3 Side Fights You Could Face, And What To Do About It

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Side hustle can pose challenges. These are some of the most common that you could face.


Key points

  • Side hustle and bustle can open the door to logistical and accounting challenges.
  • The right strategies could make your side gig much more manageable.

You may have decided to get an extra hustle to increase your income in the face of rising bills. Or maybe you have a specific financial goal you’re working toward, like buying a house or paying off your credit cards forever.

There is definitely an advantage to having a side hustle: increasing your earnings and buying yourself more financial freedom. But there are challenges you may encounter if you have a second job. Here are three that you might have trouble with, and how to handle them.

1. Not having time

When you work full time, finding hours a week to tackle your side job can be difficult. And the last thing you want to do is drive yourself to the point of exhaustion, or show up so sleep-deprived at your primary job that you compromise your performance.

Instead of trying to squeeze your sideline into your schedule, carve out time for it ahead of time. At the start of each week, take a look at your work-related and personal calendar and see where your side hustle might fit. Maybe you can only handle two hours of side work one week and five hours another week, and that’s good. It’s important to be realistic about what your schedule allows.

2. Find out what taxes you owe

Some side jobs are self-employment, which means you won’t have taxes withheld from your earnings the way your full-time employer withholds them from your paycheck. But the IRS requires you to pay taxes on additional earnings as you go, which means you may need to get in the habit of paying quarterly estimated taxes.

If you’re new to having a side hustle, you may not know how much to pay. But you have options. You can consult an accountant for help, or you can use a online calculator to determine what you must pay.

3. Feeling guilty when you’re not working

Some side hustle limits the amount of work you can do. For example, if your sideline involves content editing and the company that hires you only needs five hours of your time per week, that’s all you can spend.

But some side hustle can be done at your own pace. If you drive for a transport company, for example, you can work one hour a week or 20, it’s up to you. And that flexibility could end up backfiring on you, because what it could do is lead you to feel guilty if there are times when you’d rather stay home and relax than work your second job.

To combat this problem, try setting a weekly or monthly income goal and not worry once you’ve reached it, or once you’re clearly on target to reach it. So let’s say you expect to earn $400 monthly. If it’s the middle of the month and you’ve already made $325, then you can probably kick back on the couch for a night instead of forcing yourself to put in a few hours of hustle and bustle.

While side hustle can be a wonderful thing, it can also be difficult to manage. If you’re having trouble with any of the above, make a plan to rectify the situation so you can keep that secondary income stream.

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