How I Became a Remote Career Coach: My Story
Since 2015, I’ve been living the dream of working remotely while traveling the world—but it wasn’t always this way. I used to be stuck in the 9-to-5 grind, commuting to a cubicle each day, where remote work felt like a distant fantasy. My journey took me from a burnt-out employee facing a layoff to a remote professional enjoying the freedom to work from anywhere and live on my terms.
Today, as a remote career coach, I empower others to build their own freedom by landing remote jobs and designing lives they truly love. My expertise in remote work has been featured in major publications like BBC, Fast Company, and CNN, and I’ve been named a top remote work influencer for three years running. I even had the honor of helping Estonia create the world’s first digital nomad visa. But my proudest accomplishment? Helping countless individuals transition to remote work and find the flexibility they crave.
This is the story of how I became a remote career coach.
Life Before Remote Work and The 9-to-5 Struggle
In 2014, I found myself trapped in the same cycle so many people struggle with—commute, work, eat, sleep, repeat. I was a project manager at an advertising agency, putting in long hours and working overtime that no one seemed to appreciate. Every week was a countdown to the weekend, and the highlight of my year was squeezing as much travel as possible into my two-week vacation window.
But the constant stress was draining, and one day I realized, “I can’t do this for the rest of my life”. I was tired of feeling like my life was all work and no play. I wanted more freedom, more control over my time, and the ability to live life on my terms. I didn’t just want to travel for two weeks a year—I wanted to travel as much as I wanted, whenever I wanted.
Sound familiar?
Kate Smith in Switzerland being getting laid off from 9-5
The Layoff That Allowed Me to Chase Remote Work
Determined to make a change, I started saving money to quit my job. I envisioned my “quit day” like a scene out of a movie: I’d hand in my resignation, pop champagne, and toast to my newfound freedom. In the meantime, I booked a 10-day whirlwind vacation across Italy, Switzerland, France, and Germany. I was set to return to the grind for a little longer before making my big move.
But life had other plans.
When I returned from my vacation, my boss pulled me aside and dropped a bombshell: I was being laid off.
At first, I was in shock. But almost immediately, I felt a weight lift off my shoulders. It was like the universe had given me permission to finally figure out what I truly wanted to do. And one thing was clear—I wasn’t going back to sitting at a desk all day.
Getting on a one-way flight to Prague, Czech Republic
The Challenge of Landing My First Remote Job
After months of being unemployed and unsure of my next move, I discovered Remote Year, a program where you travel the world with other remote workers. The only catch? I needed to find a remote job if I wanted to join.
Without hesitation, I put down a $3,000 deposit to lock my spot in the program, with another $2,000 to be paid for the first month of the program and booked a $700 one-way ticket to Prague, despite having no job and just $2,000 left in savings. I had 30 days to land a remote job or I’d be sent packing back to Canada, broke and defeated.
Sounds crazy, right? It was. The pressure was intense, and each day that passed without landing a job made the situation even more nerve-wracking. But with just two weeks left before my savings ran out, I finally landed a full-time remote marketing position.
And that was it. From that moment on, I was living a life I’d only dreamed of. Over the next year, I traveled to 12 different countries across Europe, Asia, and South America—all while working remotely. I no longer had to choose between work and travel. I had both.
Remote Work in Bali, Indonesia
How Remote Work Transformed My Life and Career
Landing that remote job didn’t just give me the freedom to travel—it transformed my entire lifestyle. Suddenly, I wasn’t living for the weekends or counting down to my next vacation. I had the flexibility to work from anywhere, on my own schedule, and truly live life on my terms.
I went from feeling trapped in a small-town 9-5 routine to living what felt like a jet-setter’s life, hopping from one country to the next. And the best part? I didn’t have to be rich or famous to do it. Remote work allowed me to build a life that felt fulfilling, exciting, and 100% aligned with what I’d always wanted. I felt like I finally had freedom!
At that point, I thought I’d found my dream career. I loved my remote marketing job, the flexibility, the freedom to travel, and the financial stability. Everything was perfect.
Ready to Land a Remote Job? Take the leap with confidence! The Free Remote Job Playbook will guide you through the exact 6-step process to secure the remote job you’ve been dreaming of.
How I Transitioned From Remote Worker to Career Coach
So how did I make the jump from working remotely in marketing to becoming a remote career coach? It all started with a side hustle..
While hunting for a remote job, I started a blog to practice my marketing skills. It gave me a chance to grow my skill set and play around with different online tools and software without the fear of messing it all up. At first, I wrote about my travels and what it was like to work remotely while exploring the world. Shortly after, people caught wind of my journey (I mean a LOT of people).
