The Trunnion - Blog of Patrick McBriarty

Milwaukee or Bust?!

October 15th, 2022 - By Patrick T. McBriarty

That’s right, “Milwaukee or Bust”.  So, while not literally driving a beat-up Model-T cross-country for the promise land, echoing back to 1930s Dust Bowl days, the metaphor helps dramatize my move and internal travails to find a new home.  Temporarily living in “God’s Country” (as my cousin’s refer to Wisconsin) shifted my mindset, which has evolved over the past couple months as a post-pandemic, 50s-something.

My June blogpost “Exit Chicago” detailed uprooting myself from Chicago to try out Wisconsin while still buzzing back to the city one-day a week for appointments with Back to Natural Health and catch friends.   Living at my brother’s house gave me this option with little or no commitment and allowed a rapid escape from Chicago’s oppressive feel that spun up with Covid.  You may recall in mid-December 2021, Chicago was about to institute vaccine mandates to just sit and eat at a restaurant.  Folks were often crossing the street to avoid passing each other on neighborhood walks (for fear of the unknown).  We each endured thousands of social “paper” cuts, behavioral inconsistencies, and paradoxes surrounding Covid.  Meanwhile life in Wisconsin was refreshingly near normal, and held the promise that life in a smaller community might be better for many reasons.  The space and time in Wisconsin continued to improve my health and mental resilience (thanks for asking) and offered many additional benefits.

The interlude at my brother’s in Oak Creek, Wisconsin (just south of Milwaukee) evolved into the decision to permanently live in a smaller community.  My previous plan was to explore living in Michigan.  It became obvious I could make a significant impact in a small town or city and not have to work nearly as hard as I had in Chicago to gain traction.  Volunteering and contributing to All Hands Boatworks (AHB) in March, a 20-minute drive from my brother’s place, was already going better than I could have hoped.  They greatly appreciated my expertise, experience, and my skills which well complemented the team they already had in place.  With some distance it was clear the past several years this work had become my calling.

Nicely coinciding with my economic sense that March or April of 2022 would be my only opportunity in the near future to sell my condo and get my equity out a permanent move became ideal.  As it turned out my timing could not have been better, and the sale (at over asking) was completed with very few headaches.

My theoretical next step to explore Ann Arbor, St. Joseph, Holland and Grand Rapids, Michigan to find my ideal spot.  Past travels and sailing adventures made the eastern shore of Lake Michigan feel like ideal Great Lakes living.  Michigan seemed prettier, more lush, friendly, and more beautiful than other Midwestern states.  However, the clarion call of Teaching With Small Boats Alliance (TWSBA) and its mission to uplift kids and families by teaching building and using of small boats killed my Michigan plans.  The problem was none of the target areas in Michigan had a such a program in place.

Already having contributed to the starting-up and establishing the Chicago Maritime Arts Center over six-years, I had no interest in creating let alone initiating a startup like this on my own.  Besides, such an effort is not the best use of my skills.  I bring more value and am better fit to contribute to an ongoing enterprise rather a new entrepreneurial effort.  In additional, I was enjoying the bit I had already seen of Milwaukee and so the thought occurred…  Why not live in Milwaukee?  So, by early August I committed to working part-time for the balance of 2022 with All Hands Boatworks.

I still wanted a snowbird lifestyle to escape the winter and spend the other three seasons in or around Lake Michigan.  Unfortunately, the plans for January – March down south this winter got crushed in August.  Though I had made good progress with Back to Natural Health, but it became clear another 6-8 months consistently maintaining their holistic regimen of daily supplements and cleanses, infrared saunas, and weekly treatments in Chicago was necessary.  In consolation, I WAS feeling better and progressing week to week.  So I shifted my mindset to double-down on my commitment and building more resilience and stamina and not lose ground.  Essentially this effort is toward aging gracefully into my 70s, and for now I’m shooting to stay active and age gracefully into my 90s or beyond.  We will see…

In the meantime, I had forgotten how daunting learning a new city and meeting new friends can be despite having moved multiple times in the past.  Getting comfortable living in Wisconsin has been harder than I expected and occasionally left me feeling totally uprooted and rudderless.  These doubts and the occasional blue days had me questioning why I blew-up my 30-year life in Chicago.  In these moments my normally reliable self-confidence was shaken as twisting in my mind was a question my mother had once asked me decades ago, “Patrick, are you lost?”  And my subconscious piled-on the Bob Dylan lyric, “with no direction home.”  Attempts to flip the narrative, stay positive and embrace the feeling of being “totally” free failed.

Too many options or a myriad of possibilities bumped up against my strong sense of self-preservation, small “c” conservative sensibility, and purpose driven mindset leaving me stuck.  Add the pandemic hangover and I was uncharacteristically sitting at my brother’s struggling with jilted self-confidence and a heightened need for safety. Eventually stacking better days and time to become more comfortable with my decisions I did venture out to explore on my own terms — first in the immediate of Oak Creek area and later the City of Milwaukee.

Still I totally miss having an intimate knowledge of my surroundings, but had no real homesickness for Chicago.  This was proven week after week driving to Chicago for appointment at Back to Natural Health and returning to Wisconsin with no regrets or tinges of longing for the big city.  Don’t get me wrong, I still enjoyed visiting Chicago and seeing friends, but in leaving I was comfortable my path was elsewhere.  Further parsing my feelings, it was the local knowledge I missed and comfort of knowing what to do or how to entertain myself in my new surroundings.

While living with my brother was been incredibly helpful during this critical point in my life it was clear after about six-months I needed my own space to fully reinvent myself.  Fortunately, this sudden realization was soon solved, thanks to one of Matt’s neighbors, Missy.  I confided in her my unaddressed angst and a couple weeks later she turned me on to a second-floor apartment in Milwaukee’s Bay View neighborhood.  Bonus, the two-story duplex was in an area I had already considering as a place to live.

