How to survive the holidays as a freelancer

Rosemary Egbo
Written by Rosemary Egbo
on December 16, 2021 6 minute read

The holiday season is often a bittersweet period for many freelancers. In Nigeria where I come from, we celebrate the holidays in a traditional fashion. I travel down to the countryside to celebrate with my extended family.

I love the serenity in the countryside; fresh air, good food, and lots of events like masquerade festivals, traditional weddings, sports tournaments and the likes to attend. I know what it's like to be worried if you're going to get cash flow to pay for gifts while still trying to relax and enjoy the holidays. Only to have a relative ask me if I'm still freelancing, and why I haven't gotten a "real job" yet.

I know that many freelancers struggle with how to survive and enjoy the holidays. Some freelancers are under pressure to meet end-of-the-year deadlines, faced with a lot of financial expectations while battling to get clients to pay up on those outstanding invoices. And to top it off, close relations tend to ask prying questions about when you'll get married, have kids — and get a real job.  

I've gone through these struggles, and I've developed some mechanisms on how to survive the holidays as a freelancer. Here are my best tips and tricks for making it through the holidays without becoming a grinch.

Let's get into it!

How to survive the lead-up to the holidays

To survive and enjoy the holidays as a freelancer, you need to end the year on a good note so you can hit the ground running once you're back to business as usual. This means getting organized and wrapping things up nice and tidy with your clients so you can log off and be fully present during this most wonderful time of the year. Remember, healthy boundaries are your friends in all things — but especially with freelancing. Let's look at a few ways you can set healthy boundaries with your clients while still being professional.

1. Wrap things up early 🎁

The first step to wrap things up early is to complete your projects. and send invoices to clients that are still pending. These payment reminders are an excellent opportunity to remind your clients that you plan to be offline. Informing your clients about taking a break during the holidays should be done at least two weeks before you sign off for the year. That way, it'll give them enough time to adjust to your absence.

That said, I've worked with clients who don't respect boundaries no matter how early and often I tell them about my plans. It can be hard not to just agree to help them with that "one little thing that just came up"— but take it from me, it's much better to be firm and politely remind them, "I'll be back on (date of planned return).

And finally, don't make the rookie mistake of thinking you'll immediately return to where you left off in the new year without missing a beat. Write down notes about meetings you had, possible future projects with clients, to-dos for the new year, etc. Don't leave it to your brain to remember because all that merrymaking in between will make what happened in December a foggy memory come January.

2. Show your clients how much you appreciate them

If you're a newbie, giving gifts to your freelance clients might sound a little strange. I felt the same way when I first considered gifting my clients during the holiday season.

I barely knew my clients and they have way more money than I do — they don't look like they have any need for my gifts. Despite my misgivings, I went ahead and gave small gifts to my clients — and was pleasantly surprised by how appreciative they were!

This simple act of kindness strengthened our client-freelancer relationship, which influenced them to recommend me to other clients.

Sending tokens of appreciation to your freelance clients during the holidays is a good client retention strategy, and also shows you value them.

And the best part is that you don't have to break the bank to make this happen!
You don't need to get your client an expensive gift to make them feel appreciated. Photo by Surface on Unsplash

6 gift ideas for freelancers to give to clients during the holidays

  1. A compelling read

    A book is something many people cherish, especially when it's a book they've been meaning to read. But gifting the appropriate book can prove challenging in the client/freelancer context.  Personally, I give books to the freelance clients I'm close with — the ones I've known the longest and have a better understanding of their interests. Here are a few of my favorites to give to clients:

  1. A gift card to their favorite coffee spot
  2. Keep yourself top-of-mind by sending customized swag
  3. A heartfelt holiday email letting them know how much you appreciate them
  4. A bottle of wine (just make sure they drink)
  5. Give to a cause close to their heart
    I did this last year for a client that owns an NGO that's involved in the fight against breast cancer. She was super excited and told me that was one of the best holiday gifts anyone could give her!

