685: 10 Questions to Pick the Right Side Hustle for You

21 Jul 2025 · 13 min

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Podcast Summary: The Side Hustle Show - Episode 685

Episode Title 10 Questions to Pick the Right Side Hustle for You

Episode Description In this episode, the host Nick Loper discusses a systematic approach to choosing the right side hustle from a plethora of ideas. The focus is on evaluating potential options based on various practical criteria to help listeners prioritize effectively.

Key Takeaways

  • Common Dilemma: Many aspiring entrepreneurs either struggle to find a side hustle idea or end up overwhelmed with too many options.
  • Objective Evaluation Framework: Loper introduces a scoring methodology based on ten questions to help listeners objectively compare and evaluate their side hustle ideas.

Methodology Overview

Loper suggests using a scoring system from 1 to 4 (with 4 being the best) for each of the following ten questions:

  1. Excitement Level
  2. How excited are you about the idea?
  3. Example: Niche email newsletter may score a 2, while a YouTube channel might score a 4.
  1. Path to Sales
  2. Is there a clear path to your first customers or sales?
  3. Example: Freelance services may score a 4, while a niche newsletter could score a 1.
  1. Time to Launch
  2. How much time will it realistically take to get off the ground?
  3. Consider the speed of development and market entry.
  1. Startup Costs
  2. What are the potential initial costs to start the business?
  3. Low-cost ideas (like freelancing) could score a 4, while higher-cost options (like vending machines) might score lower.
  1. Revenue Potential
  2. What is the upside? Estimate three to five years out.
  3. Consider whether the opportunity is worthwhile relative to the effort required.
  1. Ease of Operation
  2. How simple or complex is the operational side of the business?
  3. More operationally simple ideas score higher.
  1. Automation and Delegation Potential
  2. Can the business be easily automated or delegated?
  3. Digital products score well here, while service-based businesses may score lower.
  1. Scalability
  2. How easy is it to add more customers or clients?
  3. High scalability (like digital content) scores higher compared to physical product-based businesses.
  1. Shutdown Ease
  2. How easy is it to pull the plug if the business doesn't work out?
  3. Digital businesses typically offer easier shutdown options.
  1. Sellability
  2. Is the business something that could be sold in the future?
  3. Businesses with tangible assets or digital products tend to score higher.

Conclusion

  • Score Calculation: Loper encourages listeners to total up the scores for each side hustle idea to identify a clear winner, facilitating an objective decision-making process.
  • Next Episode Preview: Loper hints at discussing marketing strategies in the next episode, helping listeners find their first customers.

Additional Information

  • Free Resource: Audience members can download a free Side Hustle Selector Worksheet from the episode’s show notes to help implement this scoring system.
  • Sponsor Acknowledgment: The episode was sponsored by Intuit, which connects tax and bookkeeping professionals with meaningful opportunities.

Final Note

Listeners are encouraged to subscribe for more actionable insights in future episodes, as the podcast aims to provide practical strategies for entrepreneurs to succeed in their side hustles.

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Transcript

Automatic transcript. May contain errors.

0:00This episode is presented with limited commercial interruption by Intuit. How cool is that? Whether you're looking to grow a side hustle or switch things up full-time, Intuit helps tax and bookkeeping professionals chart your own path and connect with customers in meaningful ways. Head to intuit.com slash expert to learn more or apply now. Year after year, without fail, half the people I talk to are still looking for a side hustle idea. The other half have too many to choose from. And it might be surprising that I found myself on both sides of the fence at various points. Like if I only had that killer idea to focus on, I know I can crush it, but what's been more common lately is being on the other side.

0:37Hey, there are way more ideas than there is time. And then there's the challenge of focus and direction and choosing where to allocate your time and attention. So last week, we talked about finding your side hustle niche and some exercises and frameworks to generate those potential ideas. You can go back and tune in to that one if you missed it. This week, armed with those ideas, I want to give you a methodology to pick which one to work on first, to remove the subjective guesswork from it and help take action and prioritize your limited time for maximum impact and result. This methodology actually came from a Side Hustle Nation reader years ago who asked to remain anonymous, but he sent me this note.

1:17He said, my partner and I keep a running list of potential business ideas and then we then baseball score them, which he called single, double, triple, home run, on a different criteria. And so for the sake of this exercise, we're going to assign a number score, one through four, with four being the best or home run being the best for each of these 10 questions. So what it'll look like is a spreadsheet. And to help you set up this file, you're going to list your potential side hustle ideas across the top, number one, two, three, four, five, however many options you came up with. And then down column one is the list of questions that we'll get into.

