2014

The past twelve months have been the most intense of my life. 2014 began on a rooftop in Chiang Mai, drunkenly lighting Chinese lanterns with friends I’d met that very evening. People who, even if I’d only known them for a few hours, already inspired me. They still do, now a year later.

That evening is a surprisingly accurate metaphor for what my year has been like. I’ve spent half of 2014 in Southeast Asia. The first time over, to experience things completely foreign to me. I lived on farms, spent ten days in silence, taught English in Laos and whatever I knew about entrepreneurship in Vietnam. I learned to ride a motorcycle and drove it down the country, worked on an island with fluorescent plankton in Cambodia, witnessed Songkran in Bangkok and flew back through New York to meet my family (and discover I’d gotten bedbugs in the only expensive hotel I’d booked in six months).

First day of driving down Vietnam.

First day of driving down Vietnam.

Doi Suthep on Buddha Day, or our night out during the meditation retreat.

Doi Suthep on Buddha Day, or our night out during the meditation retreat.

I then spent six months back in Montreal. No more than two weeks after arriving, I was back to working 60+ hour weeks. I got my first apartment there, turned twenty as a squirrel was living in our house, ate tofu sautes nearly every night, went to my cottage whenever I got a chance, all while managing a team of ~15 people, wondering what I’d gotten myself in.

Squirrel and I on the night of my birthday.

Squirrel and I on the night of my birthday.

I signed up for business school, and canceled a few weeks before the start to switch to an online computer science program (which I’d also cancel, a few weeks after getting to Indonesia). I switched apartments, found some bridge under which I could park my car and not get towed, Catherine and I decided we’d leave again to “start a startup”.

Move to Indonesia where many people ran their business remotely. Stop by in New York before to understand startups a bit better, then leave.

A month or two later, we were leaving Montreal. Early in the morning, we caught a train and that was it. We were gone.

Those six months I spent in Montreal feel like they went by in a blink. Some days felt excruciatingly long and at times I wondered if this summer would ever come to an end. Yet somehow, in retrospect it all seems to have lasted no more than a couple weeks.

We spent ten days in New York visiting startups. Seeing these companies from the inside, meeting the people who created and ran them helped us understand the effort and passion necessary to build something great from the ground up.

Kickstarter has a movie room and it's huge.

Kickstarter has a movie room and it’s huge.

It also made us question every decision we’d taken so “far”.

After cancelling our tickets to Indonesia and rebooking the exact same flight about 18 hours later, we were off. Back to Asia.

It’s a bit harder to analyse what’s happened in Indonesia since we’re still in the middle of it.

From figuring out where we’d stay, doing it again (and again, and again), getting serious about learning to code, starting off with Bringers, meeting people who’ve raised our standard of what we should be up to dramatically and realizing that we’re either going to be here for longer than we thought, or back home broke sooner than expected … it’s been intense.

When I stop to think about it, the amount of things we’ve learned since leaving Montreal three months ago blows my mind. But I’m equally impressed by the challenges ahead.

Working from Indonesia has it's perks !

Working from Indonesia has it’s perks !

The small victories do add up, though. We’re starting to see the incremental progress over that leap we’ve taken, and that’s good.

Looking back, 2014 was a year of discovery, non-linear learning and scattered challenges. I tried to push forward in whatever direction I could and widened my understanding of the world as a result.

I’m grateful for all the opportunities I’ve had in 2014 and how they’ve shaped me as a person. My goal for 2015 is to make all of these learnings converge into something larger than myself. To put all of these seemingly random things together into a project that impacts people’s lives.

My motto for 2014 was “learn a little about a lot”, this year, I’m changing it to “make it happen”.

Cheers,

Tim

Last hike of 2014 : Mt Rinjani on Christmas Morning

Last hike of 2014 : Mt Rinjani on Christmas Morning

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Jumping Ship

I believe doing the things you want to do has more to do with what you forgo than what you involve yourself in.

The reason we don’t pursue what is meaningful to us is not that we don’t want to, it’s because something prevents us from doing so.

There’s always a constraint, an obligation, a sacrifice to be made. But that’s the easy part.

Recognizing the things that unconsciously halt us is where it gets complicated. When your job is such a central part of your life, you’ve never given thought to quitting it, when in a  relationship, options that accommodate the both of you become defaults.

Getting to the point where you can have sufficient distance from yourself to see what core aspects of your life truly hold you back is the challenge.

Montreal, Canada – June 24, 2013

I’m having lunch with Catherine at an event our friends Diane and Danny organized. They’d worked on every last piece of decoration for the event for weeks, from the promotional video to the chopstick holders. They had the chef explain thoroughly how he chose and prepared his fish. They showed us how to wrap a basket with cloth so that you can carry it around. They had even made small baskets with gifts for every attendee.

Catherine and I were both struck by how different their lives were from ours. How they’d spent weeks working on this project, while we’d been routinely managing our businesses.

As a reward to myself, I had planned a 2-3 month trip during my painting company’s upcoming low season. During that lunch, we talked about it, and suddenly it came up : Why didn’t I ditch the painting company altogether and leave for a year?

I’d been doing the same thing for over 18 months, and that was the first time I actually realized I could go out and do something completely different. That what was holding me back was not some exterior force, but a self-imposed constraint that I’d internalized.

A few months later, I was off.

With a one-way ticket.

Bali, Indonesia – October 14, 2014

Substantial change logically has to come at the expense of some other important aspect of one’s life. Rarely does it come through increments, it is usually drastic, revolutionary.

To get to where you want to be, convincing the entire crew to change course is never as effective as jumping ship.

And therein lies the challenge : giving up, on all the right things.

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