I’ve had to say “goodbye” a lot in the past few years…

I guess it comes with the territory when you live in four different countries in a short time.

When I first started my journey into entrepreneurship and location-independence, I wanted to be able to live anywhere at any time. I still do.

But I didn’t account for the downside of that lifestyle: constantly leaving people I care about. In every city and country, I meet cool friends who I enjoy spending time with. Then, inevitably, I have to leave…and say “goodbye”.

Just yesterday I had to say “goodbye” to a few close friends. Tomorrow, I have to say “goodbye” to my family.

Then I’m off to San Francisco, then back to Medellin, Colombia where I’ll connect with some old friends. Eventually, I’ll have to bid them farewell again, too.

I’m not complaining – I’m living a helter-skelter lifestyle of adventure and travel, while working on stuff I care about. It’s what I wanted. But part of me wonders if the growth and perspective I gain from travel is worth the lack of stability.

On one hand, it’s helped vault me to success. For example, the connections I made in Vietnam have helped me tremendously in the year since, and completely changed my trajectory. Plus, I thoroughly enjoy the travel experience. On the other hand, I may have achieved the same level of success even if I just stayed in Boston. Plus, I’ve been forced to leave some potentially amazing relationships before they got a chance to blossom.

It’s important to pause and reflect on your motivations, especially in the midst of big life changes.

Whatever the case, it never gets easier to say goodbye. No matter what excuses you have, no matter what big dreams you need to chase or what you need to cross off your bucket list, it’s always bittersweet.

But that’s okay, and probably how it should be. There’s no real art to saying goodbye, you just have to do it. It forces you to reflect on the past, as well as the new future you’re heading toward.

All in all, I think I’d like to say goodbye a bit less. And I’d also like more stability and the chance to have longer relationships with people. That means, after this next round of travel, it’s time to pick a place where I’ll stay in for a longer period of time. That may be Boston, or it may be somewhere else. Time will tell, and a lot can still change.

But for now, it’s time to welcome to the next adventure…