Building an Incredible Legacy: With Lindsay Gafford

With the drastic increase in remote work these days, the profession of the digital nomad has become much more common. Unfortunately, many digital nomads seem to run into a common problem: self-doubt.

Welcome back to The Frame of Mind Coaching™ Podcast! Lindsay Gafford, Operations Manager for the Forum and Learning Team at YPO, is with me and I couldn’t be more excited!

Lindsay has been thriving as a digital nomad who travels all over the world, but she’s also struggling with self-doubt. She has built herself up in so many jobs that she no longer knows if those experiences actually match what she wants for her future.

She needs to journal about what her past experiences have in common, what her legacy has been, how it'll affect her work in the future, and how she can make everything work towards her goals.

Episode Transcript

[00:00:05] Kim Ades:
Hello, hello. My name is Kim Ades, I am the president and founder of Frame of Mind Coaching™ and you have just joined The Frame of Mind Coaching™ Podcast, where we invite leaders from all over the world to come onto the podcast and get coached live and in person.  

Today, my guest is Lindsay Gafford and she comes to us from Vermont. She is with YPO and we love YPO, and she is the Operations Manager for the Forum and Learning Team. Lindsay, welcome.  

[00:00:32] Lindsay Gafford:
Thank you so much, Kim. I'm happy to be here.

[00:00:35] Kim Ades:
So, I want to know a whole bunch of things. You're in Vermont, but you shared with me earlier that you are a... what did you call it? A digital nomad.  

[00:00:45] Lindsay Gafford:
Digital nomad, yes. Even before– 

[00:00:47] Kim Ades:
What does that mean?  

[00:00:49] Lindsay Gafford:
Before the pandemic YPO was 90% remote. So, I came in as a fully remote employee and it has allowed me to travel around the United States and work wherever I happen to be. So, over the course of this year, I've gone to Idaho, Montana, Utah, Texas, Kansas. I'm currently in Vermont, as you said, and in January I will be heading to Colorado. 

[00:01:14] Kim Ades:
So, how do you travel? Do you have like some kind of a bus or something? [Chuckles] 

[00:01:19] Lindsay Gafford:

[00:01:19] Kim Ades:
How do you get from one place to the next?  

[00:01:22] Lindsay Gafford:
Actually, I just have a standard, you know, small SUV that almost my whole life fits into, and me and my dog. And we do long-term Airbnbs or short-term housing that's geared toward traveling professionals. So, just kind of move from place to place as my heart takes me [chuckles].  

[00:01:46] Kim Ades:
Where's your heart takes you. And how has it been? Like, what have you learned from this experience? I think is fascinating.  

[00:01:54] Lindsay Gafford:
It's been wonderful and really one of the unexpected benefits is that I've gotten to meet coworkers that live in different parts of the country that I probably never would have interacted with in person otherwise. 

But it's also just allowed me to see where I might want to make my home eventually and to experience different parts of the country. And, for me, most important thing, how they relate to the outdoors and have an active lifestyle. So, it really varies from place to place. And I'm so glad I've gotten to experience that for more than a day or two at the time. 

[00:02:30] Kim Ades:
Have you considered Kelowna or Canada?  

[00:02:34] Lindsay Gafford:
You know what? I actually love that idea. If you can get me a connection with the immigration process, I'm all about it. [Laughs]  

[00:02:40] Kim Ades:
You're all about it. Okay, we'll talk about that after. 

[00:02:43] Lindsay Gafford:

[00:02:43] Kim Ades:
I'm connected. I'm not that well connected, but we can talk. 

[00:02:46] Lindsay Gafford:
[Laughs] Okay.  

[00:02:47] Kim Ades:
For those of our listeners who have no idea what YPO is, can you please fill them in?  

[00:02:53] Lindsay Gafford:
Yes. YPO is an organization that serves leaders in high-level positions, in their companies. So we're talking CEOs, presidents, C-suite level people, giving them a place to have learning opportunities, peer to peer connections and confidential forum opportunities, which is the team I'm on, which allows them to express things with peers that they might not be able to otherwise, and create networking opportunities. And there's just a lot we can offer. And it's a really cool organization for people in these positions.  

[00:03:28] Kim Ades:
And YPO stands for?  

[00:03:30] Lindsay Gafford:
Young President's Organization. Although, now I think we just operate as YPO. So...  