The following week in driving to see the apartment I felt a good vibe getting into the immediate area.  The neat little homes on tree lined streets with large hardwoods arching over the road and sprinkles of sunshine appealed to my sense of ascetics.  Two blocks from Lake Michigan the area had good energy and my sense of possibility grew as I approached the apartment on Indiana Avenue – named after the state in which I was born.  The landlords were super nice and Amy (the better half of the couple) was welcoming and long-time friends with Matt’s neighbor Missy who connected us.  As Amy graciously walked me through the space and shared a history of the apartment felt very easy, and impulsively I offered to take the apartment by the end of the tour.

Later that evening they texted me to say the apartment was mine if I still wanted it.  Of course I replied, “yes,” as it felt like a no-brainer.  The rent was reasonable and located so close to the lakefront, walking distance to South Shore Yacht Club (where I had already done some Lighting sailing this summer), and steps from the lake shore bike path it felt like an ideal place to stay for the next year, while I figure out Milwaukee.  The whole thing came together so organically and Missy was even further help volunteering her husband, John, and their 20-something son, Alex, to help along with my brother to move in on October 1st.  Additionally, the street block party was in progress that afternoon so met several of my new neighbors, who were most welcoming, and made it feel like the stars were aligned.

This is the first time on such a significant decision I totally trusted my gut and did not checkout all the options to later confirm my initial instincts.  Several times prior to this, on a certain level it also felt given Milwaukee’s small size and ease of getting around, it almost didn’t matter where I lived this first year.  The point was to commit to a place of my own and begin — making connections, learning, exploring, and get comfortable with Milwaukee for it to become my new home.

In the meantime, economically paying rent will be a good investment to buy time and remain flexible.  It makes sense to wait at least a year or two as the housing market will certainly cool off and there will be better real estate deals in the future.  Besides I rationalized six-months of rent is about equal to the real estate taxes I would have paid owning real estate, not to mention avoiding an additional $3K a year in condo assessments.

So hey, if you are in the area, stop by for a chat or “book” a stay in the spare bedroom here on Milwaukee’s south side and see what this new adventure entails.

5 Responses to “Milwaukee or Bust?!”

  1. Bob Segil Says:

    Hey Pat,

    Good going. Sounds nice. Good luck!

    Deanna and I have been on the road for 20 months now. Exploring Montana, Idaho and Colorado for that perfect town to retire to. I’m drawn to the smaller towns and particularly like Whitefish, MT. That said, we skied in British Columbia last Winter and the small town of Revelstoke was really something special. But we ain’t moving to the middle of nowhere.

    While in Coeur d’Alene we stumbled across a good sailor, a great guy and the owner of a J29 which he sails on beautiful Lake Pend Oreille. He sails out of the *other* Bayview Yacht Club. This guy and his wife bought 40 acres of land in the “middle of nowhere”. Set up a teepee to live in. No electricity or plumbing for a couple of years. And with hand tools and a chain saw he built a log cabin. We had dinner there and it was quite something. It takes all kinds.

    Anywho, it was a blast racing with him. He couldn’t have been nicer and appreciative of our Chicago sailing skills, focus and intensity. It was nice to hear compliments just like Paulie used to generously bestow.

    The people in northern Idaho are often quirky, so I fit right in. Generally they are warm and welcoming. Coeur d’Alene is one town that’s caught our interest. It’s gotten a bad rap as a white supremacist magnet. We never experienced any of this. Yeah there are lots of American flags, but there are also a lot of long-haired millennials operating cool, small businesses. The boat owner and his wife are ex Peace Corp peeps. So, there it is.

    We enjoyed sailing with our new friends so much that even after we moved onto Missoula for six weeks, we drove back to Lake Pend Oreille to race in the world famous Spud Cup Regatta. We won our section and ate a lot of baked potatoes too.

    Anyway, wishing you the best of luck. I Admire your sense of adventure. Keep it up!

    Bob Segil

  2. Richard Cahan Says:

    Hi Patrick. It’s wonderful that you have made these bold moves to start a new life. Always great to read about you and your journey. To health and future adventures. Rich

  3. Cynthia Ogorek Says:

    Hey, Pat,
    Congratulations on taking the “big step.” I relocated from Chicago’s Southland to Danville, IL, three years ago. I have never regretted it. “Illinois Is My Happy” place as the sign in my sunroom attests.

    These small-to-medium-size towns have all the amenities and next to none of the aggravations of big city life. I’m so glad to be here! Danville has a symphony orchestra, a light opera company, art league, tons of county, state and local parks, a National Scenic River [the Vermilion], garden club, lots of blue sky, a superb local library, an assortment museums, and very laid-back residents.

    What’s more, I’m close enough to the “old sod” that I can see friends and relatives within a couple of hours. And I have had more of them visiting me since I moved than I ever had in my old place!

    Hope you continue to enjoy your new place.

  4. Patricia Skalka Says:


    Welcome to Wisconsin!
    I moved to Milwaukee three years ago and it’s feeling more like home every day. Not so much a small big city as a big small town. I miss the Chicago pizzaz, the spectacular views along LSD, and the active writing community but enjoy the MKE slower pace and convenience, being close to family, and having the same Great Lake at the shore. I’m on the north side near the old water tower and Bradford beach. A great walking area. We should meet for coffee.


  5. Kevin Ratigan Says:

    Hi Patrick, good to see your voice again. Congrats on the new apartment in Milwaukee. Looks like a sound decision that will strengthen your confidence. New opportunities to find your community. Close to the water with all the urban amenities that we love. Hope we get a chance to visit soon.

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