1:51And I've actually got a free version of this template in a Google sheet. If you want to grab that, just head over to the show notes for this episode and make a copy. You can add it to your drive so it's customizable, editable, all that jazz. The show notes link in the episode description will get you right over there. But the first question, super important one, is just how excited are you about the idea? Remember Sarah McCaffrey's line about motivation being temporary, how excitement usually has an expiration date? And if you're not excited about something, how likely are you realistically to give it the effort necessary to achieve liftoff.

2:26So you're going to rate your side hustle ideas one through four on how exciting they are to you. Maybe the niche email newsletter is a two, vending machines are a three, the YouTube channel is a four, the freelance service is a two. You get the idea. One through four, four being the best, four being a home run in this baseball scoring methodology. Question two is, is there a clear path to your first sales or customers? Step one is the idea. Step two is the execution. Is it obvious what you're going to need to do to make actual sales? Do you already know your potential customers? Are people already asking you for this service?

3:01Or is there a more murky question mark filled path on how you're actually going to monetize? In this case, the freelance service might be a four. The niche newsletter might be a one. That's question two. Is there a clear path to your first customers or sales? Question three is how much time will it realistically take to get off the ground? Speed can be a weapon and making meaningful progress creates this positive feedback loop that helps you keep going. How much time is it going to take? Because you don't want to run out of gas. You don't want to run out of excitement before you achieve a liftoff.

3:35In the case of my shoe shopping site, it took months, months of development before we even had a semi-functional minimum viable product version of the site that I could begin to market and drive traffic to. Is there a quick and dirty version of your product, of your service that you could launch quickly? Is there a way to pre-sell something? Again, you're going to rate your options one through four on the question of speed. How long is it realistically going to take to get traction? Question four is the startup cost question. How much capital is it going to take to get it off the ground? And you might be able to fill this in with actual dollar figures if you have an estimate for that or for the sake of consistency keep it with that one through four baseball scoring system only for this one let's make for a really low startup cost and one being a more expensive business to start and thankfully most of the side hustles we cover are relatively low startup cost businesses especially in the realm of the examples we've been talking about youtube channels email newsletters freelance services probably would all score a four unless you need some special new video equipment or something and maybe that bumps it down vending machines have some upfront equipment and inventory costs, but maybe you explore some financing options and you don't commit to buying the machine until you've secured a location.

4:49So maybe that's a two or a three. It's all relative, but that's question four. How much capital is it going to take? The initial version of the shoe site, for the sake of reference, was around$10 ,000 in development costs. Today, with the different website builders and AI tools, it would probably be less than$500. But that's why we're asking these 10 questions because just because something has higher startup costs doesn't necessarily mean it should automatically be eliminated from the conversation. Are you looking for a flexible income stream and one with real career potential? I'm excited to partner with Intuit for this episode because they're actively recruiting Side Hustle Show listeners to join their world-class network of tax and bookkeeping experts.

5:32You know Intuit as the maker of TurboTax and QuickBooks, and maybe you're one of the 100 million people who use those products yourself. I know TurboTax has made a few of my Aprils a little bit easier, but as an Intuit expert, you can work virtually on a flexible schedule and get the support you need from an experienced and credentialed team. Plus, you'll get free access to Intuit Academy, their free self-paced training program where you can build your confidence in tax prep and bookkeeping skills to start or grow your career. Whether you're looking to grow a side hustle or switch things up full-time, Again, Intuit helps you chart your own path and connect with customers in meaningful ways.

6:06Sound like your next move? Head to intuit.com slash expert to learn more or apply now. That's intuit.com slash expert, I-N-T-U-I-T dot com slash expert. Okay, we've gone through four questions so far to help you objectively compare and evaluate different side hustle options. How excited are you? Is there a clear path to your first customers or sales? How much time is it going to take? Is there going to be a long product development or audience building phase? Or can you earn revenue right away? And how much startup capital is it going to take? Question five is, what's the revenue potential? Very important question is to consider the upside.

6:44We tend to be very focused on the downside, which is also important, right? To make sure a failure doesn't bankrupt us. But sometimes we skip the, well, what if it works question? So if you project out three to five years, if everything goes well, if everything goes according to plan, what does success look like? Is it a$10 ,000 a month business? Is it a$100 ,000 a month business? What's the ceiling here? What's the revenue potential? And the reason you want to ask this is you want to make sure you're pursuing an opportunity that's big enough. And that's going to be relative to everybody, but big enough to be worthwhile, because it's going to take a lot of effort and energy.

7:22And if the best case scenario, or even the most likely case scenario outcome isn't life-changing for you, why do it? You're probably going to run out of motivation. If it's not, I think Noah Kagan called this the million dollar rule. And you might adjust that number higher or lower depending on your circumstances. But it was something like, if I don't see a path for this business to make a million dollars, I'm not doing it because it's going to be hard. So one through four, what's the revenue potential for each of your ideas. Question six is how easy is it to operate? And you might not know the answer to this having never done it before, but it's kind of your best guess.

