Gandalf the Grey arrives in the Shire to recruit a Hobbit burglar.

Dwarves, men, elves… all manner of folk immediately discount the little Hobbit, even Gandalf is unsure about the adventure in store. But soon they all discover just how brave this little Hobbit is and how far he’s willing to go for relative strangers:

“I have a home. You don’t have one,” Bilbo tells the dwarves who have been turned into refugees by a rampaging dragon. “It was taken from you and I will help you take it back if I can.”

I’ve always liked the Hobbits the most. So too, did Gandalf: “I've found it is the small things, everyday deeds of ordinary folk that keeps the darkness at bay. Simple acts of kindness and love. Why Bilbo Baggins? Perhaps it is because I am afraid... and he gives me courage.”

All the Hobbits knew one another, they treated normalcy with an irreverence that made everything a spectacle, and they loved eating so much that they required seven meals a day: breakfast, second breakfast, elevensies, luncheon, afternoon tea, dinner, and supper. I could thrive as a Hobbit, I’m sure.

Ignoring the fact that I am 6’4”, I resonated with them and their more simplistic way of life because of where I was born and raised. Growing up in the Upper Peninsula of Michigan (UP) has been a blessing and a curse in many ways. Much like the Shire, the UP is a quiet and rural swath of land.

16,377 square miles make up the only land I’ve ever truly known as home. I always wished that a Gandalf would arrive outside my door and whisk me off on a grand adventure of my own. If you know me at all, you’ll know that I often joke that I’m “a city slicker who’s been stuck in the country his whole life.”

Obviously, that’s a statement meant to be entertaining more than it’s meant to be accurate; but it does shed a light into the world I find more enticing.

I am a guy who likes symphonies, theatre, musicals, exploring museums and libraries, and having vast restaurant options. Some of the happiest weeks of my life were the weeks I stayed in Green Bay, Grand Rapids, Milwaukee, Chicago, Boston, Orlando, and Dallas (to name a few). The exposure to a more varied and lively life gave me jolts of energy that’s naturally harder for me to find in my current, comfortable environment.

I discovered in those wonderful weeks that my extroverted self would benefit from a lengthy sentence spent in a big city.

—

I still remember the day I learned that the Business Professionals of America (BPA) chapter I was president of had won first place in Michigan for the Video Production competition.

As a result of our victory, we had earned the right to go to Boston for the 50th BPA National Leadership Conference.

I was ecstatic. I was so giddy with excitement as I spent the next couple of months with the rest of the club fundraising and planning out our week in Boston which was set to happen in early May of 2016. The time just flew right on by!

We’d get to go to Fenway Park. We’d take a historic haunted tour around Boston proper. We’d go out whale watching. We’d get a special BPA member-only concert with fabled band X Ambassadors (consequently one of my favorite bands ever). We’d get to test our mettle against the best and brightest from all over the country. We’d get to network and explore life in a city. We’d get to eat lots of AWESOME FOOD!! I’d even get to have my first-ever lobster dinner.

It was almost perfect…

—

My grandfather passed away a few days before I was set to leave. It was sudden. I was torn, and unsure if I should leave. Then I looked at the little note he gave me a few weeks prior and the hundred dollars. “Good luck in Boston, Steven.” he wrote.

So I wrote a eulogy on Facebook:

Grandpa Roger was a ‘one of a kind’ character, and he taught me a lot.

One of the greatest lessons I learned from my grandfather was to never lose your sense of humor.

I don’t remember a time that he was not full of smiles and laughs. He had a lewd (yes, lewd) and sarcastic sense of humor that cracked everyone up.

Whenever my ma would take my grandparents to town, I was often there. My ma would be busy with Grandma (a story for another time) while Gramps and I would chill in the car, at McDonald’s, or go for an adventure of our own.

He would tell me stories, make remarks about others (often quite comically), and/or complain about the women (My ma and Grandma) taking too long. “They must be buying the whole damn store!” he’d say with mock anger.

I will miss those moments, but most of all, I am just going to miss my Grandpa.

Then I got on a plane and flew to Boston.

It was everything I dreamed of. I loved every second of it. I just wish I would’ve been able to share stories of what I’d experienced with my beloved Gramps.

After that trip, I realized that I could thrive in a place like that. A city with a million things to do and a world of energy for me to tap into, I could really find my best self out there.

I endeavored to take advantage of any college opportunities to get out into the wider world and prepare myself (mentally, financially, and physically) for a potential journey into the concrete jungle someday soon (my original target year was 2024). I had been working towards renewing those experiences ever since.

Then Covid-19 hit.

—

All the experiences I had mean nothing in a Covid & Post-Covid world.

My desire for comfort was fading before Covid, but it’s not fading anymore.

Now I am grateful I’ve had the shelter and security of the Yoop. I am grateful that I am employed in an industry currently enduring the Coronavirus. I am grateful for the fact that my family has only felt moderate economic and virtually no medical impact from this pandemic (so far). Furthermore, those were all experiences:

I had as a straight, white man, which allowed me the power of the Ring.

I had a strong family and friend support group around me, which was like having my own Fellowship around to protect me.

I had been granted purpose through official college club activities, which gave me a Quest to make the most of my time there.

I’d say I’m still intended to be a city slicker someday but maybe I wasn’t exactly “stuck” in the country this whole time.

Maybe there was a little more “luck” involved in the environment I was born in.

Maybe I’m right where I am supposed to be now, and as long as I keep pushing myself then I think my path will reveal itself in time.

Maybe I am a Hobbit because I was born in the Shire…

P.S. I wrote this story originally on Medium but I can’t keep up with a million different platforms so I decided to share this masterpiece on here.

The rundown will be back next week. Thank you for reading (and/or listening)!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit stevenlippold.substack.com