The best career advice book I’ve ever read is How To Fail at Almost Everything and Still Win Big by Scott Adams (of Dilbert fame). One of his core arguments is that every skill you acquire doubles your chance of success (ie, Bill Gates was an incredible developer AND incredible at business).
Hopefully that argument is true because by both necessity and planning, I’ve done a lot of stuff and acquired a lot of skills before hitting 30. Although I can’t compete with the likes of my friend Matt Moore went it comes to number of jobs had, I have a lot of people ask exactly how many projects/jobs I’ve done over my career.
So here’s the list of every job I’ve ever had, and every money-making project I’ve ever had a “solid go” at and what I’ve learned at each as of December 2014.
Driving Range Ball Picker & Cashier
When I was 13 years old, one of my Uncles co-owned a driving range with my Grandma. My Grandfather ran it day to day. I wasn’t on the payroll, but I got the chance to earn money picking up golf balls and serving customers at the cash register.
It wasn’t much, but it was enough to get me hooked on working and making money.
Running Internet Ads for Money
During the first Internet Bubble, a lot of advertisers were overvaluing “eyeballs.” Toolbar revenue sharing was an outgrowth of the craziness. You could install a toolbar that just ran ads on the top of your browser while you were online and then the toolbar maker would pay a cut of the revenue.
It was a tiny payout, something like $0.10 an hour, but it was something I tried. I took it a step further by running this tiny script to keep my browser “active.” It would randomly click every few minutes to keep the toolbar running. I gave up on it because it slowed down my computer so much – and the whole Internet Bubble burst. But I learned how to hack around with toolbars and basic scripts.
Homestead.com – AoE Website
Also back in the early days of the Internet, I was obsessed with having my own website. However, hosting back then was really expensive (especially for a 14 year old) and I was lazy with HTML for some reason.
There was a site called Homestead.com that offered free websites. It was a classier version of GeoCities back then. I put up a small Age of Empires fan site. It only got a few visits, and I ended up shutting it down for some reason (I loathe Nate from the past sometimes).
The reason it qualifies for this list is that this website was where I came across the meta keywords tag and did my first dabbling in what turned out to be search engine optimization. Unfortunately, I didn’t think you could actually make money (much less a career) at it, so it fell by the wayside. I did pick up a bit of experience in website-hacking-around-skills.
Buy & Sell on eBay
eBay started to get huge around 2000 and I first tried it out in 2001 I think. My first experience was as a buyer, but I quickly tried selling a flag I think. I made like $10 profit and got hooked. I proceeded to sell basically anything worth more than $2 in my possession.
When I ran out of stuff to sell, I started buying random stuff overseas (like Buddhist statues from Cambodia that I’m pretty sure were either stolen from some archaeological site or were completely fake) and re-selling them with better copy/ratings/shipping.
The whole process was fine and a great learning experience but I never took the next step to really look at it as a business. The margins were slim and not very profitable at an hourly rate, so it slowly fell to the wayside.
One of my other Uncles owned a plumbing business (this is when I was in high school/college). He hired me to work during school breaks and summer time. I got paired with one of his plumbers to do some repair work, but mostly new construction (this was during the housing boom).
It was ridiculously tough work, but I learned more than I could write here. But really more than the plumbing and the job, my main lessons were from my cousin Mike and co-worker Kelly on how to work. Think before you do. Work smarter, not harder. Use the right tool. If you don’t have the right tool, don’t work until you have it. Work intensity matters more than work hours. Pay attention to details.
I also learned all about the day in and day out stresses and pleasure of being a small business owner from my Uncle. He was generous about showing me the business side of things, and really planted the “own a business” bug in my mind while also tempering the starry-eyed unrealistic dreams of “entrepreneurship” that so many of my peers had/have.
This project barely makes the list since I didn’t get far with it. I did learn a good bit with it. I heard about how watermelons sold for like $10 per up North – like New Hampshire. At the time we lived in rural Oglethorpe County Georgia where roadside watermelons were $5 per.
I thought I could buy 100 watermelons, put them in my family’s minivan, then drive to Philadelphia to sell along the roadside. I’d clear $500 for like 25 hours of driving. I proceeded to drive around and find a supplier, get the cash, and went back home to get the van set up for the trip.
And then my Dad started asking about inconvenient things like oil change, mileage reimbursement to him, and gas costs for a loaded minivan ($2.50/gallon at the time). By the time everything was said and done, I was left with like $5 per hour.
