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Seven side hustles I’ve done (and what I learned)

There are lots and lots of side hustles out there — so many that it’s impossible to try them all out! Here are the ones that I tried out …

Side hustles. There are so many of them! Here are seven that I tried, and what I learned from the experience ...

There are many ways to make extra money through side hustles. To get an idea of the breadth of what people will do for money, just check out Fiverr.

We can’t do everything. We must specialize. There are only so many hours in a day, and so many days.

Here are most of the side hustles I’ve tried, and what I learned.

1. Silk-screen designs on clothing

About 2005 or so, my wife and I had the idea to do funny/cute baby clothing.

And, not knowing any better, we pretty much immediately bought a six-color silk-screening machine.

I can’t remember exactly how many pieces of clothing we got out of the thing, but it wasn’t many. The cost per unit ended up being well over $200. I don’t think we ever really got the hang of it. We just flat-out didn’t know what we were getting ourselves into.

We eventually gave away the screen printing machine and materials, after making a few t-shirts here and there for a cemetery club. (That’s sadly funny, actually!)

Yeah, so this one bombed pretty badly.

What I learned: At the time, my mindset was to cut out the middleman as quickly as I could, in this case by doing my own production.

That was foolish for a couple of reasons. First, manufacturing is labor-intensive. There’s a big learning curve for pretty much everything, and that learning curve costs money. This is true even for people far more successful at manufacturing their own stuff (see Steve Chou’s podcast with Ron Eiger of Secondly, I should have started out far, far smaller: get some designs, put them up on CafePress or Zazzle, and see if there was a market for them. Heck, maybe I would have even been happy making $200-$300/month at $0.73 a unit or whatever and letting them do all of the hard work and heavy lifting.

2. Tutoring

One of the side hustles I've done is tutoring.

Since college, I’ve tutored people in physics, chemistry, algebra, calculus, and statistics. Before I got my current job, I was tutoring for not a whole lot of money (mainly because my expectations were lower).

My last tutoring job as I’m writing this happened a couple of nights ago. The customer paid $60/hour for two hours of my time. I netted $42/hour, since sent me the business. Still, nothing to sneeze at for doing something that measurably helps someone else. That, and I kind of enjoy doing math problems!

I wasn’t always getting that much per hour, though. In graduate school, I would go out for as little as $10/hour. I guess my expectations were lower (my stipend in grad school in the late 1990’s was about $13k/year, and I lived off of that). A few times I made $25/hour, which was really nice.

This side hustle is perfect for people who’ve excelled academically. Getting paid for being a one-on-one teacher is pretty cool like that.

What I learned: Charging more gives you a great chance of being treated better. I learned that there was a direct relationship between what I charged and how much the students (and parents) valued my time.

Back in grad school when I charged $12/hour, those people either just didn’t show up, or worked me down to $10, and eventually tried to pay me in ripe bananas. (I’m not making this up.) When I charged $25/hour, they treated me far better.

Same thing twenty years later. Now my rate is high enough that I’m not running all over the place all the time, and people get down to business when we meet.

There’s a lot less downside to charging too much than charging too little.

3. Playing music side hustles

One of the side hustles I've done is music.

Ahh, the true gig economy.

I’ve played in a number of bands throughout the years, and done solo performances for weddings and funerals. My first paying gig was in high school at a local restaurant.

The most I’ve gotten paid for a single gig is $300. I’ve done this twice, and both times it was on New Year’s Eve. Most of the time, though, it was more the stereotypical “Load $5,000 worth of equipment into a $500 car to drive 100 miles for a $50 gig” money.

Musicians gotta do music, and to some extent, they’ll do music regardless of the money. For me, as long as the work/pay balance doesn’t get too far off, it’s good.

What I learned: As I’ve gotten older (and I’ve learned better how to play my instruments) I’m wanting to get out and play without a whole lot of rehearsal. A few times I’ve gotten into a sunk-cost situation where I’ve invested so much time in a group without pay that it will never be profitable. (I’ve gotten a bit better at it recently.)

If you join someone else’s group, they hold the cards as to when the group goes out for gigs, and that can take a while. In the meantime, they’re already at the rehearsal location (i.e., their house) and everyone else is traveling there, on their dime. I have been fortunate enough to get into some groups that get out without a whole lot of rehearsal, and that’s a blast.

4. Give music lessons

This one is related to tutoring (and to music). I’ve given piano and trumpet lessons off and on for younger students. It helped that most of the time either the student came to me, or it was walking distance to their house. No gas and very little unpaid travel time, and it pays about as well as tutoring.

What I learned: One thing with music is that there are an awful lot of good musicians out there. It’s competitive, and this drives prices down. (That, and music is pretty much entirely a discretionary expense so it’s easy for people to drop it.) So it’s either enter the fray or get a unique spin that encourages people to pay more. For me, it’s more something to do, so entering the fray isn’t too bad.

5. Run a vending machine business

One of the side hustles I've done is vending machines.

I got into a small vending machine business as one of my side hustles for a while. I had a few machines that dispensed bulk candy (M&M’s, Skittles, etc.)

Some of the locations were great; others hardly got any action at all. But they were all pretty much on the way to work, so I was going by those locations anyway.

One thing I did right was not buy the machines from a business opportunity magazine; there are usually several packages for high-four or low-five figures that give you more machines than you can place immediately. Instead, I bought them off of eBay one at a time.

What I learned: I learned that this could be fairly profitable but, like anything, you have to pay attention. If the candy stays around in the machine too long, people don’t buy it. If you get too cheap with how much the machine dispenses, people don’t buy it. I did this unintentionally one time when I swapped out a machine but didn’t check the settings in the machine I swapped out. It dispensed like three Skittles at a time for a quarter. Oops!

6. Reselling on eBay

At one point I had an eBay store with (mostly) back issues of magazines that I got free, or for a low price. The store worked for a while until our local post office held to a pretty strict definition of media mail, which made my shipping costs uncompetitive with sellers whose post offices were laxer.

Now, I’m taking it a bit easier and taking advantage of the 50 free listings per month for people who don’t have stores. It makes things more leisurely without ongoing fixed costs. I can list fancy serial number bills, yard sale finds, thrift store finds, or things I just want to get rid of, start high, and bring it down as slowly or as quickly as I want.

What I learned: Side hustles like these are hard to scale — meaning that if I want to sell ten times as many things, I need to work pretty much ten times as much. With physical goods, it turns into a fulfillment business, and that’s labor-intensive. I’m an integral part of the system, or I need to pay someone to do those things for me.

7. Blogging

One of the side hustles I've done is blogging.

This is the side hustle I know the most about, probably because I’ve done it the most consistently over the years.

Blogging has the potential to snowball as more and more people hear about what you have to provide. More content and more value engender more trust and more influence. One offshoot of all of these “mores” can be … more money. Mostly for the same, consistent level of effort.

It’s not a quick road, but nothing of value is, really. However, getting started in blogging has gotten way easier than when I started. It’s possible to get started in just 15 minutes with a real domain name and real hosting for less than the cost of a pizza per month. (No more hand-coding HTML, gosh!)

What I learned: I’m still learning how to do this blogging thing, and it’s been almost 14 years since I put my first article on the Web for anyone to see.

One thing I learned the hard way was that your readers are precious. Treat them right! I look back to see seven or more comments on a post and not one response from me. Ouch!

Another big thing I’ve learned is that nothing is forever. No way of making money is forever, and no source of traffic is forever. Watch out for single points of failure. Google could algorithm you out of existence, or Facebook could delete your page.

Your turn!

What side hustles do you have, and what have you learned?

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