life management

Why I Left Portland and Moved Back to Milwaukee

Living on the West Coast of the United States is a dream for many. Temperatures are mild, nature is accessible, and the food is incredible. So, why in the hell would anyone ever leave the West Coast?

Well, I’ve left the West Coast twice in my lifetime. I grew up in Southern California—I spent ages 2-20 in San Gabriel Valley—and I moved to Texas in December of 2001. Most recently I spent 6 years in Portland, Oregon and moved back to Milwaukee, Wisconsin…where I lived from 2009-2014.

In other words, I moved to Texas right after 9/11 and I moved to Wisconsin in the middle of COVID-19. These are two of the most tragic and impactful moments I can think of in my lifetime. But, they are NOT the reasons I moved away from the West Coast.

Deciding to Make the Move, Then COVID Happens

Because of the timing of my Portland-Milwaukee move, a common reaction was: “I hope you didn’t have to move because of the Coronavirus situation.”

I can tell you one thing with absolute certainty: Now is not the time to pack up your shit on a whim and move across the country. This is one of the most uncertain times any of us has ever experienced, where everything rapidly transpired on a global scale.

Moving turns your life upside down…and the COVID situation has basically turned us all upside down, inside out, and spun us around. But, sometimes you just have to pack up your shit and move.

(And if you do have to move, here are some Coronavirus moving tips I shared to help you know what to expect and how to plan.)

moving during coronavirus

Moving across the country takes a lot of deliberating and planning. It’s expensive and disruptive, so it’s important to talk things through before making such a big effing decision.

Mr. H and I aren’t spring chickens anymore. Uprooting your life as you get older is less about the next adventure—it’s more about being strategic so you can live the life you really want.

Mr. H and I started talking about leaving Portland in the summer of 2019. Once we knew we wanted to leave, it was a question of where we wanted to move to. Because our business, Superneat Marketing, can operate from anywhere in the world…therein lied the problem of choosing a new home base.

Milwaukee was nowhere on our radar, because we had already lived there before. We wanted a fresh start in a new place. Here are some of the places we seriously considered moving to:

  • Valencia, Spain
  • Austin, Texas
  • Charleston, South Carolina
  • St. Petersburg, Florida
  • Chicago, Illinois

…yet, we ended up back in Milwaukee, Wisconsin.

Because of the Coronavirus pandemic, I can’t tell you how relieved I am that we made that decision. Moving to an unfamiliar place, where we didn’t know anything or anyone, would have amplified stress levels to the max. In Milwaukee, we knew how to live there.

And, even though we can’t see our family and friends because of the quarantine, having everybody within a few miles feels a lot better than feeling completely isolated.

bird sculpture milwaukee

Why I Left Portland

Okay, now that we cleared up the COVID moving situation, it’s time to get back to the real reasons for leaving the West Coast and coming back to the Midwest—which most people in milder climates tend to think is the North Pole. (It’s not.)

Friends and acquaintances were shocked that I left Portland. “But, you love Portland so much. I’m surprised that you left.”

For years, I was one of Portland’s biggest champions. Most of those years were spent during the honeymoon phase, right after we moved there from Wisconsin.

It’s Gonna Cost You

Living on the West Coast is not a cheap date. Portland used to be one of the more reasonable cities to live, until everybody and their dog moved there. Mr. H and I contributed to this major population growth spurt, having moved there in 2014. But, we didn’t understand our new financial reality until we got settled.

Cost of living in Milwaukee is very, very kind. When we moved to Portland, we more than doubled our cost of living. Rent was the biggest whopper. Taxes were higher, along with the cost of food and healthcare.

Although the job economy was healthy, a ton of ambitious professionals are competing for these jobs so they too can make ends meet. We moved to Portland on one salary, which is not a viable option even in the short-term. I knew I wanted to pursue a marketing career and I applied for almost 100 jobs before I landed one.

To Survive, You Have to Hustle

I like to say that Portland is where I learned how to become an adult (yes, I’m a late bloomer at 38). I also like to say that Portland is where I earned my MBA through life experience. Portland was where I learned to hustle.

Unlike living in Milwaukee, I needed to make a higher income to survive. I used my writing skills to my advantage and became a content marketer, which was a new marketing role at the time in 2014.

I worked for a marketing agency, a tech startup, and eventually, started my own content marketing consulting business, Superneat Marketing with Mr. H. I juggled full-time jobs while moonlighting as a freelance writer until I took a leap of faith, quit my salaried job, and ran my business full-time.

I got laid off somewhere in there, which was legitimately terrifying because of the high cost of living. Just thinking and writing about these hustle years makes me unconsciously hold my breath.

All Work, No Play

If you read between the lines, I worked my ever-loving ass off. I worked harder than I ever worked before in my life. I worked too much. I struggled to maintain balance in my life.

Anything that didn’t generate revenue, like this blog or my novels, took a swift backseat to work that paid the bills. I still managed to keep up with yoga, hiked weekly, and started taking ballet classes again. But often these activities were something to check off my basic wellness needs list. While working out, I almost always thought about work.

