202: How to Choose the Best Side Hustle for You

[00:00:00] If I asked you right now, what side hustle should you start? Could you give me a one-sentence answer right off the top?

If yes, if you already have a specific side hustle in mind, then this episode will serve as a quick reality check to make sure it's a good fit for you.

But if you haven't yet nailed that down, today I'll be sharing with you the process that I use that I've refined over the years through working with people one-on-one to guide them in figuring that out, and I'll give you my perspective on an often asked question: Should you turn your passion into a side hustle?

If you've been looking at building a side business for any length of time, chances are you've invested a lot of time and thought to an overabundance of ideas. We're certainly not short of options. this show alone has over 200 episodes full of ideas, and if you were to drop an AI prompt into your favorite search engine, well, you could be handed over 500 of them in 0.2 seconds.

So coming up with the ideas typically isn't the problem. It's deciding which one, and most importantly, deciding which one [00:01:00] is the right fit for you. This episode will help clear away the confusion of which one to pursue to the next step so that you walk away with a solid direction, not another list of 100 ideas to add to the pile.

You'll have decided on a single one, or at least a real short list for which side hustles are worth your time. If you've been stuck in analysis paralysis, jumping between ideas and never quite committing to one, let today be the day that that ends. I'm Joan Posivy, and this is Side Hustle Hero.

If you've been listening to the show for a while, you've probably already got a list of potential side hustles, maybe in a notes app on your phone or hand-scribbled in a notebook, or maybe it's 42 tabs open in your browser right now. Uh, drop shipping, freelance writing, craft workshops, pet sitting, vending machines, uh, the list goes on and on.

Any one of those has the potential to be enjoyable and lucrative, but only if it's a good fit for you. If it's not, if you eventually [00:02:00] do launch, when you come up against the inevitable challenging times with it, whether that's in a few weeks or a few months, you'll give up and let it die, and likely you'll tell yourself, "That was a dumb idea anyway."

So which side hustle is the best fit for you, your strengths, and the life that you want to build? I have two essential areas you need to explore. But first, this tip. To make the most out of this episode, listen or watch it the first time through in its entirety, and then schedule time in your calendar to work through the questions and exercises starting right at this timestamp.

First up, let's start with interest and inspiration. Think back to any of those side hustle idea lists that you've come across or do a fresh search. As you scan through them, write down the ones that sparked your interest, even if they seem out of reach.

Actually, especially if they seem out of reach, because the very thing that might be the best one for you, you could be holding [00:03:00] yourself back from pursuing because of a self-limiting belief. "Oh, I could never do that." Write it down. At this moment, you're not committing to anything.

And while you're doing that, ask yourself a couple of things, because you could use AI to generate a list of the best side hustles that fit you, and, and that's a good starting point. But you need to go much deeper and further from there on your own, uh, because it can only work with what you feed it. It doesn't know that you'll always stop scrolling when a gardening video pops up.

It doesn't know when a topic lights you up in a conversation. That insight and inner knowing, that has to come from you. So here's what I want you to actually ask yourself. In addition to specific side hustle ideas you jot down, start a second column to consider what industries you find yourself naturally drawn to.

Uh, like if you're scrolling and you stop when you land on an article about wine or woodworking or [00:04:00] AI developments, and you actually read it instead of scrolling past And start yet a third column. Are there skills that you have That your day job never uses. Maybe you're an awesome public speaker who could really capture the attention of a crowd, but your job has you buried in spreadsheets.

Or maybe you're incredibly organized, but nobody at work ever sees that side of you. Also, consider what you would do for free that offers value to others. , What would you be excited to talk about or learn about or, or do more of even without getting paid? If there was zero money involved, what would you do that would be of service to others?

Write that down too, even if you don't know at the moment how you'd monetize it.... Is there something that you've always been a bit curious about but never actually pursued? Write all of it down.

Don't edit yourself yet. Be brave. At this moment, you're simply gathering ideas.

The second area I want you to explore is one that is not often [00:05:00] considered, and sadly is another reason that side hustles fail before they've really even had a solid chance to succeed. That's lifestyle alignment. Here's what I mean. Think about your day-to-day right now.

