How to Take Time Off as a Freelancer: Medical, Maternity, and Sabbaticals

This blog summarizes learnings from The Future is Freelance Forums. These forums are where stakeholders from all levels of the freelance ecosystem (freelancers, agency leaders, coaches, platform CEOs, enterprise leaders, etc.) come together to surface and solve the biggest problems facing independent work. These summaries serve as a place to house our collective wisdom on these topics. As such, I want to credit everyone who attended this forum for these insights. 

Taking time off as a freelancer feels impossible. When I asked people signing up for our recent forum to answer the question "How do you take leave as a freelancer?", nearly a third of responses fell into one category: "I don't."

That's why I'm here, they said. That's what I want to find out.

This stood out to me because in all the forums I've run, this was the first time so many people admitted they genuinely didn't know how to do the thing we were gathering to discuss. And honestly? That tells us something important about how challenging freelancer leave really is.

I brought together three incredible freelancers who've navigated different types of leave to help us unpack this together: Helen, who's taken maternity leave and now runs a fractional marketing business; Anna, who had to take unexpected medical leave for brain surgery earlier this year; and Lucy, who's managed three different maternity leaves plus the chaos of caring for an aging parent while running her business.

Here's what we figured out together about taking time off as a freelancer.

Key Takeaways: How Freelancers Can Take Time Off

• Build PTO into your pricing from day one you're running a business, not just selling hours
• Save 3-6 months of expenses in both personal and business emergency funds
• Design systems-led processes so your business doesn't completely depend on you
• Know your contract terms regarding subcontracting before you need coverage
• Consider disability insurance or create your own self-insurance fund
• Plan based on leave type: maternity leave needs months of prep; medical leave may need community support; sabbaticals require long-term business design

Why Taking Time Off as a Freelancer Is So Difficult: The Mindset Challenge

We started by asking everyone: What's the conversation you have with yourself when you're considering taking time off?

The answers were telling. The internal narratives we carry around leave are often more complex than the actual logistics. Things like:

• "Will my business still be there when I get back?"
• "What if clients move on without me?"
• "Can I really afford this?"
• "Do I even deserve to take time off?"

Anna shared that her biggest fear when she had to step away for surgery was exactly that first question. She had to tell all her project-based clients she'd be gone for an undetermined amount of time and that she understood if they needed to find someone else. The uncertainty of whether her business would survive her absence was real.

How to Plan for Freelancer Leave: Building Time Off Into Your Business Model

Intentionally creating a business where leave is baked in from the beginning is crucial. 

This isn't just about having an emergency fund (though that's important). It's about designing a business model that can actually support you taking time off, whether that's planned or unplanned.

Have money set aside. This means both personal savings and business reserves to cover expenses. We talked about how employees often have paid leave built into their compensation, and as freelancers, we need to build that into our pricing structure. When you're setting your rates, you should be pricing in your PTO, not just your working hours.

Your business model has implications. Project-based work looks different from retainer work when it comes to taking leave. Some of us have more flexibility to front-load work; others need to find coverage. Understanding the constraints and opportunities of your specific model is key to successfully taking freelancer vacation or medical leave.

One participant shared how she's reframing her retainer contracts as annual investments rather than monthly ones. This helps both her and her clients understand that some months she'll work more intensely, while others (like when she takes that June sabbatical) she'll step back. The value isn't in being chained to your desk every single day.

The Catch-22 of Being Indispensable as a Freelancer

We had a really interesting conversation about being the "unicorn" in your business. On one hand, being irreplaceable feels like job security. On the other hand, as Úna pointed out, "feeling that you're irreplaceable creates massive pressure and a huge burden."

Helen learned this the hard way. She had systems and processes to delegate work to her team during maternity leave, but what she didn't realize was that people were buying her. "My clients knew my team, but nobody had the authority or inclination to have strategic commercial conversations."

