Fortune Favors the (Thoughtfully) Bold

Three years (and one week) ago, I embarked on what I thought would be the greatest adventure of my life: I moved to Hawai‘i.

I am a cheesy human who likes celebrating small anniversaries like that, so it’s ironic that, each year, I have been off-island on May 1st (and always for a TFA trip!). I always end up celebrating my move to the island by being forced to leave it.


And maybe that’s a good thing. Sitting here, in my parents’ place in Kona (one of the many changes over the past 3 years), I’ve been rereading my blog from that time in my life. Doing a time-warp is always fun, but I was struck not just by the sense of adventure I had, but also how frenetic I now remembered that time was.

Moving to Hawai‘i was, in fact, the biggest, most adventurous risk I had have ever taken. I don’t have close family here, I didn’t have any close friends out here. I was jumping into a job that dealt with organizing things, laughably my worst skill on earth. I was making ridiculous decisions with little thought to the outcome.

And it was hard. I downplayed it then, but my first 6 months on island was probably some of the hardest growing up I have done. Yes, being a crazy “twentysomething” is something I look back on with fondness, but also know that I barely made it through that time without throwing up my hands and calling it quits. I made choices that were wrong for me, I “took risks” that I knew would probably hurt me in the end (spoiler alert: they did).

Mostly, I missed people, and realized how much I had taken for granted little things: being able to attend spontaneous family gatherings. Being able to see my parents’ faces after a bad day at work. The friendships that, as someone who’s pretty introverted, it had taken me so long to build.

Obviously, though, I regret nothing. Moving here is one of the best decisions I have ever made. I am a much better, happier human who has been fortunate enough to find people and a career I deeply love. As long as this life in Hawai‘i will have me (and I can afford it), I think I’m building roots in a forever-home kinda way.


In the past 3 years, I have come to learn that now, risk looks different. When I was younger, taking risks and making tough choices were the obvious ones you see in coming-of-age stories like mine: move to an island, take a crazy new job, try getting to know new people, ~discover yourself~ etc.

Once you start growing roots and, frankly, growing up, risks are different. Taking a chance doesn’t mean, as it once did, doing the craziest thing. Now, the questions shift. Instead of asking, ‘am I brave enough to leave and trying something “crazy” and “new”?  I feel like the question is: are you brave enough to stay?

Yes, doing something crazy like moving to an island was a risk. It was hard. But deciding to put in the work and build relationships– romantically, platonically, with a place even– is also really hard, and I think we forget that. It’s easy to forget that the film doesn’t end at the climax, but continues through denouement, resolution, and into new stories (sorry, I just taught the plot mountain this morning).

Once we “discover ourselves,” or “find what we really need,” or whatever new age phrase we use: the story doesn’t end there. There is still a lot of effort needed to make those things continue working for us. 

And that’s a risk too. I am, in some ways, even more vulnerable now. The stakes are higher; I’ve put time, effort, and heart into this. Sometimes, it actually looks like it’d be easier to throw my hands up and jump to the next adventure, the next crazy idea, the next new thing. Who doesn’t love the thrill of embarking on new journeys?

Right now, though, I am deciding to to take the risk and plant myself more into this life. I know that it means the work gets even more real now. Yes, there are a lot of “bold” things I could go out and try– quitting my job to travel (even though I have no money), cutting ties and starting over somewhere, refuse to tie down anywhere.

The thing is: that’s not who I am. I don’t really want to do any of those things. They just look appealing when my life here gets less-than-easy.

Now, I see that fortune doesn’t just favor crazy, fortune favors a thoughtfully bold approach. Fortune favored me when I found a willingness to jump into the things I knew I needed, but maybe were to scared to dream I could have.

So, Hawai‘i, this crazy life and love I have now, it’s pretty clear: I need you. I choose you.

I hope you keep letting me make that choice every day.

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