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 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.

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.

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.

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.

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.

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.

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