[00:03:36] Kim Ades:
Yeah. And just so for people to understand who you are and what you're about, some of our listeners are YPO memebers, but not all of them are, so I just want to make sure everybody's up to speed. All right. So share with us today. What is your challenge? What do you want to talk about today?  

[00:03:52] Lindsay Gafford:
Well, my challenge has been that I have a Bachelor's and Master's in Liberal Arts degrees and entered the workforce in 2008 in the middle of the recession. So it's basically been a... Take what you can get kind of situation for me, not having a business education background. I've had to kind of claw my way up to the position I'm in now, teach myself, practically mentor myself and work to get myself out of very niche positions that didn't have a lot of growth opportunity. 

So I guess my challenge is how do I move forward with such a varied background while respecting the position I'm in. If that makes sense.  

[00:04:36] Kim Ades:
So what's interesting is you're an operations manager, that's quite a business position. Wouldn't you agree?  

[00:04:43] Lindsay Gafford:
I would, but I've had to pretty much teach myself the skills that it took to get to this place. And luckily I'm a quick learner.  

[00:04:50] Kim Ades:
Okay. So, I actually think you're in a very, very unique position. But before we talk a little bit about that, tell me about the past positions you've had.  

[00:05:00] Lindsay Gafford:
Well, I worked for the Federal Government to start doing benefits for veterans. I worked at a nonprofit in Colorado that did homeowner counseling for people facing foreclosure. I was the event Manager at a brewery in Dallas. I worked as an Operations Coordinator at a law firm. And I was a Research Analyst, the job I had before this, when I was a Research Analyst at a consumer marketing research firm. So it's nothing consistent. [Laughs]  

[00:05:34] Kim Ades:
Nothing consistent, but very, very interesting, wild and wide array of experiences.

[00:05:43] Lindsay Gafford:

[00:05:43] Kim Ades:
And so, if you were to go back to those experiences and really kind of study what is it that you achieved, what did you do, what were the results you got, would you be able to identify those clearly?  

[00:05:57] Lindsay Gafford:
I think in each position I've had, I have been able to identify a process that was not working as it should or was ineffective, and create something new that improved it and that I was able to leave as a legacy. That is kind of recognizing this as I came into YPO is how I was able to focus in on operations as a place that I wanted to be in and grow in. 'Cause a lot of operations is process improvement and identifying those areas of business that need help.  

[00:06:35] Kim Ades:
Yeah. So, what you've done is actually exactly what I would recommend, is to kind of look back at all of these roles and say "what did I do?" Rather than look at "what are my shortcomings", which is kind of how you came into this conversation, right? Like, "I come from this background, I don't really have business experience. How do I get ahead?"  

The truth is that the world is changing and what we're more interested in is not so much your education, but you know, what have you done? What have you achieved? What are you good at? And how can you show us that you've done this and accomplish these things? And if we look back at your history, what would the people behind you say about their experience of working with you? And my instinct is that you've probably left an incredible legacy in each of those places.  

[00:07:27] Lindsay Gafford:
I certainly hope so. I don't know. I guess that is part of my challenge now is I'm only just now kind of coming into this, my own power and my own strengths, right? And I'm almost 40 years old. So, I do still have that self-doubt–  

[00:07:43] Kim Ades:
You look great! No wrinkles. 

[00:07:45] Lindsay Gafford:
[Laughs] Thank you! [Laughs] It's because I don't have kids, Kim. [Laughs]  

[00:07:48] Kim Ades:
Okay, I'll take that one. [Laughs]  

[00:07:52] Lindsay Gafford:
But it's really only been in the past year, I think, where I've been able to kind of recognize my worth and my value, but that still competes with over a decade of feeling like I didn't really have a direction or know what I was doing. 

So, I guess that's the challenge now is how do I move forward in this without reverting back to those same mindsets.  

[00:08:16] Kim Ades:
Yeah. So, you're a hundred percent right. Like, you've done well. In each of your places, you've done well. And now you're in an environment of like, I think YPO is incredible for infusing you with learning. 

[00:08:30] Lindsay Gafford:

[00:08:30] Kim Ades:
Right? So it's almost like going to do your MBA, because you have access to the right people, you're in learning environments, you're hearing from, I'm assuming, a whole bunch of speakers with a whole bunch of experience. And so your job right now is to soak it in, but also to make sure that you're delivering your greatest talent to this environment. 

