Freelancers Need a Plan for Time Off

4 min readJun 4, 2023

Freelancers and business owners need a backup plan in order to take time away from their business. It’s vital for your mental and physical health — and to be there for others if the need arises.

a woman reading a book while lying on a beach — Photo by Chen Mizrach on Unsplash

Welcome back to my series of lessons learned from 15 years of running a freelance content marketing agency.

If you missed lessons 1–9, don’t worry: each lesson is a self-contained story that you can read for its own value or as part of the series. You must read this series if you’re a freelance writer, graphic designer, or business owner.

This series was inspired in part by our 15th anniversary. I own and operate Seven Oaks Consulting, a business-to-business (B2B) technology content marketing agency. We just celebrated our 15th anniversary in 2022, and to give back to the freelance community, we decided to run these lessons on Medium.

Plan for Time Away from Work

The call came on a sultry July day. It was my sister. Her usually cheery, peppy voice sounded strange. Strangle. Hoarse. Like she had been crying.

“I need to tell you something.”

That something was a rare, aggressive, mean form of breast cancer that, but for the grace of God, may have killed her if not detected early. She had gone in for her routine mammogram and discovered the tiny tumor by accident. By the time she called me, she had the worst news she could get: yes, it was breast cancer, and no, nobody knew how or why she had it. They did know that she was headed for a year (and now more) of chemotherapy and a double mastectomy.

And me, sitting in my office 400 miles away, blanched.

I wanted to be with her.

I wanted to rush over with food, a box of tissues, our favorite movies, and a blanket and curl up with her and cry.

And I couldn’t.

Because I am a business owner. Self employed. An independent contractor. I provide 99% of the services we offer. I had no one who could do precisely what I did for our clients. It was next to impossible for me to leave my business.

Okay, correction: I could leave the business. But I would have lost significant revenue.

I realized I hadn’t had a vacation in over 10 years. And I could not travel to be with my sister unless I made some significant changes in how I ran my company.

Have Someone Who Can Take Over Your Work in an Emergency

This led me to the revelation that although I had a great team of freelance writers worldwide who could produce the content, I was the only person on the team who knew the clients, their accounts, what they did, and what they needed.

Four tech companies and two marketing agencies partnered with me, reliant on my services, with no “plan B” if I should be out.

Teach Someone to Be Your Second-in-Command

Fortunately, I was able to find someone who could step in when I needed to be out. But it was an eye-opener for me. Should I be sick or have to have an extended leave of absence, there had been no one to take over the business for me.

Lesson learned: I now ensure that for every account, someone on my team understands who they are and what they do. I have a backup plan if I have to be out for an extended period.

Lesson 10 is simple, but one many freelancers need to pay attention to. If the entire business depends on you, your absence means it can fail. Don’t fall into that trap. Have a backup plan so you can take a day off, a vacation, or run to your sister’s side when her world falls apart.