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Here's what I learned from my worst online jobs

Here's what I learned from my worst online jobs

An online, work from home side hustle always sounded nice

I am an independent person, so the idea of an online, work from home side hustle has always sounded nice. The idea of being able to make my own hours -and work in my socks if I want to- has always appealed to me. But, as an ambitious person, it’s also about controlling my earnings. If I want to make more, then an online job or side hustle would allow me to work more and make more.

It’s a simple concept, but the problem is that there are so many potential online jobs. Over the years, I’ve tried a few and there was always something that just didn’t work for me. And frankly, they all paid so little that it wasn’t worth my time. I did eventually come around to blogging -which has been a fantastic, $200 an hour side hustle for me- but this post is about the missed steps and fuckups along the way. Usually, those are more interesting anyway.

My first attempt at working from home: The commission only sales job

When I was in college, I needed money. Badly. At the time, I had a mentor through the house that I lived in who was working in a little corner of the shipping industry called “less than truckload” or LTL shipping. It’s not complex: less than truckload shipping is when someone pays to ship a pallet from one place to another.

Anyway, my mentor was a scrappy, young, good looking guy who was a quintessential salesman. He worked as an independent contractor for a number of LTL companies and air freight forwarders, the biggest of which was a company called Earthtrans. At the time, as a pimply college junior with absolutely no money -but the desire to make some and be an entrepreneur- he looked like a badass. He had his own condo on the beach, and drove a blue BMW 330ci. Girls loved him. I mean, this guy had made it, right? He made his own hours, worked however and with whomever he wanted to, and seemed to always be onto some other scheme in shipping that would make him even more money.

So, when he offered to take me under his wing, teach me his tricks, and get me into the LTL game working for Earthtrans I was DOWN.

The only catch? I was going to be an independent contractor on 100% commission. Basically, I would call around to manufacturers and other people who might ship stuff, and quote them shipping through the Earthtrans portal. Hopefully, over time I would actually sell a few shipments and maybe earn permanent customers who would call me up and give me business every day. In return for my efforts I would get 5% of the total value of the shipping cost. Of course, my mentor would get a few bucks for every sale I made as well.

He taught me a few tricks, took me out cold calling on a few customers, then set me loose.

I immediately bought a headset and got to work, calling every single manufacturer I could find on Google Maps. I called and called and called. But, with no sales experience I was totally screwed. I probably put in 200-300 hours working the phones and striking out every day. Finally, I made a sale when a friendly shipping manager at a steel extrusions company let me ship a pallet for her. It was a $200 sale, of which I was owed $10.

The catch? Earthtrans would only pay out if I earned over $200 total. Feeling bad for me, my mentor took me out for coffee and gave me my $10 out of his own pocket. It was a nice gesture, really, but all I could think was “Screw this guy.” I felt betrayed that he had made it all seem so easy, promised me the moon, and left me to figure it out and fail on my own.

The bottom line? I realized that I wasn’t cut out for sales, but more than that I saw that I needed something where I was guaranteed to be paid to make it worth my time. I was giving my time away to someone else, and it felt like I was selling myself short in the process.

After I graduated with my degree in economics in 2009, I looked for a real career job in finance but there was just nothing available after the financial crisis. Luckily… VERY LUCKILY as it would turn out, I was able to use my Excel skills to land a job as a marketing data analyst in working for a small startup called Tableau in Seattle’s Fremont area, making a smoldering $30k a year.

My second attempt at an online gig: Reviewing Google results

With so little in my pocket, I was just as desperate for cash as I was in college. And the idea of an online job or work from home gig still sounded pretty nice!

Enter Leapforce. Leapforce was a contractor to Google who was paid to evaluate search results. Working for them I would log into their portal, and then I would be shown a query and two search engine results of which I would then choose the most relevant and pertinent to the query. It was basically training the algorithm. In return for my efforts, I would be paid a very small amount for each query I reviewed. Over hundreds and hundreds of queries, I would make around $10-15 per hour. Not a fortune, but certainly enough to make it worth my time given that I made less at my day job.

So, I worked and worked at Leapforce and managed to take home an extra $500-800 per month, which made a huge difference when I was making so little at my day job. That went on for about a year, but over time I got a few raises, and ended up spending more time at work, so Leapforce made less sense as time went on.


Although Leapforce was guaranteed money, it wasn’t good money for my time. What’s more, there was no leverage. Every query that I reviewed I got paid for, but I would always have to invest more time to make more money. As I moved up the ranks at work, time became my most valuable asset, and it wasn’t something I was willing to part with for so little. Then, when Tableau went public I suddenly had a windfall from my stock options (LUCKY, I know), and I was able to focus 100% on my day job.

What I learned from the worst work from home jobs

As those of you who read the blog know, I am obsessed with how much my time is worth. Quite frankly, I think it’s worth a lot. Even when I made way less money than I do now, I always inherently valued my time significantly more than I was getting paid, which is why I worked so hard at my day job to get ahead.

My first online job, the commission only sales job, held the promise of high earnings if I worked it hard and built a customer base. But, with limited sales experience there just wasn’t any way I was going to convert enough people with little to no differentiating benefits to the product I was selling. The bottom line: I had absolutely no guarantee of income. By the time I quit with my $10 bill in my pocket, I had made maybe five cents an hour over the course of a very long and fruitless Summer. But I had learned an important thing: never, ever work for someone else for free. If you’re on the job, you’re getting paid.

Leapforce was a better experience, admittedly. I was taking in a decent amount of money each week, and at the time that was an important supplement to my rather disappointing day job earnings. But like I said, I have always valued my time highly, and I knew $10-15 per hour was a wage that was much lower than I deserved, which is why I quit once I started to make a little bit more at work. At the end of the day, the total lack of leverage made Leapforce unattractive. Although I got paid for every hour, after I was done working that hour I would never get paid for it again.

In the end, the lessons I learned at mu crappiest online jobs led me to blogging. I’ve been determined to devote myself to blogging every week, and over time I have built a consistent stream of traffic from Google that I convert into income with online advertising. It’s simple, it allows me to work in my socks, it lets me make money in my sleep (because there are visitors to the site at all hours, whether or not I am “working”), and at $200 an hour it is very much worth my time.

Ask yourself: is my side hustle worth my time?

The only way that you can know if your side hustle or online job is worth your time is by knowing how much your time is worth. Luckily, I have a calculator for that. Below you can input your responses to a few questions that attempt to get at the value of your time. What would you pay to avoid waiting? How much would you fork over to get home early? These questions will give a range of values from your time, from the lowest per hour to the highest, with an average in the middle that you can use as your everyday value for time.

So, are you making enough from your online gig? Is it REALLY worth your time? Only you can know.

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