I Am An Aspiring Snowbird

On the first Friday during my mini-retirement that I wouldn’t receive a paycheck, I found myself in Hood River, Oregon with a good friend at a garden party.

My friend introduced me as her “friend from Boston who had paid off all her debt and saved up a year’s salary so she could take a mini-retirement to travel the world and write about it.” The hostess, who was gracious, vibrant, and shall we say inquisitive, took an interest in talking with me after that.

She began to ask me a lot of questions about why in my 30s I was calling my unemployment a “mini-retirement.”

I replied that not rushing find another job after my contact expired had been intentional, which usually raises eyebrows and hers did too. I continued by saying that at the rate humans are destroying ecosystems and depleting resources, it was unlikely I was going to be fortunate enough to retire safely and peacefully at 67, as world markets may be very different at that time. I told her that I didn’t want to take the chance of never experiencing the feeling of freedom to pursue personal projects and being “time-rich”, something I pointed out that she appeared to be, which she seemed flattered by. 

She congratulated me on making what she called a “courageous choice at such a young age,” and proceeded to tell me how she was spending her retirement.

“We spend the summers here in Oregon and then we close our beautiful home down for the winter and head for Tucson, Arizona to wait out the grey rainy winters. By May, we’re back in the Pacific Northwest. I guess you could say we’re a couple of Snowbirds now, isn’t that right, Tom?” she said gesturing to her husband who nodded and beamed with what looked like pride…or smugness, or was that my own jealousy talking?

It probably was. For the last five years I’ve been plotting to be a snowbird. 

“I’m working on being a snowbird too, you know. How are you liking it?” I asked her. Turning back towards me she chuckled like Miranda Priestly but covered it up with a hand on my shoulder as she leaned down a bit too demonstrably to me standing at my usual 5”3.

“Sweetie, you’re too young to be a snowbird,” she said flashing one of those kind-looking Pacific Northwestern toothy grins that looks genuine but actually carries a jab with its accompanying words. She continued half jokily, “In fact I’ll be a little mad if you figure it out at your age because frankly, it took me my entire life to be able to ship off to warmer climates during the winters and I’m in my late 60s now!” She laughed like she had just told a clever joke and looked at me as if she would pinch my cheek or pat my head like a toddler, then asked if I needed a refill on the red wine I was drinking and disappeared into her enviable big kitchen leaving me confused and offended.

Was I too young to be a snowbird? I thought, throwing back my last sip of red wine.

Is there some rule book that says that only retirees have suffered enough 9-5 bullshit to have earned the right to migrate like geese to warmer climates when they sense the harsh winter approaching?

The Rub

I live in Massachusetts which has an average cold season spanning nearly nine months now that the climate has changed. Despite generations of tough, cold-indifferent New England ancestors, I’m not built for the cold. I can never seem to get warm and I don’t sweat much in heat anyways. My hands and feet are never warm to the touch, (many a lover has pointed out) and the idea of hurling myself down a mountain in cold, slippery snow on flat metal rods sounds like cruel and unusual punishment to me.  

When Fall fades to Winter, I slip into a depressed hibernation and feel sorry for myself going about my business trying desperately to stay warm, wishing I had the courage to start my life all over someplace where it’s warm year-round. 

But what would I do for work? I always think coiling myself up into a tight knot of inner frustration.

Over the years I’ve noticed the unhealthy and unhappy cyclical pattern I fall into as winter approaches. Sure, I could take a pill to deal with it, but it doesn’t change the fact that it just doesn’t seem natural to me to fight as hard as we do in New England to just carry on through the long winter with basic tasks. Going against your basic nature for years on end inherently will cause difficulty.  

I remember during a year of record snowfall, people still showed up to work on time, despite probably having woken up at 3am to shovel two feet of snow off their vehicles and driveways for the 4th weekend in a row just to get to work at 8:42am for the 9am Monday meeting.

