Big career changes ahead — Goodbye InfoSec.

As some of you know, Brady has recently celebrated his 1st birthday. It’s been a long year and as it’s worn on, my commute (two hours each way end to end) has often left me frustrated due to the lack of time with my son. More and more often, I have wondered, despite loving my current job and the people that I work with, if it was worth the time it was taking away from my family. Yesterday, as I had to telecommute due to the epic flooding that shut down Route 140 I was able to play with my son before getting him ready for bed. It was during this I had a moment of clarity: It wasn’t worth it.

After putting him to bed and discussing it with my wife, I started weighing my options to figure out a way to allow me to work near my family, make my own hours, and hopefully live comfortably. After thinking about it more and more, I came to the realization that InfoSec lifestyle wasn’t cutting it anymore and that I was essentially fighting a losing battle. I’ve always been a bit of a chaotic neutral person and thusly I came to the conclusion that the best way to get what I want is to switch sides and move over to the darker realms of the Internet. As in my old job I monitored them daily, it was easy to reach out to my former adversaries and start inquiring about positions within their organization. They were very receptive and were happy to get someone with my portfolio, so I was able to negotiate a tidy signing bonus as long as relocation costs.

Yes, you read that right, relocation. We are all moving to Estonia. This may seem like a big move, but I have always wanted to set out and blaze a new trail beyond my comfort zone, so this was right up my alley. With Brady just picking up Portuguese and English, adding Estonian on top of that will do wonders for his development. Finding a new house would be a worry, but thankfully Peeter, my new boss, has an associate, Mikhail, that was able to get me a a killer deal on some waterfront property in Hiiumaa. He was even able to get the seller to go way below their asking price! Plus, they have a very decentralized structure are fans of working from home, so I should be able to get away with only showing up to meetings a couple times a month off-island. This is an ideal situation and everyone in the Jackson household is excited.

I know this might come to a shock to some of my InfoSec friends and it may seem like I’m abandoning them for “the other team” — and I’m sorry if you feel this way. This was the best option available to me to continue working in the field I love that will allow me to be close to my family. I sincerely hope that despite now me being an adversary, we can still remain cordial and reasonable to each other and can remain friends. Of course, trusted friends should feel free to contact me if you are interested in joining me on this great adventure, as we are currently looking for people who have experience in the field and like to work in the trenches.

I’ll be chronicling the move and the adventure of emigrating int he upcoming weeks, this should be interesting on so many levels. I need to start researching how one gets an Amateur Radio license in Estonia.


  1. April Fool’s :)

  2. Ben,

    It seems a bit far for my tastes but I am glad that you will have more time with your son. I have unfortunately been out of work for about a year and a half bit I have spent every minute with my daughter. It has been GREAT! I wouldn’t trade it for the world.

    I wish you and your family the best of luck and hope everything turns out how you want. Enjoy your time with Brady and your wife.


  3. Tom, as much as I do want to spend more time with Brady and Marina, going to Estonia to work for a crime syndicate isn’t in the cards. ;)