How I quit my job to travel: The Washington DC lawyer

Gina Dowd explains how she left her high-paying, high-pressure job to island hop around the world – using her legal skills to pay her way.

Gina Dowd was standing on Washington DC’s Pennsylvania Avenue, near the White House, when an idea that had been swirling around in her head crystallised into a decision. She would quit her high-paying, high-pressure job as a DC-based financial lawyer to travel the world.

It was January 2009, the night of US President Barack Obama’s first inauguration, and after a nearly 24-hour work day, the people crowding DC’s streets and filling its cabs and trains for the event were making the task of heading home impossible. Dowd’s life had become engulfed by her work, and this was her breaking point.

She scrapped her plan to buy a house, and instead spent the next 12 months saving money and selling nearly all her possessions. She gave her employers a month’s notice – double the customary two weeks. “I knew I didn’t want to go back, but I thought if I have to, I want good references,” she said.

Along with her good career sense, Dowd started off with a healthy sense of adventure. “I had a couple of Lonely Planet books and I wanted to go to Australia – that’s all I knew”.

She began her trip in Hawaii and island-hopped her way to Fiji then Australia, taking surf lessons, diving the Great Barrier Reef and visiting eucalyptus rainforests along the way. A highlight was driving around Tasmania for two weeks with a traveller she met on the road, seeing the wildlife, enjoying the culture and sleeping in their rented car most nights. Together they took a boat to Maria Island off Tasmania’s east coast, where they stayed in a converted prison. One night, Dowd woke up and walked out to a clearing in the middle of the grounds to discover a group of kangaroos and wombats sleeping, nestled in the grass.  

“This so amazing, I’m so lucky to get to experience this,” she thought at the time.

After three months, Dowd knew she needed to go somewhere less expensive if she were to continue her journey. Though she had no initial interest in going to Southeast Asia, many fellow travellers encouraged her to visit for both the experience and the comparatively lower cost.

Dowd’s first stop was Phuket, Thailand, where she began taking on freelance clients, spurred on by the fact that friends and acquaintances had started contacting her for legal advice. As she continued travelling through Asia, exploring Malaysia, Singapore and onto Europe, including living for seven months in Seville, Spain, she branched out to freelance websites oDesk and Elance to find foreign clients who needed an attorney for US matters.  She focused her services on business, intellectual property, financial regulatory work and e-commerce, which consisted of tasks like contract negotiation and drafting – work she could do anywhere.

“In addition to being a great way to fund my travels, these projects were very interesting in some of the same ways that my travels were – they gave me glimpses into lives and cultures that were very different from my own”, she said, giving the example of a Nigerian client who shed light on the struggles of running a business in a country plagued by corruption.

To keep her new business afloat, Dowd relied on technology and advance planning.

“All I needed was my laptop and a wi-fi connection. For phone calls we would talk via Skype,” she said. “If I had a deadline or needed to talk to a client, I would make sure I was staying somewhere with a reliable, secure wi-fi connection (and not too expensive), where I could have some privacy.”

 Dowd’s international stable of clients meant accounting for time differences, so she often found herself working odd hours. However, this suited her new lifestyle perfectly. In fact, many of her clients were world travellers themselves, and they liked the idea of using a lawyer who understood their world.

Though Dowd said she was never able to turn finding new clients into an exact science, she worked to maintain long term relationships with the ones she took on. When she finally returned to the US in September 2011, she was able to support herself with the stable of freelance clients she had built.

It wasn’t long before Dowd met someone who shared her entrepreneurial spirit and love of travel. She met and married a former Navy Seal who owns a software development company – one of the areas of practice she focuses on. Together they have a young daughter and plan to travel long term again in a couple of years, armed with the knowledge and experience Dowd has already gained.

“I never once regretted leaving my job,” she said.