April 3, 2026
Jamie Sylvian: Building Freedom Beyond the Boardroom
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Send us Fan Mail Jamie Sylvian is the author of The Executive Nomad Operating System and founder of Executive Nomad. With more than 30 years of executive-level consulting experience across sectors and countries, including board-level advisory work, he helps senior leaders rethink what comes next after corporate life. Jamie works primarily with executives aged 40 to 60 who are transitioning out of traditional roles—whether through redundancy, burnout, or choice. Rather than guiding them toward...
Jamie Sylvian is the author of The Executive Nomad Operating System and founder of Executive Nomad. With more than 30 years of executive-level consulting experience across sectors and countries, including board-level advisory work, he helps senior leaders rethink what comes next after corporate life.
Jamie works primarily with executives aged 40 to 60 who are transitioning out of traditional roles—whether through redundancy, burnout, or choice. Rather than guiding them toward another job, he shows them how to convert decades of leadership experience into location-independent advisory businesses through consulting, coaching, mentoring, non-executive director roles, and workshop facilitation.
His approach centers on intellectual property extraction—the idea that a career is not just a timeline, but a body of commercial IP that can be structured, packaged, and monetized. He helps clients navigate the psychological shift of leaving corporate identity, rewire their sense of authority outside organizations, and build flexible, portfolio-based careers without relying on influencer models.
Known for combining strategic clarity with practical execution frameworks, Jamie speaks on topics such as the challenges executives over 50 face in securing equivalent roles, the hidden identity shift required when leaving corporate life, and how to turn career disruption into opportunity. His work resonates with experienced professionals seeking more autonomy, purpose, and control in their next chapter.
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15:14 - (Cont.) Jamie Sylvian: Building Freedom Beyond the Boardroom
Transcript
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Listeners of the Randomness of Nothing podcast, Rashad Woods here, and thank you for your time as always as a dedicated listener.
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I think this episode is going to resonate with a lot of business professionals on this episode, and I've been really looking forward to this interview.
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He is the digital nomad expert.
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He is the gentleman that tells people when they're between 40 and 60 that if you feel stuck or if you had felt like you've peaked, it is not the end.
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It is a very great opportunity for a beginning.
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Jamie Sylvian, thank you very much, sir.
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Pleasure to be here.
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How are you doing?
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That's fantastic.
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You have one of those stories that I think resonates with somebody who's making that coffee, who's sitting back and saying, doing that self-assessment, and wants to see where their life is headed.
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So please share your story and your expertise.
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Yeah, so uh name's Jamie Sylvian.
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I am not a digital nomad as such, because there's a difference.
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I'm an executive nomad, and the the difference is uh, and I can say this because I have a niece Rashad who's 25 and she is a she's a digital nomad.
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She spends her life looking for flitting around barley looking for free Wi-Fi.
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I apologize for the misnomer.
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That's fine, that's fine because it because there are so many overlaps, and honestly, I was a digital nomad before I became an executive, so you know it's it's it's not an insult by any means.
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I um I uh I'm an executive nomad and I I own executive nomad.com.
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And the difference between the two is simply that I I do all the the travelling.
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Uh this uh last year I think I was in nine different countries.
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Um I've just spent the winter in Malta.
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I'm now in Bulgaria because it's we're coming out of ski season into the into the springtime, and the springtime is beautiful.
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This this part on this side of the world, Bulgaria and the Balkans, is stunning at this time, you know, for the um for the spring.
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The difference is is that I work at boardroom level.
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I've worked for um British Gas in the UK, I've worked with big uh large publishing companies, venture capital businesses, all at board level or upper management level and above, and I charge the fees of a of an advisor in in that space.
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And that means when I do travel, I'm not looking for free Wi-Fi in Bali.
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You know, I go for I go I go for two months to a to a nice place, I get a nice apartment, and 20 minutes after I land, or I land at the apartment, I'm ready for business.
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I'm in exactly this environment.
