How Not to Side Hustle During the Holidays


Last December, I picked up what I thought would be an easy holiday side gig: a two-week cat sitting job that paid $30 per day. It sounded like a low-stress way to earn extra money that I could use to get ahead in the New Year—except it wasn’t.

While nothing went terribly wrong, the holiday hustle ended up compounding an already hectic season. Here are the rookie mistakes I made, and how a little planning can help you avoid them.

1. I stretched myself too thin professionally.

The holidays really are a great time to side hustle, thanks to an influx of high-paying opportunities. So I eagerly accepted several gigs to boost my income, including an on-site proofreading job a few afternoons a week and test proctoring at a local university. As a result, I raked in an extra $1,500 in just a few weeks’ time.

However, working a total of four jobs including my regular freelance writing gig—and not sleeping at my own apartment while cat sitting—left me feeling displaced, constantly pressed for time and exhausted. That led to me having to decline additional writing assignments (which generally pay more) because I’d already committed to on-site jobs with a set rate.

What to do instead: Be strategic about what jobs you accept, so you can make the most of your (likely limited) time during the holidays. This year, I’ve decided to focus solely on my regular freelance writing clients. This way, I can write in the comfort of my own home or local coffee shop and take on the highest-paying assignments, while still enjoying the holidays.

2. I overbooked my social calendar, too.

During the same two-week span, I RSVP’ed yes to several holiday functions that were near my apartment, but on the other side of town from where I was cat sitting. Fighting L.A. traffic to trek across the city multiples times ultimately sucked up a lot more money (in gas) and time than I’d anticipated.

I also failed to consider that attending nighttime social events meant I spent more time away from the cats than felt comfortable, given that I was being paid to hang out with them. Of course, they were always taken care of—but I swear they side-eyed me anytime I got home late.

What to do instead: Working a holiday side gig doesn’t mean you have to sacrifice your social life. For some, saying yes to fewer commitments is truly worth the chance to earn more. For others, knowing upfront that it’s tough to do everything might mean cutting back on working hours instead. Acknowledging the tradeoffs upfront can help you feel better about the choices you make.

3. I mistimed my deliveries.

Another logistical threat: While I remembered to put a hold on my mail while cat sitting, it didn’t occur to me initially that I’d miss several package deliveries set to show up at my apartment. That led to even more time spent driving back and forth across town to track down packages I needed for various parties and gift exchanges. Staying on top of cards and gifts was tougher, too, on top of juggling all the side gigs and social commitments.

What to do instead: Make a list of all the gifts you need to get early in the season (like now) when you can devote the time and thought to it. If your holiday side hustle will require you to be away from home for long hours, order gifts you’ll need to hand out in person (or anything else you’re ordering online and need by the holidays) early on to avoid the hassle of having to track down missed packages later. Or consider shipping them directly to where you’re working.