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8 Questions to Ask When Starting a Side Hustle

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Thinking about starting a side hustle?

I’m all for it and judging by the number of people who have side hustles (it’s about 40% of Americans in case you’re wondering), I’m not the only one.

And why not start a side hustle?

You may want to make some extra cash to bolster the household budget. Or you might be looking for something that offers a creative outlet.

A side hustle can do both of those things for you.

When I started my freelance writing hustle as a stay at home mom, it was because I wanted to make a little money on the side. But I also wanted to have something that was just for me.

I jumped in without knowing what I was doing. And eventually, my hustle grew into a full-time online business. But it was a lot of trial and error, not to mention some serious hard work.

And sometimes, starting a side hustle isn’t right for everyone. Which is totally okay but it’s something you probably want to know before you go all in.

So to make your life a little easier, I’ve put together a little side hustle quiz to help you decide if having a side gig is a good move.

8 Must-Ask Questions for Starting a Side Hustle

start a side hustle1. Why Do You Want to Start a Side Hustle?

My “why” for starting a side hustle was about making money and staying busy. But yours might be something totally different.

So take some time to think about your reasons for starting a side hustle.

Is your family in a tight spot financially and you need extra money to cover the bills?

Are you a stay at home mom who’s hoping to become a mompreneur?

Do you have some skills that have gone unused for too long and you just need to put them out there into the world?

Whatever your reason (or reasons) for starting a side hustle, get clear on them. And don’t feel like you have to explain them to anyone else.

2. What Are Your Side Hustle Goals?

If you’ve ever read any of my posts, you know that I’m a total goals geek. I love setting goals for just about everything and challenging myself to crush them.

You can totally start a side hustle without any goal or goals in mind but…I don’t recommend it.

Because if you’re going to put your time and energy into something there should be a purpose to it. And you need to have some way of measuring whether you’re realizing that purpose.

That’s what goals help you do.

When you’re setting goals for starting a side hustle, get really specific. The more detailed your goals are, the better.

So, instead of setting a vague goal to make extra money you might set a target to make $1,000/month from your hustle.

Or if you’re starting a side hustle to pay off debt, your goal might be something like I want to earn enough money to pay down $5,000 in debt in six months. 

Just make sure your goals are realistic.

For example, I set some ridiculously high goals for myself when I started this blog. And I didn’t hit any of them because they just weren’t realistic. (I didn’t understand a thing about blogging. 🙂 )

So guess what? I quit blogging for a while because I got totally frustrated.

If you want your side hustle efforts to pay off, you can’t give up in the middle of it. And setting realistic goals that you can actually achieve matters for staying motivated.

Don’t forget to track your progress either.

Break your goals down monthly and weekly. Check in regularly to see what kind of results you’re getting as your hustle grows.

3. What Side Hustle Skills Do You Have?

The great thing about starting a side hustle is that there are just so many things you can do.

For example, you might try:

  • Freelance writing
  • Being a virtual assistant
  • Proofreading
  • Transcription
  • Graphic design
  • Customer services
  • Mystery shopping
  • Dog-sitting or dog-walking
  • Babysitting
  • Selling things on Etsy
  • Reselling on eBay

Every side hustle requires a different skill set. Some take a little more know-how than others but there’s a lot of flexibility when it comes to what you can try.

When I first started working from home, it was as a virtual assistant. One of the things I did was a VA was writing sales copy and I eventually decided to make writing my niche.

Freelance writing was a natural fit for me because I’d always been a writer in some capacity. I wrote for my college newspaper, I wrote a ton of research papers in grad school, then after college, I wrote short stories.

Writing became my side hustle because it fit my skill set. So think about what skills you have that you could turn into a side hustle.

Brainstorm some ideas and try to get down as many as you can. Then, go back through your list to see which ones are most interesting.

If you need some help coming up with side hustle ideas or figuring out how to get your side hustle going, my free Side Hustle Checklist is for you. So grab yours now!

4. Can You Earn Money From Those Skills?

If you’re starting a side hustle to make extra cash, then you can’t skip this question.

Go back to your skills list and pick out 2 or 3 that you’re most interested in. Then do some research to find out what kind of money you could earn.

I can tell you from experience that I was able to earn between $1,500 and $3,000/month from my freelance writing side hustle. And that was putting in what I’d consider to be minimal effort.

Just keep in mind that some side hustles are more profitable than others.

Earnest did some research and found that 85% of side hustlers make less than $500/month. The most lucrative hustle, at least in their opinion, is renting rooms on Airbnb.

But if that’s not for you, don’t worry. There are lots of other money-making options.