How to plan for next year

It's no longer news that the great resignation is upon us. And some of these employees are quitting full-time employment to become freelancers. From my forecast, the competition among freelancers in 2022 will be stronger than it was in 2021 — I know many people who quit their jobs this year to start their own freelance careers.

Here are a few tips to hit the ground running in 2022:

1. Invest in "me time"

It's the holiday season, and you'd likely be surrounded by friends and family which will leave you with little alone time. You're on a break to rest and come back better in 2022. 

It's important you squeeze out some time alone with your thoughts. Find a quiet environment to be present and have a heart-to-heart with yourself. You can take notes, but it's most important to be honest.

2. Review and reflect on the past year

To make better decisions, it's good you visit the past 11 months. Review your wins and losses, lessons you learned (especially the hard ones), the clients you lost and won, collaboration and networking opportunities, building your personal brand, etc.

Note the good, bad and ugly to gain an unbiased review of the year. This isn't for you to start feeling regretful while counting your losses — rather it's to have a clear picture of how the year went and how you can make 2022 even better.

3. Map out a plan for 2022

After reviewing the past year, now it's time to answer some questions that will help you come up with a solid plan for the coming year.

  • What's your business strategy?
  • Who do you want to work with?
  • Who do you want to stop working with?
  • Are you niching down in 2022? 
  • Are you keen on collaborations?
  • What courses are you taking to improve your skills?
  • Are you improving your personal branding?
  • Are you scaling into an agency?
  • What strategies or coping mechanisms can you employ to help you manage your mental health when things get stressful?

There are so many questions to ask yourself while you plan for 2022. And your plans will be effective if they are realistic, honest and actionable.

4. Set realistic time frames

Goals are wishful thinking if you don't add time frames to them. The trick here is to take them one at a time — you'll be overwhelmed and tired when you try to achieve every goal at once.

Add realistic time frames to the plans you've written down. I usually dedicate the first three months of the year to learning new skills and upgrading existing ones. I have come to understand that for me to grow, I have to continuously improve my skills.

How to set boundaries during the holidays

If you're the type of person who spends the holidays in a traditional family setting, it's important you set boundaries. There will be contrary opinions, people will get emotional, and if care isn't taken, it might ruin your holidays. 

Let's see how you can set boundaries with family and friends — and your bank account — during the holidays.

1. Think your financials through beforehand

The season comes with so many expenses that if you don't weigh those financial decisions, you might wind up broke. That means having to politely turn down invitations and requests you don't have the financial capacity to fund.

Have a budget for the holiday to reign in that holiday spending. That way you won't have to start 2022 burdened by the debt left behind by a too-expensive Christmas.

2. Mentally prepare for those triggering conversations

As a freelancer, you'll likely be asked when you'll get a real job. Friends and family might bring up triggering topics, and you have two options:

1. Swallow their triggering comments, and choose to stay quiet or

2. Let them know how you feel about those comments.

Whenever they mention your weight or marital status, tell them how happy and healthy you feel. Swallowing those triggering comments can ruin your holidays and puncture your self-confidence. So while it's nice to keep the peace, don't be afraid to stand up for yourself by having a hard (but respectful) conversation.

3. Be realistic about your expectations

It's fine to expect the best this holiday season. It's also fine to understand that humans will be humans — you can control what's within your control, nothing more. 

On this note, I'll implore you to relax and savor every moment, spend time with your loved ones, go on a vacation, read non-work related books, and try out those meals you watched on YouTube — but haven't gotten around to making yet.

Here's a quick recap:

  1. Sign out early
  2. Let your clients know you appreciate them
  3. Invest in "me time"
  4. Review and reflect on the past year
  5. Map out a plan for the new year
  6. Set realistic time frames
  7. Think through your financial decisions
  8. Mentally prepare for uncomfortable conversations
  9. Be realistic about your expectations

Congratulations on making it to the end of 2021. I wish you a blissful holiday season and a prosperous New Year!