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I'm doing, I'm I'm working on consulting, I'm working on coaching, I'm working on as a non-executive director, I'm working as uh I'm setting up workshops.
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So as long as it's in this environment, an online environment, I still do it.
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Um and I and I work at the very highest level I can, but I travel, I travel the world to do it, and that's what I executive nomad is about, the framework that I've developed.
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Well, you know, I like I said I apologize for the miswording on my and I even had it written down, and I just you basically still went to the same wording I'm used to.
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I do I saw one of your interviews, and it was with a woman by the name of Lisa Urbansky, and it talked about how burnout can actually be a gift and that people are somewhat institutionalized.
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And I say that because you know, people reach a certain peak level in their career, particularly if they reach executive levels.
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Those are very ambitious people, they're very driven people, and they've accomplished many things.
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Having said that, it's very structured and rigid at that level.
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So, what did you discover at an early age that allowed you to be the executive nomad that you so I I was doing the, I was following the executive path.
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Um, and I was at the same time wanting to travel.
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I was kind of uh as my uh as my girlfriend at the time said, I'm very I was very much a Gemini.
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I wanted all of the the corporate stuff, the flashy watch, the car, the house, I wanted all of those, all of the toys, but I also was a little bit of a hippie and I would go off in the other direction or want to travel for for months at a time.
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But you know, you're sort of forced, not forced, you're you're encouraged to be heading into the corporate world by your parents, by your schooling, by by college and university, and so on.
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And and so that's that's where I ended up.
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And I I ended up at a very young age running a business and um as a partner in a business, and we worked with corporates, and I continuously saw people who were who would be younger than me now, but were a lot older than me then, and I could see that they were they were they had they had everything on the face of it, but they were so stressed out, which had been burnt out, and they, you know, they just wanted to, they were just sort of stuck in their role, and I and I that really scared me at the time.
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Uh, and then I found I just by chance I came up across a book by a guy called W.
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G Hill, and it was called Perpetual Traveller, which was the precursor to executive to digital nomads.
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Um, and it spoke about a way of life that you could live in one place, have a company in another, your clients around the world.
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And this was pre-internet, it was a couple of years before the world.
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That's amazing.
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Yeah, right.
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So it was it was fax machines, it was it was deals by letter, contracts in the post.
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Going to the hotel lobby, right, and just like faxing all you know exactly that, exactly that.
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So I really loved the idea, but it was it it was hard work, you know.
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I remember getting so excited when I found an internet cafe when I was traveling from Spain, thinking I think technology had peaked.
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Yeah, so um, yeah, so that but that's what I got into it.
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So when I first I I started to sort of mix the two, so I was living in Spain, but traveling back to London where my business was, I had a virtual office address, so it wasn't a real address, I didn't go there to work, it was just a central London address.
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Um, and I I would fly into London and I would stay there for a week, and then I would fly back to Spain, and then I you kind of get to a point you say, well, if I can be in Spain, I could also be in Italy, I could also be here, and I could also be there, and so on.
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And that's how I started to to develop this thing out.
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I honestly didn't give it a name.
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Clearly, I wasn't a digital nomad because it wasn't digital at the time, I was more of an analogue nomad.
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But uh over time, as you know, as things progressed, and I was more and more and more travelling.
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I went off to as as life became easier technology uh-wise, I I would work with companies in London, but I was living in Chiang Mai in Thailand.
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Right.
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I would work with companies in in Baltimore while I was living in Spain, and it it became more and more online, it became more and more a business that I thought this is an actual thing, this is what I can do, and you know, to create my life and just live wherever I want.
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Work where I you know, work where I'm inspired.
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Did you find what was the reception early for clients when that was your business model?
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You know, was it what was the reception?
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It was tricky at first, so I lost so I lost deals, and I do remember specifically speaking to a very nice deal I was working on to you know with a publishing company in London, and everything was fine until the the the the conversation.
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I said something like, Oh, I'm GMT plus two, you know, time zone.