My best tip is to go online and do a simple search for “profitable side hustles”. That can give you a starting point for how much money you could make. (And here’s one article for inspiration.)

5. How Much Time Can You Put Into Your Hustle?

This might be the most important question on the list.

Starting a side hustle can take up a little of your time or a lot of it, depending on which hustle you start.

With freelance writing, I probably worked on my hustle a couple of hours a day to start. I had a newborn and a toddler so that was plenty for me.

But something like blogging or being a virtual assistant can be way more time-intensive.

So be realistic about your days and what kind of time you have. If you’re a stay at home mom, for example, how much work could you get done if your kids are home with you all day?

And if you’re already working a 9 to 5, how much time you could squeeze in?

Again, be specific. What days could you work on your side hustle? Could it be an everyday thing or just a weekend thing?

And think about how much time you want to put in.

I spend a lot of time working on my blog, which I consider an unpaid side hustle right now. All of my income is from freelance writing.

And I won’t lie — some days, I don’t feel like doing anything with it. Even pinning a single thing on Pinterest is way overwhelming.

But I push myself to at least do one thing every day. Otherwise, I’d never see any results.

So ask yourself what you’re able and willing to put in time-wise. Being honest with yourself about that can help you keep your goals and expectations about starting a side hustle in perspective.

6. What Do You Need to Get Started?

Online side hustles are my personal favorite. A lot of them don’t require anything other than a computer and an internet connection to start.

That’s all I had when I started freelancing and it’s still pretty much all I need now. But other side hustles might come with more of a shopping list before you can get started.

For instance, you might be interested in doing transcription work online. You’ll need a computer for that but you’ll also need transcription software, plus several other pieces of equipment.

In other words, you’ll need to spend some money before you can start making any.

If you’ve decided on a specific side hustle, make a list of everything you’ll need to get started. Then check your budget to see if that’s doable.

If you can’t make a big investment, consider whether you could start a different side hustle with low or zero startup costs. Then, start saving the money you earn from that hustle to buy the equipment you’ll need for the one you really want to do.

7. Do You Have Any Support?

Having support is hugely helpful when you’re starting a side hustle.

It could be a friend, family member, sibling, spouse, someone you meet in a side hustle group on Facebook. Your support system can help you out in lots of different ways.

For example, your spouse can handle parenting duties solo for a few hours a day or a few hours a week while you work on your side hustle.

Or you could bounce ideas for growing your side hustle off your best friend or sister.

I like to go to the different Facebook groups I belong to for mompreneurs and bloggers to ask questions when I’m stumped on something blog-related or to just vent about a struggle I’m having.

See who you can round up to offer support as you get your side hustle act together.

Even if that person’s only job is to offer you encouragement, that can be enough to help you stay motivated. And it should go without saying but don’t share your side hustle plans with any Negative Nancies who aren’t supportive.

start a side hustle

8. What’s the Long Term Plan for Your Side Hustle?

So, when I first started side hustling I never thought it would turn into a business. But then life surprised me and I had to make a split decision about what to do next.

Hopefully, you never find yourself in that spot and you have more opportunity to think about what’s going to happen with your side hustle.

If you want to eventually grow it into a full-scale business, ask yourself what you need to do for that to happen.

For example, would you need to learn some new skills or start marketing yourself differently? Target a different kind of client? Start investing money into your hustle to grow it?

It’s a lot easier to work toward the result you want when you’ve got some specific action steps to follow.

Something else to consider is how you’ll handle your side hustle if it ends up being less profitable than you hoped or you just end up getting bored with it.

Will you bail out altogether or stick with it? And if you decide to stick with it, at what point will you say enough is enough?

Starting a side hustle is fun but it can also be a lot of work. So figure out what you’d like it to be six months down the line, a year from now, five years from now.

Then, ask yourself if you’re committed to making that vision come true.

Do You Have Questions About Starting a Side Hustle?

This list covers what I think are the most important things to ask when starting a side gig. And hopefully, they’ve given you a better idea of whether side hustling is a good fit.

But if you have a burning question I didn’t answer, head to the comments and ask!

I’d love to share what I know with you to help you get your side hustle up and running. 🙂

And please remember to pin and share this post if it helped you!

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Hi there, I'm Rebecca, homeschooling single mom of two. I built a six-figure freelance writing business from home and now I teach busy moms how to make money, save money and master the family finances! I'm so glad you're here and don't forget to grab your FREE money-saving guide!


  1. Really liked this post. Some really important questions steps to making any hustle successful. I find that research is so so important! Pinned 🙂

    • Thanks Lisa! I think people sometimes think starting a side hustle is an easy money-maker — and some of them are. But if you want to grow your hustle into a business or make more than just a few hundred dollars a month, it takes some work.