What does it actually look like? If you work remotely and most of your day is just you, a laptop, and maybe a dog or a cat judging you from across the room, you might crave a side hustle that gets you out and around people, something social, something hands-on, like running a booth at a weekend market, or hosting a workshop, or being a tour guide.

But if your job has you back to back in meetings and managing people constantly on, you might crave the opposite, something solo, something more chill, like freelance writing, or bookkeeping, or high-ticket dropshipping.

You want to choose something that will complement what your life looks like and or what you aspire it to look like. So here are some questions to ask yourself. Do I want to work mostly solo or with other people? Do [00:06:00] I prefer working at home, in public spaces, or somewhere else? Indoors or outdoors?

Flexible schedule or set appointments? Local or location independent? Will this side hustle energize me or leave me drained after my day job? Do I want to use this side hustle to meet new people, build a community, learn a new skill? A lot of side hustle advice treats good side hustle ideas like a fixed universal ranking, like there's a top 10 list, and you just pick from the top.

But the reality is it's something that takes work, a good dollop of it. So you want to choose a side hustle that inspires and enlivens you.

Yes, there are going to be tough times and hurdles to jump, problems to solve, and tasks you do not like to do. But overall, it needs to be a business that has a positive impact on you and your life. So pick the version of the side hustle that fits the actual shape of your life, and not the version that is [00:07:00] necessarily trending or sounds impressive at a dinner party.

Most of my favorite side hustles are easy to understand and generally boring.

Should you turn your passion into a side hustle?

I get asked this quite a bit. You've probably heard both sides of the argument, "Do what you love and the money will follow," versus, "Don't you dare monetize the thing that you love. It'll ruin it!" Both of those sides have a point. It depends on you, and it depends on the passion. Let me tell you about two people. First, a friend of mine. He worked long, demanding hours in the restaurant industry. Outside of work, though, he was an incredible downhill skier. I mean, really skilled. At one point, he actually had the chance to buy into a local ski hill.

On paper, that sounds like a dream, right? Turn your favorite thing in the world into a business. But he took a pass. Why? Because skiing was his escape from work. It was the one thing that let him breathe after a brutal [00:08:00] shift. He knew that the moment that skiing became a business with schedules and customers and spreadsheets attached, it would stop being his escape.

It would just be another job. So he said, "Nope, not gonna do that." Even though it might have been financially beneficial to him mentally and emotional, it wasn't worth the trade. Now, compare that to Lucy Slater. You might remember her from episode 73, Paws, Profits, and Tails of Pet Sitting.

Lucy loves dogs. She can't live without them. Instead of protecting that as some separate thing, she built it directly into her side hustle. She pet sits while working her full-time remote job as a social media manager, staying at clients' homes while they're traveling. To her, it doesn't feel like a second job at all.

In fact, she tells us it feels like a paid vacation. She's getting her actual work done from someone else's living room with a dog asleep at her feet, effectively getting paid from two sources at the same time. [00:09:00] Not a bad scenario. So in the case of the skier and the dog lover, one said no, the other said yes, both made the right call for them.

So here's the actual test you want to run. If turning your passion into a side hustle adds joy, go for it. But if it risks draining the joy from something you love, maybe instead protect it, keep it sacred, and go build your side hustle somewhere else.

At this point, you've got your list of ideas that spark interest and inspiration. You've determined your lifestyle filters. For example, social versus solo, energizing versus draining, and you've been honest with yourself about which passions want to stay passions, and which ones are ready to become something more.

Review your lists and strike through all those that aren't a fit, and highlight the ones that feel a match. It's very possible that one idea jumps off the page, almost embarrassingly obvious, like, "Why didn't I see that sooner?" If that's you, congratulations. That's your [00:10:00] shortlist of one. Go.

If not, take a look and ask, is there a combination sitting in there, a skilled pair with an interest or a side hustle idea that only really clicks once you attach one of your interests to it? Maybe project management is one of your skills, and houseplants is one of your interests, and suddenly you're looking at organizing local plant swaps.

