No Time For Regret

I’m really good at making decisions for myself.

Amanda Zimmerman
Dresses With Pockets
5 min readMay 24, 2015

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  • Unless influenced by others’ indecisiveness, I can generally look at a menu and figure out what I want to order in under a minute.
  • I spend approximately 3 minutes choosing what to wear each morning (and NEVER plan the night before).
  • Heck, I decided to make 4 Months X 4 Cities happen just 2 days after my best friend and I came up with the concept back in December!

It’s usually not the things I do that keep me up at night, but the things I don’t do. My personal regrets are rooted in an eerie feeling that if personified would be a looming finger about to tap my shoulder letting me know that I could have done better — that I didn’t take advantage of an opportunity or that I spent a beautiful day cooped up inside when I could have, perhaps, done something spectacular.

We are in charge of how we live our lives. Of course, there are socioeconomic circumstances that make this statement less true for some compared to others. But the wonderful things that come with freedom and privilege can also be burdened by responsibility and guilt.

Because I am free, I am in control of how I live each day. Because I am in control of how I live each day, I should be able to make the choices that result in never-ending perfect days…right?

A few weeks ago, I was feeling a lot of regret about how I was spending my time in Chicago — my last city. Even though I had some of my closest friends in the area, I was lacking a sense of ownership of my journey — spending afternoons on my friend’s couch, just hanging out, rather than exploring and meeting people in the way that I had in New York, Austin, and San Francisco. I felt a huge plunge in motivation and stopped pushing myself with the same intensity that I had in the past three cities. I was frustrated with myself and chalked up my decline in motivation to being tired — which was totally valid.

I was tired of traveling and having to lug around all my crap, tired of not having my own kitchen with all the spices and appliances I needed to make my go-to recipes, tired of having to get acclimated with my surroundings, and tired of having to ask for favors.

But being tired and unmotivated was no way to spend my final month of 4 Months X 4 Cities. I knew that. And I knew that if I didn’t change my attitude, I’d regret not taking advantage of my time in Chicago.

What got me out of my funk? Three people.

Over the course of the past few months, two people reached out to me via my blog and Instagram — both happened to live in Chicago. Now, two people showing interest in what I’m doing may not be enough to call myself famous, but it’s still a nice ego-booster. It felt kind of awesome to have people reach out to me instead of me reaching out to them — something that I’ve gotten quite used to over the past four months.

Within the same 24 hours, I met up with both 20-somethings over pizza/coffee and just chatted with them about their lives and what I’ve learned so far from my journey. Hanging out with both of them totally reminded me why I was doing what I was doing. This journey came to be because I needed it, and transformed into something that could teach others that the society encouraged hop-on-and-never-get-off conveyor belt wasn’t the only option — there was more than one path.

The third person that helped pluck me out of my funk was Dana. You may remember Dana’s name from one of my first 4 Months X 4 Cities blog posts. I was introduced to Dana via a mutual friend back in February while I was living in New York. Dana lives in Chicago and has been traveling a bunch screening her incredible film The Empowerment Project. Over the past four months, Dana and I emailed and had two hour-long phone conversations that revolved around anything from her documentary tour, to our personal stories, to what I was doing during 4 Months X 4 Cities. After the first 10 minutes of chatting with Dana, I knew she’d become someone I considered a mentor and role model. She was the first person outside of family and friends who expressed unconditional encouragement as I started my journey. The funny thing was, we’d never actually met in person…until the other week.

There are very few times in my life that I can remember meeting someone for the first time and getting that cheesy feeling like I’ve known them for much longer. But of course, I got that feeling when I met Dana last week. We sat for hours in a tea shop, just chatting and asking each other questions. At one point, I told Dana how I’d been feeling this looming regret about how I was spending my time in Chicago. And as if she’d read my journal, she responded by telling me:

“Forget about it, it’s in the past, keep moving forward.”

Coming from her, it was unsurprisingly EXACTLY what I needed to hear.

So if you’re like me — extremely hard on yourself and unreasonably harsh about how you spend your days — here’s a little method I use to get myself out of those nasty funks: (1) Ask yourself if there is anything in that exact moment (or in the near future) that you can do to alleviate your negative feelings about whatever is bringing you down. (2) If there is something you can do…then force yourself to do it. (3) If there’s nothing you can do, then the only thing to do is get over it.

This post is part of 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 May 24, 2015.

For more posts in the 4 Months X 4 Cities series, check out the tab on the Dresses With Pockets Medium profile.

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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.