  2. Loved the post and loved how you have broken down into things to think about. A very useful guide for someone thinking about starting one, especially with the time. We tend to underestimate the time it takes to launch a side hustle

    • Hi Sush, some hustles can be quick and easy but if you want to turn it into a business or make more than just a few bucks, you definitely have to put some time into it! I would probably do some things differently if I were starting a freelance writing side hustle over again, which is why I wrote this post. Always trying to save people some time and energy so they don’t make the mistakes I did!

  3. Very detailed and informative. Thanks for sharing a step by step guide since I sometimes think about doing a side hustle but to clearly ask why and what’s the goal are very good questions to ask.

    • Hi Mitchelle, you’re so welcome! I definitely think it’s important to have a why and some goals, at least one or two. It’s the same as blogging — you need to have a roadmap you can follow in the beginning. The vision might change but if you can reconnect to your why, then it’s a lot easier to move forward and make progress.

    • Hi Margaret, I’m a fan of side hustles and side jobs for anyone who needs extra money or is just motivated to try and start something that could become a business. 🙂

  4. Hi Rebecca,
    It is so true that it’s important to know the purpose of your side hustle and how much time you can devote to it. I can totally relate to that feeling of being overwhelmed and somedays just not wanting to do anything with it. These are all such important questions to ask yourself…and answer! Also, I agree that it’s extremely important to be realistic in your goals. I was curious, how long did it take you to turn your freelance writing hustle into a full-time business? Thanks for sharing!
    DeShena @ExtravagantlyBroke recently posted…How To Save Money Like A Frugal Millionaire!My Profile

    • Hi DeShena, the overwhelm with blogging as a side hustle is definitely real for me. There’s just so much to do! I didn’t have much of a purpose when I started my freelance writing hustle, other than to make a little extra money and stay busy. That changed when I suddenly became a single parent. That was the moment I started treating it like a business. At that point, I was making around $2200 a month from my hustle and I was able to grow that to $5,000 in about six months. It’s continued to grow steadily ever since then but I have to show up and treat it like a business every day.

  5. I’m starting to get more into freelance writing at the moment and, honestly, I’m finding it hard to get started. I’ve signed up to linkedin, have pitched some brands/ideas and have come up cold. I would love to pick your brains at some point about the whole thing and how you got your foot in the door, so to speak!

    These are some wonderful questions to ask yourself if you ever are going for a side hustle! And very valid ones!

    • Hi Nyxie! We’ve chatted about this already but I think you’re on the right track with trying to grow your freelancing side hustle. And these same questions can work if you’re trying to jump ahead and start a business too. It’s all about having a plan — once you can nail that down, you’ve already put yourself way ahead of the game. 🙂

  6. Great informative post, Rebecca. I think a lot of people don’t take the time to sit down and answer these questions which are extremely important to be successful. In everything, we do we need to sit down and evaluate ourselves and our goals and even though I’m terrible at doing this part we need to write those down. thanks so much for these great questions!

    • Thanks Jenn! It is important to ask the right questions for anything you’re doing or planning to do, big or small. Starting a side hustle can seem like a small thing but sometimes it can turn into something bigger and you need to be prepared for it!

  7. I am really interested in starting a handmade toy company and I feel like I have thought about all the points you mentioned. What’s stopping me now is the legal and financial side of it. Safety testing and startup costs are holding me up… It would be awesome to earn a little extra income on top of the creative outlet that making these would be but I just cant get started!

    • Hi Megan! That sounds like an awesome idea — have you tried crowdfunding to raise a little money so you can start developing your prototypes? Or maybe doing another hustle that could generate some money that you could then use to invest in your toy idea?

  8. I loved this post, Rebecca! It’s imperative to ask yourself these questions to make the best decision about starting a side hustle. One job can be demanding; however, when you add a side hustle to the mix, it can be even more challenging to manage! When you’re passionate about your side hustle, you dedicate a lot of time to it. This can lead to burnout, so it’s really important to factor in how you will deal with that. Self-care is so necessary. Thanks for sharing your suggestions on things to consider before moving forward with a side hustle!
    Keesha recently posted…From Employee to Entrepreneur: Points to Ponder!My Profile

    • Thanks Keesha, you’re so right about all of those thingS! I didn’t have a full-time job when I started my side hustle but I was a stay at home mom, which had its own demands. You definitely need to be passionate about it, otherwise you will totally end up burned out. That happened to me with blogging and I think a lot of side hustlers get frustrated when they don’t see results quickly. And self-care is always a must when you’re trying to grow a side hustle or a business. 🙂

  9. Awesome post! These are all great things that need to be figured out before diving into a side hustle. When I first started looking into side hustles, I was dabbling with a little bit of everything and didn’t have any defined goals. I didn’t start having any real success until I drilled down exactly what I was trying to accomplish. These are really great, thorough questions. Thanks for sharing!
    Marissa recently posted…The Secret Twitter Formula to Skyrocket Your Blog TrafficMy Profile

    • Thanks Marissa! I just dove into my side hustle without knowing anything either and I didn’t have any goals or direction. It took me a long time to figure it out! Asking these kinds of questions before starting a side hustle can help you get clear on why you’re doing, why you’re doing and what you hope to get out of it.