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And and the guy that I was putting the deal together, he said, Well, where are you?
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And I said, I'm in I'm in Spain.
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He said, Uh oh, all right.
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And clearly it was pouring down, you could see the rain in his backdrop, and I was in I was in the sunshine, Rosham.
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And um that kind of that really he just said, Well, look, when next time you're in London, let me know and we'll get together.
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We were at signing stage and I lost the deal.
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And that kind of went right along to COVID, where people say, Where are you know, where are you?
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You know, what are you doing?
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That was always the first question on on conversations like this.
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And when I then when they realized I was in a different country, that that became not always, but sometimes became a problem since COVID, never a problem at all.
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Don't even get asked anymore.
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You know, this is a very normal way of doing business now, which is lovely.
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Yeah, and what I thought was fascinating about that was that you know you have people now where it I always find it funny when people are ahead of the curve and then things become normal, right?
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So, you know, it's always been available.
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Like Skype, I remember Skype, I'm I'm 43, and Skype was available when I was in college, and that was you know 25, almost 25 years ago.
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So the idea that somebody could have webcasting calls were always there, but at the time people only assumed it was just so people, a lot of foreign students students were calling their family back home.
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And here that was a business model setting people in their faces, right?
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To to do those type of things.
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Yeah.
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Is there a difference because you you are the executive nomad when it comes to doing business with a US customer, uh client, excuse me, and then you have time zone differences, maybe there's some sort of currency differences.
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Like how different does it become to also pitch your services too?
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Is it worth a mouth?
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So yeah, um, I do have I do get a lot of word of mouth, Yos, but but actually I I have a US phone number.
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Um, so and that's wherever I'm in the world, it's a VoIP number, it rings.
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It's like Sky, you know, the modern Sky.
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Yeah, yeah.
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I have I do work with uh companies in Canada, I have a Canadian number, I have a Central London phone number.
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Wonderful.
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So I'm sort of meeting them where they are.
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So so even now I have a uh I've had a London business address for 20 odd years, never changed.
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I've been there probably three times because something was sent there by accident, you know, to actually go and get something.
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But it's just I never have to go there.
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Time zone, yes, but but usually I'll do meetings sort of their morning, my afternoon, every now and again.
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If I'm in Europe, it's fine.
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If I'm in Asia, it gets tricky because of the very big time time differences.
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Sure.
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You've got to meet them where they are.
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And for you know, if I charge, if I'm having a if I'm working with an American client, I'll charge in US dollars.
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That's it, and I'll, you know, and I take the hit if there is a hit when the exchange rate happens.
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I just use wise.com.
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That that means I've got every currency that I ever need.
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Um so everything, as long as you sort of you you need to make a few steps to go towards them, as long as you do that.
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What they're paying me for, Rashad, is not where my bum is.
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They're not paying me to be in a room, they're paying me for the experience that I've got in strategic communications, which I've done for for many, many years.
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So that's that's what they're paying for.
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They know my results, they know where I'm coming from, and and everybody accommodates everything else.
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Are there particular industries that you specialize in when it comes to your clientele base?
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No, um, no, because my my consulting stuff, to be to be clear, I'm I'm mainly focused on executive nomad as a brand and teaching other people now.
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But for 20 odd years, I was in comms.
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Understood.
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No, um, I specifically didn't go after specific after industries.
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I found myself in the gaming online gaming industry, um, just because somebody said I somebody suggested talk to Jamie.
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So I was in the comms.
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So I did I did workshopping, I did um mentoring.
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So so I used to go into I spent a lot of time in Malta and in uh Gibraltar and in Cyprus because that's over this part of the world where the gaming companies are.
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Yeah, it's weird.
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I've noticed that, right?
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Like, you know, it's it's it's centralized over there.
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Yeah, because it's tax advantages.
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It was great for these small islands who who don't have a lot of ways to make money.
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That was a that was a an absolute gift for them.
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But that means I found myself there.