[00:08:51] Lindsay Gafford:

[00:08:52] Kim Ades:
So, the question becomes is, "how do I move forward?" I think you're moving forward just fine. You've done a great job of moving forward. It's not a moving forward problem. It's a problem where you say "Hey, my background doesn't match with my future goals". And that conversation in your mind says "am I really equipped?" 

That creates a little bit of self-doubt for you. That's the lag. Right? That's the thing that's slowing you down. It's not the actions you've taken. It's not your history. It's not your environment. You're in a beautiful, incredible environment! People would love to be in your shoes because you're surrounded with so much rich learning and so many cool people and so many people who are driven and who are accomplished. So you have mentors at your fingertips if you want them.  

[00:09:42] Lindsay Gafford:

[00:09:42] Kim Ades:
And what your job is to do right now is to build relationships. Right? Because those are the relationships that are going to propel you to the next place. 

[00:09:52] Lindsay Gafford:

[00:09:52] Kim Ades:
You know, every single time that there's a course that's possible for you to take through YPO, take it. Every time you can have a one-on-one conversation with one of the YPO members, have that conversation. And ask, you know? "What's the next step for me" or ask, you know, "what's the greatest operational change you made in your organization", like, learn from them, right? So that you can take that and apply it to your own work.  

[00:10:17] Lindsay Gafford:

[00:10:17] Kim Ades:
And the third thing is ask yourself, "what do I believe to be true about myself?" Because right now, what you believe to be true is, you know, you're clawing your way up. Wow, that doesn't sound like fun.  

[00:10:31] Lindsay Gafford:
No [laughs] it hasn't been fun up to this point on, honestly.  

[00:10:36] Kim Ades:
Right. But you're in a place now and you're still thinking about clawing. You don't need to do that anymore. And sometimes our history, we replay our history over and over and over again, even when we're in a completely different place. And that replaying of our history kind of slows us down. It has us repeat our history over and over again.  

And so, your job right now is to absolutely enjoy the benefits of YPO, and it has many, many, many to offer. And then you want to ask yourself "so now that I'm in this learning environment, what do I want? What's my next step? Do I want to start a business? Do I want to work for a larger organization? Is there someone here who I really truly connect with? Is there a business that I want to endorse and support? What is it that I want?" and your job is to look at all of the opportunities.  

So one of the things we do with our coaching clients is we ask them to journal in an online journal with their coach. But I encourage you to journal and ask yourself that question: what do I want? What's my next step? What do I want to learn? Who do I want to be around? What do I want to experience?" And you're doing that from the standpoint of traveling from place to place. You're trying to explore, like, "what do I want personally", but do the same thing professionally. So be a digital nomad in your profession.  

[00:12:03] Lindsay Gafford:
I like that. I love that. I hadn't thought about it like that.

[00:12:07] Kim Ades:
So, you're learning, you're soaking in each environment from, you know, where did you go? Utah, Idaho, Montana, you're soaking it in and you're going "yeah, I like this thing from here. I like these people from there" and you're kind of like, you know, I call it going– you're going shopping. Right?  

Like, imagine you're in a grocery store, you're going shopping. You're putting things in your basket. Right? You're going down the aisles and you're putting things in your basket. 

[00:12:31] Lindsay Gafford:

[00:12:31] Kim Ades:
"Oh, I'd like some broccoli. Oh, I'd like some chicken", I don't know, I'm making it up. But you're not taking everything in your basket. You're being selective. And in that basket is the life you live or the food you eat. 

And so, the same thing goes in your profession and you're in an environment where it's like an amazing grocery store, you get to select from incredible isles. So think through like, you know, who do I resonate with? Who do I want to learn from? What am I taking from this experience? What really speaks to me? When I listened to some of the speakers, what do I want to learn more about? What do I want my life to be about? What is the legacy I want to leave behind?" and on and on and on.  

[00:13:12] Lindsay Gafford:
I feel like you read my mind on the legacy, because as I move forward, now that I'm in a place to kind of stop clawing and just, you know, move forward in a less painful way, I also want to leave the legacy for people behind me who maybe were in a similar position that they don't have to do that, you know? 

And so what are your recommendations as I am looking forward to also kind of apply that behind me for people who come behind me, particularly other women or non-binary people who may not have the same opportunities that men have moving up into a world of operations, honestly, you know?  

[00:13:56] Kim Ades:
Well, here's an interesting thing. Do you write, at all?  

[00:14:01] Lindsay Gafford:
Sporadically. Not regularly.  

