‘The only trips I regret are the ones I didn’t take’
Guest blog post from Felicity Leo
‘The only trips I regret are the ones I didn’t take.’
This powerful statement was shared by Anna Fishman, the visionary behind Olegana Travel Boutique, during a fun and meaningful episode of her popular podcast, Permission Slip.
Episode #2 goes into women’s relationship with joy—emphasizing the importance of granting themselves permission to live fully and unapologetically take time to travel.
Whether a Foodie Adventure in Southern Italy, Puglia or exploring castles of Scotland, travel enriches our lives with beauty, resilience, adaptability, and a deeper appreciation for both the world and ourselves.
Many women aged 25 and older often find themselves asking questions like, ‘Am I allowed to want all the things? Am I allowed to desire more money? Am I allowed to be more ambitious?’
Many have stopped waiting for approval and consent for what they desire and want to pursue. Even when there’s leeway, it won’t matter if we don’t grant ourselves permission first.
Often, we hesitate to take trips because of inconvenience, fear, or perceived responsibilities. But when we look back, the discomfort fades, and the memories of the adventure, the new perspectives gained, and the people we meet stay with us.
Let go of the limiting beliefs we impose on ourselves that keep us second-guessing our choices. "I almost went to Italy." "I almost started a business." "I almost signed up for painting classes."
You never hear someone come back from a trip saying it wasn’t worth it. More often, they say, “Why didn’t I do this sooner!?”
Especially if it’s a place they’ve always dreamed of visiting—a chance to taste new cuisines, meet new people, and immerse themselves in a different world.
Travel always leaves you with something special—experiences that bring happiness and joy long after the trip ends. These moments become a part of you and can never be taken away.
“Material things might be fun and spark joy, but it's the experiences that truly stand the test of time.”
Anna recalls an opportunity to visit Japan when she was 21—a trip she chose to pass up. Looking back, she realizes the only trips she truly regrets are the ones she didn’t take. So, the next time opportunity knocked, she made it happen. She visited Spain and, in the process, discovered her amazing gift for travel planning.
The Permission Slip Podcast explores how transformational travel can be. Sure, you may have an itinerary of places to visit and things to do, but as Anna says, “The feelings you’ll experience? You have no idea!”
With 10 years of experience in luxury travel, Anna has seen firsthand how people become completely immersed in the moment. Watching their faces light up with joy and wonder is an unmatched experience.
As Sara Walton, Business Coach, affirms: “The attention to detail at Olegana Travel Boutique is truly extraordinary!”
“Encourage women to do what they love , take time to travel!”
Doing so brings happiness and satisfaction, filling their cup and renewing their sense of being. It provides inspiration and patience to take on their world with fresh energy.
After all the luxury trips and women-only journeys they had experienced over the years, these women told Anna that their trip with her group was one of the best of their lives.
That was Anna’s aha! moment—a realization that this was exactly what she was meant to do with her life.