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So I was in Gibraltar a lot working with billion dollar companies at at the boardroom level, at owner level or board level.
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And I would go, I would either go down there for once every couple of months and do a workshop, literally in the room with people, and then I would mentor some of those people who were kind of not getting it, and they were so they needed communications work, excuse me, Russia.
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So they needed communications help, they needed work, you know, some sort of advice and stuff that went on.
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So um I found I I worked with um VC companies, venture capital companies, helping other businesses buy other businesses.
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It's just about communication, so the writing, the you know, putting the the comm strategy together, which is all on my laptop.
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I don't have to be in any room.
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Well, you know, and I think and and this segues into my next question.
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So you have now that you're helping executives, right?
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And you have, you know, I don't I don't hate the stereotype people, you have the guy or woman who's had it all.
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They graduated in the top 5% of their class, they have their MBA or their masters, they they've done very successful financially, personally, and yet they still feel empty or they still feel trapped or they still felt burnt out, right?
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And they're looking at it and sit back and saying, despite all of my accomplishments, I still have to be in these amount of meetings, my schedule's still dictated by this, and what's next for me?
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So when you when you have those conversations with those successful people, what what's the what's the what's the intro call like?
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And it's gotta be some raw emotion that really comes out because they kind of have to put on an act at their current profession, but then they get to be the real you when they talk to you.
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It's absolutely fascinating.
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I have spoken to just some of the highest people, you know, half a million, million plus in salaries, and you take them out of a very, very boxed arena that they're working in, the nice office and you know, all of that stuff.
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And they they actually they're quite lost.
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Once they're going through the process and they they don't know what to do without that corporate badge which has defined them for 10, 15, 20, 25 years.
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And so they step outside of that and they say, now what?
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And and I've spoken to people who thought, well, I thought, you know, I thought I'd get a franchise, I thought I'd start a business.
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I thought, you know, they're they're they're looking at things because they're just not sure.
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Because the entrepreneurial world, you know, the the solopreneurial world is very, it's vastly different.
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It's not it's neither better nor worse.
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It's but but if you've been in a corporate world, when you wanted printing done, somebody down there did it, when you wanted some accounts done, somebody over there did it.
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You know, when once you become doing your own thing, um then that changes.
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But what they're really, really afraid of is losing relevance because they've got the relevance of their badge.
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Because their inbox is funny.
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People are coming to them saying, uh, you know, how do I do this?
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I mean, how do I do that?
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So with executive name mode, with the framework Richard that I put together, is I actually I call it rewire, repackage, and repurpose.
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And rewire is where we go into in a in a conversation like this, we're looking for some wins, losses, and lessons in their career.
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Because if they and they can't, this is a real challenge for people because they did it just as a part of the job.
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So they're not seeing it in a in and of itself.
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There's you know, so we extract that and say, that thing you did, you know, in you were working for a logistics company and it was a there was a takeover and it was all messy, and this thing you did that is a consulting business, that's a coaching business, that's a mentoring business, that's a workshopping business.
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Let's extract it out.
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Once you've got that, once you do that, that it's really interesting mindset, um, mind shift is that they go, Yeah, actually, yeah, I could do that.
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And all of a sudden that relev that relevance still stays there.
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So you say, right, that's exactly that's exactly what we're trying to do here.
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We're giving you a series of services that you can package, which is the second part, you actually give them a name because ringing somebody up and saying I'm a consultant, well, there's a million of them, and who cares?
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But when you actually give your give your um what you do an actual name, so I'm the logistics oversight guy, I'm the um, I'm the um gaming company strategist, I'm the something serving something, right?
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Yeah, that's what they that's what they see.
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And the third bit, so that gets people excited, right?
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The third bit is simply to repurpose all of that so you can do it into different industries, which is in answer to your earliest question, did I specialize?
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No, I didn't.
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That's why.
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Well, because process there's a reason why people can jump from you know Coca-Cola to to you know Unilever to Procter and Gamble.
