Every Business and Job I Failed at Since I Was 7 Years Old
I like money. I grew up broke, and always wanted more.
It wasn’t for toys, video games, or anything sensical. I was young and craved security. Things only got harder as the years went on (but that’s a story for another time).
Since I was a kid, I’ve been an entrepreneur. People rarely talk about the ugly side of entrepreneurialism: all the failures that it takes to find your footing.
I’ve by no means “found greatness” or any of that hyperbolic shit, but I’m happy, I’ve capitalized on my successes, and I’m building a business that can help secure my family’s future. This is what I’ve learned through all my failures over the last twenty-two years.
Trash Can Collection
I was seven. I convinced my neighbors to let me bring their trash cans out the night before collection came through (which was once per week). Then, I’d bring the barrels back in when I got home from school the next day.
Five bucks a house (in 1999–2000), seven houses on the street. $140 a month as a kid.
Too bad I didn’t make it past the third week. I would later find out that I have horrible ADHD, and I forgot every one of my neighbor’s trash the night before pickup.
I was a kid, they were nice about it, but as you can imagine they no longer needed my services after that.
Write things down. Make reminders. It took more lessons to really cement this, but I was pretty bummed that I messed this up for myself.
My dad let me learn the lesson on my own and didn’t lecture me. I always appreciated that, even though it took more time to learn the repercussions for myself (properly).
I was eight years old, out after 3:00 PM on a Monday with my best friend. We had a bucket, two cloths, and knocked on doors. Two (hopefully cute) kids asking for $10 to wash your car in your own driveway, what could go wrong?
It was winter. It was 27° F out, and we were trying to wash cars. At 4:35 PM as the sun was going down, the 15th house finally told us what we were doing wrong.
“Boys, you’re going to freeze people’s doors shut,” and we went home.
Yeah, a 95-minute runtime. We were going to try again in March, but by then, it was on to the next grand idea.
Understand that you can’t sell a service unless there’s a need for it. There was a reason all the car washes in our part of Massachusetts barely ran in the winter.
The next brilliant idea was a pranking service. I made $95 from this when I was ten years old, but the problem was liability.
My friend and I were paid $10 to prank a guy’s wife. She was on her way home from work, and he thought it would be funny if we did the invisible rope trick.
We did it. She slowed her car down to a halt, looked onward for about forty-five seconds, and when she realized there was no rope, she was pissed.
She pulled into her driveway and actually called the cops on us.
Don’t ever say “Yes, I think it’s funny” when a cop asks you “Do you think what you’re doing is funny?” — they tend to not like that.
I worked at a convenience store. My job was to bag ice from the ice machine out back, fill a mini shopping cart, wheel it out front to the ice chest, and stack it.
I did this consistently, but I label it as a failure. I worked about forty minutes a day, three days a week. For a thirteen-year-old kid, that’s not too bad, but it required a lot of time dedication since it was early in the morning before school.
It added up to around $20 a week. Then I had another task (which we’ll get to in a minute).
My time, attention, and reason to show up should be worth a lot more money. The only reason I stopped this one task is actually because I got electrocuted at fifteen.
The ice chest in the front of the store had a leak. There was a small puddle behind it.
I thought I’d be a good employee and clean it up. I leaned down with paper towels in my hand, and got zapped for a few seconds.
Thankfully I was able to pull away and all’s well, but it freaked me out.
Same store, just a different job. I filled up little ketchup cups at the deli, cleaned up the back room, and organized the shelves.
I would also fill the soda bottles in the chest up front. Still not a lot of consistent work, but it was something.
This is around the time my ADHD really started kicking me in the teeth. I made mistakes, I repeated those mistakes (even though I thought I fixed them), and I wasn’t a good employee.
I was very distracted, not very good at my job, and I made the same errors over and over again. I didn’t implement it immediately, because I was fifteen, but it taught me to build systems.
I know my faults. If I build a system to counteract them, all goes well. Well, most of the time.
Nonprofit Door-to-Door Sales Work
I was seventeen, and I read an ad on Craigslist. I went to a shady office in Boston, and met a bunch of college kids who were about to drive to Rhode Island and knock on doors for money.
It was a grassroots campaign. I hadn’t become a people person at this point, so I tagged along with an experienced sales worker (I don’t know what to call their position at this point).
I knocked on one door on my own. I had the script, and when the guy answered the door, I completely fumbled it.
“Hey, I’m getting paid $10 an hour to beg you for money to fix pollution in the nearby bay, but I doubt much of your contribution will actually fix anything.”
He gave me advice. I got fired by the end of the day. We rode back to Boston, they paid me for a half-day, and that was that.
The guy told me something about sales. He said, “You’re too honest to sell to people. Try marketing instead.”
Well, low and behold, I write for marketing companies and have my own media company now. So I suppose what he said actually stuck with me.
Coffee Chain Manager
I started working as a coffee slinger and doughnut lord at the counter. I worked solo, and it was nestled inside of a convenience store (separate business).
This is where I learned how to talk to people, strike up conversation, and my customers even gave me tips. I was seventeen when I started, and I actually loved this job.
It turned into a management position at another coffee company. First Assistant Manager, then Store Manager.
Long story short, I had the toughest store in the network. I left because I wasn’t getting any help and took a demotion to overnight baking (which is where I was able to freelance while I cooked muffins at 2:00 AM).
Both GMs for the entire franchise couldn’t leave that store for six months because of how hectic it was. It validated my struggles, but I wasn’t done yet.
I was shit at asking for help. I made things harder on myself, and I let my perfectionist tendencies ruin an opportunity for me.
Also, it was $13.00 per hour and highly stressful with no benefits or bonuses, so in the long run, I’m glad I’m not there anymore.
Content Marketing Agency
I built one, then I failed. It didn’t last long, but I put hundreds of hours of work into this content marketing agency startup idea.
I designed a website, I wrote blogs, I had email marketing set up, proposal templates, a fulfillment pipeline: the works.
But I had no idea how to market it properly, which is pretty ironic. I closed shop on this idea, and realized that the further I got from the frontline (actually writing and editing content), the less happy I would be.
You don’t have to “advance” to the next phase in everything you do. You can maintain a title, especially in freelancing, and simply refine and hone your craft.
That’s when I realized it’s better to put all your efforts into one focused venture at a time instead of dabbling in an entire portfolio of aspirations.
Consistency. That’s the key to success.
So, Here I Am
Freelance writing has been there for me since I was eighteen, and it’s where I’ve found my calling. While it’s expanded to forms of passive income mostly through different online writing outlets, it’s held true the longest.
Everyone fails, and if your failures don’t get you excited, then I have bad news for you. It’s going to be a lot harder to take rejection smacking you on the face in the future.
Take principles and lessons from every failed endeavor, and never let it stop you from going on to the next one. Today, I own websites, average over $20K/month as a freelance writer, and sell digital products while also working on courses and YouTube video content as well.
Keep innovating. Never stop trying. You’re always one step away from greatness, and you never know it until it happens.