HuskyHacks On Hiatus – I’m Leaving MIT to Hike the Appalachian Trail

Is it particularly strange to start a blog, ready to fill your little corner of the interwebs with all of your weird and wonderful (and probably wrong) ideas, only to have the first post talk about how you’re going to be leaving soon? Maybe, but I don’t care. I’m Matt and this blog is going to chronicle my fail-forward attempts at becoming a better cybersecurity practitioner. Or, at least, it will chronicle that after I return from the Appalachian Trail in late-summer of this year.

Wait, let’s back this up for a proper introduction. I’ve been steadily chipping away at building a knowledge base of IT and information security since about 2012. I enlisted in the military and was assigned as an IT specialist supporting the air wing of the Marine Corps. I also trained as an information security specialist and intelligence analyst during my tour.

I completed my enlistment and moved home to pursue my degree at Northeastern University in Boston, MA, where I found undergraduate life to be a nice break from the grind of the military. But during my final year at Northeastern, chance would have it that I stumbled into one of the coolest jobs that I could have imagined; I applied for a co-op and, in turn, was offered a full-time job at the MIT Lincoln Laboratory as an embedded cybersecurity analyst in its Space Systems and Technologies division.

“We won’t stop you from applying for the co-op if that’s what you really want,” the HR rep told me, “but your military experience in IT and intelligence analysis makes you a good candidate for these other full time positions. You don’t have to decide right away.”

I decided right away anyway.

Chock full of enthusiasm but lacking even basic technical acumen, I accepted this position. I didn’t feel ready at all; to this day, I still feel bouts of imposter syndrome regarding my level of competency for the work that I do. I’ll save that discussion for another blog post and talk about how I deal with that, but for now just know that it was tough for me to walk around the halls of the Laboratory and feel like I shouldn’t have even been there in the first place. This led to a tough adjustment from the relative ease of undergraduate life to the high-stakes of the cybersecurity of Laboratory assets.

My main areas of responsibility, among other things, included the cybersecurity of the MIT Haystack Observatory. The Observatory has two world-class radio imaging telescopes that are used in radio astronomy and classified Department of Defense research efforts. These telescopes are multi-million dollar projects and, somehow, I was the lead embedded cybersecurity analyst assigned to safeguarding them. This can’t be life.

I realized that I would have to get good. And thus began a two year plus journey to gain any amount of competency that I could scrape and claw to in this fascinating, complex, and fantastic field. I completed my undergraduate degree while working full time at the Lab, studied on nights and weekends, attended certificate courses and conferences, and even took up arms with a Kali Linux image to begin the quest to achieve OSCP (I failed my first exam but, again, this is a post for another time). And while I have a long way to go, I can’t help but feel some amount of satisfaction with how far I’ve come.

That’s the beauty of this field – everyone has a long way to go, but you’ve always come a long way from where you started. Even if you started yesterday.

On January 2^nd, 2020, fresh from the holiday break, I called a meeting with my supervisor and manager at the Laboratory and gave them the news; I would be leaving this year in February to attempt a thru-hike of the Appalachian Trail, something I had dreamed about for many years. They were perplexed, to say the least, and asked me if this had to do with the culture, workload, or quality of life at the Lab.

And the honest answer to this was no, this was a deeply personal decision and has very little to do regarding my satisfaction with working at MIT. I loved working at the Laboratory and could easily have stayed much longer, but I can’t ignore the feeling that I absolutely need to do this. And additionally, this year has presented my partner Emily with a fantastic set of potential opportunities to pursue her PhD in the fall. So knowing that I would be moving in September anyway, and that a thru-hike generally takes about five months if one starts in Georgia heading north, it was clear to me that the stage was set; I’d give my notice in January, prepare to hike in February, and then be on the trail starting in early March. Weather and bodily health permitting, I will finish in midsummer to get home just in time to pack up our stuff and move.

The academic community recognizes the value of the sabbatical; it is an extended break afforded to seasoned academics to allow them to withdraw, reflect, ponder, and return with a reinvigorated sense of purpose. The paces of the world I’m leaving and the one I’m stepping onto could not possibly be more different. I expect this is going to be an adjustment. It’s also hard to step away from your career when you feel like it is starting to catch fire, but even though it’s compelling to stay and keep working on my craft, I know that all of this will always be here when I get back.

Can the same be said about the Appalachian Trail? Maybe, but I fear not forever. So before its pre-historic magnificence is erased from the Earth, I’m going to go see it with my own eyes.

I’m Matt, and I’m HuskyHacks (or HuskyHikes?). Thank you for reading and please stay tuned!