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It's because they understand process, they understand strategy, they understand people.
00:15:58.840 --> 00:16:02.840
So that in itself is already 80% of what you need to know, right?
00:16:03.000 --> 00:16:11.000
And then it becomes because you know, for all intents and purposes, those are all you know publicly traded companies, so the profit and loss statement all reads exactly the same, right?
00:16:11.159 --> 00:16:19.159
Yeah, you just have to be able, and at the end of the day, you're just trying to refine whatever processes and remove any flaws, so to speak, that are currently in said process.
00:16:19.399 --> 00:16:38.440
What I find fascinating is, you know, because I think this really hits home with a lot of people because you know, when you you'll look on LinkedIn and you'll see people at a certain age and now younger, you know, in particular, yeah, definitely that are like for sure, and then you know, they're like, oh my gosh, I kind of need to, you know, break the glass kind of deal and see what's available out there.
00:16:38.840 --> 00:16:42.279
Have, and maybe you don't know this, but I just have to ask this question.
00:16:42.519 --> 00:16:47.000
Are it how is the business world responding to people who are doing things like this?
00:16:47.080 --> 00:16:53.799
You know, now you could be in college and you can sit back and say, I don't want to do this internship, I want to get with Jamie early in my life.
00:16:53.960 --> 00:16:56.519
How do businesses adjust to this new normal?
00:16:56.840 --> 00:16:58.679
Okay, now that's a really good question.
00:16:58.840 --> 00:17:06.360
Um, and it's the the value of the executive nomad is so so I'm gonna answer what you just asked in in two ways.
00:17:06.840 --> 00:17:09.559
The value of an executive nomad is pattern recognition.
00:17:09.720 --> 00:17:19.000
When when I'm in with a new client and I'm talking to them about what their problem is, their challenges, whatever, I can help them because I've seen it five years ago, ten years ago, fifteen years ago, right?
00:17:19.240 --> 00:17:21.159
I can I've seen what they've done and they haven't.
00:17:21.240 --> 00:17:23.400
They're going, well, you know, how on earth do we get out of this mess?
00:17:23.480 --> 00:17:25.320
And I'm thinking, right, I know exactly what to do.
00:17:26.200 --> 00:17:26.679
That's the value.
00:17:27.079 --> 00:17:41.319
Yeah, so so when you go back to somebody who, you know, the intern and and and what have you, the the trick now, if they're doing that, is for the next couple of years, is to get their network going because the network is your easiest place to put your position yourself as an executive nomad.
00:17:41.480 --> 00:17:46.279
Because you can just call they already know you, they know what you can do, you've got you know, you've got their phone numbers and all that.
00:17:46.440 --> 00:17:55.960
So we're looking at for me, 40 plus is the right place to be, and it changed, you know, the the the services you offer changes in that art from 40 to to 60, 65.
00:17:56.359 --> 00:18:05.799
Um but when you're younger, you can start laying the groundwork so that you know you you don't have there's no age for this, and you don't have to travel the world doing this, you can do it from your kitchen table.
00:18:05.960 --> 00:18:13.559
But if you want the executive, that's the executive bit, if you want the nomad bit, that's that's when you're gonna need to sort of work it all out how this is gonna work for you.
00:18:13.640 --> 00:18:16.200
So it's answered in two ways, if if I did that right.
00:18:16.440 --> 00:18:26.599
Yeah, yeah, and you know, and because I think that you know, if anybody who's gone on LinkedIn and you see some of these people, you know, who are who have high-level credentials, I think they would benefit for your services.
00:18:26.680 --> 00:18:53.480
So I hope people who are listening, you know, with with the ebbs and flows of how life operates, would I would encourage you all to reach out to Jamie because I think that if you are lost or stuck and you you know you're at a certain age and skill set level, like I'll see some of these people and you know, you know, high-level UX developer and and and you know, high looking for you know director position, like people have to realize that the higher the scale of pay, the less like the less available positions.
