I’m Shipping Up to Boston

Three days ago I delivered a letter of resignation to my boss at the big telecom company where I’ve worked for the past six years. I’ve accepted a new job as a technical writer at a startup ISP in Boston, and I needed a few days to process my thoughts on the change.

Out with the old…

When I started working at the big telco back in 2012, I had been recently laid off from the advertising agency I worked at for five years after they had lost one of their major clients and 30% of heads were cut company-wide. I still had my side-gig writing for Lifehacker, but with two kids, a wife, and a mortgage, I needed to find full-time employment quickly.

An old friend from high school got my foot in the door, and the hiring staff manager had read my work at Lifehacker. I started out as an entry-level analyst in the Network Operations Center (NOC), watching equipment alarms on a display in a darkened room on third shift. After a little over a year, I worked my way into a network analyst role in the VoIP NOC, learning a lot about networking, telecom, scripting, and UNIX.

Fast forward another year and I’ve started a Dungeons and Dragons game after hours with a couple of work friends and several higher-ups at work–the same staff manager who read my work at Lifehacker and a Senior Director who needed someone to rehaul their organization’s postmortem process. I end up getting a promotion and spend three years writing over 2,000 Root Cause Analysis investigations.

This is the most evocative image search result for “telecom equipment” so I’m going to use it even though I’ve never done anything relating to satellites

Six months ago, I finally work my way into a position where I get to do work that is more meaningful and exciting–working to brainstorm the best methods to improve communications and collaborations within the entire Engineering division (1,400 or so employees) where I created training videos on various software platforms, acted as a project manager, and had a lot of fun lecturing executives on why email and meetings are horrible. I was enjoying my work and not looking for a change, but my former boss, the one who hired me from the D&D game, was now at a new company in Boston and wanted me to join him.

During the month of December, I went through a few phone interviews and the week before Christmas, I was flown up to Boston and went through a battery of six interviews in three hours. I had come down with a wicked case of laryngitis the day before and sounded a bit like Louis Armstrong, but plenty of coffee and perseverance saw me through and I felt I had done well in the interviews. I had six hours to kill before my flight left for home, but I was so miserable with the cold, I just took the subway back to the airport and crashed in the terminal until my flight left. Instead of exploring the culinary delights of Chinatown as I planned, I instead had a cheeseburger at the airport Wendy’s.

Hopefully I won’t need to chuck tea in the harbor to perform well in the new gig

I received the verbal offer last Friday and the formal written offer on Monday. I’m going to be in charge of overhauling the technical documentation for the entire engineering division of this much-tinier company. They’ve only been in business for three years, but they’re already providing internet service in 7-8 cities and the company’s future looks pretty bright. I got a pretty good offer that includes stock options so I will have a lot of skin in the game to make sure I help continue their meteoric rise.

It’s kind of strange to process my feelings at leaving the old company for new one. When I gave my boss my notice, I picked the worst possible day–there was a major (14%) layoff, and I could tell the layoffs were putting weight on his conscience. Nevertheless, I persisted and went forward with my resignation. He was extremely gracious, agreeing with me that he would have taken the same offer, asked me to help recommend someone who might be able to fill my role, and offered that if this new position didn’t work out for whatever reason that I should call him first the next time I’m looking for a new job. I’m really going to miss working for him, and I hope we can continue to chat back and forth where we nerd out on productivity and tech gadgets.

I told a friend it felt like I was saying to my old company, “thanks for providing a living for my family for six years, but now I’ve grown beyond you. Nothing personal, I hope we can still hang out maybe, sort of, not really“. I’m going to keep in touch with many of the great coworkers and managers I’ve had there, but I’m glad to be leaving the company behind.

…and in with the new

The new company has a startup culture, which is both good and not-good in various ways.

The company headquarters is in an old historic building in downtown Boston where everyone works in an open office setting, even the VPs sit out with everyone else and are also wearing hoodies and jeans, and there’s pretty good coffee and free beer and wine. They say you have unlimited vacation time, but that’s almost always code for “you’ll have so many responsibilities that you’ll never have time to take a vacation”. That’s all fine, I know what I’m getting into. I know how to figure out what matters and what doesn’t, create systems to produce what is needed, and figure out how to carve out time for myself. I’ve been doing that for years.

I don’t have to move to Boston, thankfully (that was one of my conditions laid down with HR at the first interview). I will work remotely from my home in South Carolina, and one or two weeks a month, I’ll be flown up to the office in Boston. This will be my first time doing much work travel, and at this point, I’m very much looking forward to it. I’m looking forward to being able to get up and have my morning routine before stepping out of the hotel and walking to the office, working for the day, and then getting to know Boston. I’ve never lived in a metropolis before, I don’t really want to, but it’ll be nice to get to know what it’s like to live in a big city in bite-sized doses. It’ll be hard on my wife and kids with me away (it’ll also be hard for me to be away from them), but we’ll survive, and I’m honestly looking forward into having a dichotomy between solitary days on the road where I can spend time writing in a cafe after work or going to museums or plays and my normal family life at home.

It’ll probably be tougher than I’m expecting it’ll be–there will be times when I’m sure my wife and I will resent each other a little–when I’m stressed from work and she’s stressed from her work at home and we end up taking it out on each other–but I’ll also be home with them for the majority of the time and we’ll have the freedom to go work from anywhere when I’m not on the road.

All in all…

It’s a change. A pretty big one for me, anyway. I’m looking forward to it, and I know it’s not going to be all sunshine and roses, but it’ll be a worthy struggle that will hopefully bear fruit on multiple levels. I’m hoping to take you guys on that journey with me if you’re interested, otherwise I’ll mostly just keep talking about books, writing, and tech stuff.

In case you’re wondering about the post title, educate yourself this classic Celtic Punk song:

I’d also be remiss if I didn’t mention another song, Boston and St. Johns, which was the first dance my wife and I had at our wedding. It’s the song of a sailor heading out to sea and convincing his love that he’ll be back before long because “there isn’t too much ocean between Boston and St. Johns [Newfoundland]”. I’ll be expressing the same sentiment to my wife for the foreseeable future, so I thought it’s appropriate, and I’m always up for introducing people to Great Big Sea:

3 thoughts on “I’m Shipping Up to Boston

  1. Use the T to get around (Boston drivers are way worse than SC ones!) and don’t be afraid to venture out of Boston to sample the history outside the city. (I particularly like Salem!) The weather will be different, of course, especially being right there on the water. Dress warm until spring!

    I grew up just southwest of Boston and have family to the north so I get to go back every so often.

    Congrats on the new job! Tikatu


    1. Thanks, Tikatu, those are great tips!

      I’m definitely not driving in Boston–I’m stoked to be able to ride the T, and if I end up over the weekend in Boston, I’d love to go explore Salem, Concord, or go visit Maine.

      Dressing warm is on the agenda! I need to get extra long underwear, wool socks, and a real coat.


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