7:57Or you might talk to other people doing similar things to what you're considering. But is it operationally simple or complex? What does the sales funnel look like? What kind of delivery logistics are involved? How many different software tools might you have to duct tape together here? A simple solo freelance service? Probably a four. A newsletter? Maybe two or three, only because you have to constantly recreate the product every day or every week. But how easy is it to operate? One through four on that question. Question seven is how easy is it to automate or delegate? And it's probably never as easy as you think or as easy as the passive income gurus would have you believe, but is the model you're considering ripe for automation or delegation?

8:39For example, kind of hard to automate a service business like pressure washing or mobile car detailing, but it's a service that could probably be delegated. Digital product business, like selling printables, much more automated, probably scores a four on this matrix. But question seven, how easy is it to automate or delegate? Question eight, how easy is it to scale? And when I think about scale, I think about the ease of adding an additional customer. For example, if I have a YouTube channel or a podcast or an email newsletter, extremely easy to scale. It costs zero or almost zero to add that incremental viewer, listener, subscriber.

9:19And your production costs are the same, right? It costs the same to produce an episode that 10 people listen to or that 10 ,000 people listen to or that 100 ,000 people listen to. Very scalable. So those kinds of businesses would earn a four, where a vending business might be a two, right? You can use your existing systems and distribution network, but it's still a new location to onboard and lots of one-on-one sales calls to make that scale happen. So how easy is it to scale? Freelance service, maybe a one or a two. You can sell additional clients, but then you've got to find the time to fulfill the work.

9:53Question nine is the shutdown question. How easy is it to stop operations if you find out it's not working? This is the pull-the-plug question. If it's a website, I mean, you can just stop updating it. You can stop paying the hosting. Pretty easy. If it's a physical product business, do you have to liquidate the inventory? Do you still have to honor any product warranty issues? Got a few more moving parts. If you sold a membership to something, do you have to issue refunds? Do you have to continue providing access to a dashboard or a product? One through four, how easy is it to shut down if you need to, with four being the simplest and easiest in this case?

10:29And question 10 is, is the business something I could sell down the road? How sellable is it? Solo freelance business? Probably not very sellable. Personally branded YouTube channel? Probably not very sellable. Library of digital products? Maybe more so. Profitable vending machine route? Absolutely. Online newsletter with a hands-off production system? Absolutely. My only experience in selling a business was my virtual assistant business, and it was absolutely not a consideration when I started, probably should have been. With that in mind, I probably would have put better bookkeeping and revenue tracking in place.

11:07And you may never intend to sell your business, but operating it as if it were a sellable asset is probably going to make you a better business owner anyway. And that exit could be a pretty substantial wealth building event. So don't discount question 10, even if you're not thinking, I'm just in the startup phase. I'm trying to get something off the ground. But don't discount question 10. Is the business something that could potentially sell down the road? Again, you can download a blank version of this matrix with all these questions at the show notes for this episode. And then you can just plug in the business ideas that you're considering across the top.

11:42But here's where it gets fun. Now you can total up the score for each of these columns, for each of these side hustle ideas, and objectively see which one won. because it's going to give you a clear numerical winner. And what else is cool is if the one you wanted to win didn't, that's a great gut reaction to go do that one instead. The one you wanted it to win. You can even manipulate the weighting of the different criteria to massage the data because ultimately it's your side hustle. You get to choose. I think this will be an eye-opening exercise for you. If you're an overanalyzer, if you're debating between different options, it gives you, hopefully it gives you mathematical permission to proceed if you're the permission seeking type.

12:23And you can't argue with math. And once you've got that side hustle selected, you're going to want to tune in next week as I walk through 10 ways to shrink the internet, to do some marketing, to get your first customers. I know it seems like a big, scary place, but with these 10 strategies, you can find your people and you can start to make some more money. So be sure to hit that subscribe or follow button in your podcast app so you don't miss that or any other other awesome upcoming episodes to help you add more profit to your pocket. Big thanks to our sponsor Intuit for helping make this content free for everyone.

12:52Intuit, the maker of TurboTax and QuickBooks, is inviting Side Hustle Show listeners to join its world-class network of tax and bookkeeping experts. To learn more or apply now, head on over to intuit.com slash expert. Once again, that's intuit.com slash expert. That is it for me. Thank you so much for tuning in. Until next time, let's go out there and make something happen and i'll catch you in the next edition of the side hustle show hustle on

From the publisher

Too many side hustle ideas? Here's how to objectively choose which one to tackle first.

We'll cover factors like excitement, ease of operation, scalability, and more.

Free Bonus: Download the Side Hustle Selector Worksheet

Full Show Notes: 10 Questions to Pick the Right Side Hustle for You

Sponsor: ⁠Intuit — Join Intuit's world-class network of Tax and Bookkeeping Experts⁠!

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