My post about my 6 month job search generated some attention and conversation. The comments helped me clarify some of the more specific lessons I’ve learned recently; or that I knew but were reinforced by the experience. After taking time to organize them into a somewhat coherent structure, I’m ready to share. Here’s the first lessons on the list.

As always, if you have opinions, corrections, or experiences you want to share, please do so in the comments below.

I get this question (“should I start looking now?”) a lot, both from people fresh out of school or boot camp; folks who are in their first or second job but aren’t sure whether they should make their next move; and people who have been working at the same place for a while, but wonder about the color of the grass beyond the fence of their organizational borders.

I tell everyone the same thing:

It’s never a bad time to look around the airplane and check where the exits are located and the parachutes are stored.

As far as I can tell, there’s nothing to lose by semi-seriously applying for jobs that look interesting and seeing where things lead. At worst, you’ll find out a job you’re not a good fit for or a company where you wouldn’t want to work. At best, you’ll know your value in the market and have a flattering offer in hand.

“No, Leon. The worst is that I apply, someone blabs, and I lose my job.”

Look, I’m not an employment lawyer, but if that happens, it seems like you might need one, because that kind of sh… tuff is patently illegal. Yes, it’s a hassle nobody wants or needs. But it’s also incredibly uncommon. The risk of taking out production with your next change control is significantly higher.

The secondary benefit of applying often – at least once every 6 months but better if you can swing it once a quarter – is that you keep your interviewing skills sharp in a low-stakes situation. If you bomb the interview, you still have your current job and nothing is lost. But even if you bomb, what you’ve gained is valuable insight into what happened, and why, and how you might approach that situation different.

It’s hard to understate the value this mental preparedness has when you’re in a situation where you NEED (or really really WANT) the job you’re interviewing for. Being a veteran of 4 interviews a year, you enter each conversation with a set of stock answers to common questions. Every question from every interviewer feels less like an surprise quiz, and more like a conversation. The calmness and confidence this instills can make all the difference.

“That’s a pretty fairy tale, but what happens if my company finds out I’m interviewing? Am I just supposed to tell them I’m doing it for fun?

Yes.

To be honest, I have started telling the companies where I work that I do this, up-front, just to avoid surprises. I’ll admit, this is a HUGE function of the privilege I carry and I know it. Please use caution.

That said, I tell them for a few reasons: First, I often interview because I mentor folks who are looking for jobs and I want to be able to talk about the interview process credibly.

Second (and this is the more controversial part) if my interviewing makes my employer nervous, it says more about their feelings of how I’m being compensated than it says about my loyalty to the company. Again, I know how risky that attitude is, and caution you to carefully consider following in my footsteps.

The upshot of all of this is that if you are wondering if it’s time to interview, it probably is. I’d love to hear what you think in the comments below.