Editor's Note: I first met Daniel Ross back in December of 2019 in New York City during a black-tie dinner on the Intrepid. We rubbed shoulders with travel influencers and celebrities. Carly Rae Jepsen performed. It was a magical evening.

Little did we both know it would be the last time we'd see each other until March 2022. Our travel schedules finally intersected, and we had the chance to sit down in Miami for this conversation at the stunning EAST hotel in Brickell.

This interview has been edited for length and clarity. Listen to the full version here.

I was living what I thought was a dream. I had the job that I loved, and I was travelling all the time. But looking back from where I am now to then, I wasn’t happy.

On Dan's Pandemic

Cornelius McGrath
Hello, everybody. And welcome back to a very windy edition of the Junto. We're not in the Windy City. We're actually in Miami. It's raining. It's 90 degrees, and it's the windiest it's been all weekend — classic when you're trying to record a podcast.

Daniel Ross

You brought the wind with you.

Yeah. We have our first ever northerner on the show.

Geordie. Oi. Oi.

Daniel Ross. A man I've only met twice. This is the second time. He's a travel coinnessuer. A really brilliant bloke. A man who speaks way more languages than me. Excited we could have you, man. And glad we linked up in Miami.

Thanks for having me, man. I'm glad we got to hang out. I believe that the universe brings people together at certain times in certain places, and I feel like this is one of them.

Absolutely. So last time I saw you, we were in New York on the Intrepid.

Random!

Very random. It was a different time for both of us in our careers. I was getting EE off the ground, and you were working in travel, albeit in a different space. So I'm curious, what's changed since December 2019?

There were a couple of things. A global pandemic came along. That changed a few things. But what's changed mainly for me is that the pandemic helped me take control of my life and make it go in a way that wasn't being controlled by anybody else anymore. I was able to make sure that I was going in the right direction, not being held back by anything or anyone.

What was life like for you before the pandemic?

I was constantly chasing my tail, trying to keep up with everything. Getting that work-life balance was just impossible. When I was employed full-time, I struggled with that a lot. I was living what I thought was a dream. I had the job that I loved, and I was travelling all the time. But looking back from where I am now to then, I wasn't happy.

I was living vicariously through myself. I wasn't ever really present in what I was doing. It was always like, "what's the next thing? How can I be better at this? Or how can I do this?" And I was never focused on the now. I was always focused on "more, more. I want more." Now, I've stripped it all back and started from scratch. And now I appreciate everything day by day, rather than looking to the future all the time.

So, where were you when the pandemic came?

I had just come back from Brazil. I'd been working remotely there for a while, and I was looking for a place to live in London. My lease was up. I was staying with some friends who have now got a little daughter, and I was staying in their spare room at the time. And they were like, "oh, you can stay with us as long as the pandemic happens." And I was like, "guys. It's now April. We locked down in March. We all need our own space."

And so I was looking for somewhere to live in London, but live on my own because it was a pandemic, and I was like, "this isn't gonna blow over anytime soon." So I decided to leave London, where I built a life for myself, my crew, my friends, and all my social life. Everything. My whole life was in London, and I decided to go back and move into my childhood bedroom at my Dad's house. That was April 2020, and that was a real pivotal moment. Because it was like, "okay, I'm 30 years old and completely back to basics. I'm now living in my childhood bedroom. What am I doing with my life?" And so, yeah, that was when everything started to change.

I flew on my own for the first time when I was 13. And I remember being dropped off at the airport and just having this like sense of freedom. 

On Dan's Origin Story

Tell us the story of your upbringing. You went to Loughborough, were an interpreter, and worked at Manchester United. You speak three to four languages and are teaching yourself Greek. Now, you're a freelance travel producer. There's not much you haven't done, but what's the arc? What's the why? What are you chasing?

That's a good question. What am I chasing? 

Doing something every single day that I'm passionate about. And that brings me joy. It's that icky guy people talk about a lot these days. Combining something that you love with something that you're good at and something that can be used by someone else or someone else needs.

And if you can get all those three together, you've got the icky guy - like that perfect balance. And that's sort of what I have with what I do now. I absolutely love travelling. I've studied aviation and got a masters in it. Airlines and airports, I know that inside out. People come to me daily and ask me questions about booking a flight, what insurance to get, or how to use their points and miles. I feel bad because I don't have the time to sit through my Instagram and answer all these questions. But it's really humbling sometimes when I get messages from people that I don't know or people even that I do that say, "Hey, Dan, just wanna let you know I'm here because of you or I did this because of you." And that's the third part of the icky guy, that what you do is useful for other people. And that makes it all worthwhile for me to be doing what I'm doing.

You keep saying, "ikigai". What's that?

