Lessons I Learned Starting Over

It’s been 11 years – more than a decade since I moved from Los Angeles to Chicago. Most of the people I know who relocated made the move for a job, partner, or had some sort of connection to their new city. Then there’s me. I made the somewhat irrational move because Chicago seemed like a great city, I didn’t need a car, and couldn’t afford both a car and an apartment. 11 years later, I have a husband, two children, friends, and a home. Here are the lessons I learned starting over in a new city.


The Lessons I Learned Starting Over in a New City


I was about to turn 28 and could not have felt more stuck than I did. After almost a decade in an extremely toxic relationship that I just couldn’t shake, and growing up in a pretty toxic family, I had to get away. I was a little (read: very) broken and in desperate need of a change. I wasn’t thinking this far out – to where I would be in 5 or 10 years. There wasn’t a plan to stay, settle down, start a new business, because I was just trying to find happiness and figure out who I was.

When I first visited Chicago in November 2009, there was something about the city.

The reality is that NYC would have been first on my list, but there was no way I could afford it. The energy of a big city, but smaller, friendlier, and more affordable. I couldn’t imagine uprooting my life to a city where I didn’t have any connections and the concept of winter terrified me. The blogging world connected me to a few people in Chicago, and one had a friend who was looking to rent her Condo, so I came back for a month on Feb 1, 2010. If I could survive Chicago in the winter, I could do this, right? I loved the city but it took some time to get the courage to make the move, and 5 months after I returned home to LA, Buddy and I made the move to the midwest.

I wanted to figure out my career in a new city.

When I was designing blogs, I made enough to cover basic expenses. It wasn’t my passion and I wasn’t good enough to take my business to the next level. My blog had been around since 2007 but I didn’t start monetizing it until 2016. I’ll talk more about that another time. Today, I want to look back at the last decade + and share some life lessons I learned in my 30s after moving halfway across the country and starting over in a city where I didn’t know anyone.

You have to put yourself out there.

This is a tough one for most people. I don’t really like going to events and loathe small talk but chances are that you won’t meet new people sitting at home by yourself. I’d rather meet a new person, sit down, get to really know them, and talk about everything. I want to invest my time with friends and not having a pointless conversation about nothing with someone I’ll never talk to again. I’m sort of a homebody but if you want to meet new people, you’re going to have to try new things. I once went to a party where I didn’t know anyone (so, so not my thing) and met one of my closest friends there. I met one of my best friends when I saw her walking in the parking lot by my ex-boyfriend’s apartment, all because I pulled my car over to say hi. We live thousands of miles apart but talk every single week.

Set some boundaries and learn to say no.

It took until I was later in my 30s to get this one and I’m about to contradict the first point a bit, but hear me out. Yes, you need to put yourself out there, but it’s ok (and good) to say no. I talked more about boundaries in this post, but even when life isn’t where you want and even if you’re looking for new friends or a partner, you can’t be in a constant search. It’s ok to have a quiet night in. There was a time when I was single and felt like I had to go out Friday and Saturday but I eventually learned that it’s a good thing to be able to spend a Friday night alone at home. To slow down. To not take on the extra project when you’re feeling burned out. In my late 20s, I pushed myself to the point that I got shingles, so take it from me. Sometimes, you need to slow down and that’s ok.

Starting over in a new city is lonely.

Living alone might not be for everyone and even though I had some lonely periods, I loved it. I’m so glad I experienced living on my own. Developing a routine and enjoying that time on my own made me so much stronger. Time alone helped me figure out who I was  and what I wanted without someone else. Learn to enjoy your own company and enjoy doing whatever you want.

Friends will come and go.

This is a life lesson, but one that feels magnified with new friendships. There are friendships that will last forever and others that will fade away. Some friends just come into your life for a season, but there’s always a reason we cross paths with someone. Right after I moved from LA to Chicago, I met someone who, like me, had just moved from LA. We were basically instant best friends, but she eventually moved back to CA and we lost touch. It felt a little sad at the time but there weren’t any hard feelings at all. Sometimes, there are friends that seem like they’ll be around forever and it can be a bit harder when things fade. I’m still struggling with this one, especially this year.

Keep your old close friends close.

Want to put a friendship to the test? Move to a new city or experience a big life change. Distance can make it really difficult to make new friends, but it can also grow friendships with those who live far away.

Stop holding on to stuff.

I was one of those people who held on to articles of clothing that I never wore and you’d think moving to a new apartment almost annually (I know, I know) would have taught me to get rid of things sooner, but it took a while. There’s so much joy in owning less. I love selling or donating things I no longer need or use – it feels so freeing.

It’s ok to ask for (and accept) help.

It’s ok to let friends help you and it’s ok to ask for help when you need it. Let friends pick you up after surgery or bring you something if you’re sick. Reach out to a friend if you’re feeling lonely and need to see someone. And don’t forget to show up for them, too.

The worst case isn’t that bad.

Let’s say you move and it’s not for you. Maybe the job doesn’t work out or the city doesn’t start to feel like home the way you hoped. Not working out is not the same as failing. It’s better to try than to stay put and wonder what could have been. I’ve created a great life in Chicago, but would be open to moving somewhere new with our girls. You always have the option to go back home, but maybe a new city or new job will be the change you needed.

You are stronger than you think.

People told me how brave I was for moving to a new city alone but trust me when I tell you that you, too, can do hard things. Back in my 20s, my confidence was so low. But now I know I can handle hard things. I took myself to the hospital for knee surgery, went through the fears of starting a new business, left that business, spent holidays alone, and there was that time Buddy almost died and I had to figure out how to pay almost $6000 in medical bills. And guess what? I did it, and you can, too.

I’m so grateful I took a somewhat irrational leap and decided to move to a new city because the people I’ve met (and created – how crazy is that to process?) along the way are my everything. I don’t know who I’d be without them.