The Ideal Side Hustle

Hakeem Gunn
The Side Hustle Club
7 min readDec 18, 2022

Creating a system to select the right side hustle

A light pink background with a blue question mark off to the far right.
Photo by Towfiqu barbhuiya on Unsplash

In an era where options to make money via side hustles continue to expand, what has become essential is the system you use to vet them.

GET INTO THIS NOW! FIVE SIDE HUSTLES THAT WILL MAKE YOU $1K A MONTH! HOW I MAKE $5K A MONTH WITH THIS SIDE HUSTLE! DON’T MISS YOUR CHANCE TO MAKE $100K FROM THESE 5 SIDE HUSTLES!

Does any of that sound familiar to you?

The never-ending amount of options can be overwhelming, especially if FOMO kicks in. You don’t want to miss the “it” side hustle. Like Newsbreak when it was churning out thousands to writers without batting an eye. Those days are gone, but what remains is an endless amount of side hustles to choose from. So, how do you gauge whether a side hustle is worth your time or not?

This is my system. Tweak it or make your own. It doesn’t matter to me. What matters is that you have a system to rule out what is sub-par and cling to what will accrue some decent income.

#1. Entry Cost

Questions to ask:

  • What is required out of pocket to get started?
  • Do I need to purchase equipment?
  • Are there any additional fees to watch for in the future?

You don’t want to be in a position where you have to cough up a lot of money as you’re trying to make some. Of course, there may be things to acquire over time but you shouldn’t be forced to scale too quickly.

If I have to dish out too much in the onboarding process, then the side hustle drops a couple of places on my list.

What’s too much? That varies. Is it a one-time fee or monthly? If it’s a one-time fee, though the charge may be $100+, if I see the opportunity to easily make that back then I’m all for it. However, if that’s a monthly payment with a narrow road to breaking even then that’s a no-go. Maybe I’ll circle back to it when I’m a millionaire.

Take Medium for example. There’s a really low entry fee but what do you get in return? The opportunity to make a profit, build a following, expose yourself to a plethora of different writing that ranges in quality, skill, style, and topics, an awesome community, and much more. That’s a great investment, even if you never make your profit back via Medium. The benefits you receive from the platform set you up for success elsewhere.

#2. Pay Period

Questions to ask:

  • How long do I have to go without getting a check?
  • How frequent is the payout?
  • Is the payment process seamless?

This is tricky because it depends on the side hustle. The majority of us desire a fast return on our input. On OfferUp I get paid immediately when I sell an item in person, we’re talking cash in hand or Zelle on the spot. If I ship items then usually I’m looking at a few business days, payment for that method is a direct deposit to whatever bank account I have on my profile.

Some side hustles don’t allow you to get paid until things really get going for you. This isn’t necessarily a bad thing, just take it into account when vetting them.

As most of us know, YouTube won’t allow us to monetize our content until we hit 1000 subscribers and 4000 public watch hours over the past 12 months. Some channels hit that within a few months and some unicorns within a few weeks. The general public? Years. Though there is no entree fee if you’re looking for a quick payout this may not be the way to go — unless you’ve done your research, niche down, etc, but even then there’s no guarantee.

If the future payoff or additional benefits are enough to hold me over in the meantime until I can make some real income, then I’m all for it. Plenty of niches will take months at times but primarily years to give a great payout. In those cases, you’re likely able to scale to something more sustainable when that payout begins coming in. An example of this would be writing books on Kindle Vella.

In the beginning, you’ll go through the dry phase but after years of creating content, building a community that loves your writing, and familiarizing yourself with the platform and your writing style, you’ll be in a position to make some serious income. Though a great payment isn’t immediate, the long-term payout is worth it.

This all depends on you though, how long can you go without income from your side hustle? I work full time and that takes care of my bills. I can put a year or more into something without immediate payment because my essentials are situated.

Never, and I mean never, use a side hustle as a primary source of income if you’re just starting off. That’s the whole point of it being a side hustle, it’s supposed to be supplementary, not primary — though your side hustle can grow to take the primary income source’s place.

#3. Effort & Gains

Questions to ask:

  • How much effort is required before seeing gains?
  • What do those gains look like: cents, dollars, or bills being covered?
  • Based on the required effort, can I consistently do this?

This is connected with #2 but here’s the difference: if I have to take on a million Upwork jobs before getting decent pay, we have a problem. That’s an exaggeration but you get the point. How much effort is required before seeing gains? Also, what do those gains look like once they come in?

Survey sites are notorious for this. You spend hours thumbing through so many surveys only to get a few cents on a dollar. Sure, it’s better than nothing but how much more could you have made via another side hustle within the same amount of time?

Your time cannot be refunded, spend it wisely.

Also, even though you made some profit by burning some serious hours on a survey site, is that sustainable? Can you consistently do that per day, week, or month, and be content with the time/pay/effort ratio?

#4. Long/short-term advantages

Questions to ask:

  • Is it scalable?
  • Is it evergreen or will this income stream dry up?
  • Aside from the financial benefit, what other advantages does this side hustle give me?

Let’s use OfferUp again. No entry fee, the pay period is fast, and the physical effort required is based on the type of product you desire to sell and how far you’re willing to drive.

Short-term benefits:

  • Fast payment system
  • Alleviate clutter in my house
  • Making money off things I would otherwise throw away or someone else was throwing away
  • Teaches you negotiation skills, communication, how to price products (factoring gas mileage, shipping fees, etc), and more

Long term

  • Potential to scale operation: opening low-cost storage, flipping free larger items, niche reselling, etc
  • Potential to expand into different selling avenues: Facebook marketplace, flea markets, auctioning antique items, pawn shops, eBay, Amazon
  • People will always be looking to get rid of “stuff” so though the future of the platform isn’t set in stone the concept is. If you can master negotiating, selling, and healthy business practices via OfferUp, you can take your talent elsewhere even if the platform tanks

#5. Legitimacy

Questions to ask:

  • How long has this side hustle been around?
  • Where can I find verifiable data? Earning reports, real testimonies, state/Fed regulations
  • What type of pertinent information do I have to give up and why?
  • Have I done my due diligence? Why am I confident in betting on this? Why am I willing to take the risk of losing my time/effort/money on this specific platform?

Wait, you mean every side hustle mentioned on Medium isn’t legit? Get out!

Sarcasm aside, please be careful. Some of these so-called side hustles haven’t been properly researched, they just get thrown into a slew of other side hustles to make up a listicle.

I love a good listicle and will comment when I see one but I’ve also seen some pretty sketchy posts or posts including an unreputable company.

Do you know of a company that was investigated and turned out to be built off some shaky foundation? I can name a few, the one that comes to mind the quickest recently tanked in the crypto space.

Christopher Grant wrote an article about “The Urban Writers” who were paying authors $1.00 for every 100 words. Yup, if you did the math that’s a penny a word. I can make more on an egregious survey site!

The moral is before you dive in test the waters. Make sure what you’re getting into is legitimate by doing your due diligence.

This is the method I use to gauge whether or not a side hustle is worth getting into. Sometimes I’m wrong, though I filtered it through my system years later it turns out some that I passed on were actually good income earners. Those times are few though and I’ve learned to trust my gut but more specifically my system and continually tweak it. Plus, the number of times I’ve avoided trouble, wasted time, and wasted funds make up for the times I’ve been wrong so my system has solidified its reliability for me.

What about you? What’s your system?

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