The 7 Worst Ways I've Ever Made Money

I've decided that this year I'll try to be a little more humble. I know, here is this Leo, larger than life, deciding to admit to a few of my failures, or rotten experiences, in life. I've always been a bit entrepreneurial. But there have been times when I got into things, that looking back, I can't exactly say were "highlights" in my career.

Here's my Top 7 Worst Ways I've Ever Made Money:

7. Pizza delivery guy.

This job loved me. Only problem was, it didn't pay well. The good news was that it was pretty low stress after getting fired from my Florin Mall Marketing Assistant Job. I wasn't fired from the marketing job for being a crappy marketing assistant -- I was fired because the books got messed up, and it made the Director look stupid in front of the merchants association. Of course, she never admitted that the whole reason the books were messed up was because she hired this guy to be an intern and he stuck his imbecile head in the books. Before I realized what he'd done, he was two weeks into it and made a complete mess of things! With his screwups and my not really being a guru on accounting, it cost 20 hours at $100 per to get it straightened out with the accountant. Back to the pizza delivery, this was okay, but people really ought to have their money ready when they order pizza. I hated waiting there while it grew cold. Pay: $5.95 an hour + tips. Sweat: low. Worst side-effect: smelling pizza all day long, getting chased by dogs and small children. I never had anyone named Spicolli order a pizza at school, though.

Best lesson learned: Distribution is much more profitable when you're delivering high-ticket, high-value items.

6. Selling lemonade on a street corner.

Like many youngsters, this lemonade job idea was my first entrepeneurial approach at making money. I was about 10 at the time, and I thought it would be really cool to sell lemonade. I was offering cups for about a quarter. I sat out there with my sign, table, and lemonade for about 5 hours. The only problem was: I lived in the country. My customer total after those 5 hours was only THREE customers. I'm surprised I sat there that long, looking back. Afterwards, my Mom told me that the lemonade cost $1.50 at Scolari's grocery mart, but she wouldn't charge me for it. Thanks, Mom. Pay: crappy. Sweat factor: not high. Worst side-effect: being bored to tears!

Best lesson learned: no matter how good your product and marketing might be, you won't make sales unless you product or service gets noticed by a lot of people. And that can't happen if you are marketing out in the boon docks.

5. Cleaning toilets at camp Fox boy scout camp.

Now, here's a doozy: once upon a time, I actually volunteered to clean toilets! Well, not exactly. I just wanted to go to Camp Fox. My older brother went and asked me to come. He thought it would be a good idea to get me out of the house during my summer vacation. Turns out that I had two choices as a volunteer: KP or maintenance. Riding around in the jeep looked like fun, until I realized that the jeep drove to the bathrooms. My brother lasted three days. I stayed the week. Pay: zero. Sweat factor: medium. Worst side-effect: ew. You really don't want to know...

Best lesson learned: People love free help, but offering free help doesn't create profit. I'd rather work for money than volunteer, unless the volunteering connects me with another job I might love and that might be highly profitable.


4. Selling door-to-door security systems for retail.

Now, this one doesn't show up on my resume. Not because I got fired. The boss loved me. In fact, he told me I'd written the best sales plan he'd ever seen in his life (I now offer that as a service to ARRiiVE Business Solutions clients). What sucked about it? I can't put my finger on it, except that selling retail security systems to busy small business owners just seemed like a weird way to sell. It didn't help that my head was all messed up from my divorce - never an easy time to start a new job. Pay: decent. Sweat factor: high. Going door to door increased my respect for the Kirby salesman. Worst side-effect: getting chased by the black doberman guarding a used car lot. Now I know how postal delivery workers feel!

Lesson learned: Make sure you understand the work you'll be doing and want to do that type of work before you sign up for the position.

3. Selling timeshares for an ego-maniac.

Actually, selling timeshares can be fun. The schedule isn't too grueling (you're usually out in less than 8 hours), you get to work at plush resorts, and the pay can be fantastic. You're talking about people's dreams. And sharing dreams and what other people love most in life ought to be fun, right? Well, sort of. You're forgetting that I was selling to people! This means people who often have serious issues. And many people are not pleasant to be around, including some of the people who manage you. I won't name names, but this one particular manager was so awful that he didn't let me go to a wedding, called me a slacker, and threatened to fire me -- of course, I was at work on valium with a wrapped-up toe (I'd just had surgery on my foot three days earlier), and he'd already promised I could go to the wedding right up until the minute I was walking out the door. Yep, he was the worst boss I've ever had.

