266. Don't Wait to Travel, Take that Vacation With Anna Fishman

It is time to travel. It is time to get back out there and enjoy what this world has to offer, from amazing food, the sound of different languages to vibrant cities. If you've been feeling the travel itch, you’re going to love today’s guest.

Anna Fishman is founder of the Olegana Travel Boutique. With a passion for crafting unforgettable experiences, Anna has redefined luxury travel, making it accessible to families, couples, and now an exclusive community of women. 

She calls it her second wind career. She had worked in daycare, police departments, she did taxes – and her last corporate job was in marketing and advertising compliance.

“I didn't love any of those experiences, I never felt at home when I was at work and never felt like I was making a difference,” says Anna. “I remember sitting in my last job in a cubicle thinking, is this it?”

Having her first baby flipped her life upside down. She says looking back, she had postpartum depression. Returning to work after maternity leave had her dreading going into the office week after week. But on paper, she says everything was great. Anna took some time to get honest with herself. 

“I asked myself if I didn't have to do anything … if I don't have to pay for mortgage or care for the baby. What the heck would I do with my life?” asked Anna. “Travel. It's always been travel. Good times, bad times. You know, like I travel to forget. I travel to celebrate, I travel, I just travel.”

With that realization, Anna used her four-hour commute each day to research how to start a travel business. She had no experience running one, but she says for the first time in 15 years, she felt alive. She credits the support of her husband as being the most important catalyst on her journey.

“His belief in my vision, his belief in giving me that freedom to quit my corporate job a year and a half into this … if he didn't show me that support, mental, financial, emotional, … if I didn't have him, this would never have happened. So I want to stress how important it is to have that support,” says Anna.

“We're fighting against the market, the clients, the suppliers. But we're also fighting this invisible fight at home against our partners who are not supporting us. Unfortunately, it will never work if you're fighting on if you're divided on two fronts,” she says.

Six years into her travel business, Anna started focusing on small group trips for women. The camaraderie and connection she found was powerful.

“Being in a destination with the client who comes alone, was a little nervous, a little shy, doesn't know anyone, maybe just lost a partner, maybe just, you know, got divorced. … That said, ‘that's enough. It's time for me to put me first and take this crazy step.’ … We have all kinds of interesting people that come on our trips, and then seeing them, open up like a flower throughout the trip and really start enjoying life again, if I may say that, … It's such an incredible, powerful experience and emotion and feeling,” says Anna.

The experience allows her clients, who might be burnt out, to get a reprieve from decision fatigue. Anna says her job is really to know the client and what they’re looking for, and she has many conversations with women about not waiting to retire to travel. 

“Women who come on our trips are a little bit older, but I don't want to wait till I'm in my 50s,” says Anna. “I don't want to wait to retire, to live my life. I need to fulfill myself now so I can be better for my kids and for my husband and for my clients.

“I don't care if you block it ten years from now, or one year from now, or three months from now, unless you get on the calendar and say, ‘this is when I'm going to Italy or Greece’ or whatever you want to go, it will never happen.”

Connect with Anna Fishman : https://www.oleganatravelboutique.com/ 
Anna is off