“It started with a date” – The Coffee Shop Conversation that Doomed My Desk Job

"It started with a date" The Coffee Shop Conversation that Doomed My Desk Job

It was early January 2014. The holiday season was now behind us, and it was back to life as usual. On Monday I’d return to work after 10 consecutive days off. But I didn’t want to go.

The topic had come up several times over the course of the year. Preliminary conversations had begun. Ian had resigned from his steady, full-time job the year before to try his hand at entrepreneurship, and together we dreamed about both of us having that freedom. But it didn’t feel like a real option until that day. 

Ian and I planned a coffee shop date to see what we could do to make it happen. Four coffees, three pastries, and five hours later, we had a plan.

It started with a date.

Without knowing where else to begin, I picked a date. March 1st, 2014. It was an arbitrary selection, but in two months time it would mark the official day my freedom began.

Then we crunched some numbers. If I was going to quit, we needed to make some lifestyle changes and start saving money. We had already begun living more frugally since Ian had taken the leap. But for both of us to forfeit a stable paycheck? That sounded tricky, but not impossible.

Lonely Speck had just begun to gain momentum. Ian’s most popular articles were starting to get reshared by popular photography blogs, and his December affiliate revenue had reached an all-time high of $167. The outlook was good for writing to become a viable financial support for us. But we weren’t there quite yet, and there was more we could do to increase our chance for success in reaching our goal date.

We considered all the ways we could save money. For starters, I could sell my car. I was riding my bike to work every day, and the weekly parking shuffle for street cleaning was a hassle anyway. No more car payment = $250/month saved. No more car insurance payment = $100/month saved. Plus, I’d end up with a net positive $2,300 after paying off my auto loan if I sold it for KBB value. With almost $1K in savings, cashable vacation time, and a canceled monthly cell service plan, I was in good shape to save enough money to cover one year of my student loan payments — plus three months of well-budgeted world travel for the two of us — all before my arbitrarily projected quit date.

We ditched our commitments — except the one we have to each other — and found a way to make our travel life happen.

There was just one more thing that needed tending to.

Health insurance. Even with the Affordable Care Act, if your recent income is well over the poverty line, it’s expensive. As it turned out, though, I didn’t need it. If Ian and I departed for our overseas adventure right after my quit date, a much more reasonably priced health insurance plan would cover me while traveling abroad. We splurged and got the covers-nearly-everything plan and together paid only $368 for three months of overseas coverage.

As we took our last sips of coffee and packed up to leave, I felt an eagerness and excitement unlike any I’d felt in my life. We didn’t just have a dream. We had a plan. And I was determined to stick to it.
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Want to know what happened next? Read about what the next two months entailed in “7 Steps to Quit Your Job & Travel Full Time.”

You may also enjoy “10 Reasons I’ll Never Regret Quitting My Job to Travel.”

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About the Author

Diana Southern
In March 2014, Diana called it quits on her traditional American working life and set out to explore the world with her partner in crime (and love of her life) Ian Norman. They now live a sustainable life of full time travel, working for themselves and seeking adventure at the same time. Here on North to South, Diana documents their journey in achieving and maintaining this "road less traveled" way of life.

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