. That’s why it’s so important to protect it, through registration and tight contracts.

This is one of my favourite things to help people with! If you too would like to take more breaks and make more money, let’s do a deep dive into your business to figure out how you can use the law to make this a reality. Book a Legal Audit consultation with me at Henry Business Law.