People were reaching out to learn how I was able to make money while traveling the world so they could do the same too. I started jumping on free calls to help them out. That’s when I realized there was a real demand for this knowledge. My story and digital nomad lifestyle started getting picked up in major press and publications. The BBC even wrote an article about ME. Then CNN, Fast Company (multiple times), CBC, podcasts, interviews - you name it.
Remote Career Coach, Kate
People wanted remote jobs! I started constantly getting emails and messages from people reaching out with one big question: How do I get a remote job, too?
But people didn’t just want tips—they wanted a clear path to landing a remote job, and I was in a unique position to guide them. When I saw the impact I could make, my focus shifted. I started offering career coaching sessions for about $25 an hour at first (crazy, I know!). For context, I now charge $3,497 for my 3-month 1:1 remote career coaching program.
As I made this shift into remote career coaching, not only did I enjoy helping others, but being a remote career coach was EXTREMELY fulfilling. I LOVED my marketing job, but helping others create their own career freedom? That was next-level fulfilling. This wasn’t just work—it was a passion. Over the past six years, I’ve put EVERYTHING into fine-tuning my coaching program, building out resources, worksheets, and frameworks that actually make landing a remote job achievable.
Watching clients secure remote roles, grow their income, and experience real freedom has been the most rewarding part of my journey. What started as something I loved has grown into a full-fledged career coaching business that’s helped countless people make remote work a reality such as:
Tyler, who landed a remote job in 90 days or…
Marcy, who doubled her income when she landed her remote job or…
Becky, who also landed a remote job in exactly 90 days or…
Kayla, who landed a remote job so she could live abroad and have the freedom to travel the world or…
Denis, who landed a remote job because he wanted to beat the LA traffic…
What I’ve Learned About Landing Remote Jobs
I know how overwhelming it can feel when you’re trying to figure out how to land a remote job—especially when you’re transitioning from a traditional office role. It can seem like the remote job market is an entirely different world, and in some ways, it is.
But it’s not impossible.
The key to successfully landing a remote job is having a clear, structured approach. My 1:1 remote career coaching program is designed to help you streamline the remote job search process, so you don’t waste time applying to remote jobs without hearing back or feeling lost in the endless search. I’ve developed frameworks, resources, and strategies that guide my clients through every step (that have been constantly and meticulously refined over the years!)
I’ve designed my remote career coaching framework to be simple and structured. I map it out precisely for you. My goal is to make the process of landing a remote job straightforward so that you can get more results in less time (and without all the overwhelm). And dare I even say, a little fun or exciting? Here's an email from one of my recent 1:1 remote career coaching clients:
It’s not a matter of IF you can land a remote job, it’s a matter of HOW.
If you’ve been applying to endless remote jobs with no results, there is a high chance:
Something is broken (not working/being done incorrectly) or missing in your process to land a remote job, or;
You’re not effectively communicating your value to employers
Now, of course, this is among a variety of other considerations (but those are the top two).
The challenge is that most people were never taught how to land jobs, let alone remote jobs. It’s not your fault! You’re doing the best you can with what you know. Having a proven remote job roadmap and framework to rely on can help keep you on track throughout the process and help you land a remote job faster than trying to figure it out on your own. You can create your own or use mine, which includes over 70+ action prompts so you know what to focus on and when with your remote job search.
Regardless, as you go through the process, check in with yourself regularly to reflect on what’s working and what’s not so you can make continual improvements and adjustments to your job search strategy.
The remote job search has also changed even from when I first started coaching people on how to land remote jobs. It’s important to stay aware of these changes so you can set yourself up for success.
Ultimately, when you know the right steps to take, the process becomes less scary—and even a bit exciting.
See Real Results! Check out how my clients have successfully transitioned to remote work with these inspiring success stories!
How to Get Your First Remote Job
So there you have it, that’s my story on how I became a remote career coach. If you’re sitting there wondering how to land a remote job, know this: it’s absolutely possible. I went from a burned-out 9-5 worker to traveling the world while working remotely, and you can too.
It all starts with taking that first step toward change. Whether that’s updating your resume, exploring remote job boards, or even reaching out for guidance, remember that it’s within your reach.
If you’re ready to take control of your career and unlock the freedom that remote work offers, I’m here to help. My 1:1 remote career coaching program is designed to give you a clear path to success, so you don’t have to figure it all out on your own. Or maybe a self-paced program like my Remote Career Accelerator is more your speed!
P.S. Don’t forget to subscribe to my FREE weekly newsletter, where I share new remote job postings, tips, and all the latest news on remote work. Let’s get you one step closer to landing your dream remote job!