It struck me as misguided Herculean show of strength to pull that off but I didn’t see that as commitment, dedication, or professionalism. I saw it as a bizarre form of martyrdom or professional masochism. Really? I thought, you literally lost sleep to get up early enough to clean your car, probably threw out your back and risked your life in these conditions to save face with colleagues you don’t even like nor will you remember in 7 years? For what, exactly? Fear of repercussion from managers who also experienced the legendary snowfall totals that month? For bragging rights so you could prove that you’re tough enough to be there at all costs to strategize about the upcoming initiative to enhance customer experience and reduce call volume?


There is so much more to live for than work.

When I reluctantly showed up late after driving 50 miles in 5 foot snow shocked and frazzled by the sheer terror, I figured everyone would be understanding about my tardiness after such a storm, but they acted as if it was just business as usual and I was late and overreacting.

That’s when I knew I was different.

I would never be a true New Englander like them because I just don’t want to fight that hard for my dayjob.

That’s when I started to plan for an alternative future of remote work.

I simply can’t understand why, in a state with such severe public transportation issues, companies were still so resistant to embracing remote work in the 2010s. There are 6.86 million people living and commuting to Boston in single-occupancy vehicles simply because they have no other option living in townships like I do outside of Boston with no easy city access.

Without the option to take any public transportation that would get me to work’s doorstep in under 3 hours each way, I was forced to pollute the earth in my 4-cylander kicking and screaming the entire time because it was so asinine that someone as low as me on the food chain still had to make an appearance to further my career when all I was doing was designing digital materials that would never be printed.

I was not curing cancer nor holding notorious corporate pillagers responsible for what they’re doing to our society and our planet and yet, my body had to be present for my manager to mostly ignore except for the weekly one-on-one she called to maintain her sense of control.

Why, as white color workers do we need to be in an office anyway? To make the company look productive? So someone can control our every move like they did with foremen in now defunct old New England textile mills that my grandmother worked in? Because connections are so important for networking?

I call bullshit. On all of it.

We don’t need to burn fossil fuels every day driving alone 100 miles a day just to make a paycheck on someone else’s electricity bill and computer. We don’t make that many human connections at the office anyway. People generally stick to their team and form cliques and habits following the same pathways to and from their desk and facilities every day. 

It’s rare for an office worker to actively reach out to make new friends. When was the last time you introduced yourself to a stranger in the cafeteria? Or scrolled through the Directory on a whim looking for someone with an interesting title to send an introductory email to?

Colleagues might be introduced to each other from other departments in an in-person meeting but that relationship then largely continues via email and instant messenger at this point anyway.

For someone like me with a daily 4-hour roundtrip commute who doesn’t want to manage people or projects, and who conducts most of her business digitally, is it really the best use of my time and talent to force me to report to an office where face time detracts from my work?

It definitely is not.

Those Damn Millennials

I had a conversation with an old friend from 8th grade whom I still see occasionally and he told me that he hated working with millennials as a middle school history teacher. I laughed heartily thinking he was being sarcastic until I realized he wasn’t. He actually thought that we weren’t included in that age bracket when we, in our early 30s, are the very first generation to embrace internet socialization which is the very thing that makes millennials different from previous generations.

I had to remind him that he used to “flirt” with me on AOL Instant Messenger using only words and web links back in the early 2000s, to which he blushed. I reminded him that we would hang out at each others’ houses and instead of painting our nails (or doing whatever it was boys did) like in previous generations, we’d all gather around the family’s computer innocently downloading illegal MP3s to rock out to while we harassed each other on AIM for fun.

We knew how to text on “dumbphones” when it was like a modern form of Morse Code your fingertips could memorize without looking while driving home from high school. We had beeper codes that meant “I Love You”, “I miss you”, ”What’s up?” We created and embraced a whole language and culture our parents had no way of knowing, which has only evolved with the younger Millennials today and yet we’re still social beings who turned out just fine with lives, jobs and children now. The same will be true for his most annoying students.

