How to Pick the Perfect Side Hustle

When I was in college, I had a lot of little hustles. It was college so there was a lot of downtime.

I’ve written about the most interesting of the side hustles, when I used to gamble online. Nothing focuses the mind like losing a thousand bucks on a single hand of Blackjack (for what it’s worth, I’m even on my two bets over $1,000)!

I also used to flip things on eBay, including bootleg copies of the Transformers TV show because the DVD-boxed sets were available.

Those side hustles never grew to anything bigger. I didn’t become a professional casino promotion chaser. I didn’t become an expert seller on eBay. I graduated, went to work, and stumbled my way into an entrepreneurial streak of online businesses.

The internet loves the idea of side hustles. The internet loves them because there are so many of them out there. With the advent of the gig economy, where you can drive people around on Uber or take on small jobs from Fiverr, you can start a little something on the side and earn some extra cash.

There are, however, good side hustles and great side hustles.

Table of Contents
  1. Good vs. Great Side Hustles
  2. Know Your Why
  3. Good Hustle: Driving for Rideshares
  4. Great Hustle: Blogging
  5. Can Good Turn to Great?

Good vs. Great Side Hustles

The good side hustles enable you to turn more of your time into money. These are the second jobs, ridesharing gigs, and the paid survey sites. If you work a job where you can’t just put in extra hours to earn more, a side hustle is a way to extract more value out of your free time.

They’re good because it enables you to earn more. You can use that money to pay down your debt or put more towards saving – we could all use more of that.

There are, however, great side hustles if turning spare time into spare dollars isn’t a game-changer for your financial situation.

The great side hustles are those hustles that can become more than a simple transaction. They are more than turning hours into dollars. They enable you to build equity in an asset that can immediately or in the future be a source of income.

There’s just one problem… a great side hustle is one that reaches that future point where it generates income. The great ones have a higher expected value but like doubling down on 11 in a casino, it’s never a sure thing.

This is why the perfect side hustle is a hustle that not only has the potential to become more than a time-for-dollars trade but will teach you a valuable skill while you build it.

Know Your Why

Why are you pursuing a side hustle? Is it to earn a little extra income so you can retire early? Or to pay down some debt?

Is this a short-term need or something where you can and want to build something long-term?

Maybe when you were stuck at home because of the pandemic, you wanted a side hustle you could do from home.

A good side hustle is inherently short-term — it’s trading time for money and you get it immediately. A great one has the potential to scale but doesn’t necessarily generate income immediately. A good side hustle may be better for your needs because you can’t wait on the income to build up a great one.

We must make decisions based on our circumstances. Don’t feel like you’re shortchanging yourself by doing a good side hustle today because you need the cash (you can always build a great one later!).

Let’s look at some prime examples of both:

Good Hustle: Driving for Rideshares

Driving for Uber is a good side hustle.

I’ve met a lot of fantastic people who drive for Uber because it’s a way for them to monetize their commute. According to the U.S. Census, the average commute time is 26.7 minutes. That’s nearly an hour each day!

If you can turn that hour into cash while meandering your way home, that’s a very good way to do it. You just roll the dice and hope your next Uber ride doesn’t take you farther away from home!

Or, you could drive for a program like HopSkipDrive, is a technology company that connects parents with on-demand rides for transporting kids to and from school or extracurricular activities. Since you can choose your rides up to seven days in advance, you can plan around your schedule rather than waiting for rides to call you.

But driving for Uber or other rideshares is not a great side hustle because it’s not scalable. You have to drive every dollar you earn and when you only have 24 hours in a day, there’s an upper limit to what you can earn. It’s great for earning some side cash, to monetize a commute or some downtime, but it doesn’t scale.

It also doesn’t strengthen too many career skills — although it’s not a complete loss in the skill-building department. You will improve your ability to make small talk (a nice social lubricant) as well as your driving and navigational skills. But it’s likely not going to be a game-changer on either front.

Great Hustle: Blogging

What’s an example of a great side hustle? Blogging.

What’s fascinating about blogging, which is true about every pursuit, is that there are so many layers to it. On the face of it, blogging seems to be about writing. You have to come up with ideas, you have to formulate those ideas into an entertaining and engaging post, and then you need to format it in a readable way that pulls people in. It’s a constantly evolving process.

But then you realize that to get people to your site, you need to network with other bloggers in your niche, get involved in social media, learn a little about search engine optimization, and integrate an email newsletter so you can reach those folks who discovered your site and want to learn more … the list keeps on going.

It seems simple and straightforward until you dig into it.

What makes it great is what you learn. If your blog fails, you will become a better writer, a better organizer of ideas, grow your network, and improved your understanding of social media and other online technologies, among other things. These are all skills you can use anywhere and it’s a valuable by-product of your time and energy. You could even take these skills and start freelancing for other bloggers. For example, you could become a freelance writer, social media manager, or SEO consultant. Here are some more ideas on how to become a freelance blogger

If your blog succeeds, it is scalable. Your blog will earn money while you sleep because it’s a storefront that never closes. You can use that stream of income to build up your investments, and maybe you can sell it one day for a nice balloon payment that changes your financial trajectory.

In either case, you are better off.

Can Good Turn to Great?

Yes, and very easily.

Caitlin Pyle was a freelance courtroom transcript proofreader making a pretty good living at it. It was her full-time job

When I interviewed Caitlin Pyle about earning $17+ an hour as a freelance proofreader, I was fascinated by her journey into that world. It turns out I wasn’t the only one.

It’s the classic “good” side hustle – you’re proofreading. You get paid for a unit of work, which in her case was by the page of the transcript. You could scale it by hiring people but nothing stops them from freelancing on their own.

So how do you go from good to great? Teach people what you know.

She now runs several courses, one of which is Proofread Anywhere, which teaches people how to do exactly what she did. If you have a successful side hustle that is going well, it’s not a huge leap to decide whether you want to put your on-the-job training into a manual or course. You can then sell that course and take advantage of the size and scale of the internet.

In late 2016, Caitlin revealed in her first income report ever that she earned $1.7 million in just two years. That’s a lot of proofreading pages. 🙂

(Also, her earnings were not just from proofreading. It’s also from teaching people how to proofread.)

It’s by no means easy… but the potential is certainly there.

So the next time you’re considering a side hustle, ask yourself why and make sure you start the right one.

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About Jim Wang

Jim Wang is a forty-something father of four who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Empower Personal Dashboard, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

>> Read more articles by Jim

Opinions expressed here are the author's alone, not those of any bank or financial institution. This content has not been reviewed, approved or otherwise endorsed by any of these entities.

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