The “play” aspect of my life became escapism. My alcohol intake increased. It was very easy to adapt to Portland’s craft beer/cool restaurant lifestyle.

I kept myself in check with booze breaks over the past 3 years. I’m in the midst of my longest alcohol break, celebrating 10 months as I write this…during the COVID crisis.

milwaukee lincoln center of the arts

Why I Moved Back to Milwaukee

Chicago was actually the place we decided to move to. Mr. H and I were moments away from signing an apartment lease in Chicago when Milwaukee came up in one of many exhausting moving discussions we had.

Mr. H said: “You once told me some of the best years in your life were spent in Milwaukee. Why don’t we just move back?”

Calculating Risk and Reward

Moving to Chicago was going to be a parallel move financially. As of today, Portland and Chicago have about the same cost of living. Chicago is technically a lower cost of living (crazy, right?). But it all depends on where you live in the city (and that’s a big ass city).

This also made Chicago a risky move for our business, since we didn’t have many connections AND it was expensive. In Portland, we were well-connected so business was good (pre-COVID, of course). In Milwaukee, we know lots of people and the cost of living is significantly less.

Stress was creeping in and we hadn’t even signed a Chicago apartment lease yet. Milwaukee’s pros list outweighed Chicago’s list by a longshot. Plus, Chicago is a 90-minute train ride away whenever we want or need it. I love Chicago and it’s hands-down one of my favorite cities…to visit.

A Simple and Manageable Life

The biggest mental hurdle I had to get over was this whole idea of moving back to Milwaukee being associated with “moving backwards.” I was stubborn about moving forward, moving faster—I was trying to one-up myself and my life. It was a mindset I had adapted to survive in Portland and I was still clinging onto it.

Mr. H’s point about Milwaukee being the best years of my life kept bringing me back to reality. What kind of life did I want to live? The answer was…a simpler life. For life to be simple, it needed to be more manageable.

Cost of living was a logical part of that. So was being close to family and long-time friends. So was being back in the place where I spent some of my happiest years.

In Portland, I practiced yoga. In Milwaukee, I became a yoga teacher. I wrote three novels while I lived in Milwaukee and I started this blog in 2012. Portland was where I became a content marketer. Milwaukee was where I became a writer.

music store milwaukee

Unchanged and Unspoiled

This music store says it all. It’s still here, down the street from where I used to live on the East Side of Milwaukee. The dog statue is the same, a simple dog who enjoys sniffing musty old records for eternity.

In a way, Milwaukee is frozen in time. So much of it remains unchanged and unspoiled.

Portland was growing, changing, building higher and higher. Out with the old, in with the new. Milwaukee has seen its fair share of construction during my absence, but not nearly on the same scale as Portland. Historical buildings stand in beautifully stoic positions—weathered and wise.

There is something deeply comforting about a place that holds onto its history rather than charging full speed ahead toward the future.

Milwaukee is understated, a lesser-known miniature Chicago, it’s NOT the coolest/hippest city. I cherish Milwaukee for all of these reasons, and more that I won’t bore you with.

lake michigan selfie milwaukee

One of my all-time favorite movies is A Good Year, with Russell Crowe and Marion Cotillard. At the end, Russell Crowe’s boss asks him this question when offering him a partnership opportunity:

Now what’s it to be: The money or your life?

After the past six years, I have the answer to this one. Money is a tool and I’ll use it as needed. Beyond that, I’ll take life. No contest.

lowering your cost of living love your enthusiasm

Because this blog has been so popular, I did a spin-off about lowering your cost of living on my podcast, Love Your Enthusiasm.

In this 20-minute solo segment with yours truly, I share my experiences from loving and leaving the West Coast twice—along with other tools and ideas to help you achieve more balance with your finances.

In this episode, I share:

  • How maintaining a higher cost of living diminished my enthusiasm for writing blogs and books and pursuing new passion projects and businesses.
  • My financial relief since returning to Milwaukee and how this has reignited my creative passions.
  • The importance of being balanced in your finances, which often gets overlooked or ignored.
  • Ways to decrease your cost of living, including looking at how you spend, where to save money and time, and moving to a cheaper city.
  • How I increased efficiency in my business by spending on resources.
  • How the Wheel of Life helps you visualize all areas of your life at a glance to see opportunities for improvement—finances being one of these areas.
  • Why trying to achieve financial freedom by earning more money isn’t the best approach.

You can find Love Your Enthusiasm on your preferred podcast app (Apple, Google, Stitcher, etc.), or jump over to the website.

Listen Now

30 thoughts on “Why I Left Portland and Moved Back to Milwaukee

  1. Welcome back to the Midwest. I moved to North Carolina for a couple years and when I came back to Michigan all I could think was “There’s no place like home.”

    1. Dorothy was onto something, wasn’t she? The West Coast is where I had happy childhood memories, but the Midwest is where I had happy memories as an adult. It’s a good place to be!

  2. Milwaukee is a great city! A bit too cold for this Florida gal. Ultimately isn’t it about what makes you happy and fuck all that other noise…..easier said than done- I know. You should be proud of yourself!