It is natural for us to connect with each other with the typed word and occasional GIF just as well as if we were gathered around the same computer sharing funny memes or snapchats. That’s why I don’t think it’s super important to physically report to an office for certain professions like mine. We’ll get to know each other via chat or video conference just as well, if not better than in person.

When you talk to somebody at work, you communicate with their personality anyway, not their body (hopefully). When you talk about someone you know, you’re referring to their mind and personality first so if their image is a bit hazy via video conference it’s fine because that’s how they’re going to end up looking in your fading professional memory anyway.

Additionally, if you don’t really have much in common with your colleagues on a personal level, interacting remotely removes that awkward obligation to physically socialize with teammates you really can’t stand.

Due to my digital upbringing, I’m confident I know how to transmit my personality and working style across fiberoptic cables. Nothing about remote work turned me off except for the sheer elusiveness of companies with open positions who saw things as I did when it came to getting work done efficiently.  

Keeping a Foot in the Door

My intention for my year-long mini-retirement was to unwind from professional strain, a symptom due to the exhaustion and anger I felt about nearly a decade of epic commuting.

To do that I would first stop wearing a watch and kill my alarm clock so that I could wake up whenever my body felt like it.

Next, I’d travel away from my routines to reconnect with my love for spontaneity and adventure and far-flung friends and family.

Lastly, I’d write about it all: the ups, the downs, the struggles, the blessings. I’d write about it so that anyone who wanted to take time for themselves between jobs to truly live, would have a look at what it’s really like to step away from building a career to reconstruct your sanity and well-being.

I told myself I was just going to have fun and not think about money or work or my career.

Easier said than done for a person who fears financial insecurity, but I told myself that when I was ready to jump back into the workforce, I would, but I would never commute like that again.

I had my sights set on a remote job, no matter what I had to give up to get it. I was prepared to earn less money in exchange for a guarantee that I was not required to commute 2 hours to the office. I was prepared to do contract work which meant I’d have to pay for my own health insurance and would have to manage my own investments.

None of that mattered. I’d handle it. As long as I could do my job remotely, I’d take it.

So I tweaked my LinkedIn profile, set it up to attract recruiters and began fielding phone calls regarding different roles that I’d be a good fit for. I took phone interviews by the pool and hung up if they only offered 1-2 days remote. I knew what I was looking for and I had enough reserve funds to support my lifestyle for a year, so I was prepared to make demands and take no shit.

It felt a little disingenuous doing this while I was supposed to be enjoying my mini-retirement on the road, but it’s hard to turn off that part of you that enjoys your career, if you’re so fortunate to feel that way.

I figured it didn’t hurt to keep my foot in the door now that I knew exactly what I was looking for.


As I stood there at the garden party people watching, waiting for a refill, my phone vibrated with a message on LinkedIn from a recruiter who got me a job in the past.

“Good News!

I think I’ve found you the perfect fit! It’s doing what you love with a fantastic, small team with an experienced leader. Bad news: There’s a salary cap and its $20k less than what you make now…but did I mention that it’s 100% remote?

Call me.

– Erica”

The hostess returned with a bottle of red wine and refilled my glass.

“So, honey, what did you do before you “retired?’” she asked, using one hand to make air quotes.

“I worked in an office,” I said not lying “designing courses for training programs. I used to commute 4 hours a day just to do that, did you ever do that for a job?” I asked.

“Four hours?!” she exclaimed. “No, I’ve never commuted more than 30 minutes to work, honey.” She paused as if considering the weight of what I’d just said.

“You poor thing” she said as she frowned and patted my shoulder with her free hand.

“That’s why I’m going to land a remote job after I feel satisfied with my time off so I can be a snowbird like you,” I said smirking at her.

“And I’ll do it before I turn 34, too. Thanks for the refill!” I said, as I raised my glass to her feeling closer than ever to my snowbird goal and I excused myself to call the recruiter back.

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