The solution? Thinking about your business more systemically. As Úna said, for a business to grow, "it needs to be systems-led, not founder-led." This doesn't mean you can't maintain your unique value proposition, but it does mean thinking about:

• Automated marketing that runs without you
• Partners or subcontractors who can cover certain aspects
• Passive-ish income streams (though let's be real about how "passive" they actually are)
• Contingency plans for different scenarios

Freelancer Maternity Leave vs. Medical Leave vs. Sabbaticals: Different Approaches for Different Situations

The amount of preparation time you have varies wildly depending on the type of freelancer leave you're taking. Someone planning for maternity leave might have months to prepare. Anna had six weeks to figure everything out before surgery. Some medical emergencies give you days or less.

This matters because your preparation strategy will differ:

Planned leave gives you the most runway. With maternity leave, you can spend months front-loading work, setting up systems, briefing backup people, and communicating with clients. You have time to build that financial cushion and put automated systems in place.

Crisis leave means you need to know how to accept help quickly. Think Lucy's setting up a Buy Me a Coffee link, or Anna's GoFundMe. When you're in the middle of a medical crisis, having easy ways for people to support you matters.

Sabbatical leave requires the most intentional business design up front. You're choosing to step away, which means you need your business model, systems, and financial planning in place well before you take that time off.

Practical Strategies for Taking Time Off as a Freelancer

Here are some concrete strategies that came up:

Strategic timing. Some work is naturally seasonal. Lean into that. Take advantage of slow periods, holidays when clients aren't responsive anyway, or natural breaks between projects. Many freelancers find the weeks between Christmas and New Year's or summer months work well for extended time off.

Work-life blending (when appropriate). For planned vacations, some of us prefer to check email once a day rather than come back to chaos. This isn't for everyone or every situation, but it can work for certain types of leave and helps maintain client relationships during time off.

Insurance and backup plans. In the UK, Helen pays £26/month for income protection insurance. In the US, freelancers can get long-term disability insurance through the Freelancers Union. Or you can set aside your own self-insurance fund. Either way, have a plan for if you can't work.

Know your contracts. If you're thinking about having someone cover for you, check whether your contracts actually allow subcontracting. Anna's don't, her clients are specifically paying for her. That's important to know before you're in crisis mode.

Have unofficial backup. Even if you can't formally subcontract, having peers who can help field questions or handle small things can be invaluable. Anna and I share the same VA, so when Anna was out, the VA could ping me with questions about Anna's systems.

Ask for help. Both Lucy and Anna shared how community support made a real difference. Whether that's a Buy Me a Coffee link, a GoFundMe, or just letting people know what you need, don't be afraid to let your network support you during medical or other crisis leave.

Essential Mindset Shifts for Freelancer Time Off

The conversation kept coming back to fundamental mindset shifts freelancers need to make:

From employee to business owner. You're not just selling your time. You're running a business. That means your pricing needs to include overhead for things like PTO, just like any business would factor in employee benefits. 

From hourly to value-based. Moving away from hourly billing to retainers, packages, or value-based pricing gives you more flexibility to take time off without directly tying your absence to lost income. This is especially important for planning freelancer maternity leave or sabbaticals.

From indispensable to sustainable. Yes, your unique value is important. But building a business that completely depends on you being available 24/7 isn't sustainable or healthy, and it makes taking any kind of freelancer leave nearly impossible.

Taking Time Off as a Freelancer: Start Planning Now

Taking leave as a freelancer is hard. There's no getting around that. No one “gives” us built-in PTO or sick leave; we have to build it in ourselves. We're carrying the mental load of worrying about whether clients will be there when we get back. We're navigating business models that often weren't designed with extended leave in mind.

But here's what I took away from this conversation: taking time off as a freelancer is possible. People are doing it; managing maternity leave, medical leave, and sabbaticals successfully. And the more we talk about it, share strategies, and support each other through it, the easier it becomes for all of us.

The key is thinking about this before you need it. Don't wait until you're in crisis mode to figure out your leave strategy. Start building it into your freelance business now:

• Build margin into your pricing to account for time off
• Set aside emergency funds (both personal and business)
• Think about your business model's flexibility for different types of leave
• Cultivate relationships with peers who could help during emergencies
• Research your insurance options for disability coverage
• Give yourself permission to take freelancer vacation time—you deserve it

Because at the end of the day, we're not just running businesses. We're living lives. And sometimes life requires us to step away, whether we're ready or not.

Want to join the next conversation? Click here for information on the next Future is Freelance Forum.