[00:14:04] Kim Ades:
So given your background in art, it's not a writer. Is that something that is appealing to you in any shape or form?  

[00:14:11] Lindsay Gafford:
It is. It's just a matter of being able to focus my thoughts is where I struggle. I feel like there's so much happening up here that to like, narrow it down and really start doing anything I kind of freeze, and so then I don't do it.  

[00:14:25] Kim Ades:
So, that's where journaling plays an amazing role, because you can take all those thoughts and just put them down and you don't have to organize them and they don't need to be focused and they don't need to make sense and they don't have to serve a purpose. You just need to get them out of your head. 

And what you're going to notice over time is that there's a bit of a theme. And with that theme, you're going to say "okay, this is really what I want to be focused on". Because what you're going to do is you're going to look back and you're going to start reading your journals. You're going to say "oh, you know, this is what I'm about. This is what matters to me. This is what the legacy specifically that I want to leave behind".  

And that legacy could be a project that you do for younger people that are behind you. It could be that you start a podcast. It could be that you start a business. It could be you write and you publish your articles in something like It could be a million different options. But when you're writing it down just for you, nobody else needs to see it, you're exploring what that could be. 

[00:15:25] Lindsay Gafford:

[00:15:25] Kim Ades:
And what I think is happening for you is you have a lot of thoughts, like, you know, they're firing and you're not capturing them anywhere. And so they're repeating themselves, right? They play over and over and over and over again in your mind. And it sort of sounds like "I'm still clawing in some ways", and we want to put that down. We want to let that breathe. You don't have to claw anymore. It's over. It's done.  

[00:15:50] Lindsay Gafford:

[00:15:50] Kim Ades:
So stop holding on to that ideology because that holding onto it makes it happen over and over again. You don't need to do that. And I'm going to throw one more thing at you is that you're in an environment, again, with all these incredible opportunities. Think about how do I serve these people? Because when I serve these people really, really well. That's the gateway to the relationships I get to build, and that's the gateway to learning and that's the gateway to stretching my talents and my skills. 

So you've been given an invitation. You're invited to the party. Stop wondering whether or not you really should be there, 'cause that is what's happening right now.  

[00:16:33] Lindsay Gafford:
It absolutely is [laughs] imposter syndrome, there's a moment of it every day, at least. So you're absolutely.  

[00:16:41] Kim Ades:
Yeah. And, you know, the battle you're having is not with the world, the battle you're having is internally. And what I'm here to say is you deserve to be at this party, start having fun, start dancing. 

[00:16:54] Lindsay Gafford:

[00:16:56] Kim Ades:

[00:16:57] Lindsay Gafford:

[00:16:58] Kim Ades:
And that's really my greatest kind of coaching for you is to say "I'm here, what do I do with this amazing opportunity in front of me? And how do I become a digital nomad for my profession? What's my next move? What else do I want to learn?" And make it a fun experience, right?  

[00:17:18] Lindsay Gafford:
Right. I love that way of looking at it because obviously I'm in that mindset already, in other parts of my life, so I love that and figuring out the pieces I want to keep as I go along. I love that.  

[00:17:32] Kim Ades:
Also you're a pretty frickin fascinating person, right?  

[00:17:36] Lindsay Gafford:

[00:17:36] Kim Ades:
You're living a life that so many people dream to live, right? To get to travel to all the places and experience all the things. Like, to me, you're looking for a mentor, you're already a mentor.  

[00:17:50] Lindsay Gafford:
I guess that's where it's– that's hard for me to reconcile within myself because that's something I've wanted for so long is to have that mentor and to think of myself in that way, without having ever officially had that in any capacity is hard. 

[00:18:09] Kim Ades:
Well, let's look at it a little bit differently. Like, you're thinking about a mentor as some human being who kind of takes you under their wing. And you know, I've never had a human being who's taken me under their wing, but I've had lots and lots of teachers in my lifetime and they've come in so many different forms.  

You know, it could come in the form of an author I really love reading, who has messages I want to take on. Or it could come into like, I've listened to one podcast or one webinar from one person and I'm like "wow, that one lesson really made a difference and made me do things completely differently".  

And so think about the idea of not having one mentor, but having like, teachers everywhere you look, cumulatively. 

[00:18:56] Lindsay Gafford:
For sure.  

[00:18:57] Kim Ades:
Right? And I like that better anyways, because I don't like having the input from only one person anyways.  

