How to Travel Cheap in Retirement and Still Hit Bucket List Trips w/ Jillian Sidoti
episodePreviously titled “How to Travel Cheap in Retirement w/Jillian Sidoti” — renamed by the publisher on Aug 5, 2026
Wealthy After 40: Retirement Planning and Budgeting for Gen X
25 min
2 speakers
7 chapters
transcribed 1 month ago
Transcript
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Transcript generated automatically by AI and may contain errors.
What is the main topic discussed in this episode?
Welcome to the Wealthy After 40 podcast, the show for Gen X women and couples who are ready to ditch financial stress and feel confident about retirement. I'm your host, Dailene Higgins, money coach and retirement strategist, to help you gain clarity and confidence with your money by creating a spending plan that aligns with your financial goals and dreams so you can spend intentionally, save consistently, and feel at peace about your future. Join me every week to understand your money, simplify your decisions, and take intentional steps toward the life you want.
Jillian Sadati is an entrepreneur, traveler, and co-founder of Last Life Ever, a platform built on the idea that you shouldn't wait for retirement to live well.
Who is Jillian Sidoti and how did she go from lawyer to travel entrepreneur?
A mom of three based in Rincon, Puerto Rico, she shares her adventures at At Last Life Travel and helps people design lives full of meaning experiences. Thank you for joining us here today, Jillian. Excited to talk to Jillian. She is, quote, a travel expert. So we're talking about traveling today. And I know many of us, as we head into retirement, that is something we really think about, are thinking that's what we're going to do. So I thought, you know what, Jillian would come and share. She's set up some amazing travel trips. I'm sure she'll share those with you. And then basically how to plan and prepare for So Jillian, before we jump into the questions I have to get us talking about those things specifically, share who you are and what you do and how you got into the really the travel side of it all.
Yeah. So it's interesting. I was an attorney for 15 years and my life was like pretty, pretty miserable. It was interesting because I was having this really great career and I Yet I found myself just wishing I didn't have it anymore. I was making a ton of money and I just didn't want to have it anymore. I ended up going to a conference and I met this guy who's now my business partner. And he said to me, oh, yeah, I used to be a lawyer. And I remember thinking, oh, yeah, I want to be, I used to be a lawyer. And he told me a story about how he, and this is his story, but I'm going to tell it anyhow. He told me a story about how he was a bankruptcy attorney, a very successful bankruptcy attorney. And he got really sick when he was in Peru at Machu Picchu, got home and found out he had leukemia.
and thought he was going to die and went through all of that, the chemo treatment and whole nine things.
What travel turning point convinced Jillian to prioritize travel with her family?
And when he came out of the fog of leukemia, he realized, I'm just, I'm not going to do this attorney stuff anymore. Not only that, he had to file for bankruptcy, right? So it was like this whole, what am I doing with my life? And he was already committed to traveling and And for me, I wanted my kids to have a life of travel that I did not get when I was a child. I grew up in a very middle class situation, but I was also the oldest of five kids. So our idea of travel was getting in the station wagon and driving, fighting the entire down the I-95 and fighting the entire way and then ending up somewhere. Yeah. Or minivan, whatever it was that year. And I remember thinking when my kids were born, you're not waiting.
I think I was 20 when I got my passport for the very first time. And I remember when my youngest was born. I have three kids. My youngest was born. He literally, he was fresh out of the womb. I still have his first passport. And I got him a passport almost immediately. And that's really when I started going, I'm going to travel and I'm going to travel forever. hardcore, I'm never going to say no to travel opportunities. And that became even more clear when my husband and I planned a trip that we had been planning for all intents and purposes our entire life. lives together, right? We'd probably been together at that point in time. My oldest was seven. So we'd been together for about 15, 16 years at that point in time.
We won an auction, a church auction. for a trip to Italy. And this was a trip that we had planned to take before my oldest was even born, right?
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Chapters
7 chapters
1
What is the main topic discussed in this episode?
0:06–0:59
2
Who is Jillian Sidoti and how did she go from lawyer to travel entrepreneur?
0:59–3:06
3
What travel turning point convinced Jillian to prioritize travel with her family?
3:06–7:11
4
How do you set a specific travel goal and deadline instead of saying 'someday'?
7:11–9:44
5
What practical strategies can make travel affordable (where is the dollar worth most)?
9:44–15:44
6
How can travel points and AI hacks reduce costs and improve hotel upgrades?
15:44–25:01
7
How can you find meaningful adventure close to home without long flights?
25:01–25:51
Speakers
2 identifiedMore from Wealthy After 40: Retirement Planning and Budgeting for Gen X
How to Overcome Retirement Decision Overload
Retire Confidently With a Money System That Works
Retirement Planning for Gen X: 4 Things to Map Out Now
4 Signs of Quiet Financial Stress That Delay Retirement
Why Do You Fear Retirement? The Answer Might Surprise You
Why Your Retirement Number Should Be Personalized