A Solopreneur's Guide to a Holiday Season on Your Terms
How to manage your workload and stress.
Most solopreneurs I know feel like they work a lot of hours or don't have good boundaries. They'll work in the evenings or on weekends — anything to make clients happy or get their business off the ground. While I'm not a big fan of hustle culture, I get it: you do what's necessary to keep your business afloat.
The holiday season (late November through the start of the new year) is a different story for many reasons. You may want to take time off to spend with friends or family and you need to set proper expectations with clients. Our minds may be elsewhere, but that doesn't mean our clients or our businesses are elsewhere. The last thing you want is to get into a situation where you're forced to do client work when you'd rather be celebrating.
Here are a few things to think about as you approach the holiday season: how you can feel less anxious and how you can prep each year.
Decide in advance how much time you'll take off
If you plan to take time off, it shouldn't be a last-minute decision. Decide on your last working day of the year and start communicating to your clients — early and often.
I stop working around December 20th every year and don't resume until after January 1. This was my schedule long before I became a solopreneur: I have kids, and they have winter break from school. It's nearly impossible to get anything done with them at home.
Once I became self-employed, I had to figure out how to maintain my desired holiday schedule while still meeting client expectations. I start communicating my availability around late November (before U.S. Thanksgiving). Because I end up not working for around 1/3 of December, I need to make sure my clients know I won't be available during that time. This typically ends up kicking client work into high gear for several weeks, because clients want to complete projects before I'm unavailable. Sometimes I feel like I'm limping over the finish line, but it usually adds to my December income (which I'll talk about later).
If you're delivering work for clients, you may need to build in some time for feedback before your holiday break. For example, I'm a freelance writer. If I deliver something on my last working day of the year, clients don't have time to review it and request revisions. I have to let clients know the last day that I'll deliver any new work and the last day I'm working overall.
In addition to taking time off, think about your response time during the holidays. Will you still check your email, or will you wait until you return to respond? I'll typically set an auto-responder that my response time will be delayed until January 2, but I'll keep an eye on email. If something urgent comes in (like a prospective client), I'll reply and acknowledge that I received the email and let the person know that we can connect in January.
Budget for your holiday break
Many solopreneurs face the same situation I face: if you don't deliver any work, you don't get paid. This can add financial stress to the holiday season because you feel like you can't afford to take time off. I usually have really busy weeks leading up to my holiday break, but it's not enough to offset the reduced income for two or two-and-a-half weeks at the end of the year.
Ideally, you want to be in a situation where you don't feel pressured to work. If you're able to, set aside money every month in a separate savings account. During the holidays, or whenever you take time off, pull money from that savings account so you can "pay yourself" and don't feel any sting from reduced income that month.
You should also plan for the time it takes to "ramp up" once you return after your holiday break. When I resume client work in January, it takes a bit for my clients to have work ready for me. They're usually returning from their own holiday breaks or consumed with year-end reviews and reporting. I don't know that this would necessarily change if I worked throughout the entire month of December, but I have to be prepared for a lag in January.
If that's the case for your business, you could take the time to reflect on your own year, plan for the upcoming year, or do some internal/admin work. That way, you can keep your business moving, even if you are slow with client work.
Reach out to your clients
Every year, I send a holiday email to my current clients. I thank them for their business and share anything I've been up to outside of their working relationship with me.
Sending a holiday email is a simple way to stay connected with your clients and remind them that there's a human on the other side of the invoice. You could also include past clients that you wouldn't mind working with again, to remind them that you were a great asset to their business. Sometimes, clients may simply not have the budget to work with you, or you lost your internal contact with a company. If the relationship didn't end on bad terms, so it's worth including the past client in your holiday email.
I maintain an email list throughout the year, so it's easy for me to send an email to my clients in early December.
Holiday marketing
If you sell digital products, courses, or coaching, the holidays are a great time to market those products and earn a bit of extra money. People are used to Black Friday deals, so you can offer a discount to draw in new customers.
Keep in mind that holiday marketing takes some planning. You'll need to schedule some social posts and an email campaign to go out, which might include graphics or videos you'll need to create. You'll want to schedule them over several weeks, depending on your offer. If you need some inspiration, The Consistency Corner has a free holiday marketing planner.
You'll also want to market anything you plan to launch in January — especially if it means collecting money in November and December. A business coach I know created a workshop for freelancers looking for help as they set goals for the year. She created content around year-end reviews and goal-setting that she published throughout December, driving her audience to sign up for her workshop.
Anna Burgess Yang
Remove the guilt
Ultimately, you know best how you want to work throughout the holidays. Maybe you only take a step back. Maybe you fully unplug and don't look at your email again until January.
Whatever you do, commit to the boundaries you set. Otherwise, you might feel guilty if you reply to a client's last-minute emergency on December 23rd. Give yourself permission to do what's best for you and your business, and don't apologize for the decisions you make.
Need to review the health of your business? Check out my quarterly planning checklist for solopreneurs.
