A Nomadic and Free-Spirited Person

The term Digital Nomad irritates me. It feels branded, packaged, and sold back to me. It feels like an Urban Outfitter’s festival style guide. It takes an experience that we’re all trying to figure out and define for ourselves and tells us what it’s supposed to look like. It takes the spirit out.

It’s also useful for explaining what I’m doing and finding resources about how to do it well, so I’m reluctantly using it where it’s useful. I read a lot before I set out and still ignored some really sage advice. In this post, I’m going to reflect on my mistakes a little, share some surprises and hopefully provide some useful info for someone considering this lifestyle.

Mistakes were made, more mistakes will be made, and everything is temporary.

I try to remind myself of the impermanence of depression, the unimportance of possessions and ephemerality of life. I try to be zen about mistakes and be self-compassionate, but I’m just not quite there. So please forgive how many times I’m about to call myself an idiot. I have a real knack for finding inventive new ways to blame myself for everything and for being really hostile and unsympathetic with myself (I promise I’m working on it!).

I overpacked. I really, really overpacked.

Heres something I’m ready to recognize is a little funny: I packed seven pairs of shoes. I know that sounds ridiculous, but my reasoning seemed good at the time. This is is my entire life we’re talking about and I have a lot of hobbies. I wasn’t trying to be a minimalist, I was trying to be prepared. I need my cycling shoes, my climbing shoes, comfortable wedges, going out heels, black flats, knee high boots, and rain boots. Yeah, that’s right, I didn’t even pack sneakers or hiking boots. I am a foolish, silly, ridiculous person. They were acceptable losses for me and I really needed room for my three coloring books! There’s a lot of other things that are probably funny (hoop, yoga mat) but everyone is different and your packing list is going to reflect your values.

I read tons of packing lists and suitcase reviews and really sought out of tons of information and I ended up figuring it out from my yoga teacher.

Yogis are smart.

I have exactly what I’m supposed to have.

I’ve given tons of stuff away, I’ve acquired a few things, and I’ve replaced a lot of things with a few things. It’s okay that I overpacked and sure it’s hard to let some things go, but not as hard as I thought. I move about every two weeks and if I haven’t used it in two weeks, I’m trying to let it go. The only thing you can do wrong is think about it too much. You can research and plan for weeks and no one else’s packing list is going to be right for you. Just know that it’s going to be fine.

I took my eyes off my things.

What kind of idiot is so obsessed with getting their activity tracked that they just have to charge their apple watch at a damn bar? This one. I’m the idiot. It’s me. There’s just no excuse for this. There’s these incredibly convenient plugs under the counters with hooks at a ton of bars in New York. I’m not saying you shouldn’t use them, I’m just saying you should keep an eye on them. Be vigilant with your possessions. Especially if they’re expensive or sentimental.

I didn’t do a good job of telling people I was leaving.

I don’t have a good excuse for not communicating with my friends and family earlier and more clearly. The whole experience of solo traveling is a pretty selfish endeavor. I guess I didn’t know what to say. Of course my friends and family are amazing people who just wanted to spend time with me and share in my excitement. I still don’t feel like I’ve done a good job of telling people what’s going on, I hope this helps — I love y’all!

I tried to mix vacation with working remotely.

I think this may have been my biggest mistake. I couldn’t be truly present for the vacation part or truly productive with the work part. I did my best and my friends and family know I love them and I know I made my work commitments. I know everyone is different but this was the most stressful experience that I’ve had so far. I thought I could have lunch with my cousin and work through the afternoon before dinner with my friends. It’s just too much. Everyone is different but I need structure to do my job successfully and trying to do vacation like activities on lunch breaks and never having an evening off was brutal.

I had no idea this would happen.


Outside of Burning Man I don’t know if I’ve ever experienced many moments in my adult life where I truly felt like there wasn’t something I ought to be doing. With all the research, planning, negotiating, and budgeting I had to do to make this happen — I never stopped to think about the fact that all that planning means I now I have days where I have nothing to do. In Portland, there was always laundry, deep cleaning the bathroom, baby showers to go to, kitchen gadgets to buy, Ikea trips, and the eternal Comcast box that was supposed to get returned two months ago. There’s a lot less of this in my life now and it’s the most delightful surprise imaginable. There’s lots of work in spurts to get the next month planned out but it’s a lot more fun to spend time on Airbnb looking of the perfect place with a hammock, dog and pool than it is trying to find an apartment anyone can afford in Portland anymore.

Medellin in 4d

I’m going to Medellin, Colombia in 4 days.

I’m planning a post about all of my preparation for this and why I chose Medellin as well as one all about my time in New York City.

Thanks for reading!