  10. These are great questions to ask! Having the right mindset is a must for entrepreneurs. I love how you talk about your real experiences and emphasize the EFFORT we really must put forth to see results!

    • Hi Starr, thanks! The mindset really does matter, whether you’re just starting a side hustle for extra money or you want to do something that you could turn into a full-fledged business at some point. I didn’t have the mindset to be an entrepreneur until I had to become one but once I got it, it made a huge difference in how I approached growing my hustle.

  11. Thank you, Mama. I would add Network Marketing is also a side hustle to consider for those who love to promote and sell products they love. It also allows for great support and meaningful connections. Your article is inspiring. I have several side hustle and so far so good. I would change that for nothing.

    • You are so welcome Charlotte! Side hustles really are great and if you can do more than one at a time, that’s awesome! I consider blogging my side hustle, as freelancing is my main business. It took me a while to get to this mindset and it’s still a struggle sometimes to juggle both but I totally wouldn’t change it.

  12. This has given me much to think about. I used to work at home pre-kids. I often wonder if now that they are older I should try again. We homeschool, too, so they are still here all the time. I’m very torn.

    • Hi Valerie, I’m glad you found it useful! I started side hustling with two babies in diapers so I definitely think it could be doable with older kids. My kids are 10 and 11 now and they’re so used to me working from home that they don’t even blink. Having a routine really helps, with set hours for work time, set hours for school time (if you school that way — our best friends unschool) and set hours for family time. They know they can always come to me if they need something but they also know that they need to find ways to keep themselves occupied while I’m working.

  13. I simply love this post and everything that you have explained here is on point. Starting a side hustle might seem overwhelming at first but if you stick to it, it pays off. You just need to figure out what is the right side gig for you depending on your circumstances. I love blogging and can’t think of doing anything else other than that as I wanted to start something where I can be there for my kids while having a side hustle that can make decent money on the side.

    • Hi Nadia, thanks so much! You definitely get out of your side hustle what you put into it but what kind of side job works for one person may not work for someone else. That’s why it’s so important to know your why and what your goals are, as well as what you’re good at or could make money doing. I love blogging too, to the point it’s becoming an obsession and I’d love for it to be a profitable side hustle at some point!

    • Hi Rami, thanks so much! No, I haven’t considered podcasting yet. I’m a super introvert so talking freaks me out a little. It’s a lot easier to frame your thoughts and say what you mean to without stumbling in written form. But you’ve given me something to consider. 🙂

    • Hi Diane, thank so much! Absolutely, you need to be clear no your why when starting a side hustle or any kind of business. It’s especially true with blogging, where you often make a big investment up front but wait a while to see a return.

    • Thanks Chris! You definitely have to think it through — starting a side hustle can be a big undertaking or a little one but you still need a plan. Otherwise, you’ll end up giving up as you said!

  14. You raise some great points that people really should consider. Finding the balance between the time required and the financial benefit of any side hustle is so important. If you’re taking something on solely because you’re looking to bring some extra money in (not just because you enjoy it) then you don’t want to be putting a ton of time in for little gain!

    • Hi Britt! Yes, you’re so right! When I started freelancing I always assumed I’d make money. Blogging is so different! But if you’re committed to your hustle and putting the them in, then you’ll eventually get a result. But you definitely have to enjoy it, otherwise, you’ll end up frustrated and burned out.

  15. This is an absolutely amazing article Rebecca! Some super great tips if you’re thinking about starting a side hustle for sure. Thanks again for some more amazing content!

  16. I started blogging just for fun, but then I kinda liked it more than I thought I would. So now I’m the process of exploring if this could lead to some extra cash. This is the perfect quiz for me today. You have inspired me to think about this more and make a better plan.

    • Hi Jenny, thanks so much! Blogging is fun, right? At least when it’s not super frustrating. 🙂 I think blogging for money is still doable in this day and age of everyone blogging if you have a plan for it and you’re committed to doing what it takes. I’m still working out my plan as well and fine-tuning to figure out where to go next!

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