I decided to take on a few more hours at the Rec Sports Complex and ditch the idea – and always remember to calculate out real costs.
Sports Complex Supervisor
This project was my first real job for a non-family member. I was an incoming freshman to the University of Georgia and needed a reliable way to pay for gas, books, etc. I applied and got a job at the Recreational Sports Complex at UGA.
It was pretty much a dream job in many ways. I had trained for cross-country all through high school there and loved the park & fields. It was active, outdoors, interesting, above minimum wage, and kind of unique. I had a great boss. I had some actual responsibility (like being the annoying guy that kicked people off the fields when it rained). I also had some downtime to get reading done.
I learned that you could seriously impress your boss, coworkers, and customers by just being more interested, more curious, more flexible and the first one to help.
I ended up winning Rec Sports Complex Manager of the Year at the UGA Employee awards. I left during the summer after my freshman year to chase higher pay and more fun working at Campus Transit, which I’ll get to momentarily.
The summer after my freshman year I was working at Ash Plumbing, but wanted to start my own business again. My sisters had recently started working for a cleaning company and told me how much their boss charged.
Not yet having fully learned my watermelon arbitrage lesson, I offered to go into business with my sisters as a cleaning company. I bought a commercial grade vacuum cleaner and some cleaning stuff. I took over the marketing – going pretty much everywhere in town where cleaning companies advertised and put up flyers. We got some leads and my sisters cleaned a few houses while I tried to figure out how to pitch the big target – apartment complexes.
In Athens, every single apartment complex “turns” in July, so there’s a ton of cleaning to be done and a lot of money to make. I figured it up and thought that we could close 1 complex and we’d be set. So I started pitching. Door to door pitching was pretty much the worst thing in the world – and really inefficient in hindsight, but I learned from it. I got some interest and some follow ups, but it turns out that property management companies don’t want 3 random teenagers to take over cleaning for their complex.
I gave the equipment to my sisters and started my new job at Campus Transit at the end of the summer.
Disability Van Driver
I applied to Campus Transit for a bus driver position on my 19th birthday (minimum for in-state CDL). July 23rd was a bit late in the summer to train for a bus, but I was offered the disability services van driver position.
I took it, especially to get into the elite campus club of Campus Transit. The pay was $2/hr less than bus drivers, but I was told I could definitely move up Spring semester. The van driving job was super-easy to do, and also one where it was easy to impress passengers/supervisors. I also got a lot of schoolwork done while working which freed me up to do other projects.
After discovering how much money I could save by buying textbooks on the recently launched Amazon Marketplace, I thought it’d be a pretty cool place to run a small business. I owned a ton of books; knew the market; and it was something that made intuitive sense.
I posted every book that I could bear to part with (so really not that many), wrote sales copy, and posted them. After shipping, I made a decent profit per book given how little time it took, so I thought I’d try to grow my operation.
I needed a source of used books – library sales! At the time, libraries held these friends of the library sales to raise money. All the books were flat rate priced, so there were some incredible finds if you knew what to look for. I’d go up to one on Saturday morning; try to buy books for $1 per, then post and sell on Amazon for $10 per. I’d lose money on books that didn’t sell, but at even small volumes, I’d still make a profit.
I did this operation for quite a while – more than 6 months. In my mind, it was a cool operation. Libraries got immediate cash (often for books no one else was buying) while I took on inventory risk and shipping for a profit. But I ended quitting because people at these sales pretty much despised me. I mean, it got really awkward, like I was taking candy from kids and reselling it.
I learned that library sales aren’t so much sales as community gatherings. There’s a whole subculture surrounding them with a social code that you don’t mess with by bringing profit into the equation.
I ended up phasing the operation out and always asking librarians if they had looked up market price on Amazon before putting books out. Most libraries market price their books now, which I think is a great thing. Either way, I learned a lot about pricing, sourcing, customer service – and on how money and marketing affects community.
Shivar Storm Windows
The summer after my sophomore year while I was training to be a Bus Operator, I heard several people complaining about how awful storm windows were and how much they’d pay for someone to clean them.
I told a few people that I knew how to clean storm windows and asked for referrals. 3 days later, I had made a 3 appointments and was scrambling to buy cleaning supplies and to learn what a storm windows actually were.
A week later, I had made $600. I had 3 happy customers. And I was 100% done with storm windows. They are the worst things ever invented by anyone. I learned that there are fun and not fun ways to make money.
