9 Questions to Find Your Best Side Hustle

So, you want to start one of the best side hustles? Let me be the first to congratulate you! Starting a side hustle is an exciting process, and it can be a pathway to personal development, skill development, and some extra income along the way. For our purposes, we will use Merriam-Webster’s definition of a side hustle.

“Work performed for income supplementary to one’s primary job.”

Merriam-Webster

The key here is a side hustle requires,

1. work and

2. is supplementary to your job.

There are lists all over the place, “50 unique side hustles”, or “25 side hustles to do from home”. These are great to get inspiration, but you shouldn’t pick your side hustle just based off of a list of what “makes the most money”. The side hustle has to complement your lifestyle. Ask yourself the below prompts to help nail down which project you should pursue.

Questions to Ask Yourself Before Starting Your Side Hustle

1. Are you scratching your own itch?

Are you pursuing this side hustle idea because it interests you, you need quick cash or because it is the trendy thing to do? For making quick cash, it is okay to do something you wouldn’t define as ideal. Usually clearing your unused items and selling them online is a great way to make quick cash.

For building a long-term business that can generate consistent income every month, you have to like the topic. You will have to find your project interesting, and in the worst-case scenario, even if there are no customers for the first several months, you are at least researching your interests. Pick something that you are interested in and pursue that above all else. This side hustle will be with you for years. You might as well do what you want, not what is trendy.

2. How much time and energy do you have to commit to the side hustle?

This project has to fit into what you are already doing in your life. Having a side hustle means sacrifices in other areas. Dedicating time to your side hustle takes away from your free time. If you are on an extended break with ample time, you could invest in making something unique like a book, or art piece. Or if you are limited on time, maybe that means picking up the occasional gig or making things that do not have to have a lot of manual steps.

Figuring out how much time you have is why in college I started doing Redbubble Print on Demand. I was going to school full-time and working. I didn’t have consistent time to dedicate myself to building out a brand, but I still got to work on my art and make some side income with it. It wasn’t as intense as what my entrepreneur friends were trying to do with their side hustles, mine is even a little clique, but it worked for my busy schedule and was fun. The side hustle has to work for you, otherwise, it becomes a chore.

Also, your life changes. After graduating, and only having to work full-time, I found I had more time to work on an ambitious project. Hence, this blog! As you move through life, you might have more time to work on more ambitious projects, so might as well start learning entrepreneurial skills with something small.

3. Does thinking about the side hustle bring you joy?

Putting aside the potential extra income, does thinking about doing the actual work bring you joy? If the side hustle sounds like a chore before it even starts, that idea is not for you.

Look for or think of an idea that excites you. Remember, since this is something that is done in a supplement to your career, the side hustle will have to be worked early in the morning, late at night, or on the weekends. It has to be something you look forward to doing even early on a Tuesday morning.

4. What unique skills do you have?

What skills have you developed that you can leverage in a side hustle? Maybe you are good at writing, synthesizing data, programming, selling, or creating art. Instead of re-working the wheel and developing a new skill, use what you already have to create your side hustle.

Ask yourself what skills you have and how you could leverage this into a side hustle that would help you stand-out. Maybe you are artistic and good at marketing. Then an Etsy or Shopify store might be perfect for you because you could have better business acumen than most of the other sellers in your niche. Use your strengths to stand-out.

5. What skills do you want to develop?

It is the Catch-22 most entry-level employees face, you need to have prior experience to gain the entry-level role where you can learn entry-level skills. The best way to get these roles, or to transition to a role that has this skill, is to develop it on your own. I

If you want to work at a video game studio, your side hustle could be learning to code and making small indie games to sell. That way you are developing skills you will need and can demonstrate proven success to potential employers. Plus, you can also see if you would be happy to make a career out of this industry because most of the time we don’t even know what our “dream job” entails. Check-out this post on how to investigate your dream job.

A side hustle where you are developing a new skill could be less profitable in the short-term than other ideas since you have to take time to learn. However, it can lead to long-term payoffs if that talent is what you need to transition to your dream career.

6. Do you have a clear path to monetization with first customers or sales?

The point of the side hustle is skill development while also making discretionary income. I use some of the blog’s income on working towards financial independence, for instance.

If no one is willing to pay for the service or product, you will never see the extra income.

To provide an example, I like planning out planted aquarium tanks, but no one is going to pay me to design tanks for them. However, I can monetize a blog that talks about how to develop your ideal life. See which ideas excite you and see which have the most potential for making money.

7. How much capital will it take to create this side hustle?

I am a big fan of keeping the side hustle small. Chris Guillebeau has tons of resources for how to start a side hustle under $100.

Starting small and scaling up is better than spending thousands of dollars on an idea that turns out to be unprofitable or something that turns into a chore for you.

With the Redbubble example, I already had my iPad and Procreate, so for me, the cost was just time. With the blog, I got three years of website hosting for around $100. Keep things small to see if you, and potential customers, like the idea before spending tons of money.

8. How will pursuing this particular side hustle fit into your life?

When will you make time to work on it? What does working on it look like? Will you bring in others to help with this process? Think about how your week will change if you make time to dedicate to this task. Most likely, this side hustle will push you out of your comfort zone, so keep in mind it will take more energy and time than you might initially expect. Factor an extra 10-20% on whatever you estimate.

9. What are your realistic goals with this side hustle?

Set goals. What does success look like with this side hustle in six weeks, six months, two years? Set markers to see where you want this project to go. Does it align to the life you want to build for yourself?

Maybe your focus is on skill development or making a long-term passive income generator, or maybe even to build and sell the business. Know what your end goal is in mind before starting.

Main Take-Aways

• Side hustles are a lot of work, and they can be a very enriching part of life.
• Poorly chosen or planned side hustles can be major energy, time, and money drain that does not last or work for you.
• Think about how your side hustle fits into your life. It should complement your life and your goals, not detract from them.

Action items

Write down your top three side hustle ideas. Run through these questions with each of them. Which one do you see adding the most enrichment to your life and goals? What can you do today to start that side hustle?