3 Ways to Get Through the Holidays When You’re Self-Employed

Three strategies for making it through the holidays when you're self employed without undue stress to your spending, your schedule or yourself.


If you’re working an office job, the holidays are the time that you can finally relax, take some of that hard-earned PTO and generally act unemployed for a few days.

But for those of us that, like me, work for themselves – the holidays can quickly morph into six straight weeks of anxiety, stress and constant work. Or worse, not enough work (but all the anxiety and stress).

I’m saying all this from experience. The holidays are the one time of the year that I frequently wish I worked for an employer. An employer that would pay me to lie on my couch in a onesie watching cheesy Christmas movies (like every other person on Instagram).

I’ve been self-employed for three Christmases now, and while I’m far from mastering the holidays, I’ve learned a few tricks to make them bearable.


Say No to Your Family (Even on Holidays)


I don’t know about you but my holidays are 99% parental guilt-trip and 1% cookie-face-stuffing.

Stuffing my face full of cookies is here to stay but the family guilt has GOT TO GO.

Seriously. I spent years falling for it. Getting up early on Thanksgiving to help cook. Staying the night on Christmas Eve so that “it’s just like old times,” and driving miles in holiday traffic to see relatives I barely know.

That’s a lot easier to do when you’re on paid vacation. But when you work for yourself, your time is your money.


Four hours at a Christmas party for your mom’s second cousin’s neighbor is four hours you could be earning, planning or decompressing.


The same policy applies to your spending. You have permission say no to spending extra money (on your family, your friends, even yourself!)


If work (and/or income) tends to slow down during the holiday season, it’s probably not the best time to ramp up your spending.


In fact, adjusting your budget to spend less can go a long way in reducing holiday stress. (For tips on how to avoid overspending this December, keep these 4 strategies in mind).


Plan Ahead So You Can Plan to Relax


Yep, the only way to relax and stop planning is to…plan.

Early in November (Um, like, right now. Today. This instant), you should be planning your World Takeover strategy for 2017.

Do you know which clients you need to follow up with on January 2nd? Which pitches you need to prepare? What your key points of focus are going to be for your business? The improvements you want to make?

The reason I used to find the holidays stressful is because I wasn’t actually prepared for the following year.


I would spend weeks feeling scared and unfocused and unsure because I was scared and unfocused and unsure.


Get your ducks in a row before you get into your onesie and turn on Love Actually.


January starts on January 2nd


If you’re working for a company, your holidays might linger on into the second week of January. Everyone is on sugar-overload, still dealing with family in town and trying to recover mentally from the holidays.

If you’re self-employed, it’s a different story.


On January 2nd, make sure you’re at your desk first thing, computer charged and ready to work.


You didn’t pick self-employment because it’s easy


If you’re working for yourself so that you can enjoy restful holidays, long summer vacations and weekends taking long leisurely bubble baths, it might be time to consider a different career path.

Sure, you might get some of those perks (or even all of those perks). But figuring out when you can actually work them into your schedule may prove difficult and even inconvenient. You might work all of 4th of July weekend, then find yourself bubble-bathing on a random Tuesday morning.

Just last Christmas I found myself frantically trying to break away from the holiday festivities to respond to an unexpected email from a Fox News producer. Thanks to that holiday hustle, I made my Fox & Friends debut two days later and got to plug my book to the show’s 1 million plus viewers.

It was a good reminder that I didn’t get into working for myself to enjoy lazy Christmas evenings, but to exercise my passion, creativity and yes, my slight obsession with the hustle.

Keep that in mind this holiday season and you’ll have lots to celebrate!



10 responses to “3 Ways to Get Through the Holidays When You’re Self-Employed

  1. These are all really great points! There are pros and cons to side hustle vs. self-employment, and I definitely feel the cons. It’s important for me to focus on the pros for the time being (consistent pay, benefits – PTO(!)). When you are self-employed I think it’s important to do the same thing. Don’t dwell on the fact that you don’t have PTO or clients are slow to respond (if at all) the second half of December. Think about all the pros you have such as setting your own schedule, being able to say no to things, etc. You aren’t trapped at a desk 40-60 hours a week! It’s important to celebrate those things, especially around the holidays.

    1. Absolutely. I’m a huge fan of self-employment and would take it over a 9-5 ANY day, that said, it’s important to know it’s not all sunshine and rainbows 🙂

  2. Be less social.It can be really easy to get distracted with your social accounts, but if you really want to make the most of the time you have in the working day, try to take a step back from Facebook, Twitter, Instagram etc.

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