10 min 18 sec

Corporate Marketer Plans Worldwide Trips for Women

Frustrated with climbing the corporate ladder, a marketer finds adventure waiting for her at the bottom when she starts a travel planning service for women.
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What It's About

When the disillusion sinks in, this corporate marketer finds her calling planning trips for other women.

Business Model
Skills Required
Research & Organization
Profit Potential

Words of Wisdom

Mary has learned a lot of lessons along the way. When we asked her if she would do anything differently, she said that she would have started Living Big Travel much sooner than she did.

She used to look at successful entrepreneurs as having everything “figured out,” but what she discovered is that despite the outward projection of success, everyone is just figuring it out as they go. In her words, “if there’s something that you’re passionate about and have a general idea of what you’d like to do—just go for it. You’re never going to feel 100% ready, and if you wait for that moment, it may never arrive.”

Fun Fact

In 2015, Mary took nine women to Costa Rica. When her usual chef who hosts an empanada-making lesson said his restaurant was out of action, Cecchini told him how much the ladies had been looking forward to it. “So he said ‘I don’t think my wife would mind,’ and offered us his home kitchen! We ended up having a great time and holding his kids....”

As part of a reunion, the Oregon-based women all came to Cecchini’s house in the spring of 2016 and made empanadas again.

Notes from Chris

Episode 416

Mary Cecchini did all of the things that she thought she was supposed to do. She went to college and earned a degree, and she eagerly jumped into the workforce working for major brands. But after 5-8 years of climbing the corporate ladder and chasing promotions, she wanted something different.

Mary was successful, but she didn’t really feel that she was the one guiding the ship. She felt that she was drifting further and further away from what she wanted her life to look like.

She’d always wanted to travel; she felt that doing so might give her the clarity she needed, but her 60-hour work schedule and limited time off forced her to put that on the back burner. So she made a promise to herself—by 2013 (one year’s time) she would quit her corporate day job and see the world.

And she kept that promise. She traded in her heels and briefcase for a set of comfy set of hiking shoes and a travel pack and spent five months doing a solo trek through Europe, starting in Turkey and heading West.

Over on her blog, there was an overwhelming number of responses from women at all walks of life who wanted to do the same thing but didn’t have the time to plan or were held back by their reservations about traveling solo. And this lit a spark for her.

She thought back to all of the stops she had made along the way and decided that she could plan these trips for other women and make it easier for them to have the life experiences that they wanted without the burden of having to a) plan it themselves, or b) go it alone. She’d put together group travel experiences for women and plan every step of the way from hotel stays and where they’d go to eat to the activities they’d do along the way.

Mary’s mother had always told her, “love big, live big,” so when it came time for her to name her women-only travel company, she decided to call it Living Big Travel as a tribute to her mother.

Since then, Mary has helped plan vacations for around 150 women on 15 different trips to places like Switzerland (which happens to be her favorite destination because she loves the mountains!), Iceland, Croatia, Thailand, and Italy, and she’s even added some domestic trips and options for people who are looking for some assistance for solo vacation planning. Most of her trips fall between $2,000-4,000 depending on whether the trip is domestic or international and they usually include 6-7 full days of jam-packed adventure.

One day, Mary would like to turn Living Big into her full-time passion project, but for the time being, she’s been happy growing her brand slowly and intentionally. She’s also grateful to have the marketing contract work available to her so that she didn’t have to put pressure on Living Big. She feels that if she did, money would have played a bigger part in her decisions. If she didn’t start this as a side hustle, she might not have been able to make decisions based on what was best for the company.

Maybe this is another reason for a side hustle … maybe this is another reason to look at your life and ask yourself, “Am I fulfilled? Is there something missing? If so, what steps should I take next?”


  • Living Big Travel: Trek on over to Mary's website to learn more about the trips she plans for women
  • Wordpress: Mary used Wordpress to form her website for Living Big Travel, and here you can learn how to install your own Wordpress site in 5 minutes


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"When women make connections with other women who are very different than they are, it’s an invitation to see the world through another woman’s lens, to see all that we have in common, and an opportunity to develop more empathy and compassion for women, and the world around us."
—Mary Cecchini #SideHustleSchool

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