Speaking of having fun while making money, I got a Class B CDL license with Passenger and Air Brake Endorsement to operate a 40 foot mass transit bus for the University of Georgia Campus Transit.
At 19, that was so much fun. There’s also nothing like driving 20,000 lbs with 80 passengers late for class on crowded streets to knock a serious sense of responsibility into you. I learned a lot about working closely with people, customer service and turning tedium into fun.
I also learned a good bit about working within a large organization, and what type of management I work best with. I kept working at Transit off and on – including as a full-time employee for quite a while.
Bus Driver Trainer
I was recruited to help train new drivers on how to drive buses, and ended up doing it for a while. I learned a lot about coaching, teaching and supervising.
Philippine Travel Resource
I had just returned from a trip to the Philippines so I decided to put up a small resource site. It was basically a personal blog promoting Amazon books. If it had been on its own domain (not Blogger), it might have grown a good bit by now, but I shut it down after a while.
I learned a bit more about websites and I dabbled in my first actual bit of search engine optimization.
Lumber Store Manager Trainee
I graduated from UGA in May 2007 and took my first “real” job at 84 Lumber, a large building supply retailer. It had nothing to do with my degree or previous experience (except maybe plumbing).
I justified taking the position because it was near Athens, GA and promised rapid promotion & bonuses (this was the tail end of the housing boom). I was also interested in their new international division.
My initial position was a Manager Trainee at the Monroe, GA store. I was in that position for 4 months, but it felt like 3 years with everything I was doing and learning. My boss was incredible and taught me anything I wanted to know. I did everything from loading trucks with a forklift to working on P&L sheets to managing temporary employees.
I also rapidly learned what it’s like to work for a large corporation, and all the associated Dilbert-style politics. Unfortunately, Summer 2007 was the last major crackup boom for housing. In September, 84 Lumber stopped expanding stores and their international division. There could only be 1 Manager Trainee at each store, and we had 2 of us. My boss pitched my on becoming a Contractor Sales Rep. I took it.
Lumber Sales Rep
My job as Contractor Sales Rep was to find contractors building houses and sell them building supplies. I had base pay plus commission. In hindsight, this job was really an insane job to have in Fall/Winter 2007. I had never done sales – much less B2B sales…and much less building supply sales. 84 Lumber was also distinctly uncompetitive. We were also on Home Depot’s home turf.
Since I had no idea what I was doing, it allowed me to be a bit unorthodox with sales and marketing. We were judged by 2 metrics – dollars sold and credit accounts opened. Within 1 month, I was the top sales guy in our area by credit accounts opened. The only guy ahead of me in dollars was a sales guy with 1 huge account building an apartment development.
In December 2007, there were exactly 0 building permits pulled in Walton County. And 84 Lumber started shutting stores fast. I shifted gears to find & sell to remodelers. In February 2008, a VP showed up at 6am to shut down our store. He offered me a transfer to a different store or take severance. Given the change in pay structure, new boss, and a generally bad vibe for the company, I took the severance.
I wasn’t totally unemployed though, I had started several other projects and jobs. I also ended up going back to Campus Transit while I shifted gears back to the Internet (and that ended up taking a while).
In November 2007, even though I was the top sales guy at 84 Lumber, my pay was not great. I also saw the writing on the wall with housing going into a freefall.
My original plan with my International Affairs degree was to go into the International Trade sector of the economy. Although I couldn’t find a job in that area, I decided to go at it freelance style.
I found this guy who ran an import/export business out of China who was hiring commission-only brokers. I signed up and proceeded to fail. I nearly had a couple big deals, but the work was not fun for me. The default approach was either relationship-based or cold selling. For some reason, I didn’t break out of the recommended box and run my own operation. Either way, I quit with a lesson in hindsight to do things differently.
Bookstore Customer Service Rep
Also in November 2007, I was hired at Borders Bookstore as a holiday customer service guy. For those who remember bookstores, the job was everything it appears to be. You don’t get paid much; it’s an amazing work atmosphere; you spend all your paycheck on books. Also, the best perk of the job was the ability to check out any book from the store like it was a library.
I was the one of two holiday temps they offered a permanent position after Christmas. I also got employee of the month several months there. I got involved with merchandising, the coffee shop, inventory, and marketing. Even though it was a physical store, I actually learned a lot that I’d apply digitally.
I also gained a lot of respect for coffee baristas. That’s a tough job.
