The Best and Worst Times to Side Hustle

StressIn the personal finance world, there’s a lot of discussion regarding “side hustles”, also known as extra income opportunities, side jobs, survival jobs, etc.

You can only cut back on your expenses so much, but your earning potential is practically unlimited. There’s always an opportunity to make more money which is why many take on side hustles as a way of maximizing that opportunity.

Side hustles can range from babysitting to web designing to freelance writing to soap making- basically anything you can charge for can become a side hustle. As a professional actress, I’ve had to become a side hustling pro to sustain me through periods of un- and underemployment. Through my personal experience I’ve learned that side hustles, just like anything else, are prone to good times and bad times. Anyone looking to maximize their extra earnings should consider these factors when approaching their own hustle.

The Best Times To Side Hustle…

In the Last Minute.

Nothing gives you the upper hand in a negotiation quite like your services being desperately needed, as soon as possible. Leaving yourself open to side hustle opportunities that pop up at any time, particularly in the last minute, may not always be convenient but can pay off big time. Not only are you in a position to negotiate a better rate, but you can specify any additional terms you may find beneficial– certain hours, breaks, rush fees, etc.

Holidays and Occasions.

I was once asked to babysit for a New Years Eve party. I didn’t get to spend midnight at a bar or kissing someone special, but about an hour later, I walked away with $300 in my pocket. If you’re willing to give up some of your regular traditions or even a few weekend nights, you can charge that side hustle time at a premium.

The Worst Times to Side Hustle…

In a Time Crunch.

If your side hustle involves some kind of preparation and/or travel for you to get there and provide your service, it may not be worth your time if you’re not guaranteed a certain amount of hours or amount of work. For instance, if you were asked to babysit for two hours, but you had to commute an hour each way, would it be worth four hours of your time for only two hours of pay? (Tip: If you side hustle hourly, consider setting a minimum with your employer that makes your travel time and expenses worthwhile. That way, even if you only wind up working an hour or two, you’re still guaranteed your full minimum)

When Your Unemployed.

Oddly enough, side hustling when you’re unemployed doesn’t always make financial sense. If you take on part time work while collecting unemployment you have to report it and give up a quarter of your weekly unemployment pay for each day of part time work, no matter how few hours or how little the earnings. For example, if I make $400 a week on unemployment and I was offered a babysitting gig for one day that week, I would have to make at least $100 in that day of babysitting; otherwise I’d be operating at a loss. Yes, it seems counterintuitive to disincentivize people from working, but unfortunately, that’s the way the system is currently set up.

When You’re Exhausted.

Working a full time job in addition to cultivating a side hustle, along with everything else you do (working out, cultivating hobbies, raising a family, etc), is A LOT. Sometimes a break and time to do nothing is more valuable than constantly filling your time with more work- even if it means less money. Nothing is more important than your health- physically, mentally, and emotionally; don’t stretch yourself so thin that you jeopardize any of those.

What are your best side hustle timing tips? What has worked to your advantage? What hasn’t?


The Best and Worst Times to Side Hustle — 10 Comments

  1. Soo true. The times when people do not want to work are always the best times to make that extra income. Moving away from my family/friends during college, it was pretty easy to pick up extra work during those times when others were taking off for holidays.

  2. I don’t side hustle jobs, since my regular job takes all the time that I want to spend on earning income (plus it pays a lot, so I don’t really have to side hustle.) But your tip that the best time to negotiate a side hustle is “in the last minute” is germane to any type of work. If a client is having a hard time meeting a deadline, they will often be willing to hire consultants and freelancers to get the job done. Just look at what happened with

  3. In France they have made calculation so you don’t lose so much money for working alongside unemployment, because before you could be better off doing nothing at home than working. They count the hours you worked over the month and deduce part of it from your check so you are always better off working.

  4. My most fun and profitable side hustles are started when I already have a stable job. I started blogging while I was full time employed and fit in blogging whenever I could. Then I turned that online work into self-employment. Now I am self-employed, business is stable, and I’ve started a pet sitting side hustle. It’s made about $1200 in less than a month. Obviously, I can work best with a side hustle if I have a full time job to keep me stable the rest of the time. 🙂

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