My Story: I Work from my Laptop from Anywhere

Dreams do come true. From a very young age I set a goal for myself that I wanted to be able to work from my laptop remotely from anywhere. The past year I’ve done exactly that and is one of the biggest accomplishments of my professional career. It wasn’t easy reaching this goal but has been as rewarding I had hoped it would be. Looking back I’m thankful for all the experiences along the way in reaching this goal and wouldn’t do anything different on my pathway to arriving here. I’ve managed to create a life/work balance that affords me the happiness I desired from the freedom of workplace. In this post I’m going to discuss getting to this point, what it’s like now, and what the future holds and future personal/work plans.

This story is long, and by no means the whole story, but I think paints the picture well enough to post here.

Becoming Location Independent in my Career

Early days: When I first set this goal for myself I don’t think personal laptops even existed yet. Getting my first hand-me-down Compaq PC from my Uncle was a game changer for my life to come. Before that I had a neighbor my age who at his house had a few computers already and I was always going over to his house to play with them. He’s now one of the top enterprise cyber security professionals in the nation who handles all the work at his company none of his associates dare to touch. He was always into hacking and engineering as where I took a route of mostly gaming background (that’s what kids do) which lead to an early interest in Web Development with technologies, like GeoCities, Lycos, Netscape, Excite, Tripod, which are responsible for basically paving the way for the modern internet. It was at this time I also had a pirated copy of photoshop 6.0 which I would later go on to earn a Bachelors Degree in Graphic Design to compliment my web technology skills.

I soon became that neighborhood kid all my friends parents would call over when they needed any sort of technology help. So I guess you could say I’ve been doing this a long time.

Making progress: In college I had a roommate who shared my desire to be able to create websites from designs. Together we purchased the ‘Adobe Dreamweaver’ book, which I read it no-time, and realized the only real way to learn this skill was by doing. To be challenged with real-world projects and learn by completing those. I had built a few websites already some with HTML and soon discovering WordPress switched to using that technology. I was enrolled in a Web Design I course at my university and our final project was to create a 5 page personal portfolio website we could use to showcase our graphic design work. I already had built myself one of these so I decided to instead build a site for the beach candy shop I worked at part-time (don’t judge me haha) for the project. Lucky for you, I was able to dig up that candy shop website which you may view and laugh at here.

Funny enough, it was that website, and that candy shop job, that would play a huge role in shaping my professional career from there forward. The story goes, while working one night at the shop a group of people came in seemingly from one of the neighboring bars on Newport Ave., it was like 4 gals and a dude. While the ladies ‘taste-tested’ the chocolate covered gummy bears from the bulk candy bins, the guy who was with them approach me at the counter and mentioned he worked at the surf shop right across the street and handed me his business card which I think his title was ‘Website Manager’ on the card. He mentioned if I ever needed anything at all to not hesitate to hit him up.

I have to pause in the story right there because at the moment I had no idea what a huge impact that statement “if you ever need anything at all” from this random bald guy would have on my life to this day. You’ll understand later in this post why but when looking back it literally chokes me up thinking how things for me would have been so different today had I not been working at the candy shop that night.

Shortly after I quit the candy shop after working there part-time during college for a year. I ended up being required to complete an internship for my college requirements. I remembered that night at the candy shop and furiously dug around for that business card. When I found it I sent an e-mail re-introducing myself and asking if there was by chance an opportunity to internship for the Web/Marketing department at the surf shop, a core shop in the surf industry since 1974. I may sound like a nerd but have always been very into the action sports industry so this would be a dream internship opportunity.

I heard back from the surf shop, but it was from another guy who mentioned the guy I met at the candy shop was no longer working there and told me to come by for an interview and I did. At the interview I looked over their company website with them and rifled off about 10-20 things I could do to improve it during my internship and they were visually very stoked to have me get to work. After completing my internship requirements they began paying me to continue working for them which became my new part-time college job. I’d go on to manage multiple other website interns for them and build their online presence into what you see today. The opportunity given to me by the surf shop and the people there is one of the largest milestones in my professional development leading to my work today.

From then till a year ago: After I graduated college I moved from San Diego back to where I grew up in the Pacific Northwest to help with a family business and spend the winter snowboarding. I was mostly doing freelance web development and marketing work, including for the surf shop still, and living a pretty lean lifestyle living in the back of a little market store my parents owned. Through my work at the surf shop I was reconnected with the bald guy who I met at the candy shop and we kept in contact. He told me that the work I did for the surf shop was better than anything he ever did for them as website manager, which, I disagreed as he paved the way and built a solid foundation that gave me incredible leverage to do a great job there.

One day he reached out to me and said if I wanted he had a job for me in San Diego working for a startup company with a innovative business model doing performance based SEO work. Winter was over, no more snowboarding, my parents were selling the family business and I was ready to move to back to San Diego so that’s exactly what I did. I interviewed, got the job, and we killed it for 6-months. The guy I met at the candy shop that night was closing leads and I was fulfilling the work and we grew this startup by some unbelievable amount during this time.

A business dispute with the CEO of that start-up led to us both leaving and bootstrapping our own startup company and taking our clients with us.

