Should I take the jump and join a large company or small startup?

Two Paths Diverged in the Woods

Should I take the jump and join a large company or small startup?

I’m at that stage in my career where I need to take a big jump and get a job with a large company or exciting startup. I’m an MCSE+Internet and an MCT. I’m good at my job as an NT admin working with IIS, Proxy Server, clients (Windows 95/98/NT Workstation), and database design and implementation (thus far, using Access). I also do some Web design (database-driven using Active Server pages and Access/SQL on the back end). I’ve completed a Cisco router course, but I haven’t had any production experience on Cisco yet.

My present project is ending, and I either need to look for another job or go back to school for something in demand, like Windows 2000, Cisco (CCNA?), or a database administrator. What would be the right career move for me at this stage? It seems that there’s an endless list of skills I should possess: Linux/Unix, Cisco, Microsoft Site Server, SMS, SQL, hardcore Exchange...
—Brad Suneja, MCSE, MCT
Senior IT Systems Administrator
Walnut Creek, California
Great River, New York

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I’ll bet most of us, those of us in the U.S. anyway, took American Literature in high school, which means we read Robert Frost’s poem, “The Road Not Taken.” You remember, “Whose woods these are I think I know…” about two paths diverging in the woods. One of the most frightening moments we come to as adults is having to choose. 

Some choices are trivial: If I choose vanilla ice cream instead of chocolate, who cares? Anyway, it’s a non-exclusive choice because I can always have chocolate tomorrow.

Career choices, on the other hand, are neither trivial nor non-exclusive. When you look at all the things you could be, whether professional wrestler, dude ranch cowboy, or IT professional, one choice excludes the others—at least for some substantial period of time. One thing I hear in your question, Brad, is that there are many technologies you want to be good at. As Greg points out, however, unless you want to be a generalist (jack of all trades, master of none) you need to make a choice and commit to it.

Fear arises because a choice, for the most part, excludes all the other known possibilities, but even more so because you might be passing up future possibilities, like the next hot thing. Well, you can dismiss that fear right now because no one knows what the next hot thing will be. Take an example from the past—you could have committed your future to video-on-demand. If you remember, Oracle and Microsoft made a big deal about this a few years back.

The point is, you have to specialize to get ahead, but your choice of specialization should be based on three factors: 1) what you like to do, 2) what you have the ability to do, and 3) what you can do that makes you attractive to employers. With regard to Microsoft technology, specialization can either be intensive or extensive. Intensive involves drilling down into some aspect of Microsoft technology. Extensive complements your Microsoft experience with something else, like Cisco or Linux.

It sounds like you have some background in database technology and Web thingies. To me that spells e-c-o-m-m-e-r-c-e. Is there a demand for that right now? To quote one of my favorite beer labels, “Ya, sure, you betcha.” Again, the point is to build on your strengths. Also, what kind of company do you want to work for? End-user? Consulting firm? This will help further determine what else you need.

So you’re not a specialist yet, but you know you need to be. Being a good specialist means having the knowledge and experience in your particular technology. You have some knowledge and some experience, but it doesn’t sound like you’re at the specialist level in any of them. Gaining the knowledge on your own is relatively easy but expensive; gaining the experience on your own is nearly impossible. My suggestion at this point is to find a company that values what you already have and that is willing to invest in making you the superstar specialist they need. Not easy, but it can be done.

Oh, and I completely agree with Greg’s comments on large company vs. exciting startup. Assess your risk tolerance carefully. Also, consider where you’re located and whether you want to stay there. Some places just aren’t great incubators for technology startups. Some final advice: Startups usually don’t have the time or the resources to “bring someone along”—they need the experienced pro. Perhaps a stint at a larger organization would give you the seasoning and intensive experience you need. Then, after you’ve maxed out your 401(k), you can hitch your wagon to a startup. Good luck!

About the Author

Steve Crandall, MCSE, is a principal of ChangeOverTime, a technology consulting firm in Cleveland, Ohio, that specializes in small business and non-profit organizations. He's also assistant professor of Information Technology at Myers College and a contributing writer for Microsoft Certified Professional Magazine.

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