Sometimes the winning idea isn't a standalone, it's two or three things on your list that were meant to go together. But if you're looking at a few ideas that all still feel very viable and you genuinely can't tell which is the one, you're not the only one. That's actually quite common. Here's a process that I found extremely helpful. I stumbled on it at a time early in my career life when I was legitimately torn between two career paths.

At the time, I was working in the banking industry, and I knew I wanted something different, and I came upon that proverbial fork in the road. One path was to be [00:11:00] a professional competitive bodybuilder, something that I had been doing on an amateur basis. I really enjoyed it. I loved the feeling of strength and physical power and genuinely enjoyed working out.

The other path was as a professional speaker and trainer in the personal development space, essentially sharing with people the connection between the way we think and the results that that generates in our life.

Through what I had been studying and applying on this topic, I had become the youngest branch manager of a financial institution in Canada at the time, and then a successful entrepreneur. As you can appreciate, those were two very different career tracks, and I felt that I could not go all in on both of them at the same time.

I had to choose. And while I was debating this in my head, on a conscious level, it seemed I wasn't getting anywhere. One day it was, "Yes, bodybuilding pro," and then the next day, "No, seminar leader," until I did this. I allowed myself to drop into a very relaxed state, and once I was there, I saw [00:12:00] in my mind's eye what my life would look like as a professional bodybuilder, what I would be doing day to day, how that would make me feel, and the level of satisfaction that would be derived from that, and the service that I was providing. After I took the time to really feel what that felt like, I set that aside, and then I brought up the image of what life would look like as a speaker and trainer in the personal development space, how I would be connecting with people, where I would be traveling, how that would cause me to feel.

And it was only then, after comparing those two pictures in that state, there was absolutely no contest. It was obviously the path of the personal development. That's where my heart was calling me, but while the debate was happening in my head on a conscious level, I really couldn't connect that deeper feeling.

And once I did, it was no contest. I knew exactly which direction I had to go. So if you're feeling torn between two or three different side hustles, do that exercise. Find [00:13:00] a place where you can really relax, and pull up the image on the screen of your mind of that first side hustle. What would it feel like?

How rewarding would it be? How would it affect your life?

Notice how it affects the lives of those around you. Then set that aside and do that for the next one, and potentially a third, if that's the case for you. ... And through that process, you should get a better indication of which one to pursue. Because it's possible that your fear and self-doubt is holding you back from the one that in your heart of hearts you would really like to pursue.

If this is your first listen-through, take some time now to actually work through what we covered today. Get your list down, run it through the lifestyle filter, sit with the passion question, and if you're torn, try that visualization exercise. But here's the thing, even once you've got your shortlist or your one clear answer, that's still just the starting line.

An idea can look great on paper and still fall apart the second it meets the [00:14:00] real world. So how do you actually know if it'll work before you sink your time and money into it? That's what comes next. Figuring out which side hustle to pursue is just the first of seven essential steps to bring it from idea to launch day.

The other steps include validating the idea, sketching out a simple plan, and mapping out your moves, just to name a few.

I've put all seven steps into a free download called Smart Start: From Idea to It's Live in Seven Steps. Go grab it at sidehustlehero.com. It's free, and it picks up where today's episode leaves off.

Well, that's a wrap for today. If our chats are sparking your entrepreneurial spirit and providing valuable insights, consider showing your support by visiting www.SideHustleHero.com/support.

That's where you can shoot me a, a virtual coffee. It's a real thing and a fun way to give the show a caffeinated thumbs up. Thank you so much. In the description, you'll find the link to the full show notes, which live at our website, [00:15:00] SideHustleHero.com.

If you’re enjoying what you’re hearing in this podcast, it’d be so appreciated if you would take a moment and leave a review and a 5-star rating at the platform where you’re listening, to let others know that there’s valuable content here for them to start or grow their side hustle, and be sure to share this episode with a friend who is in need of some side hustle inspiration and encouragement today. 

For you and I to connect, you can send a DM on instagram @joanposivy -  or shoot me an email to hello@sidehustlehero.com. Thanks for listening. And hustle on.