Coffee Education Website
In 2010, I stumbled on this new website software – a blogging platform called WordPress that some people were turning into a content management system. I decided to buy hosting and launch some websites on my own domain to learn actual web development skills, and apply some marketing ideas that I’d been learning about (specifically search engine optimization and online advertising).
I spent way too long thinking of a website idea, so I just picked coffee since I was really getting into it at the time. Either way, the site was awful. But it got some organic traffic and made my first $1 from advertising. After that, I was completely hooked. The vertical was really competitive and I didn’t really know what to do to scale up the income given the time I spent on it. I still own the domain as a sandbox/experimental site.
Music Gear Drop-shipping Website
I found a music gear wholesaler who would dropship stuff for me. I opened a Shopify account with my brother and started my first ecommerce store. Turns out that vertical is hyper-competitive. Didn’t sell a lot, but I learned a lot of assorted development skills (including selling stuff via Amazon marketplace).
The whole customer service part was awful and a I frankly was not learning enough about the business part of business to keep the project worthwhile. I migrated it to a blog/experimental site that I still own.
WordPress Tutorial Website
Partly to help myself learn and partly because interest in WordPress skyrocketed with the release of 3.1, I started a tutorial website. It was a freemium model. I got a some traffic and even got 2 paying subscribers. I learned that membership sites are really hard to run in the beginning. I didn’t have the time or money to keep it running in the short term.
Most of the content made its way into my current marketing website – shivarweb.com.
Assorted Blogs & Websites
There was a period where I just launched a lot of different types of websites. Few were planned out super well, but with each one I got a bit better with WordPress and building traffic from scratch.
Automated Real Estate Agent Website Platform
I built a platform where real estate agents could buy a prepackaged website with design templates and pulled in listings for a monthly fee. Turns out that market is huge, hyper-competitive. It was also still a bit too complicated for real estate agents to actually use. They just wanted someone to build and run it for them.
Automated Private Detective Website Platform
Same story as the real estate agent platform. The feedback I got was – “can I just pay you to build and run this for me?” Either way, it was a pretty cool product from a technical perspective for me (though I know actual developers would have been like “WTH is this?”).
Shivar Web Consulting
In October 2011, my friend Matt Moore asked me if I knew anything about search engine optimization, AdWords and websites (I did, though I was still learning). I took on EZ Dent Repair as my first client – and Shivar Web Consulting began. Oddly, before then I had literally never considered that I could sell services for a fee.
I knew how to do the work well – everything from running organic marketing campaigns to building websites to running paid campaigns to a bit of copywriting, but had really no clue about the business or management side of running an agency.
I was pretty good at marketing myself and digging up business and doing the work, but by October 2012 I realized that I still had no real idea how to turn what I had into a real business.
I had several big projects that would be wrapping up in January 2013, and decided that I really wanted to be part of a top-flight agency on a team doing either SEO or PPC for large clients.
In January 2013, I was hired as an SEO Specialist for Nebo Agency. I’ve since been promoted to Senior SEO Specialist and am the client lead for several accounts. One of my campaigns won Best SEO Campaign of 2014 from the Atlanta chapter of the American Marketing Association. I’ve learned a ton at Nebo – too much to list here. If you’re looking for a digital agency to work for, I’d recommend them.
Although I stopped taking on retainer clients at Shivar Web Consulting, I kept the site going as a place to share ideas, experiences and opinions about running a website and generating an audience. It’s also given me a platform to try new things that would be outside of scope with clients. I’ve developed my own amazing audience that regularly visits the site and subscribes to my weekly newsletter.
Bamboo Chalupa Digital Marketing Podcast
In September 2014, I started a new podcast with Brett Snyder of Knucklepuck (also my former boss at Nebo) about digital marketing. I’ve dabbled in podcasting before but audio is still a very different medium for me. We’re only 10 episodes in, but they’re really useful and really fun to produce.
It turns out that I can’t stop trying stuff. While ShivarWeb.com is my primary business, I’ve since launched several online publishing brands. Each is its own stand-alone business (or pro-bono project). Fun times :)
Even though I didn’t read How To Fail at Everything and Still Win Big until July 2014, the principles Scott Adams outlines are exactly what I’ve accidentally/purposefully done so far to achieve a small bit of career success.
I’ve definitely found the value in mastering 1 skill and specializing in a single job, but the longer I’m in the working world, the more I think the truly valuable core skill is solving problems and figuring stuff out. And that’s something that really only comes by acquiring different, complementary skills.
If you are curious about what I’ve written elsewhere – here’s a sampling.