How to Think About (And Prepare For) Long-Term Leave as a Freelancer
What if you have to take a step back?
One of my friends recently ran an informal poll: "How do you take time off as a freelancer?"
More than 30% of freelancers replied, "I don't." Others squeezed in a few days here and there, like during their slow seasons or when their clients weren't working around holidays. Other freelancers manage to plan for vacations throughout the year, embracing their flexible lifestyles.
While vacation planning and taking the occasional sick day may be on the radar for some freelancers, far fewer think about long-term leave — at least not until they need it. A serious medical issue. A family emergency. Or even pregnancy and an upcoming maternity/paternity leave.
No one should have to figure out long-term leave while they're in crisis mode. And no freelancer should think that they can go their entire careers without needing extended leave at some point. While you may not think about the exact logistics until it's necessary, you should at least consider what it would be like to step away from your business for an extended period of time.
What would long-term leave look like for you?
When I was preparing for freelancing life years ago, I wondered, "What would happen if I got pneumonia and couldn't work for two weeks?" My business is mostly project-based work. If I don't work, I don't get paid. Taking a lot of time off would impact my income.
Then I got to find out the answer to my own question, but not in the way I was expecting. I was diagnosed with a brain tumor. It was thankfully benign, but I needed surgery to remove it.
During the weeks between diagnosis and surgery, a fear kept looping through my mind: Will my business still exist when I come back?
Brain surgery has a pretty long recovery period, at least 6-8 weeks, possibly more. I had to tell my clients that I would be gone for a long period of time. I also let them know that I understood that work might not be availalbe for me when I returned. It's always a risk with freelancing: there are no worker protections. If my clients still needed work during that time, they would find another freelancer.
So there was a two-fold risk. First, the lack of income while I wasn't working. Second, that even when I returned, my income would be significantly lower due to losing clients.
Anna Burgess Yang
Long-term leave depends on your business model
There is no single version of "long-term leave." Preparation will vary wildly, depending on the situation.
- Maternity or paternity leave gives you months to anticipate and plan, but the unexpected can still happen.
- Major surgery typically gives you some notice. In my case: six weeks.
- Medical emergencies or family situations may have no notice.
- Burnout or sabbaticals require a different type of emotional and logistical planning..
Your ability to step away also depends on your business model, and this is where you can start thinking in advance of taking long-term leave.
Do your contracts allow anyone else to help you?
Whether you can subcontract work depends, first and foremost, on your freelance contracts. Some contracts expressly prohibit subcontracting. Clients are hiring you and expect you to do the work. If your contracts prohibit subcontracting, you can’t simply hand your work to someone else.
Even if subcontracting is allowed, is it feasible?
Subcontracting will depend a lot on how much you're able to interact with someone while on long-term leave. Let's say you're taking maternity or paternity leave. You're stepping away from the day-to-day work of the business, but you can still check in with the subcontractor.
If you can't interact with the subcontractor at all (such as a medical emergency), you'd need to find someone you trust completely. That person would need to deliver without oversight and be able to meet deadlines. And the project managment is just the minimum. You'd also have to trust that the person would deliver work that meets your clients' expectations.
Will new work slow down if you're not there?
Maybe you depend on a steady stream of inbound work to keep your business churning. Will the work disappear if you're not the "face" of the business?
That was a huge concern of mine when I stepped away from my business. My social media presence drives inbound inquiries. Because of this, I scheduled a lot of social media posts in advance. This kept my LinkedIn profile active, even though I wasn't around. My virtual assistant handled inbound inquiries, letting people know that I'd get back to them when I returned.
I recently spoke on a panel about long-term leave and one of the participants shared:
One of the things that I've sort of discovered more and more as I've built my business is that the more it is based on me running it, the more at-risk the business is. For the business to grow, it needs to be systems-led, not. Not founder-led. And it needs to sustain itself in the event that I'm not here.
Of course, this type of preparation is only possible if you have advance notice of your long-term leave.
How freelancers can best prepare for long-term leave
Freelancers rarely talk about long-term leave (or worst-case scenarios). If you've moved beyond the "thinking stage" to the "planning stage," here are some things to consider.
1. Build a financial cushion
My hypothetical, "What if I get sick and can't work for two weeks?" was the driver behind early (and consistent!) savings.
Obviously, I wasn't expecting a brain tumor diagnosis. But the savings allowed me to continue covering my business expenses — subscriptions, service providers, insurance, etc. — without panic.
If you’re self-employed, an emergency fund is your safety net. Set aside money every time you get paid, or once at least once a month.
2. Make sure your contracts reflect your future needs
If you think you'd like the option to subcontract work, if needed, talk to your existing clients about modifying your contracts. You'll also want to add language that allows subcontracting to new contracts.
Keep in mind: if you never want to subcontract, fine. But if you're not sure, add the language to your contracts so at least you have the option.
3. Don’t be afraid to ask for help
For all of my business savings, I never thought I'd need to take a two-month leave from my business and have zero income during that time.
I created a GoFundMe to help offset my lack of income. The response was heartwarming. I got donations from people I knew and people I didn't know. A few freelancers even shared it in their newsletters or on social media to help spread the word. The message was always the same: We need to support each other.
My business savings paid for my operational costs. Money kept flowing out of my business for things like my accounting firm and subscriptions for apps I use. I could safely walk away knowing there was enough money in the business to keep it going even when I wasn't working.
My GoFundMe paid for my life — the money I would have paid myself from my business. I also received some help from family members.
For all of the stress during that time, I didn't have any financial stress, and I'm grateful for that. I needed every ounce of energy for my recovery.
4. Look into insurance
In the U.S., freelancers can access disability insurance through Freelancers Union and other providers.
Years ago, I went through the application process. I decided against paying the monthly premium, knowing that I was disciplined enough to save on my own.
But disability insurance may be worth considering if:
- You don’t have an emergency fund yet
- Your income is unpredictable
- You’d be financially devastated by a multi-month gap in your income
Disability insurance won't cover burnout or sabbaticals, but it will cover medical leave.
Operational readiness matters more than you think
Stepping away from a solo business is rarely simple. You're all the roles in your business, from marketing to administration. Not to mention the actual delivery of work to your clients.
Even if you have no idea what long-term leave looks like (or why you might need it), it's important to think about how you can prepare. You might not bring someone in to do the work, but you might rely on a virtual assistant, for example. For that to work, you need documented processes.
If you were to take long-term leave starting tomorrow, what would happen? Ask yourself: what things can you put into place now that would make leave easier in the future.
If you need to step away from your business, this guide walks you through everything you need to do to prepare.