As for some of the tours? Some people forget to bathe. Yeah. For days. Others are incontinent. How bad do they smell? It depends. Other people think it's funny to bring their baby on tour. Some babies are cute. Other babies cry... for hours! I had one couple going through a divorce while on tour. The guy's wife decided to flirt with me. Talk about awkward. Some people that go on these tours are so old they cannot hear, see, or even say much of anything. However, they can sit there for two hours for their free gift! It didn't happen to me, but I heard one tour actually DIED during their tour. It happens. Money: actually, quite good. You can make anywhere from $50k to $400K a year selling timeshares. Sweat factor: some days good, some days bad. This job is mentally exhausting. Hours not bad, but you lose your weekends. Worst side-effect: having to endure the long, drawn out squeak from the buttocks of a 90-year-old-man as he stood there, kinda smiling at me, passing gas in the elevator. I don't think he knew he did it. If he did, well, shame on him. The job probably shouldn't make the list, because it's actually a pretty good job, all-in-all. But not when the boss is an egomaniacal jerk!

Lesson learned: If you have an egomaniacal boss, and you have a strong ego, it is probably a matter of time before one of you will have to go. Make a decision who it ought to be and then operate intelligently from that position. If it is you, find another job: quick!

2. Digging trenches under poison oak.

Now, don't get me wrong. I'm can really appreciate when someone else digs a ditch: when I see that long, three foot deep by one foot across hole carving through the landscape, it makes me very happy. Yes, a ditch, when dug by someone else, truly is a splendid thing. Now I can lay the pipe, plumbing, wires, or whatever that needs to get put in the ditch to complete connectivity. Yippity skippity! However, I must admit that I don't want to be the guy digging the friggin' ditch! Why? Because it is really hard work. I'd rather work with my mind. I'd rather sell something. I'd even rather give a presentation (something many consider worse than death). Certainly, I'd rather play my sax. Or even play video games. That's right: I'd rather do anything besides dig that ditch. Yes, I've dug ditches. But I can't say I enjoyed it. Enjoyment: zero. Hard work factor: very high. Pay: very low. Worst side-effect from this job: poison oak (Dad thought my brother and I would be great at stretching a water line 1/3 of a mile up-hill through a trench under the oak trees when I was 10 years old. Yeah, my Dad sure had a winner of an idea that time. I had poison oak everywhere for 3 weeks. I think I still have scars on parts of my body.)

Lesson learned: If you have a nasty, difficult, or particularly hard job in front of you, it is better to hire someone else to do it than do it yourself.


1. Working for Taco Bell as a "deep-fryer".


Not that it was bad, it just didn't pay a lot. I actually normally worked as a cashier (it is more like me to handle the money than the grease). The absolute worst job they have in the restaurant is the deep fryer guy. I did that one weekend when our fryer was out sick. I also almost died of heat stroke as it was 102 degrees outside and the restaurant didn't have proper air conditioning. I think I consumed 12 Dr. Pepper's in one day. I never could understand why the fryer guy seemed to enjoy his job. After all, I never met a fryer who got promoted to manager in that position. Total earned: <$500 (sucky, huh!) total sweat factor: way too high. Worst side-effect: a horrible case of acne. I think my face still has a few pockmarks from that one.

Lesson learned: Learn what the worst job in any business is and always make sure you don't end up doing it. The story of the guy who went from the bottom to the top is more rare than common.

In retrospect, I do recommend you find work to pay the bills, especially until you figure out a way to moonlight and make money doing the things you love. But, there are definitely jobs that you might enjoy more than others. Try to stay away from toilets, doberman pincers, and digging ditches under the Poison Ivy -- you'll be glad you did!
__________________________________

Post by Scott Andrews, CEO of ARRiiVE Business Solutions.

ARRiiVE Business Solutions helps executives improve sales, launch products and services, and build dynamic, cross-functional collaborative teams. For more information, contact info (at)ARRiiVE (dot) com or call us at 1 (805) 459-6939.

Copyright © 2007 by ARRiiVE Business Solutions. All Rights Reserved. You may republish this article only if you publish in WHOLE with the COPYRIGHT and ALL ACTIVE LINKS intact.

"He's quick, he's funny, he makes you lots of money." SUBSCRIBE to our feed here.