In 10 weeks, I am quitting my job, leaping out of the career race that is Washington, D.C., and boarding a plane to Chile.
Look, this has NOT been an easy decision. I’m in my mid-30s and have been on a fantastic upward trajectory in my career. I believe in Lean In. I spent the last year of my life working 70+ hours per week on a national security priority, prepping my boss for meetings with the Big Guy, and it’s been incredibly rewarding. My career is important to me.
But at some point in the last six months, I realized my life has pretty much looked like this for several years now:
Sure, I’d take vacations once in a while. But something wasn’t right.
I couldn’t stop thinking about certain pieces of advice I’d heard from mentors and articles the last year.
- Unwitting Mentor: What do you love so much, you could do it every day, without stop, forever?
Everyone has something like this, but so many of us have lost it. It’s usually something you did non-stop when you were little. Maybe it’s being outside in the sun (and now you’re in a windowless cube), or sketching, or playing a sport, or reading or baking. You know what it is. That thing that every time you do it, you disappear into the zone, hours pass, and you are at peace.
This advice came from Elizabeth Theranos, who I think is one of the most amazing and talented women alive today. She worked nonstop on her invention for years on end. She loved it so much, there was nothing else she could do but this. (Of course, she eventually got to her goal and now is a gabillionaire, but money isn’t the point here.)
Probably most of us aren’t built like that – I know I’m not – but there are things I love so much that I would like to do every day, and I’ve lost over the years. Like writing for pleasure, and not for work.
Here is a cover and a page from a “book” I wrote at 8:
2. Fully Aware Mentor: What stories do you want to tell from your rocking chair?
How you won that big account of a paper company and your grandchildren don’t even know what paper is now because it was obsolete by 2030? Or how you wrote a billion papers that were used for a total of 10 seconds in some meeting once?
Or do you want to talk about the time that you ran from a bear, you almost drowned learning to dive, or that person you loved but just wasn’t right for you? That you explored the world and made huge mistakes, but you don’t regret any of them?
I don’t know if I want to have grandchildren of my own, so I’m not entirely sure who will listen to my stories, but I definitely want to be talking Big Adventure. Big (more, already made plenty) Mistakes.
- Random Online Quote Mentor: Make new mistakes. Do what scares you.
Making mistakes is scary. I don’t think you can be human and not fear making mistakes and being judged for them.
This is probably a healthy emotion to a degree, but you have to know at what point it stops being a positive – don’t-go-down-that-dark-alley-alone-it’s-dangerous – and turns into a negative – don’t-try-purusing-that-thing-you-love-because-it’s-new-and-different.
Letting fear hold you back leads to only one thing, as far as I can tell – regret. Whether it’s starting something new or leaving something, it’s the first step that is the most terrifying.
In fairness, I’ve quit a job previously and gone to travel. It was one of the best six months of my life.
But to do it now, when my career is going so well, when everything and everyone around me is telling me to settle down, buy a house, have a family, keep that steady job and keep advancing it?
- My Mentor (and Unwitting Love) Mark Manson: Just don’t give a fuck.
I need to be honest with myself: I don’t want to be judged.
It’s kept me from making decisions before in my life. I do care what people think. And not just my family and friends, but random people I’ve never met who might theoretically learn something about me and think it’s stupid. Yea, I’m that scared of judgment.
Unfortunately, you can’t avoid it. People are going to judge you. Whenever you do something out of the norm, you’ll hear or see a reaction.
Which is why I love Mark Manson, who writes that learning the difference between when we should and should not give a fuck is essential to being comfortable and honest with yourself and others. It’s tricky. But worth it.
Unfortunately, Mark is not single as far as I can tell, so I will continue to love him from afar and recommend his articles to anyone who will listen. (Especially this one on relationship myths.)
- My Closest-Thing-to-a-Life-Coach Mentor: Visualize your two futures.
Fair warning: My friend called this technique “very Portland-y.”
Picture yourself, 10 years from now, having made one decision, on your current trajectory. Build that full picture in your mind – the job you’ve achieved, the office, the car, the family. Or maybe it’s a relationship or a place you live.
Did you feel something good in your body? Maybe you sat up a little higher, or smiled, or relaxed your shoulders? Or did you feel a twist in your stomach, a frown, or a claustrophobic sense of breath?
Now picture the other choice and the future it’s created in as much detail as you can.
How does your body respond to that future?
Your body already knows the answer.
Mine knew. It was time to leap and create a new future from the path I was on.
So I drew a new chart, composed of the kind of stories I want to tell on my rocking chair.
Even now, sitting with my decision made and out in the open, I am scared some of the time. And I feel the weight of judgment some of the time. But after a few minutes of indulging those some of the time, I either call one of my friends who supports me 100% for a pep talk, or I look at the cover of my Chile travel book.
I am to go to there.
Or I sit and write and two hours have passed and I’m happier than I’ve been in weeks because I’ve been doing something I love.
Because this life has to be about more than just work. Starting a new path will never be easier – a lot of planning and saving, yes – but the timing will never be better.
I can do good, meaningful work, AND have a good life. I am convinced.
So I’m leaping.