Reflections on Boston

It’s hard to believe that last week I was in Boston, knee deep in the history of the city and the exploration of a place that has held my heart since I was 14. (And also, since we’re all friends here, and I’m being honest – an exploration of myself, and how I stand on my own two feet.)

Coming back from the trip, I’m still glowing a bit from this self-discovery – as well as mentally packing my bags and planning my next adventure. There’s so much I learned about myself throughout the visit, and I don’t want to lose a bit of it – so I figured I’d write it down, for my own memory (but also in case anyone reading this is curious about traveling solo).

LEARNING ONE: I am capable of more than I could have ever imagined.

Traveling on my own was the ultimate crash course in self-reliance. I’ve always considered myself to be a pretty independent person, but nothing truly prepared me for stepping off that place and realizing, no one was at the gate to meet me. No one really “cared” I was here. I had no plans, no obligations for an entire week.

I travel a fair amount for my day job, so getting off a plane and through an airport alone is not too uncommon. But those solo jaunts were always quickly capped off with client visits and work obligations. Here, in Boston, instead – it was me and only me, for that jaunt… and the next seven days.

And I liked it way, way more than I thought I was going to.

Not only did I have the luxury of only doing what I wanted to do on the timetable that I wanted to do it, I was also put to the test – navigating a new, strange public transportation system and a new, strange city, opening my eyes to new and exciting things around me (even things that were – gasp! – not in my guidebook), and remaining open and social to strangers, especially when going out at night. Those chats were some of the highlights of my trip, and they would never have happened if I’d closed myself off due to fear… or if I hadn’t gone out solo at all!

Not that it always went smoothly! I discovered quickly that without the lake as a reference (Thanks, Milwaukee and Chicago!), I have an impeccable ability to get lost and walk 10 minutes in the opposite direction… even when looking at the Google map. (Oops.) (Live and learn, right?) That being said, by the end of the week – I became much more comfortable in the walking city that is Boston, and even managed to make it from the North End to Beacon Hill with minimal phone checking.

LEARNING TWO: Tuning into the world is an eye-opening experience.

During my time away, I didn’t touch my headphones from the second I landed in Boston until my morning commute two days after I got home. As someone who’s basically attached at the hip with this piece of tech (phone-keys-wallet-headphones is the frequent refrain when leaving the house every morning), this time in silence and, well, immersion is unheard of.

I’m a person who would’ve previously told you that I was obsessed with background noise. I don’t necessarily need a fan or some sort of white noise machine going at all times (although I gotta say, I don’t hate it in the office), but it does drive me crazy when I’m at home with another person – and it’s silent. We’re not talking and there’s nothing going in the background. I love to listen to music or a podcast on my commute, during the work day, at home while cooking dinner, heck – even in the shower or when falling asleep.

And that’s not counting leisure time with TV in the background, whether I’m “watching it” or not.

But while I was in Boston, I pushed myself to not “tune out” my surrounding and instead tune into them. I kept my headphones with me for emergencies but didn’t use them once – although I must admit, I was tempted during lunch on my last day. Instead, I people watched, peered into shop windows, soaked in the architecture, and wandered around to my heart’s content. And honestly, it was magic.

It leaves me wondering – I wonder if I treated Chicago with the same wide-eyed curiosity and enthusiasm, would I love it as much as I love Boston?

I’m not certain that’s the case (I mean, Boston’s pretty perfect), but it’s something to consider. And dare I say – worth a try?

LEARNING THREE: Five Days Solo is the Perfect Amount of Time (For Me)

When I started telling people that I was taking a trip solo, I got a fair share of negative response – my mother was worried about my safety, my friends thought it was ridiculous, my coworkers thought me strange (although, what else is new?). But the resounding fear was – wasn’t a week too long? What if I hated it?

To which I gotta say: rude. What are you implying, that I’ll get sick of myself? (Ok, if we’re all being honest, that was one of my fears too.)

So yes, I was tentative about going solo, and I was tentative that a week was ambitious and perhaps “too much time,” but I also felt confident that I’d like it. And clearly, like it I did.

But liking it – nay, loving it – aside, I will admit that a six full days was just one day too long for my liking. By the time Friday rolled around, I was tired, slightly overstimulated, way out of my routine and normal schedule, and ready for an afternoon at home. Which is when I learned – cut while you’re ahead, and leave the trip wanting a little more. Five days was the perfect amount of time: a weekend would’ve felt too short and any longer I would’ve gone a bit stir crazy.

Not that I would trade my Friday night for anything – that night was awesome, and a perfect send-off from this city that has my heart.

Armed with this knowledge, though, which was arguably the goal of this trip (learning more about myself and how I stand on my own two feet) – I am better able to plan future trips and make more concrete goals for the future. Knowledge is power – and I’m now armed with another little bit of it.  

LEARNING FOUR: A New Friend is Right Around the Corner

Tuning into the world and being open to strangers turning into friends were highlights of my trip. Chatting with locals in bars led to some fascinating discussions, great food recommendations, interesting touring sites, and (I hate it, hate it, hate it when people say this, but I gotta do it) an expanded worldview.

Overall, I’m a pretty shy person. I have become much more confident and outgoing as I’ve aged, but my entire childhood could easily be defined with a photo of me on a couch, reading or surrounded by art supplies; as I like to tell people, I was an indoor kid. 100 percent.

But as I get older, I do my best to push myself out of my comfort zone – and a large part of that is chatting with new people, making friends, and being comfortable doing things solo. (Helloooo, Boston trip – complete with solo travel, solo touring, solo eating, and solo drinking.) Every time I enter a social situation alone, I am gripped with anxiety…

…and nearly every time, the situation turns out so well, I meet someone interesting, and have the best time.

It’s these positive experiences, one after another after another, that make doing things solo less scary – and they’ve introduced me to people I would’ve never otherwise met or experiences I would’ve never otherwise had. (I mean, would I have found a tiny late-night Italian deli that was cash only and the size of my living room? Probably not, but celebrating a new friend’s birthday – and eating that calzone – are equally unforgettable.)

In honor of continuing this adventure here at home, I’m going to make more of an effort to step outside of my normal Chicago comfort zone – and instead of rushing around my day-to-day life all the time, slow down and do things solo once in a while. I’m sure I’ll find interesting people along the way.


SO, if you hadn’t picked up on it yet – I am completely, unequivocally hooked on traveling solo! I had the absolute best experience and can’t wait to try my hand at more adventures. I’m already saving and planning for my next trip.

It is so freeing not to be gripped by the fear of traveling solo, and I no longer am naggingly curious but paralyzed by the anxiety that I would actually hate it. Because, it turns out (and I know it sounds dumb), I really like myself – and I really like spending that much time pushing my comfort zone and spending quality time with me, myself, and I.

With Boston checked off my list, and traveling solo officially checked off my 25×25, I’m debating my wanderlust heart and the question – where to next? Part of me wants to push for a trip every month, but I’m not sure that’s realistic with my budget, work-travel schedule, and family commitments. (Plus, start small right? I can always make monthly trips a goal in the future.)

So for now, I’m committing to one solo trip (whether that’s a weekend, a long weekend, or even longer) a season. Winter, obviously: Boston. So that leaves Spring (March-May), Summer (June-August), and Fall (September-November). Current cities that have my eye: Austin, Dallas, Moab, Nashville, Sedona, Portland (the Maine one), Louisville, Santa Fe, New Orleans, Savannah….

Ahhh! So many places, so little time. So glad I’m content flying solo.

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