Many years ago I read an article by the legendary Mike Royko where he listed all the jobs he’d worked before becoming a writer.
I was fascinated with how many different jobs he had worked that had nothing to do with journalism. I’ll never forget one of them was stevedore.
Although it was never my intention to have a lot of different jobs, I ended up doing just that.
Here were my jobs in chronological order:
- Chores including grocery shopping, laundry, making dinner, drying the dishes, taking out the trash, sweeping and vacuuming the entire house, and cleaning the kitchen and bathrooms ($5-$10 every 2 weeks, if I was lucky)
- Mowing Lawns with my friend (he took a bigger cut it was his mower)
- Shoveling Snow (sporadic)
- Washing Cars (really sporadic)
- Industrial Cleaning of Giant Washers & Dryers for soiled Hospital Linens (truly disgusting but it was my first “real” job paying $3.35/hour))
- Pizza Delivery and Short Order Cook – This is where I was taught the basics of customer service, sales, and being accountable. It was here that I had my first taste of “variable income”. When we had a good night, I’d work really hard and my tips were higher. It was a lot of fun too, especially on weekends.
- Math Teaching Assistant for underprivileged high schoolers taking Saturday classes. I was a college sophomore and hungover every day I worked there.
- Lifeguard – This was a blast in the summer. I was the community babysitter for 100+ kids and worked with fun people my own age. I liked the money, the prestige, and the tan. It sucked in the winter when I was lucky to get 10 hours a week at an indoor pool.
- Roofer, cement laborer and brick pointer – Hard labor with above average pay. My coworkers who were career laborers who urged me to go back to school before I ruined my “surgeon’s hands” and became a lifer like them.
- Mail Boxes Etc. Assistant Manager – Essentially I was a retail clerk and box packer but was called a Manager so the owner could avoid paying overtime. To this day, I can pack anything and make the box nearly uncrushable (aka UPS proof). This is where I met my wife.
- Warehouse Manager/Shipper for a carnival supply and candy fundraising company. No job I’ve ever done since compares to the exhaustion and frustration of unloading an entire tractor trailer full of M&Ms only to have another trailer pull up to the dock 10 minutes later with a full load. No matter how bad work is today, it still beats unloading M&Ms.
- New York Times Newspaper Delivery – As an independent contractor, I worked 7 days a week, 365 days a year, from 1 AM to 4 AM delivering the New York Times to rich people. What initially looked like a cake job paying me twice what I was earning as a warehouse manager ended up paying me less after self-employment taxes and vehicle maintenance were factored in. Not to mention, this job destroyed my sleep cycle, my social life and my digestion for the entire year I did it. It was cool to be out at night all alone though. It’s a different world.
- Plumbing Supply worker– My brother-in-law took pity on me and offered me my first opportunity for a real career. He paid me a good salary, gave me a company van, health benefits, vacation pay, coaching, and treated me like a valued employee. I couldn’t handle it. I quit after 6 months
- Bicycle Messenger – I used to pity my customers who were cooped up inside all day wearing suits and ties while I rode around the city on a bike. This paid minimum wage plus a commission for the top riders. I never made more than minimum wage but my secret plan was to use this to find a computer related job in the city. It worked!
- Warehouse Guy for Retail Computer Store – I unloaded trucks and managed the warehouse for an Apple Retailer back when Apple wasn’t popular (early 1990s). But I made more than minimum wage, got commissions for doing deliveries and learned how to use, install and fix Macs.
- Sales Guy at Retail Computer Store- My boss gave me a chance to have a real career. He changed the trajectory of my life. The characters who worked here, who bought here and who wandered in off the street were the most entertaining in my entire work life.
- Manager of Information Systems for Marketing Agency – I learned how to present to big customers, how to manage billing down to the minute and that most of marketing is made-up bullshit.
- IT Help Desk Guy – A contract position that paid me double what I was making at the Marketing Agency. I hated putting out fires all day when I knew we could eliminate the cause with some better planning. But I had zero influence over anything strategic. The money was outstanding.
- B2B Sales Guy at a startup Internet Service Provider – I loved this job. We grew really fast during the dotcom boom on the late 1990s. I was promoted a bunch of times and ended up running a sales team of 35 across 5 locations.
- Sales Guy for an IT Staffing Company – This was a disaster. The company was a mess. I worked remotely. I took this job as a way to relocate to Florida, which I did.
- VP of Sales for startup Network Security Company – I thought this would be just like the ISP job, only better since I was joining earlier in a higher role. I was sadly mistaken. Our “product” was mostly vaporware. I hustled to sell consulting services to businesses that were buying very little during the post dotcom crash.
- Field Sales for a Title Processing software – yawn.
- Field Sales for an IT Services Company focused on SMB – I actually loved this job. Our clients were manufacturers, insurance agencies, and SMBs. We sold and services networks, servers and computer systems. I worked remotely here for 4 years.
- Inside Sales rep, team lead, manager, director for a public software company – a game changer for me. I did very well here and was promoted 5 times eventually becoming Director of Sales running a team of 175 people selling $58M a year. I made great money, learned a lot and met some good people. I also learned to despite corporate bureaucracy, politics and running a business by its “stock price”.
- VP of Inside Sales for a Startup – I joined to open a sales office and run a team of 20-40 reps in my hometown. That never materialized. My team never grew beyond 6 reps. Nor did our product ever get past being nice-to-have for a very small niche market. My job was eliminated after 3 years.
- Self Employed Consultant – What began as a blog that I intended to use as an expanded resume to help me land my next VP of Sales gig, turned into a decent consulting business. This is what I do today. I love being self-employed.
So there you have it.
My plan was to go to college, become a doctor or lawyer, and follow that path to fame and fortune.
It didn’t turn out that way.
Today I’m grateful for the variety of experiences I had with so many different jobs.
I’m sure it has cost me money. Good money only came after I specialized in technology sales.
Had I started doing this straight out of high school, I would have made more money and would be retired by now for sure.
But then again, as my wife says, “If grandma had balls she’d be grandpa”.
Although I have fond memories of the camaraderie and teamwork at my favorite jobs, I have no desire to work as an employee ever again.
Solo consulting part-time suits me just fine today. As long as I can pay my bills and help some people out, it’s my plan for the foreseeable future.