Why I bounce

Working shouldn’t feel like a prison sentence.

I am 27-years old. I graduated from college in the spring of 2010, five years after graduating from high school. During those five years, I attended five different universities. Since the spring of 2010 to current day, I have worked for six different companies, in two different industries. That may seem like a lot of different work places for someone who’s only been in the post-college “work-force” for 3.5 years and it probably would appear that I’m the sketchiest, most unemployable person out there. Before you make snap judgments on me, let me tell you why I’ve made the career decisions I’ve made.

You know how some people know exactly what they want to be when they grow-up? My oldest brother, for example, knew at a young age that he wanted to be a pilot and do you know what he does for a living now? He’s a pilot. Other people have a wonderful college experience with a Robin Williams / Matt Damon moment with a professor that shaped their career path. Well, I didn’t have any of that.

I went into business school mainly because my father was in business and it’s what I grew up around. When I finally graduated with a degree in Business Management, I was very well equipped to do… nothing. What the F*** does a management degree do for you when you’re 23? I ended up pulling some strings with a friend who had connections in the wine/spirits industry and landed a job as a Territory Manager for a large wine/spirits distributor in California. The day I started I had a meeting with a man who was my boss’s — boss’s — boss. His office didn’t have windows. That was very frightening to me. Here’s a guy who is three layers above me and he can’t even tell if it’s light or dark outside. After doing that job for a few months, I quickly learned that I was not going to do well in a large, corporate environment.

Lucky for me, I was being recruited by a smaller, family-owned distributor, around the same time I was planning on leaving the current one. I took the new position because it was little bit more money and I believed that I would enjoy the size of this new company. I hustled and worked my butt off at this new gig but I also had my first head-to-head battle with upper management. I’ve always been a techy kid, you know the one that parents call to see how to fix the DVR, burning all sorts of CD’s in middle school (thanks, Napster). When I started this job they made all of us carry these huge binders with papers and photos, to show clients. I had recently purchased an iPad and I thought it would be easier (and look more badass) if I had all my information on it. I ended up building a very basic app on the salesforce.com platform that allowed me to collect the customers order info and put it on my computer, so that when I got home I could place the orders. I’ll never forget riding around with my boss’s boss one day and he got so upset at me for not carrying the big binder that he told me to quit trying to outsmart him. The next day I resigned.

That was a big turning point for me in my career. I realized that I needed to be in a place that fostered innovation and encouraged creativity and didn’t shoot it down. Today I look back and think of both those jobs as stepping-stones and I’m very happy to have had those experiences. The first helping me realize I wasn’t built for a large corporation and the latter guided me to the tech industry.

Two-weeks later a friend of mine of suggested I go to a “hiring party” at a medium-sized startup named Demandforce. I had a blast at this event and met so many interesting people and hungry go-getters; I knew this was the place to begin my tech career. Before Demandforce, I had learned a great deal about being an outside salesman. I was good at building relationships with clients and following through on promises. While at Demandforce, I learned everything from cold calling to closing a deal on that very same cold call. The people there knew what the heck they were doing and still do. I made a lot of great friends there and made some serious money, too. I decided to leave because it was growing very quickly and I had an offer to join a company that had recently been acquired by Salesforce.com, Assistly (now Desk.com).

I told my boss at Demandforce that the reason I was going to SFDC was not because I wanted to be part of large company (I think they were roughly around 7,000 employees then) but because I wanted to learn more from the founders of Assistly and how they built the company and scaled it. The CEO of Demandforce was an amazing guy and a great leader but by the time I left the company had grown to over 300+ people and it was hard to get face time. However, at Desk.com the company was only around 50 people and there was no intention of folding them into the rest of SFDC anytime soon, so that excited me. Working at Desk.com was another wonderful experience where I gained so many valuable skills. There was training in consultative selling, meetings with the marketing and product teams and focus on growing the culture. The time I spent at Desk.com was some of the most fun anyone could have in a work place. Working along side smart and funny people never gets old. I decided to leave because my brother and I had been planning to venture out on our own and try our luck at building a company.

Talking about building a company and the startup life is something that has been discussed so many times; I’m going to choose to not focus too much on it. Short story is we raised a small F&F round, built a little team, launched an MVP and then shortly after ran out of money. We didn’t do a good job of validating our assumption and we took too long in development. What I will say (to get back on subject) is in those six months I learned things that I would have never learned had I stayed steady on a career course. Building a team, working with designers and developers, tools like CS6, paper-prototyping, Github, etc. were all things that I was forced to learn about. I also learned that working with my brother was a great thing. You often hear horror stories of people who can’t work with family members, but we worked very well together and had complimenting strengths. I look forward to whatever projects we work on together in the future.

In the past few months I’ve been consulting with a small startup; helping with support operations, social media and a number of web products. I recently ended that contract with them and that has sort of prompted me to write this.

As I begin hunting for my next gig, I wanted to put it out there, publicly, why I believe bouncing around isn’t a bad thing. In three and half years, I have learned much more than I would have ever been able to had I still been slinging booze, serving time until I got an office without a window. We don’t judge people who bounce around from relationship to relationship without serving two years, hell some peoples relationship only last for one night. If you’re feeling stuck in your current position or you don’t like the way the light at the end of your tunnel looks, get out of there. If you’re miserable at six months or curious at ten, move on. Don’t get stuck and pigeonholed into a career you don’t want. You’re not serving a prison sentence. You will land on your feet, you’ll learn new things and most importantly, you’ll grow as a person.