Solo Travel After 50: What I Wish I Knew Before I Started // 151

Are other people’s fears shaping your decisions?

If you’ve hesitated to travel solo because of warnings, doubt, or “what if” conversations, this episode is for you. After six years of intentional solo travel beginning in her 50s, Cheryl shares what she wishes she had known before she ever booked that first ticket.

Because the biggest obstacle often isn’t the world.
 It’s the voices that have never done it themselves.

In This Episode:

• Why the world isn’t as frightening as many assume
• The power of walking with confidence and purpose
• Why overplanning creates stress instead of security
• How leaving space creates better travel moments
• How solo travel rewires your brain and reshapes identity
• Why autonomy builds lasting self-trust
• Starting small in safe destinations

Solo travel after 50 isn’t reckless.
 It’s intentional growth.

When you move beyond borrowed fear and step into your own experience, something shifts. Confidence deepens. Decision-making strengthens. You begin to see yourself differently.

If you’re ready to move past hesitation and design a safe, meaningful solo trip aligned with this season of life, Cheryl works with women in 1:1 coaching to build structured confidence and realistic travel plans.

Apply for 1:1 coaching at:
 https://cherylbeck.com

Transcript

Solo Travel Reflections and Regrets

Speaker 1 0:00

Have you ever looked back on something you did in your life and thought, oh, I would do this differently next time around? And I'm not talking about regrets, I'm talking about something that maybe you enjoyed, or just something if you had to do it again, you would do it differently. For example, I feel like there are a couple parenting things I'd probably do differently, so maybe as I get some grandchildren someday, this could be something I would do for them. For example, you know wishing I had taught my children at a young age another language and so getting maybe a redo with my grandchildren. But I thought about how this relates to solo travel and there are a couple things that I wish I knew before I started solo traveling and then I could share with you so you can get out there and do it differently or better than I did the first time around.

My Solo Travel Journey

It's Not As Scary As People Think

Speaker 1 1:00

Welcome to Solo Travel Adventures. I'm Cheryl Esch. You're a certified travel coach and advocate for solo travel, so I had to think about how long have I been solo traveling? I've been actually doing it. I mean even going back to my 20s. I did some solo travel. Mostly it was road trips at that point in my life and you know, my thirties, forties probably did some solo travel. Mostly during that time of frame of my life it was maybe, maybe, to visit family or friends. I would often go to a lot of fitness conferences or workshops, uh, solo. So, yes, there I would be alone. But I didn't start truly intentionally solo traveling until my 50s and so I'm 57. And so about six years ago is when I recall kind of really intentionally planning an actual solo travel. Now I wanted to do a little solo travel before that and I'll get to kind of what happened there. So solo travel has become a part of every year. I make sure I plan more than one these days, solo trip usually. And I just have some things that through these past six years that I may pass on to you, things I wish I knew before I started solo traveling. And then the first one is really something that a lot of people perceive and I'm here to debunk that. And the one thing I wish I knew is it's not as scary as people perceive and we often believe and even listen to those voices of other people. We often believe and even listen to those voices of other people.

Speaker 1 2:46

I like to refer to a quote that is often used by Brene Brown. She uses it a lot, but it's actually by Theodore Roosevelt and you may be familiar. It's called the man in the Arena. I'll read a little bit of it it is not the critic who counts, not the man who points out how the strong man stumbles or where the doer of deeds could have done them better. Isn't that what we're talking about here? The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs, who comes up short again and again.

Walking Confidently Keeps You Safe

Speaker 1 3:26

Now there's a lot more, but essentially from this quote, and what Brene Brown often says is don't listen to anybody's advice. Who hasn't been there, anybody's advice who hasn't been there, and so a lot of people that would tell me that I shouldn't solo travel, it's scary and I shouldn't do it. There's crazy people out there and all that stuff. Actually, I look back and I think, well, they've never solo traveled, so they can't really speak from experience, and so that's really one thing. I wish I hadn't listened to those people, because the bottom line is and just so you know, if you have never solo traveled and I've been doing it six years at least, periodically earlier than in my 50s. But these are things I wish I knew, as I started to intentionally solo travel after I turned 50. But you're going to listen to the people that have actually done it, and so it is not as scary as the world makes it out to be is number one thing I wish I knew, and before 2019, I actually missed out on a trip or two because I was listening to those naysayers in my close circle and I just wish I had not listened to them because I could have been experiencing more solo travel and more experiences prior to 2019. The second thing I wish I knew before I started solo traveling and again it's a sort of safety issue that many people would assume.