It's a Japanese term thrown around in a men's mental health group that I facilitate on a Monday. There's a guy who talks about it a lot on there. You get the three parts of your life down - finding something you are good at, makes you money and that people need. They call that the ikigai.

Clearly, you now are in a very different space from when you and I first met. You're not working for somebody else. You own your time. How is that?

Owning your own time is like anything. There are pros and cons to it. If I hadn't had a job where I was so conscious of every waking hour of my day not being devoted to working, I think I would've struggled to do the freelance gig that I'm doing now. I treat my days like a 9-6 PM  job every single day. If I'm not working, I feel guilty. So that is something that I'm grateful that I had because it enabled me to have this work ethic that now I have to live this freelance life. What is amazing is that I struggled when I was full-time. If my brain isn't creative, I can't write if I'm having a black dog day or just not feeling so good, like I can't force myself to be creative.

When I was working full time for a media publication, I had deadlines that I had to hit. And if I'm having like a day where I'm feeling really low and I can't concentrate, I've got no creativity. You miss that deadline. That's a strike against you. But now, I work, get all the things done that I need to do, but I do it when my brain's working. So I might end up working. I don't know, 9:00 PM till midnight, but I'll get so much work done rather than sitting at my desk, trying to work like all day, just because they're the allotted times that I needed to work in. That has been the biggest blessing. Now, I don't really care when I work, but it's also the double-edged sword of not adding up all the time. So I don't know how much time I'm spending working and how much I'm not, but at the same time, it doesn't matter because the balance, for now, seems to be right.

Fascinating. We had a great conversation last night about family. And some of the questions we tossed around were, what were your parents' ambitions for you? Which ones did you fulfil? What is still yet for you to achieve?

I'm curious, how much of a role does family play in the only Geordie world traveller that I know? He's in a different country almost every three days. You don't really associate that archetype with the North of England. Who put that in you?

I have to thank my mum, dad and auntie for this actually. My dad would take me to the local Newcastle airport, which is like nothing like Heathrow or Miami or whatever. We'd go on day trips. Me and my brother, we'd take the train and the underground Metro. This is the day where you could go airside. So past security. You watch like the planes from the outside terrace. And I used to collect all the little notebooks from KLM and Air France and British Airways and the timetables. And I'd get home, and I'd pretend people were ringing me. This is, I was like 9, 10, 11 years old. 

I'd pretended ten people were ringing me to book holidays. And I was obsessed with flying and travel. Since then, it became my dream to be a pilot. And that's where all this started, to be honest. And then, when I was 13, we found out that my grandma had had two children. One that my mom didn't know about. And we found out about this when they were fully grown women, and somehow my mum didn't notice. One of those of my aunts lives in Spain. I'd met her maybe once in England before. And my mum put me on a plane one way with a return ticket to Spain. 

I flew on my own for the first time when I was 13. And I remember being dropped off at the airport and just having this like sense of freedom. And so the combination of the Aviation passion and that early experience of travelling on my own for the first time. Those two things together. Since then, that's all I ever wanted to do. I've tried working in finance. I've tried working in financial services. I've tried doing all the corporate jobs. But I was always just dreaming about working in this world.

We know what the 30-year-old looks like. But tell us about 25-year-old Dan.

25-year-old Dan? Wow. You know, it is crazy. I was living in London. I was racking up ridiculous amounts of debt, living a lifestyle that I like couldn't afford to live, doing things that I thought I should be doing because I was 25 years old. And I didn't have a career progression. I didn't have the desire to own my own place. I was living this fast and furious life in London, thinking I was living the dream.

Don't get me wrong. Would I change what I did as 25-year-old Dan? Absolutely not. Because all the things I've done in my twenties, all the mistakes I've made, all the people I've met, all the things I've learned have got me to where I am now. And so to think, "oh, you are a bit of a mess when you're 20." Yeah, I might have been a bit of a mess when I was 25, but look where that mess is now. And if I was going through that messy stage now in my thirties, you'd worry a bit.

I keep making sure that people see on my social media that I’m on my laptop and working. I don’t want people to think that this guy is living the big life.

Dan On Success

Is this the most successful you've been?

It depends on how you quantify success, right? Financially that's a hard one. I'm in the first year of freelance, so until my accountant sits down and tells me everything, I've only got a rough idea.

I'd say financially, I'm better off than before, but I don't know to what extent. So if you're talking about success as a financial metric, I would say, yes, this is the most successful I've been. But then success also comes down to work-life balance and getting out of bed every morning and not feeling like what you do is work. 

Some days, I'm like, "oh my God, I've got this to write still. And I'm not interested in it." And yeah, of course, I'm not going to paint this picture and be like,...