Over the next three years we would build our startup into a well-respected company with a beautiful office on Broadway in Downtown San Diego, wonderfully talented and amazing employees, and client success that spoke very well to our line of work and reputation. The company would change a lot over those years and was adaptive to the ever-changing landscape of the online marketing world. As Co-Founder and COO, I learned more from my business partner, our contractors and employees and about the industry we worked than I ever could have hoped for. I gained so much in terms of personal development that would shape my professional development. One of the more rewarding opportunities during that time for me was getting to work with a handful of really awesome interns. It took me back to when I interned for the surf shop and what that enabled me to do with my career. During my time as COO of that company I was also witness to 4 new babies entering the world out of my companies employees and contractors which is incredibly rewarding for me to play a tiny role in supporting.

The final stage for me as COO of that company was helping transition the company from our office to being a 100% remote workforce. Something our company was already partially practicing but everyone there felt we no longer required our fancy office that really did nothing for us. By the end of 2014 we accomplished this goal and the company had become 100% remote which for me and those who worked with us was a huge benefit.

My co-founder, the customer dude from the candy shop, but moreso friend, mentor, and role-model has always been a giant supporter of achieving the proper work/life balance and he taught me the importance of this. He taught me that you should first create the life you want then shape your work around that, and not the other way around. It’s easy to say this but to actually do it became my primary focus. I needed to get back to my goal I had set from an early age to be able to work from my laptop from anywhere. But more importantly, do the things I wanted with my time and live my life THEN do my work as needed when and where I wanted to support that life. Invaluable advice I’m tremendously thankful for.

The Past Year of Working Remotely from my Laptop

As of the first of the year in 2015 we decided to re-structure the company which resulted in me switching from an employee as COO to now a freelance contractor which enabled me the freedom of the self-employed lifestyle. It was my co-founders idea that I retain the title of ‘co-founder’ at the company with whatever meaning that carried with it. I still get to work with the company on a daily basis doing mostly web development and they’ve remained my largest supporter personally and professionally over the last year for which I cannot thank them enough.

As the first year of being 100% self-employed wraps up I can say that it’s been everything I thought it would be. Personally, it’s now my second winter season in a row that I’m a seasons passholder to my local mountain to snowboard. I’ve been eating better, catching up with old friends, creating more art, reading more, exercising and adventuring more, and growing into an overall better person I like to think. Professionally, I’ve re-honed my freelancing skills, been presenting with awesome new opportunities, and greatly expanded my web development skills by taking on many different types of challenging projects that fit my specializations.

In the middle of the year something unexpected happened to me that resulted in a very positive impact on my freelancing. I woke up to an e-mail that said I had been hand-selected to be a part of an elite group of freelance WordPress developers located around the world. Like that night in the candy shop, I didn’t know what this meant right away but soon learned it would be one of the biggest opportunities I’d ever had in my career. I was humbled to learn I was now working on a service marketplace platform where my associate developers were guys/gals I had looked up to for years in the WordPress development community. These are the developers who regularly contribute to WordPress core, esteemed theme and plugin developers, and influential names you might recognize from help/support articles around the web. Now I was working with them, as a peer, which for me was almost unbelievable but no matter how hard I pinched I didn’t wake up…

Not only did this opportunity improve my reputation and credibility but resulted in a new revenue stream and enabled me to grow professionally by taking on work outside my comfort zone I lived in before. You see on this platform you’re only allowed to take on work you know you can complete so you’re constantly challenging yourself with “I think I can do that…” and I haven’t been stumped yet! I’ve also built relationships with the other senior developers there and have grown my network to include some specialist who can help me and my clients in areas I’d rather not take the time to learn which is huge.

Overall, this year I put a priority on pursuing life over work and I can say I’m really happy with the balance. Could I have done more work, made more money, and helped more people? Yes. But I really wanted to see how things would go without spending all my time being a work-a-holic which I’ve been called before. And I’m happy with the results this year. As for next year…

What the Future Holds

Travel: You’d think since I’m location independent and can do all my work remotely I’d be traveling the world. I thought so too but it’s just not the case. I do want to do more traveling but honestly I love the West Coast where I grew up and live. Sure I want to snowboard in places like Chile, Austria, Japan and Switzerland but it almost seems senseless to travel for snowboarding when it’s so great right in my backyard. I can see myself traveling more in years to come to far away places but it isn’t huge on my list at this point.

Work: This year went great for me in terms of work. Next year I think I can do even better. Now that I have sort of a baseline established I definitely want to pursue some lateral opportunities and see what I can do. More challenging jobs, more challenging clients/projects, more writing, and more community involvement. Also would like to start developing a few personal brands that align with my passions.

Life: Pretty much all my possession can fit inside my car, an estate wagon. This is cool when I move seasonally and act like I’m a minimalist or something but really it’s kinda of annoying not having a place to keep my stuff. It would be cool if I could buy some land or something and build a shed to keep my things. Haha, you can probably tell I’ve thought about this a lot…


As I mentioned at the start I left a lot out here in this story. Surely this isn’t all that’s led up to my current ability to work from my laptop but that goal is where is all started. I’ve put in my 10,000 hours of practice and with that and some really great opportunities I’ve recognized I’ve been able to follow my dreams. This story serves as motivation for others who wish the free themselves from the old way of doing things and escape the 9–5 and do what makes you happy.

By Raleigh

I am really fortunate for my work that allows me a flexible enough schedule to live my life in a way that affords me much happiness.

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