[00:19:04] Lindsay Gafford:
Right. I mean, yes. That makes sense. [Chuckles] That makes sense. I am maybe one of those odd people– I do like having a boss, you know, I like having that direction comes. So I think thinking of outside of that kind of small bubble and expanding to what I'm already doing. 

I'm a very avid reader. I listen to podcasts all the time. I love to learn. So, I think repurposing those in my mind is something that as my– I am mentoring myself right through these things.

[00:19:39] Kim Ades:
Exactly. And if you even, again, I'm going back to the whole writing component. But if you start writing down, like, "what did I learn from this one thing I heard?" You know, I listened to a 30 minute podcast, what's the one thing that I want to kind of remember? Write it down. And what you're going to start to notice is that there's a trend in what you're attracted to, a trend in what you're learning, there are themes in what you're learning. You're building yourself up in different ways, but they're specific.  

[00:20:07] Lindsay Gafford:

[00:20:08] Kim Ades:
So, part of what you need to do is kind of step back and observe everything you're taking in and say "what did I like about what I took in? What more do I want to take in? I like this component, do I want more of that? Less of that? Right? And you're kind of taking a wider view of what it is that you're learning, absorbing. 

[00:20:33] Lindsay Gafford:
Absorbing. [Chuckles] 

[00:20:34] Kim Ades:
All of it. Exactly.  

[00:20:36] Lindsay Gafford:
Yes. That's a good idea. I tend to– you know, we always talk about, we don't want to do the fire hose on somebody for all of the information that I do that to myself. I know I do. 'Cause I want to know everything, but you can't know everything. And I think taking a step back will probably be really beneficial. 

[00:20:56] Kim Ades:
You know what? You're fire hosing yourself, that's fine. But what you want to do is like, "okay, so all this stuff is coming into me. What's actually getting into me". Right? 

[00:21:07] Lindsay Gafford:

[00:21:07] Kim Ades:
It's like, imagine you are drinking from a fire hose, how much water are you actually getting in? Right? It's probably going all over the place. 

[00:21:14] Lindsay Gafford:
Right. [Laughs]  

[00:21:14] Kim Ades:
So what you want to say is– what you want to ask yourself is what am I taking in? What do I want to take? Let me start to slow down and really, again, the word absorb, absorb what I'm taking in. Because when I am able to do that, I'm able to give myself better direction.  

[00:21:35] Lindsay Gafford:

[00:21:36] Kim Ades:

[00:21:37] Lindsay Gafford:
Direction. [Sighs] That's what I've been looking for since grad school. I think I'm only just now like... You know, the fork in the road. I feel like I'm finally just chose that fork in the road and it's the mindset. I'm so new to this. I'm new to this Operations Manager position even, if it's only been for a month. So, I'm still working my mind around it and accepting that I have earned this role, that I deserved this role, that I'm where I'm at to be, you know?  

[00:22:11] Kim Ades:
Somebody else certainly thought so. 

[00:22:13] Lindsay Gafford:

[00:22:13] Kim Ades:
And of course I'm biased, right? I'm a hundred percent biased. I own a coaching company. I believe that people benefit from coaches, especially the highly driven population who have things to achieve, places to go, the movers and shakers of the world. So that's something you might want to consider also.  

And for those of you who are listening and you're feeling like Lindsay, please consider coaching as well. You know, that just moves things so much faster, calms things down, helps you gain clarity and direction. So please actually come to our website,, check it out, look at the other podcasts, you know, just come and visit.  

Lindsay, I hope you got something out of this podcast. I hope that you learned something or at least got a minute to say "oh wow. I didn't think about it like that".  

[00:23:05] Lindsay Gafford:
I absolutely did. You've given me a lot of things to think about actually, and I will work on writing some of them down. [Laughs]  

[00:23:12] Kim Ades:
Amazing. And if you're really bold, send them to me and we'll see what we can do with them. 

[00:23:17] Lindsay Gafford:

[00:23:18] Kim Ades:
Thank you so much for being my guest on this podcast. Again, for those of you who are listening, if you have a challenge that you want to share on the podcast, please reach out to me. My email address is  

And if you have a challenge, but you don't really want to share it on the podcast, please reach out to me anyways. Again, my email address is  

We will see you next week. Have a good one. Thanks, Lindsay.  

[00:23:46] Lindsay Gafford:
Thanks, Kim.

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