Leave Space in Your Itinerary

Speaker 1 5:10

Again, as a woman solo traveling gosh, you're gonna you know you're gonna be a target. You're gonna be harassed. What I found You're going to be harassed what I found was walking confidently, with your head held high, I believe, has kept me from any harm. There is something to be said for that. As you walk confidently, I like to say no one's going to mess with you, because you look like you're not going to put up with crap, right, and so I believe that has played into sort of why I have been fortunate enough to be kept from any harm Now I'm not saying that and I have never been pickpocketed, but there's that could still happen, right. But if you're walking confidently with your head held high, not in your phone, then you're going to be safer in your solo travels when you're walking around.

Speaker 1 6:05

Third thing I wish I knew before I started solo traveling is a perfectly planned itinerary never goes as planned. So I guess the bottom line that I learned from this is to not plan so systematically and to allow space for free time. To allow space, because things will go wrong and so you will have to learn to pivot. Plus, a perfectly planned itinerary caused me to really rush around trying to get oh, I got to be here at this time, here at this time, and it really created some stress for me. That was in my early years and I don't do that anymore, but I felt it. Also, it limits you as well, because if you have exactly planned what you're going to see or do, it doesn't allow for you to actually see or experience something you weren't planning on and you miss what I call the serendipitous moments that occur when you solo travel. So if you are new to solo travel. I encourage you to. Yes, planning an itinerary is going to make you feel safer and more confident, but within that plan, please allow some gaps. Give yourself extra time, even for your travel getting from one place to the other, and that way it will be less stressful for you.

The Transformative Power of Solo Travel

Speaker 1 7:44

And the other thing I learned is that solo travel is more than seeing new places. There's actually, I discovered there's a mental and emotional change that happens when you solo travel and you may not notice it at first, but it's very remarkable. You might even come back and feel changed and not really understand what it was that changed you. There's so much that happens when you do solo travel and there is some science behind some of it too. But in general, the idea of you know, making your own decisions, problem solving on your own, having that freedom, the autonomy of yourself and just seeing new things will rewire your brain and experiencing new things For me that was the biggest thing is having new experiences really sort of changed me mentally, my perspective, and just that whole idea of kind of an adventure was also something that pulls us out of our mundane, and so that again will cause a change in us and we might even crave it.

The Unexpected Joy of Traveling Alone

Speaker 1 9:06

Which gets me to my final point, and I really wish someone who had solo traveled had been adamant or shared with me the beauty and the joy of solo travel, because one thing I didn't plan on and I wish I knew is how much I would love solo travel. Because one thing I didn't plan on and I wish I knew is how much I would love solo travel and that often we may initially go for other reasons, maybe because no one could go with us. Maybe that was timing, maybe it was finances, or maybe the place you wanted to go was not a popular place to visit, so no one really wanted to join you. Or maybe you went as sort of an escape. Of course, you know a vacation from your daily life, but what I have learned is I really love solo travel. I actually hate to say this, but I love solo travel more than going with other people, even though I will do that from time to time.

Speaker 1 10:04

There's just something about and you will learn this as you begin solo traveling there's something beautiful about being with yourself, even, and getting to know and love yourself, and so those are some things I wish I knew before I started solo traveling after age 50. I hope that's inspired you to get out there and solo travel on your own and maybe experience some of these things or take them to heart and know don't you know? For example, don't take the advice of someone who's never been there. You may have people that are, you know, good intentions. They are watching out for you. But if you start small, pick a place that is known to be safe for women travelers, you will be absolutely fine, and you will. My hope is that you will come back feeling the same way I did, that you love solo travel and you want to do more of it. Well, sisters, get out there and have that solo adventure.