    1. Fuck all that other noise is right! Milwaukee is a great city. We are planning to become snowbirds and come down to Florida for a while in the winter—that was our agreement with me moving back to the Midwest winter. This West Coast girl needs sunshine and beaches from time to time. 🙂

  3. Darling, you made the right choice, hands up!
    Your analysis of the whys, pros and cons is so truthful and logical, it sounds like it just made sense.

    My heart jumped at your “moving back to Milwaukee could have felt like moving backwards – when I want to be moving forward,” because it states sooooo much what I’ve been feeling at being back in France and thinking more and more about moving back south.
    You became so many parts of you in Milwaukee, it’s impressive; the city will be happy to have you back and I’m sure will offer you what you came back for.

    I smile reading you because I can sense the heartfelt logic, pull, perfect sense in that path you’ve chosen.

    You made it happen. It’s going to be fantastic!

    1. The moving backwards thing was something I had to meditate on for a while. The logic totally made sense. Cheaper cost of living and having family around? Those are no-brainers.

      But, I definitely got to a point in life where I felt like I needed to keep pushing forward…do more, try the new. I did plenty of that over the past 6 years. I would rather channel my personal growth in other ways—not give it my all just to make ends meet.

      I’m glad you found this piece relatable, hon. Remember…one day we will have travel adventures again to soothe our adventurous spirits. xo

  4. Sounds to me like you’ve really got your shit together. You don’t have to focus on the what’s most important to you. It’s who you are.

    My best to you and yours.

  5. I hope that after the cardboard boxes are neatly stacked and discarded, you’ll be able to create lots more of your wonderful fiction. Welcome home! We’ll be able to share real hugs very soon. xoxo

    1. Fiction is a ways off for me as I’m working on a new podcast (since my travel wellness publication never launched because of COVID).

      I do have the premise for book #5 and it’s more of a return to my Beneath the Satin Gloves roots. If the timing works out this year, I’d like to finally participate in a NaNoWriMo and bust out a first draft. We’ll see how the year goes!

    1. Thanks, Jilanne! The West Coast will always be home to me. I love it, but I don’t love the cost of living. Feels good to be able to slow the hustle mode down and refocus my energy.

  6. Your decisions for leaving Portland largely mirror mine. I arrived there in 1994, when it was on nobody’s radar…and left when it was one of the hippest, coolest places in the country. I got asked a lot of the same questions as you, and my answers were also the same. Good luck in your new old city!

    1. I knew many native Portlanders so I understand just how different the city used to be. Most of them are unhappy with all of the changes, but I don’t know if they will ever leave either.

      I’ve moved around enough to know when it’s time to move on. Coming back to my new old city was the right thing to do, for sure!

  7. Wow! What a great story Britt! It’s becoming clear for alot of people- simplicity is the key to being happy. I’ve experienced this and just talked to my mom about it this past weekend.

    I read the book, Your Money or Your Life and I think there are many parallels to your next focus. This book is #1 or #2 on my all-time favorite books and very influential in my life, you may enjoy it: . Thanks for the great post.

    1. Hey, Summer! I haven’t talked to you in forever. So happy to “see ” you here.

      Right now are all being reminded of the importance of simplicity. For about 9 months, we’ve been working hard to get to this point. And, we still have work to do.

      I will definitely check out this book! Thanks for the recommendation. Take care!

  8. Hurrah, and well-written Britt. You’re obviously confident you can make Superneat work from your new (old) home. It’s a truth I think I learnt some time ago now. You can keep striving, keep climbing, better this, more of that. And then you die… At some point you realise that actually, maybe you have battled enough and need to level off, to breathe, in order to connect with life again.

    And maybe you’ll be able to get back to your blogging and writing, or indeed other discretionary pleasures that you might find.

    Welcome home.

    1. Superneat is not location-dependent, so we finally had faith that our business could operate anywhere. So why not live somewhere with a higher quality of life? It definitely made sense.

      More, more, more and then we die. That is so true and I recognized that I was falling into that trap. Years were flying by faster than I wanted them to. Definitely ready to slow things down.

      I have been blogging more as you can see! I’m also working on another project, which I will reveal soon. 🙂

  9. I love that movie, too. Love it. Seen it too many times, love it. And yes to life. We have a new receptionist, and I found myself smiling at her as we got into our cars Friday evening, as I had just said, “I lead a simple life.” It’s a pleasure for me. A true pleasure. She’s a gallavant-er, which is great, but not for me. Make the life you want. These things take time to create, and it’s FINE to change your mind, cause journey and all that.
    I also love to visit Chicago, but I cannot imagine living there. Maybe one day that’ll be the perfect place for a leg of my journey — who’s to say? Right now, I love here. Be where you love. And gosh, Britt, to have the one you love with you, it almost doesn’t matter 😉

    1. It’s rare for me too meet someone who has seen A Good Year. So, yay for that!

      Make the life you want…I love it.

      Ditto on my feelings for Chicago. I feel it’s more livable than some other gigantic cities, but it didn’t feel right for us. I’m so glad we made our decision to slow our shit down and come back to Milwaukee.

      And yes, when you have the one you love with you, that’s all that matters.

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