4 Months X 4 Cities: How it All Began

Amanda Zimmerman
Dresses With Pockets
5 min readJan 1, 2017

This post is the first post in a series documenting a personal journey I created for myself starting February 1, 2015. The journey took me from New York City, to Austin, TX, to San Francisco, and ended in Chicago, where I lived in each city for exactly one month. I’m reposting all the 4 Months X 4 Cities stories — this one was originally published on January 12, 2015.

What happens when you’re a 20-something and your life appears to be headed in the wrong direction?

Well, the way I see it, you have two choices: deal with it or (the scarier option) do something about it!

Now, I really can’t complain. I have a great apartment in DC (in an awesome location). I have truly incredible friends — some that live in DC and some that are far away, but remain present in my life. I have an unbelievably supportive family — sisters, parents, cousins, grandparents — the whole shebang. But… I don’t know what the heck I want to do with my life.

So for the past few months, while I was just going along, living my life, comfortable in my routine, I couldn’t help but ignore the tapping on my shoulder of a voice inside saying, “Hey Amanda, we both know I don’t need to tell you this, but you’re going the wrong way.”

The tapping never ceased, though I tried to suck it up and ignore it for quite some time. Then about a month ago, I decided I need to take the scary road and do something about it.

I quit my job and started reading The Quarter-Life Breakthrough, a book that boasted: An inspiring career guide for twentysomethings to get unstuck, pursue work that matters, and change the world. With practical exercises and helpful resources, this book is essential reading for anyone who wants to get paid for who they are and what they believe in.

Here are a few quotes that screamed out my name:

  • The journey is the journey — there is no finish line, no top of the ladder. Your career is simply a series of journeys.
  • Being able to choose what you do with your life is an enormous privilege, and it shouldn’t be wasted.
  • Having a skill that you’re good at but that you hate doing may keep you from finding meaningful work.

I was hooked. Every word resonated with me. And so, for the entire week following my completion of this book, it was all I talked about.

I talked about it to my friends, I talked about it to my parents, I talked about it to my friend’s parents. And then, on December 21, 2014, I talked about it to my college roommate Stacey when we met up for brunch in NYC.

It was at this moment that the game was about it change. Big time.

I was going through my whole spiel about how the book was such an eye-opener and how it was changing my perspective on my future career path — yadda, yadda, yadda. Stacey stopped me mid-sentence and said:

This is kind of crazy, but I know what you’re going to do. You’re going to sign over your DC lease, and travel to four different cities in the next four months, exploring different career paths and blogging about it!

My reaction was the following:

First of all, how the hell did you just think of that. And second of all, yes, I want to do that!

So here we are, almost a month later, and I’m actually doing it. It didn’t happen overnight, and I’m not nearly done planning, but I’m signing over my lease this week and I’m speaking to someone later today about subletting in Brooklyn for the month of February.

I’ll be aiming to work at short-term/volunteer/part-time/apprenticeship-type positions in each city, exploring various career interests that I’ve always had, but never had the guts/time/means to pursue.

This 4X4 journey that I’m creating for myself is all about networking and being open to new people and new experiences. I’m blogging about it for family and friends that care to know what’s up with my life, for people like me that just need to push themselves to figure out how they can live a meaningful life, and also to get the word out.

I’ll be hitting up NYC in February, Austin in March, San Francisco in April, and Chicago in May, and in order to make the most of the next 4 months, I’ll need your help. You know awesome people living in these cities that I don’t! Hit me up and tell me who I should be grabbing coffee with or volunteering for. Maybe we haven’t spoken in years, maybe a friend of mine passed along this post to you, maybe you just came across this blog and we’ve never met — I DON’T CARE — reach out and I will be more than open to any suggestions and guidance you may have!

The way I see it, there is very little security in this plan. There’s a lot of room for error and there’s no concrete way to assure that it will go any certain way. I’ve just got to put everything I have into it and go with the flow.

And in honor of the GIRLS Season 3 premiere last night:

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Amanda Zimmerman
Dresses With Pockets

Just your average 20-something, who enjoys publicly reflecting on what it’s like to be an average 20-something.