The Long and Winding Path to Freedom… and Sleeping In

“The concept of a digital nomad in its true form has slowly gathered steam in the last decade, but always with a bit of a stigma attached to it until now.”

“…many individuals I’ve met over the years with a CEO title have often ended up there on their way to chasing something else…”

When You’re Not Fighter Pilot Material

I never thought about being a CEO as a career path one sets out to do intentionally. I know there are those who do, working their way up corporate ladders to get to the top so they can lead the charge. However, many individuals I’ve met over the years with a CEO title have often ended up there on their way to chasing something else, taking on the mantle as a necessary and occasionally reluctant step towards achieving a dream.

The label itself is inherently American… the title a man might hold at the helm of a massive corporation if we look at it more traditionally. As a career goal it holds a bit of ambiguity in its direction. It’s more akin to chasing a status or title when spoken about without context, rather than describing a specific profession. It’s definitely not the vision I had of my future when I was in school, university, or even years after I started my own business.

To be honest, in high school I was dead set on being a fighter pilot. The concept of being my own boss was so unattainable that I chased potential thrill-seeking career paths in more traditional ways. But after realising I was looking at a vertically challenged future and would not meet the (then) height requirements for flying an f14, my next wildly ambitious plan was to get a degree related to intelligence gathering and become a spy.

From Chasing Spies to Chasing Gigs

Unfortunately, or perhaps, fortunately, my journey to becoming a super cool globe-trotting intelligence officer was a long one. I drowned in readings and paperwork and constantly became distracted by some of my more creative pursuits. I already had a bachelor’s degree in multimedia which I loved but initially considered fairly useless in the grand scheme of things.

I worked constantly while I was studying, starting out as a music teacher, which somehow evolved into music promoter, band manager, and booking agent. Eventually, I ran my own little agency and a fun but short-lived documentary TV series based on my home town’s local music industry.

My master’s degree fell slowly by the wayside as I got lost in a world of live music. I lived and breathed an industry where every day was about the hustle—fighting for each and every opportunity, and usually not even for yourself but for the musicians whose music you fell in love with.

Everything I learned in my early days of business was from that period of my life. Every mistake, every rejection, every risk, and every fight to be heard was another skill I took with me. I don’t want to sit here and say education isn’t valuable, because it is—but I also know that the most valuable lessons I learned in my life until that point were never even considered in the classroom.

Life Lessons from the Real World

When I walked out of university and into the world, I had high expectations on starting my first ‘real’ job. Possibly because at that point I was leaving behind a well-paid teaching career and assumed my next adventure would be just as exciting and rewarding as well as better-paid. Unfortunately, none of my expectations were met, and reality set in pretty hard.

I worked a proper 9 to 5 (8 to 6) desk job as a graphic designer for a record label, making less than I had in any other job I’d held before. And for the first time in my life I truly understood what it felt like to be stuck—physically, mentally and emotionally. I was stuck, and I really and truly began to hate waking up to face each day. It was true that I chased this job not just because I was degree-qualified but because it helped advance my interests in the industry. But my romanticised version of adult freedom was very quickly slaughtered by reality.

It’s important to note here that even at this point, my goal was not to advance as a designer. Even though I set myself up as a freelance designer in my last year of university, I continued making life choices in favour of my bands.

I really did love designing and coding. I said yes to coding work before I even knew how to really code. I took every opportunity I could to design something, anything. Band flyers, tour posters, promotional websites, video editing effects, album covers, custom birthday cards—you name it and I tried it. I loved everything about it except for the actual going to work part. The part where I had to wake up early in the morning and drive to an office, the part where I had no clear upward trajectory and the part where (10 years ago) I was getting paid significantly less than my male counterparts who were doing the exact same job. The situation wasn’t what I wanted for myself, and I had to make some changes.

Leaving the 9 to 5 Behind

“From that moment, everything I have done has been in pursuit of those three things, starting with the first of many high-risk and extremely inadequately thought-through choices because I was stubborn enough not to accept failure…”

After working less than a year in my second and last ever ‘real’ job, I realised that expecting change doesn’t happen when you keep making the same choices. I was constantly looking and applying for ‘better’ jobs, until finally realising that no matter how good the job was, I was consistently choosing something I didn’t want.

I lived in Australia, and the concept of full-time remote working and flexible hours wasn’t an accepted form of working. In fact, fast forward 14 years later and it probably still wouldn’t be if not for a global pandemic. The concept of a digital nomad in its true form has slowly gathered steam in the last decade, but always with a bit of a stigma attached to it until now. Back then, it was a difficult concept to push your way through. But I had, by that point, decided that it was the life I really wanted.

I wanted the rush of freedom I chased in flying, the exciting global life I fantasised about while studying intelligence, and the long-held childhood pleasure of waking up and going to bed whenever I chose. Three seemingly simple yet impossible things that I could not let go of from that moment on. From that moment, everything I have done has been in pursuit of those three things, starting with the first of many high-risk and extremely inadequately thought-through choices that paid off because I was stubborn enough to not accept failure as an option. It was the only way I knew how to move forward, and I did exactly that. I stopped chasing other people’s dreams and started chasing my own.

Work Isn’t a Place, It’s an Action

Today’s weird pandemic-driven reality brings the rise of the remote worker, the remote company, and the online business. Remote work has become the new normal by force—completely out of necessity. But as I noted previously, when I first started out a decade ago, no one would hear of remote working. It was unrealistic, unreliable, and simply not how people worked a ‘proper’ job.

