Unsure What Side Hustle Is Right For You?

Three questions to ask yourself to determine which side hustle(s) best fit into your life

Lindsay R.
Freelancer’s Hub
6 min readSep 18, 2021

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Photo by Matthew Henry on Unsplash

Talk about the benefits of having a side hustle seems to be discussed on almost every online platform these days. I’ve been guilty of this myself, too.

But talk about what side hustle is right for you and your unique lifestyle, well, that seems to rarely ever get discussed. There are 100s of side hustles out there for you to pick and choose from (for ideas, try here and here) — from renting out a room on AirBnB, freelancing on Fiverr, and driving for Uber to filling in surveys and starting a YouTube channel.

So how do you know which one you should pursue?

How do you filter through the noise?

I think a really good starting point are these three questions below. They can help you to narrow down your choices by identifying the type of work that is appealing to you and actually fits your day-to-day schedule, as opposed to simply relying on “what sounds good” or what that guru in the YouTube ad was telling you would make “big bucks.”

Hopefully, by assessing these questions for yourself, you will save valuable time and resources — and bouts of misery — going after the wrong side hustle.

Question 1: What kind of worker am I?

From everything I’ve read about side hustles online, I think it is only fair to say that most probably fall within one of the following four categories:

  • Creative, mostly focused on “brainy” work (think freelancing, blogging, writing on Medium, YouTube, Etsy, eBooks, interior design, tutoring)
  • Active, mostly involving physical labour or physical activity (think car wash, gardening, food delivery on a bike, dog walking, personal training)
  • Business, mostly intent on creating a larger business, or contributing to an existing one (think Virtual Assistant, affiliate marketing, eCommerce, print on demand, drop shipping, social media management)
  • Menial, mostly repetitive tasks (think online surveys, renting out your car, Uber and Lyft, food delivery in a car, flipping items online)

Step one to finding your perfect side hustle: Figure out what kind of WORKER you are (or want to be).

Do you prefer sitting atop your cozy bed all day, writing blog posts and doing research in comfortable silence? Or are you always on-the-go, exploring and moving your body amidst the traffic of the city? Are you an entrepreneur at heart, itching to grow something long-term? Or would you rather complete a few small tasks and then sign off, knowing those activities are done for good?

Ultimately, the type of worker you are should or envision yourself becoming should fundamentally influence the type of side hustle you pick. There is no point in delivering food on a bike if you hate exercise, just how there is no point in trying to start an Etsy store if you hate creating with your hands.

So, pick one of the above categories, then identify those side hustles that fall within it.

Question 2: Scalable or non-scalable?

There is a huge fundamental difference between scalable and non-scalable side hustles.

Scalable side hustles generally require a ton of work upfront, but can generate exponential returns down the line, often with a lot less work required day-to-day and week-to-week.

For instance, starting a YouTube channel or selling services on Upwork might not bring in a whole lot of income throughout the first couple of months (or even years) as it takes time to establish yourself on your chosen platform, to create a customer or audience base, and grow your reviews or following to showcase that you are trustworthy or entertaining.

However, once established, it is generally easier to make significant income without the need for so much input — you can charge more for your proven expertise, and take advantage of the followers/customers you have. After all, it doesn’t matter if you’re pushing a video out to 1,000 or 100,000 followers: the work will be the same, but the returns inevitably different.

Non-scalable side hustles, in turn, will see you earning roughly the same income for the entire period of your engagement. This means you can earn comparatively more at the start, but also won’t experience exponential growth in the future.

Going back to the example of driving for UberEats — your hourly average will generally stay the same year-on-year. Initially, it will be a lot higher than someone creating their own blog. But, eventually, the blogger’s hourly rate will likely eclipse that of the driver by x number of times.

Step two to finding your perfect side hustle: Figure out what kind of INCOME you want.

Do you want reliable income right now, starting this week? Or are you happy to put monthly checks off for a few weeks/months/years while you grow your following without much in return? Do you even want/need monthly income reliability? Or are you content with receiving a large check one month, and a small one the next?

What kind of income you want and need is not only shaped by your lifestyle, it also shapes your lifestyle. Scalable side hustles oftentimes have a much higher earnings potential when compared to non-scalable side hustles, but they are equally plagued by income insecurities, varying pay check sizes, and many late night of working your a** off and seeing no immediate returns.

So, pick wisely as to the kind of size hustle income you want, then identify those that correspond.

Question 3: Upfront investment — yay or nay?

Some side hustles require an upfront investment, while others require none at all. Depending on the side hustle, this investment can be significant or minimal — in terms of either/and time, skills, money, or equipment.

Blogging, for instance, is comparatively investment-lean, only requiring an electronic device on which you can type, which arguably most people already have, and a connection to the Internet. Driving for Uber, on the other hand, is investment-heavy, requiring flexible access to a vehicle, insurance, a driver’s license, etc. — not a minor hurdle to overcome if you currently don’t have any of these things.

Similarly, certain side hustles, such as tutoring a niche subject, may presuppose years of experience in an industry or field, while others, such as dog walking, are more widely accessible to all kinds of people willing to put in the work.

Step three to finding your perfect side hustle: Figure out what kind of PREPARATION you want to do, and for how long.

Do you already own the equipment needed to kick off your side hustle journey? Or are you willing to invest in the equipment upfront and, if yes, what is your (financial, time) limit? Do you already have the skillset required to excel at your side hustle? Or do you see yourself first needing to take classes, attend further education, etc. before you can make any sort of money?

Knowing the level of preparation and money you are willing — and able — to spend upfront will automatically remove certain side hustle opportunities from your vision board, while others will come into focus more clearly as you eliminate non-viable options.

So, spend some time thinking about what preparation you have already done — and yet to do — for your side hustles of interest.

I hope these three guiding principles — what kind of worker you are, what type of income seeker you are, and what kind of preparation you have already completed or are willing to complete — is helpful in steering you in choosing the perfect side hustle for yourself, your lifestyle, and vision for the future.

These questions are of course not meant to be a box ticking exercise à la Buzzfeed where, after clicking on a few pictures, the final winner — and your perfect match, of course — are revealed. However, I do hope that they can help you as a general framework for narrowing down your options, and in being more mindful as to what qualifies as a good side hustle for you personally.

I now wish you the best for your new endeavour! Thanks for reading.

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Lindsay R.
Freelancer’s Hub

Fiverr freelancer | Working towards FIRE 🔥| Sharing tips on side hustles, freelancing, and making money online 💸