00:18:53.720 --> 00:18:54.119
Absolutely.
00:18:54.279 --> 00:18:56.039
I mean it's to it's and ageism is a thing.
00:18:56.279 --> 00:18:57.240
Ageism is a thing.
00:18:58.279 --> 00:18:59.799
People really struggle with it.
00:18:59.960 --> 00:19:00.279
Yeah.
00:19:00.680 --> 00:19:01.000
100%.
00:19:01.880 --> 00:19:04.440
The answer is don't don't sorry, please, Karen.
00:19:04.680 --> 00:19:06.680
No, go ahead, because I've I we're going back and forth.
00:19:06.759 --> 00:19:07.240
This is great.
00:19:07.480 --> 00:19:19.480
So the the the answer to ageism is to use age as your superpower, and the way to do that is to call yourself an executive nomad or become a something that that gets a benefit of that, and that is pattern recognition.
00:19:19.559 --> 00:19:36.359
You say, well, you can you know, you can I I I encourage everybody to write a book because if I was up against you trying to pitch him for a deal, or I should you're a younger guy, you've got a lot of advantages that I don't have, but when you hand over your business card and I I hand over my book, I'm in right.
00:19:36.519 --> 00:19:39.240
Like, you know what, but you ever seen good you ever seen Goodwill hunting?
00:19:39.319 --> 00:19:40.599
You ever seen Goodwill Hunting?
00:19:40.759 --> 00:19:54.440
Like it's it's like it's like when Matt Damon got like to that debate with the guy at the bar because the guy was trying to impress the girl, and then the guy completed and then Matt Damon completely like washes the guy because he knew he was right, and then like that's the business card versus the book, right?
00:19:54.519 --> 00:19:56.279
Like, you know, it's like exactly that.
00:19:56.440 --> 00:19:58.039
You know, so I just I laughed at that one.
00:19:58.279 --> 00:20:08.440
It's funny because in in the in the course of doing this podcast, people have asked me to write a book, and what's weird about it is I've hesitated because I didn't think I was worthy of writing a book, because I'm like, What do you why would I write?
00:20:08.680 --> 00:20:11.480
But now that you mention that, you could be the podcaster.
00:20:11.720 --> 00:20:19.960
Like, I'm literally gonna reach out to the person that's been emailing me a half dozen times now after this call, be like, I should write a book, because then it's like I'm the podcaster with a book.
00:20:20.119 --> 00:20:28.839
Like, I think people are selling themselves short of their actual potential because they think they have to be at a certain stage to do certain things.
00:20:29.000 --> 00:20:29.799
Yep, yep.
00:20:29.880 --> 00:20:39.799
And and I and also the difference is, and this is really important, this is why anyone, anyone watching and listening should should think about writing a book, is because I am now the executive nomad.
00:20:39.880 --> 00:20:43.640
That's a that's an incredibly powerful brand in and of itself.
00:20:43.720 --> 00:20:52.359
Yeah, um, and I built out as as I'm building out the brand itself, I own the dot com, I own the dot us, I own the dot Canada, I own all of that brand.
00:20:52.519 --> 00:20:57.799
So I have become synonymous with the executive nomad, the executive nomad.
00:20:57.880 --> 00:21:00.599
And that that in and of itself, but that that's just my brand.
00:21:00.680 --> 00:21:07.000
You know, you can anyone can create a brand and sort of and and build themselves around it because then all of a sudden everyone knows you.
00:21:07.160 --> 00:21:13.240
You know, anyone in your space, you're in the logistics space, you're in the engineering space, but you're you're you're positioning yourself there.
00:21:13.400 --> 00:21:17.559
You're the guy who wrote the book, you're the guy who's on the podcasts, you're the guy who's doing all that stuff.
00:21:17.720 --> 00:21:19.559
All of a sudden the doors start opening.
00:21:19.640 --> 00:21:25.240
I'm I'm I do probably five or six podcasts a week now, and most of them are inbound to me asking me if I'll do it.
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