Get your Foot in the Door

May 7, 2008

This is the story of how I jumped from young guy with no experience, to Senior Developer at a Fortune 500. You should go back and read the Lessons of the Fast Track if you haven’t already, it’s good primer material.

As I mentioned, I had been working with technology seriously for 8 years when I started college. I faced the issue of doing work that was better than the market average, but not having the documentation to prove it. I also was a full time student, so working a 9 to 5 wasn’t in the cards (not that that’s a great idea anyway). The obvious answer was to continue what I had been doing, but bring it to the next level.

I had been freelancing for clients, using my parents as a point of contact when necessary to provide the fictional context that clients need to feel confident. Now I was old enough to pull off the contact myself without pretense. I was fortunate to meet a guy who is a very bright business man, and we went into business together full time when I was about 20.

If you haven’t already, I highly recommend going into business for yourself at least once. It doesn’t matter what market you target, just come up with something you think will be profitable, and go for it. You’ll learn at a ridiculous rate. I learned to handle the paperwork of a business, deal with clients of all stripes, sell services, design increasingly complex software systems, discover the joy of due diligence, and find that the business I was in wasn’t really for me. It was an extremely valuable period for me.

It was doubly so because I was able to parlay that learning experience into a Senior Dev position at what it reputed to be the best technology employer in my city.

Think Deeply

Think Deeply

This goes back to my thoughts on getting started early. If your formative years have been spent passively consuming media, then that is what you’re likely to want to do as an adult. You will attend class in college expecting to be passively educated. You will get a job by passively seeking interviews until someone accepts you. You will spend your career passively doing your job, and passively earning small raises and promotions along the way.

On the other hand, if your world is filled with opportunities and interests, waiting to be grabbed and explored, then that world is your oyster. During my time freelancing, I learned everything I could about my craft – I was always thinking about how to improve in technology and in business.

I tried many things that turned out to be miserable failures. I poured my heart into projects that were poorly researched, ill conceived, and turned out to be shitty. I’m really glad I did all that – I understood what I was doing far more deeply than most people in the profession do. I wasn’t just thinking about how to get through the day, I always thought about the skills I’d need in the future. What if I got a bigger client? What if I had to hire a person to help me with my growing workload?

I thought about that, and learned about it before it ever came to pass. That’s how I work on everything – I work with an eye to the future.

Foot, meet Door

I had a resume that listed my undocumented experience in a context that made sense to corporate recruiters and hiring managers. I sent it to everyone I knew, and put it on job boards far and wide. I looked for about a month, I went to dozens of interviews, sometimes up to three per day.

By the time I was sitting in the three part interview with the guy who would later be my boss’s boss, I was ready. I was primed to rock the interview because I had been practicing nonstop for a month, but I had no corporate experience. I emphasized my team management experience. I told him all about the exciting projects I’d worked on, and about how comfortable I was with all kinds of technology. I had researched the company, and I knew how I could help him achieve his goals. I set the right tone, and in his mind, he had already hired me.

The other two parts of the interview were more technical, but that was no problem. I answered most of the questions without a hitch, and for those that I couldn’t answer, I took the opportunity to explain with total honesty that I wanted this job because I wasn’t sure I could do it. I was sure there were things I didn’t know, and I was hungry to learn everything I could. I didn’t know how clustered indices were implemented in SQL Server 2005, but I damn well would find out. There was no need to inflate my knowledge.

I got that job making $75,000 base salary when I was 22 years old, in a city with very low cost of living. But I didn’t do it for the money. I did it because I genuinely believed that I would learn a tremendous amount while I worked there, and it was my plan to use that knowledge and corporate experience to jump to my next job within a year or two.


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