I remember bringing up the concept to a new employer I contracted with while I prepared to move overseas; they were not at all open to a working format that did not demonstrate ‘boots on the ground’. So what do you do when you’re in your mid-20s and you’ve discovered that your chosen method of earning a proper adult living doesn’t exist in your home country? The answer’s obvious, immediately sell everything you own and buy a one-way ticket to Canada.

Working from Anywhere and Everywhere

“Essentially I started my own business because no one else would hire me to do what I wanted to do the way I wanted to do it.”

I arrived in Vancouver three weeks after I decided with absolute certainty that I had to leave everything behind if I wanted to chase freedom. I quit my job realising that I really had absolutely nothing to lose. My ‘career’ was going nowhere and I would either make it overseas, or I would end up going back home and living with my parents. I was lucky in that respect.

I got on the plane with $5000 Australian dollars, no job, nowhere to live, and if I’m truly honest, no real thoughts of failure. Whether you want to call it ignorance, confidence, or just a complete lack of understanding around the concept of a ‘plan B’—from the moment I made the choice to get on that plane I knew I would not fail. I could not fail! Three months after I moved to Vancouver I had enough freelance clients that I could work entirely from home. Actually, entirely from wherever I wanted! I’d discovered that North America was far more open to the concept of working remotely, and for the first time in my life I was doing exactly what I wanted on my own terms.

I was driven by the hustle—a familiar hustle I realised I already trained for. I wanted to design, or redesign, everything I touched. I said yes to everything. I worked as much as I physically could, and I loved every second. Passion is one of the biggest driving forces I know for success. It’s the first thing I look for now when I interview someone for a job. I wanted to build websites. I wanted to make videos. I wanted to create amazing things for as many people as I could. And just as I dreamed, I could now do it all from my living room in my pyjamas, from an amazing cafe in the middle of Europe or from a beach resort in Thailand.

Essentially I started my own business because no one else would hire me to do what I wanted to do the way I wanted to do it. And hey, fair enough. These are the perks of being in charge. You don’t need to hire the girl who wants to work from home. You may not want to employ someone located elsewhere in the world. It may make you uncomfortable to potentially pay them for doing nothing. After all, how will you know if she’s going to log in and actually do any work? I get all of it, and I know it takes time to build trust. I also know it’s not the right choice for everyone.

That said, the interesting thing about working from home is that if you have the right personality for it, you tend to get a lot more done. You probably also work a lot more than you should. And I mean A LOT more. After 18 months, I had already tripled my pitiful salary back home. I was working 12 to 14 hour days while travelling all over North America and Europe and turned into a mad tourist every weekend that I hit a new city. It was glorious. It was also the hardest I ever worked in my life as I constantly hustled for work, contracts and business relationships. This insanity was my version of freedom and my version of happiness. I wouldn’t trade it for anything, because 10 years down the road I now have choices that I would never have had otherwise. Choices that a lot of other people don’t get.

Trust and Believe in Yourself

Most of the best things I’ve done in my life have been completely mad and impulsive. In most of these instances, I spent a total of five minutes thinking about doing something before I executed it with complete disregard for any possibility of failure. I listened to and trusted my instincts.

Seven years ago sitting at a cafe in the middle of Prague, I made the next big step of my self-constructed ‘career’ and decided to split my life and business into multiple locations to see how far I could get by building a brand that could be more than just myself. A brand that could bring together others like me, those who wanted to work on their own terms but still be part of a team. That moment in the cafe, a little dream of freedom by a little Aussie girl became a proper adult business that my mum finally recognised as a real job (though she still asks me when I’m coming home).

Today, This is LD has grown into a whole team of amazingly talented unicorns around the world who all have their own unique stories to tell about how they took control of their own careers and built their lives on their own terms.

Here I Am, CEO

“To many of the people I work with I don’t really even have a face, let alone any tangible ability to inspire.”

I never thought I would be a CEO. Honestly, I’m still not even sure I am one now. It sounds a little silly to me. I spend most of my time wondering why anyone would want me to lead them anywhere. To many of the people I work with I don’t really even have a face, let alone any tangible ability to inspire. The rest of the time I’m so busy I can’t even remember why I thought having the title was remotely important in the first place.

But in those tiny moments in between, I remember that I want to be that person who drives change. Not just for myself, but for those around me as well. Even if those changes are small, seemingly insignificant things that perhaps no one else will ever notice or dwell on. As long as they are real, and hopefully meaningful, then I’ve achieved what I want from my journey. That is the CEO I want to be. I’m not the helm of an empire. I’m just the glue that holds a team and a dream together.

As a brand, the London chapter of This is LD is just the newest iteration of this mostly unknown person’s lifelong dream. But for myself, and hopefully, those who work for and with this company, it’s a representation of endless hard work, constantly evolving creativity, ongoing learning, brave risk-taking, and in our small way building a hopefully shinier tomorrow, one project at a time.

Author avatar
Lisa Eyo Andrews
http://www.thisisld.com
A tea-fuelled innovator who thrives on developing creative and integrated end-to-end solutions that cut through the clutter. Full-stack creative. Primarily a night owl who loves travelling and watching cars drive round in circles.
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