How one woman built herself a brand new career traveling the world after 21 years of working 9-5

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Cacinda Maloney, diving with sharks in Roatan, Honduras.
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Courtesy of Dr. Cacinda Maloney of PointsandTravel.com.

Cacinda Maloney has always traveled.

At the start of her 21 years as a licensed chiropractor, a business coach advised her to travel every six weeks.

She and her husband “thought he was crazy at first, especially since we had just graduated from college with our doctorate degrees and in debt of college loans at $100,000 each,” she told Business Insider in an email.

“We were go-getters who were ready to work after 10 years of college. However, the advice he gave us ended up being the best advice we have ever received from a coach.”

So, while building and running an Arizona chiropractic practice with her husband, Maloney made regular travel a priority. In 2014, she made it her profession as well, leaving the practice’s daily management to her husband and beginning a new career as a travel entrepreneur.

Maloney, who runs PointsandTravel.com and its associated Facebook and Instagram pages, is today a Travelocity ambassador who’s visited over 50 countries so far. While her husband and two teenage sons sometimes join, she takes the majority of adventures on her own.

Below, Maloney tells Business Insider what it’s like to leave an established career, the realities of a life lived on and off the road, and the challenges of building a career that sends you around the world.


She had started PointsandTravel.com in 2012 as a way to document her travels. That year, she visited eight countries and 38 cities. In 2013, she did about the same.

In Palawan, the Philippines.


By 2014, Maloney had reached a crossroads. “I was extremely busy at the clinic and then became busy at PointsandTravel.com and I knew something had to give. It was a good thing, but there was just too much work!” she said.

It’s wild out here: Wadi Rum #Jordan #goJordan #shareyourjordan

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In Wadi Rum, Jordan.


“I had been working long hours for years and was ready for a break,” Maloney remembers. “I was one of the lucky ones, who had built-in vacations every six weeks of my life for over 20 years. But still, I was tired of the same routine.”

Truly almost hard to believe you are seeing 400,000 crosses on the Hill of Crosses #bestoftheBaltics #JaywayBaltics

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At the Hill of Crosses, Lithuania.


“I knew I had to make a decision at this point, as I couldn’t do both and do both well,” she said. Work like freelance writing gigs and photography offers, brand ambassadorship proposals, and trip requests started flowing in, and “it was now or never to take the plunge.”

In the Galapagos Islands.


Maloney remembers feeling like a “fish out of water” the first 3-6 months, hoping she’d made the right decision.

In Glacier National Park, Montana.


“I was a part-time blogger for one and a half years, so the transition came naturally. Of course, it was scary for this medical professional to transition, but it was like a new adventure in many ways,” she said.

In Key West, Florida.


The hardest part, she remembers, was the “‘business of travel’: learning new technology, buying the equipment needed, learning to write creatively, learning to organize the workflow, figuring out social media, hiring virtual assistants/other writers, and planning strategy.”

In Smögen, Sweden.


Now, she’s a brand ambassador for three major travel corporations, a travel expert for a tourism board, a freelance and contributing writer, a social media manager, and a travel photographer. Her new income, she admits, doesn’t compare to what she was earning as a chiropractor, and she still maintains a partnership in the practice she built.

In Santorini, Greece.


Working with Destination Management Organizations (DMOs) means she rarely pays for accommodations, flights, or food on a trip.

In Southern Italy.


“As a travel entrepreneur, I’ve been paid to eat my way thru Sicily, gallop on camels at sunrise in Jordan, rappel a 100-foot waterfall in Costa Rica, sea kayak in the Galapagos, sail through Greece, marvel at the markets of Guatemala, swim with stingrays in the Cayman Islands, snorkel with beluga whales in Manitoba, and dive with sharks in Roatan,” she said.

I see you! #Galápagos sea lion says hello! @ecoventura @ecoventura_ec #allyouneedisEcuador

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In the Galapagos Islands.


“Plus, I drink in some of the world’s best bars, eat in elite Michelin-stared restaurants, as well as ‘dive’ restaurants and even street food. I get to explore archaeological sites and experience things I never even knew existed!”

More of the #Chichicastenango #Guatemala food market #TravelDeeper #yahootravelexplorers

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In Chichicastenango, Guatemala.


In 2016 so far, she’s visited Great Britain, Spain (twice), Monaco, France (three times), Italy (twice), Germany, Norway, Sweden, Denmark, Grand Cayman, Dominican Republic, Galapagos Islands, Ecuador, the Philippines, Japan, Mexico (twice), Dallas (twice), Montana (twice), Park City, Utah, and Manitoba, Canada.

In Manitoba, Canada.


Next, she’s off to Indonesia, Mexico (twice), San Diego, Texas, and a cruise from Nuremburg, Germany to Budapest, Hungary. She’s also trying to accept “a burning invitation” to Cuba.

In Troyes, France.


“Ideally, I like to think that 30% of my time I travel, 30% of my time I work on projects, and 30% of my time I am looking for new work with 10% of my time doing miscellaneous activities,” she said. She intends to cut back on the traveling a little in 2017 to devote more attention to the non-travel elements of her projects.

In Zipolite, Mexico.


She advises others who want to leave their careers for something new: “Invest in yourself. That one great skill you have: Use it. Do what you do and do it well. Do it better than anyone else. Strive daily to do your best work.”

Rum Point, #CaymanIslands with @nicolepajer -one beautiful soul.

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In Grand Cayman, Cayman Islands.


And, she adds for fellow travelers, “If you travel more than six times a year internationally, get global entry. Only bring a backpack and carry-on luggage. Always get travel insurance, have a spare SIM cards for your DSLR camera, and get T-Mobile, who has free international 3G almost worldwide.”

In Manitoba, Canada.