My friend Jason Shen wrote a post called You Had One Job. His goal was to point out that our parents’ generation grew up with the expectation that they would go work for one company and be loyal for their entire life. It’s obviously different in today’s world. I’m 25 and have already had more than a dozen different jobs.

As I was going through Jason’s list, I reflected on my own jobs. More interesting than the number of jobs that I’ve had, is the experience I gained from them. In many cases I learned what I didn’t want to do when I grew up. Those poor experiences pushed me in the right direction.

Here are the jobs I’ve held, and what I learned from each.

1. Bus boy, Server, Cook and Cashier

When I was 13-years-old I spent a few weeks of the summer bussing tables. That summer I made enough to purchase an original Xbox. It seemed like a monumental amount of money at the time.

I’d spend future summers of my teenage years working in similar capacities. I remember those summer days spending my afternoon waiting for the fryer timer to count down, which signaled the chicken fingers were done.

The work was incredibly hard and incredibly boring. I’m not sure if my parents wanted to teach me a lesson, but the experience taught me to avoid working in a restaurant at all costs.

Also, tip well when you go out to eat. Being a server is tougher than you think.

2. Sports Camp Counselor

Herding kids around the playground. It was one of the first jobs I really enjoyed. The only downside was that I had to watch Veggie Tales everyday.

As a kid, I always loved sports camp. As a counselor, it kind of felt like I was getting paid to go to camp.

3. Legal Intern

Like many teenagers, I thought I wanted to be a lawyer when I grew up. Where did I get that idea?

I worked for a friend of my father’s for a few weeks one summer. This particular friend was one of the funniest people I’d known. I thought working for him would be a blast. As it turns out, he spent much of the day reading through casework. No time for jokes.

He didn’t work in a giant firm. He worked independently, and his office was filled with thousands of manilla folders stacked in piles four or five feet high. My time was spent organizing and filing those stacks—a job as boring as it was tedious.

In the end, I decided that I wanted nothing to do with the legal profession. That internship saved me a couple hundred grand on an education.

4. Food Marketing Intern

In the summer of 2009 I gave working in the restaurant industry another shot. This time I was working in an office for a food marketing firm, Sunbelt Foods Company. I’d pick up hams, cases of Texas Pete and head to new restaurants and watch my boss, Adam, try and sell the owners on them.

It was much better than working in a restaurant, but it wasn’t anything I was in love with.

5. Associate News Editor

I’m told that I’m incredibly present and ask great questions in my interviews. I attribute that my time reporting at The Auburn Plainsman. Talking to complete strangers can be a daunting task. It took several months for my anxiety about talking to strangers to dissipate.

I also learned to be ruthless in my pursuit of interviews. Nobody wanted to talk to a me. I was the guy who called when you, or someone reporting to you screwed up. Remember that time a drunk person stole the Tiger Transit bus? The transit manager did everything he could to avoid speaking with me.

While working as a reporter, I learned how to use Photoshop and InDesign. Technically it was my boss, Ellison’s job to paginate the news section, but I frequently ended up doing it. I think this was the point where I became seriously interested in design.

As a bonus, I made enough to buy one extra case of beer each week.

6. Vice President of Communications

It may seem silly to put a fraternity job on this list. Yes, I got free rent and food for two years, but it was more than that. Getting elected was a moment of self-actualization for me.

I wanted to build a new website, and convinced the fraternity the alumni board to give me the money to build it. I hired a design group in neighboring Opelika to build it. I basically served as a producer, although I didn’t know that’s what it was called at the time. The Auburn SigEp site is still live, and looks pretty good for something five years old.

Getting elected put me in a position of power—or what seemed like one—for the first time in my life. I learned that the key to gaining respect is to be humble and avoid holding that power over others.

I had to fire someone for the first time. Letting someone go is never an easy task. It’s even more difficult when you’ve known them for several years. I met with our President and Chapter advisor to let our fraternity cook go. It was difficult, but a good decision for the chapter.

7. Online Editor

With a new-found love of design and experience managing a web development project, I returned to The Plainsman to rebuild our website. Rod, the Editor in Chief at the time, and I campaigned for a redesign. I wanted to replace the bulky awkward Matchbin site with a WordPress one.

