How To Know If Side Hustling Is Right For You

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Today’s guest post is by Melissa Brock. She is the founder of College Money Tipsand Money editor at Benzinga. She loves helping families navigate the college search process. Check out her essential timeline and checklist for the college search!

Thinking about picking up a side hustlebut curious about whether you’ve got it in yourself to successfully side hustle? Not sure it’s worth your while?

I spent 12 years working at my alma mater in college admission before I picked up my side hustle — freelance writing. For a long time, it didn’t even really dawn on me that I should take on a side hustle.

I’m constantly amazed by what people come up with as side hustle opportunities. I know a couple who looked for pallets on the side of the road, refurbished them into furniture and sold them. Talk about hustle — I’m awed every time I think of that story.

Once I figured out how to side hustle, I realized I was bornto live the gig lifestyle. I started freelance writing in 2017 and haven’t looked back — side hustling gives me more freedom, so I’m not always chained to a desk.

So, how do you know side hustling is right for you? Let’s find out!

Before we get started, make sure to sign up for my free resource library that includes a ton of amazing free resources available immediately. 

Here are ways to know whether you’re made for side hustling.

1. You have a side hustling mentality

Are you always scheming for new ways to make money? Always thinking about pestering your editor for more freelance work? Looking for ways to sell — well, pretty much anything?

You may be in good shape if you have that mentality, but if you don’t naturally have that bug in your brain, you might encounter some difficulty trying to pull it off. If the regular ol’ nine to five is fine with you, side hustling might not be in your nature. 

But wait — can you learn to “get the hustle?”


Fiverr is a great place to post freelancing services that you provide. Businesses can find you on Fiverr and pay you in exchange for doing work for them – whether it be related to graphic design, writing, programming, etc.

2. You have a goal in mind

How much money do you want to make with your side hustle? The most successful side hustlers write down a goal and meet it. 

Notice written down — you increase your odds substantially if you write them down.

Put your goals in front of you so you see them every day. Whether you write, “Make $5,000 this month with my side hustle” on a Post-It and stick it up on your mirror or have a spreadsheet you look at every day, make sure you have something you can commit to.

Make sure you know what you’re working toward. 

3. You tap into a skill you know you have

You don’t want to spend your time side hustling as a photographer if everyone says, “Geez, all your photos are really blurry… Like, all of them. You’re freelancing as a photographer?” 

It’s important to realize what you’re pretty good at — and what you’d best leave to the pros. You’ll have more success if you’re doing what makes you wildly happy. 

What’s the one thing that people have always said you do well? Have they always complimented your fried chicken recipe? Your acting skills? Your piano playing abilities?

Take that skill. Let’s say you multiply your earnings by 10, then multiply them by 10 again. Figure out how to level up as you go.

Do you want to start a side hustle today? Sign up for my free Work From Home eBook that includes several side hustles and remote careers you can start today.

3. You’re full of grit

Are you particularly gritty? Believe it or not, this seemingly small characteristic  can make a huge difference in how successful you are at side hustles. What does grit actually mean?

It simply means you never refuse to give up because you have perseverance and passion for your future goals over the course of weeks, months and years. 

Angela Duckworth, a grit pioneer and professor at the University of Pennsylvania, used to teach seventh grade math in New York City public schools when she noticed that her best students were not necessarily her smartest students.

With a flourish, she left her middle school classroom to become a research psychologist so she could better understand the role that foundational skills like self-control and perseverance play in achievement.

So, the ultimate question: Do you have grit? And how will your level of grit help you sustain a successful side hustle?

4. You believe that there’s a side hustle out there for you

Choosing the right side hustle for you involves knowing your skills and your priorities.

You can activate certain types of side hustles while you’re nestled deep into the recesses of your couch and others will make you completely criss-cross your town.

No matter which approach you take, each one is a viable way to increase your income. (Crazy, huh?) 

If you have a job, use that as inspiration. What already-honed skills do you have through your job that you can turn into a side hustle?

For example, I turned my writing skills and college admission knowledge into my site, College Money Tips.

Here are some other ideas:

  • Copywriter to freelancer
  • Engineer to entrepreneur
  • Teacher to online tutor
  • Mental health counselor to private practice counselor

Related article: How To Monetize Your Creative Skills

5. You’re familiar with the term “fail fast” — and embrace it

Ever heard of failing fast? It means trying different things and failing, and instead of emphasizing the failure part of it, you know that the knowledge gained from a failed attempt actually increases your probability of eventual success.

Goes back to that “grit” thing. If you fail, dust yourself off and still make a go for it on round two. And three. And 96.

For example, let’s say you start a dog walking business.

You put out what you think are great ads, only to get zero nibbles on your services. Analyze what went wrong and fix it. Then congratulate yourself — you fell fast. 

The only thing you can do after a failed attempt is to try again.

Related article: 10 Ways To Turn $100 Into $1,000

6. You know how to get the word out there

Whether you dominate with your side hustle using Facebook ads or get by on word of mouth, you know how to get your services a broader audience.

If current customers make their way for you by word of mouth or you do as much advertising to get them as you possibly can, you still know how to get the word out and build your business.

You’ve got good instincts. Use ‘em!

7. You’ve got people in your life to hustle for

Do you have others in your life to hustle for?

Now, does this mean you can’t be a single person and build an admirable side hustle? Nope.

However, sometimes having others in your life who you know you need to hustle for — kids’ college funds, a disabled child’s future, a spouse who’s working overtime to provide for your family — gives you that extra push. 

Your loved ones can be a powerful motivator. Look at your loved ones’ needs and determine how you can power forward for them. You can do amazing things when you’re working on someone’s behalf. 

Consider Jennifer Maker’s story. Maker runs the site– six months into building her site, she made $15,000 in one month on a product launch. Her income experienced a snowball effect, and by the end of the year, she made $65,000 in one month. 

The really cool thing about this story is that Maker didn’t do all of this just for herself. Her daughter has a serious medical condition and Maker needed $50,000 for a specific treatment.

She was able to pay that bill due to her blogging income. Her daughter was a powerful motivator.

Do you want to start a blog? Sign up for my free blogging course here. I teach you the most important steps to get started so you can get started making money blogging.

8. You love your side hustle

If you love your side hustle, you’re more likely to succeed. (After all, it’s pretty hard to feel motivated when you’re dragging yourself out of the house to do your side hustle.)

hat’s why it’s key to find a side hustle that you love. If you can’t imagine doing anything else, be it weeding gardens, fixing cars, maintaining websites or watching kids, you want to tap into the hustle that gets you going. 

The happier you are doing your side hustle, the more likely it’ll be that you hit your goals and make more money.

Side hustles you can start

Here are a few side hustles ideas if you’re eager to start making extra money:

Free courses or workshops that teach you how to earn extra money:

Final Thoughts

Carefully consider your personal characteristics, your level of tenacity and outline the goals you’d like to achieve.

I can’t imagine not doing my side hustle and I know a number of other freelancers and side hustlers who feel the same way. They would feel like they’re missing out on a really rich part of their lives if they weren’t able to do their side hustle. 

Figure out what you can’t live without doing and hustle your heart out. It’s an amazing feeling!

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Do you want to start a side hustle?

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