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What No One Tells You About Living and Working on the Road

September 6, 2016

What No One Tells You About Living and Working on the Road

Because of the work I do for Rockstar Finance, I skim hundreds of blog posts and news articles each week, and there are a handful of themes I see over and over again. Paying off debt, embracing minimalism, building wealth and retiring early are among the top five. But the topic of “quitting your job to travel the world and do what you love” is, without a doubt, at the top of that list.

The success stories sound dreamy. People write about how they live on as little as $1,000/month in various countries, with accompanying pictures of laptops on beaches and books in hammocks. Instagram feeds are filled with ocean views, mountain tops and cold drinks dripping with condensation during afternoon siestas. And the captions that go along with them express nothing but joy and gratitude. It seems like a fantasy come true. However, like so much of the curated content we are exposed to, it’s not the reality for the many of those who are trying to live and work on the road.

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Thoughts From the Road

September 2, 2016

Thoughts From the Road

Hello, friends! It feels so good to finally have a few moments to sit down, gather my thoughts and write my first update since leaving on my road trip. I’ve already been on the road for 19 days, and it simultaneously feels like the longest and shortest 19 days of my life. Long because my first week of driving to Minnesota seems like a distant memory now, and short because it’s wild to think the people I’ve seen and places I’ve been to are, realistically, only a few hours away in all directions.

Before I left, this trip felt BIG. I estimated that I would drive at least 10,000km in 17+ states. Not even three weeks in, I’ve already driven more than 6,000km in 14 states – and there are at least four more that I’m going to drive through (five if we include Washington, which I need to drive through a second time to get home). Because of the fast pace I’ve been moving at, and the long driving days, I haven’t had time to write a full post yet. But I did piece together a list of thoughts I’ve had so far on the road.

Some are silly, some are serious and some are incomplete – and the more time I spend alone, the more confident I am about saying that this is how my thought process works on a daily basis.

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Coffee Date With Anthony Ongaro

August 24, 2016


Hi friends! In case you haven’t been following along on Instagram, I’m officially ten days into my road trip and things are going well so far. I’ve already visited six states, and am about to enter my seventh and eighth states later today. Aside from one crazy wind/rain storm, everything has gone smoothly… and guess what? I’ve only cried once! Somehow, that feels like a win. :)

There are so many things I want to tell you about the trip already, but for now I will just say that the highlight has been my time in Minnesota. On a particularly rough day of driving through South Dakota, I texted friends to say I couldn’t wait to arrive, because I had a feeling it was going to be a special part of this trip – and I was right. On top of seeing some long-time blogging friends, friends I met at WDS last year and even some new faces, I got to stay and spend quality time with Anthony and Amy Ongaro.

You might recognize Anthony’s name because he’s written not one but two guest posts for me in the past. He’s also the writer behind the blog Break the Twitch, where he talks about intentional living and creating a life that aligns with your values. Based on that sentence alone, you can probably imagine that we have a lot in common… and we do! But I didn’t know what to expect, because we had never met (other than on a few Skype calls) before this trip.

Now, after spending just a few days together, I am genuinely sad at the thought of not seeing Anthony and Amy again for a while. I honestly don’t know if I’ve ever felt so aligned with two people, in terms of our energy levels and interests. We spent most of our time together laughing, and turning our online relationships into true friendships. And they were the most amazing hosts. I truly couldn’t have asked for a better experience.

Before I left, I asked Anthony if he would mind answering some questions for the blog, so I could share more about him with all of you. Here’s what we pieced together. :)

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