Unfortunately, the paper didn’t have $6,000 laying around, and the Communications Board didn’t see the immediate need. The Plainsman’s site is the same as it was when I left the paper.

I was terribly disappointing, but all was not lost. The weekly editorial discussions were fantastic. I got to write a few columns, which was a nice change from sweating out deadlines with hard news stories. My writing improved dramatically during this period.

I was now able to buy two cases of beer each week.

8. Digital Marketing Intern

My internship at V3 Media Group was a reason to stay in Auburn during the summer, which was always a blast.

During this time I voraciously readed any and every article posted on Tech Crunch, Mashable or Fast Company. Later I’d learn that many of these articles originated from events on reddit and Hacker News and would become avid readers on those sites.

After months and months of absorbing tech articles, I decided I wanted to start my own company. Dale Vaughn, the director of V3MG, would be my business partner and would introduce me to Thomas Gross, who would become my first investor.

9. Founder

Starting a company was a defining experience for me.

FRUGGL was a small coupon business that eventually failed. There are honestly more lessons here than I can share in these few short paragraphs. I’ve written about it in the past, but there is one realization that dramatically changed my perspective.

Nothing I had learned in college was applicable to my business. Even worse, what was the classes touted as “business classes” were completely worthless. I was trying to figure out how to create email marketing campaigns, split test advertisements, and how to sell clients. Meanwhile, in class I was learning about Six Hat Theory and other theories for business academics.

When I started my company my father had an incredibly accurate comment, and one that I tell people every time a friend tells me they want to start a business.

“What’s the worst that can happen? You’ll have a great learning experience at a fraction of the cost of your education,” he said.

10. Marketing Consultant

I learned to create and manage SEM and Facebook Ad campaigns while running my business. When it was time to look for a new job, I built a landing page and ran a Facebook ad campaign to try and get myself hired.

Eventually that led to a consulting gig with a company called CrowdFunder, which wanted to use crowdfunding as a means to fund startups. It was illegal at the time. Investors had to be accredited, which meant they needed to make $500,000 or have $2 million in assets to invest.

The JOBS Act would do away with the accredited investor, and allow anybody to invest in startups. CrowdFunder was lobbying for the JOBS Act, and needed someone to manage their media campaigns.

I grossly undercharged them for my time. With our help the JOBS Act would pass, but the Securities and Exchange Commission dug in. It would be three years before companies could raise money via crowdfunding.

11. Product Evangelist

My dream job was to work for a Y-Combinator company in Silicon Valley. I saw that drchrono was hiring Python engineers on Hacker News. I figured they might be hiring other positions as well, so I reached out to them.

After a few interviews Michael Nusimo and Dan Kivatinos decided to bring me aboard as a contractor. I’d split my time between Mountain View and Atlanta. I had three tasks: make sales, develop marketing campaigns, and help hire an online marketing lead.

I spent my mornings working on creative and setting the ads. In the afternoon I gave product demonstations to doctors. I was a lousy salesman, but I eventually helped hire Mike Haverhals, who worked at drchrono for a couple of years. He is now the online marketing lead at Twilio.

I wanted to transition into a design role within the company. Unfortunately, it didn’t work out in the end. They ended my contract and gave me some parting money. That generosity almost funded my entire trip to The Starter League in Chicago.

I still email Michael and Daniel occasionally.

12. Freelance Web Designer

It was an interesting period for me. I had just left Chicago and The Starter League, but wasn’t quite employable as a designer or frontend developer. So I decided to team up with a few friends to work on freelance projects. I’m not terribly proud of my work from this period, but we did build functioning web apps. My perspective was that people were paying me to learn.

Unfortunately, I wasn’t able to sustain myself as a freelancer. I’d have to start looking for other opportunities soon.

13. Senior Interactive Producer

Finally, we reach my current job.

I’ve been at Red Square for shy of two years. I was promoted after one. I’ve managed a range of projects—gigantic 150 page websites, smartphone apps and even games.

It is a bit early to reflect on what I’ve learned as an interactive producer. Perhaps, that will warrant another post in the future.

Posted by:Sam Solomon

I'm a designer, writer and tinkerer. I currently lead workflow and design systems at Salesloft.

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