The freelancer’s holiday survival guide

Don’t go home without it.

The holidays and freelancing have a lot in common. There’s the ability to set your own schedule, you can wear sweatpants or glitter and it’s all good, and the battle to ignore Twitter and pay attention to what’s going on is constant.

But there are some additional challenges, and we don’t mean tryptophan. For many freelancers, going home for the holidays means adopting the role of ambassador for freelancing to the confused nation that is W-2-ed family and friends. And while “okay boomer” responses to funemployment jokes are easy (and on trend!), explaining what you actually do can be trickier.

From career interrogation and taking time off, to showing up with your life basically together, we’ve put together the ultimate guide to navigating the holidays. As for the fact that you may have to sleep on a blow-up bed at least once? You’re on your own.

Get your s**t together

Open enrollment for health insurance is underway, which means you have until December 15 to lock in coverage for next year. Stop procrastinating and check out our guide to choosing coverage. Because if you keep just one deadline over the holidays, it should be this one.

While you’re in get-it-together mode, you may as well get a jump on your taxes. The IRS would like you to, so much so that they’ve launched the “Get Ready” campaign on how to adjust withholdings, gather documents, renews IDs, and set up payments ahead of time. Check out their tips for next-level adulting here.

Talk shop with confidence

Explaining the ins and out of your freelance career as you pass the mashed potatoes can get old quickly. You can’t bring your therapist with you, but you can cultivate an understanding frame of mind and assure inquiring family members that you are kicking ass on your own terms.

Don’t forget to chill

When you don’t work a traditional 9 to 5, it can be tempting to work all the other hours as well. But don’t! You, a freelancer, deserve a vacation, so make time to kick back, relax, and celebrate all you’ve achieved this year as you recharge for the next one.

Happy holidays!

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Categories: Remote Life