How to Handle These 5 Challenges in the Side Hustle Workforce

Everyday we’re hustlin’ — no, seriously we are. In fact, nearly 44 million Americans have a side job. While side hustles may be transforming the way we work, they don’t come without their fair share of challenges. These hurdles impact workers at all levels, from those juggling full-time roles in addition to side jobs to entrepreneurs trying to transition from traditional employment to self-employment. Here’s a look at some of the most common challenges side workers face and the solutions for getting around them.

1. Not enough time.

The challenge: Maybe you’re single with a full-time job and a side hustle. You might be a parent with both a job and side gig, too. I know, I know — we all have the same amount of hours in a day that Beyoncé has — but that doesn’t mean that you won’t inevitably reach a point of frustration where you feel like you don’t have enough time to do it all.

The solution: Sit down and draft out what your daily timeline looks like, hour by hour. Take into account everything you do throughout your day, including the time spent at your full-time job, with your children (if you have any), or any other commitments such as caring for aging parents, running errands, and even your commute. Do this before you commit to any side hustle, so you have a better idea of how much time you can devote to getting that job done.

2. Saying “yes” to everything.

The challenge: We have long been told not to say “no” to opportunities and that 80 percent of success is showing up. However, constantly saying “yes” to plum side gig assignments when you know you don’t have the bandwidth for it can cause you to quickly get in over your head with commitments.

The solution: Be honest. If you have a side gig where you work with several clients, like freelance writing, or graphic design, explain to them what your existing work situation looks like. It’s highly likely they will not know everything else you have on your plate and be completely understanding if you need to scale back.

3. Taking on side gigs that are a conflict of interest.

The challenge: There’s a side hustle or potential client that has expressed interest in working with you. The only problem? They’re a competitor to your full-time job.

The solution: If you’re a full-time employee getting poached by a direct competitor to your company, don’t take the gig. Even if it looks amazing. Even if it pays well. At the time of your employment, you likely signed employment contracts, non-disclosure agreements, and non-compete clauses, and you may have an understanding about your company policy that discourages these actions. Do not jeopardize your full-time job, or think you can work the other side hustle without word getting out. Trust me — it will and it will not be good for your reputation or employment future.

4. Getting paid on time.

The challenge: You submitted your invoice on time and are ready to be paid for your hard work. But, the payment is running late or the client is unable to write you a check at the moment.

The solution: Typically, most side hustles have a written agreement in place between both parties that touches on what to do next if payments run late or you are not paid at all. Follow-up with the client and, if the situation requires it, have a discussion together to see what can be done next.

5. Doing your taxes.

The challenge: Simply put, you can’t recklessly spend every paycheck you get from your hustle.

The solution: The more you earn, the more you have to set aside a certain percentage for tax purposes because it is highly likely you will need to pay something in to federal and possibly the state during tax season. If you are not confident about doing your taxes with a side hustle, you may consider working with an accountant or tax professional. These individuals will need to be paid for their services, of course, but they are experienced, thorough, and can help you find deductions you might have missed otherwise.

What challenges have you had with having a side hustle? Let us know how you tackled them in the comments!