The Startup Traveler: An Ambition Labyrinth

It’s the middle of January, and I’m sitting in a tent at the edge of Lake Wakatipu at the Frankton Motor Lodge in New Zealand.  The skin on the back of my neck has finally turned a dark brown from red and peels a little more each day.  It’s hot and sunny, but the recent storm from the night before has blanketed the Remarkables Mountain Range in the distance.

Despite the breathtaking surroundings or exceptional weather, I’m a bit stressed out.  On my laptop are three screens: my spending budget, an almost-finished marketing report and  a goal-setting worksheet that the CEO of one of the companies I contract for had sent me.

If we continue living out of a tent and living off of oatmeal and coffee, we should be able to stay under budget for the year.  And by under budget, I mean paying 75% of my income towards student loans and 10% towards a my “moving back to the high rent of San Francisco” savings fund.  But the key to this equation is that I actually have an income – any income – to work with as we travel the world and return to SF.  I’ve been jobless in the Bay Area before and it’s not a pretty scene.

What’s really stressing me out is choosing a reasonable, meaning set of goals for the new year.  The worksheet starts by looking back at what I’ve accomplished over the past year and then asks a series of questions leading me to list my goals and priorities for the next year.

2013 was easy.  I got 2 awesome jobs in Australia for the year,  made new friends, tried new foods, supported new charities, ran my first marathon, presented at the Melbourne Quantified Self group and started my own little business.  I set each of these goals meticulously throughout 2011 and 2012, writing each goal on a note card and taping it to my living room wall for everyone to see.

But 2014? My biggest goal is to not run so fast that I trip over my own feet – as a runner and traveling entrepreneur.

The business I created, Systems Arch, was really created just for tax purposes.  I don’t have so much as a website or logo created for it yet. By having a business, I’m able to contract more easily for Australian companies while living in San Francisco. The idea was to continue working for a few companies on a part time basis so I could travel New Zealand and South East Asia while continuing to making my always painful monthly student loan payment.  But as I talk to more and more people, the more I realise that with a little TLC, some positioning and the right kind of networking I just might be able to make this work!

But is that what I really want?

What about my vision of settling down, getting a cool job at a health-tech company as a Product Manager and starting a family?  Is it possible to do it all: freelance and build my brand while traveling, then dig into a super awesome job back in the Bay Area while taking on a few side projects here and there?  If I did that would I have time for starting a family and training for my next marathon, the SF Marathon in July, 2014?  I want to say yes to all of this, but the devil’s in the details.

Hyper Mobility

I promised my partner that if he moved to Australia with me for a year, we would spend 4 months traveling to whatever countries in the world that he picked.  My idea was to spend the year in Australia saving money for this trip, but the reality is that when you’re in a new country you’re have to spend some money on new experiences.

So to travel, I had to get a job.

Planning a trip and work schedule is a lot like planning a backpacking trip in the mountains.  You create a proposal, mapping out every detail and circumstance you and everyone around you could ever imagine happening.  You get all the right gear: laptop, international debit card, WiFi hotspot, upgraded Dropbox account, Basecamp account, Freshbooks invoicing account.  But at the end of the day, you’re really just looking at a mountain on a map and guessing how fast you’ll be able to climb – there’s really no way to prepare you for the experience until you do it.

A lot of people that we’ve met while traveling find it fascinating and charming that I’m able to work while seeing the world.  And it is.  It’s the biggest, most amazing adventure I’ve ever had in my life and I’m completely thrilled to have put in so much hard work and planning to make this happen.  But there’s also a fair bit of eating oatmeal for days, shivering in a tent for the 10th night in a row, hitchhiking in the rain, and yes, committing the biggest of all San Francisco foodie offenses — eating from the McDonald’s Dollar Menu.  Not once, but for a solid week because McDonald’s is the only affordable place eat and get free WiFi.

Worse than the Micky D’s Dollar Menu though is saying “no” so much.  The other week, we had planned to hitchhike to the other side of New Zealand and stay at a farm but had to stay in town so I could finish a rush of different project that had come up for work.  As I sat glued in front of my computer for 12 hours a day for 5 days, my partner patiently found small things to occupy himself as he waited for me to finish.  I know this sounds trite, especially because I love the work I do and the people I work with but man, when you’re in the mountains halfway around the world with the love of your life, work can be a drag.

So what will the next month bring to my travels and business?  What charities and sporting events will I find to participate in?  And how the hell are we going to afford moving back to San Francisco and starting a family?

I guess I should finish this goal setting worksheet to find out…

Travel woman

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