About a year ago, I had booked a trip to Asia for a month. I did this five months ahead of time not knowing what I’d be doing in terms of work or life, but had wanted to visit a friend living in Taipei and attend a friend’s wedding in Malaysia. I also realized that the only way to ever plan a “vacation” in my solopreneur life was to just book it and try to plan work around it.

In the months before the trip, I lost several projects and then lost a great project because they weren’t comfortable with me working remotely while I was in Asia.

I was feeling pretty crappy. I had turned down projects for a couple of months prior to focus on some creative projects, but was feeling pretty desperate to land some work so I didn’t feel so worthless in a busy American city.

A couple weeks before my trip, I had a client reach out about a potential project which was right in my wheelhouse. Towards the end of my pitch, I said “sooooo I have this trip planned to Asia. Would you be open to me proposing how I could still do this work remotely?

They said sure. I was shocked.

The next day I sent them a proposal to spend 25% of my time working on this project from Asia for an hourly rate that would easily support my life over the next couple of months. They accepted it immediately.

A few weeks later in a surf-side cliff town in Uluwatu on the island of Bali, I spent about 5 hour working on the project for the first time from the location pictured below.

As I worked that day, it was one of the first times I was working and didn’t really have any resentment towards that work. How could I with such a view?

It was also the first time where I felt a little silly that I had spent almost a year freelancing and didn’t think about leaving Boston or New York to explore more of the world or visit friends. Especially if I could live here for $20 a night.

Almost a year later, I visited this same place traveling with my partner and realized that this moment, this day of working remotely and abroad at the same time, was a moment that forced me to dream a little bigger and question my own limitations I was putting on my life.

And now I always wonder, am I dreaming enough now?



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