Spotlight Series: Meet Career Coach Rachel Despres

1. Tell us a bit about yourself

Heya! My name’s Rachel. I’m a Career Coach for Rebels, writer, educator, and former cubicle-dweller. I help the nonconformists of the world to break free of their desk jobs and build unconventional careers. I’m based out of Guelph, Ontario, Canada, but I work with people all over the world (thank you, Internet!).

When I’m not coaching one-on-one, running workshops, or creating content to help my Rebel peeps, you’ll find me on a nature walk with my partner, Will, and our full-of-love French bulldog, Gus; curled up in a cozy chair with a cup of tea and my nose buried in a book; watchin’ basketball (go Raptors go!); or sitting in a movie theatre full of kiddos, checkin’ out the latest Pixar film (#nevergrowingup).

2. What was your first job and how did you get it?

My first job of the professional variety was as a Project Manager at a marketing agency that specialized in working with not-for-profit clients (i.e. charities and government organizations).

Since this is back when I was playin’ by the typical career “rules,” I got the position in a fairly traditional way. After graduating from university, I researched what marketing and advertising agencies were located in the area I lived, and this particular business caught my eye. I liked the creative elements of their website and the way they talked about their clients, projects, and employees.

So I flagged their website and checked back regularly until a position became available. And when one did, I jumped on it! It didn’t much matter to me (at the time) what the position was. I was so full of new grad giddy-up to get out into the real world and start doing the work I’d spent four years learning about in school.

I can still remember how elated I was the day I received an offer letter. I had checked off the “get a good job” box and was officially an adult. Like, for real. It’s funny to look back on that moment now, and how I thought I’d do a deep exhale and cruise on through the next 40ish years until retirement. Little did I know the career journey that lay ahead of me.

3. How did you decide and get to your career today?

Being a Career Coach for Rebels was never something I set out to do. Rather, the path was born out of me fumbling my way through my own career journey and the challenges and frustrations I experienced along the way.

Like many people, I graduated from university with the idea that I’d spend the next 40ish years happily working in the field in which I’d studied. Hoo boy was I ever wrong about that! My career in marketing lasted about three years, during which time I bounced from job to job to job. Searching for, but never finding, the fulfillment I’d anticipated when I chose to study and then work in the industry.

At first, I thought it was the company I was working for. Maybe it was the wrong fit? But by the third job I knew it wasn’t just my bosses or the culture that wasn’t jivin’, it was the WORK too. The duties. The day-to-day responsibilities. And I came to the realization that no matter where I worked, these feelings wouldn’t change. Like a square peg and a round hole, it just wasn’t gonna happen for me and marketing. We weren’t meant to be.

So I made the decision to leave the industry. I didn’t have a plan. Not a damn clue what was next for me. I just took some time off to figure it out. And with the help of a career coach, I landed on the field of book and magazine publishing. Dreamy, right? It certainly was for me at the time. I’m an avid reader and stationery aficionado, so it felt like a fairy tale career.

I went back to school and did a one-year postgraduate certificate, which I LOVED. I was so sure that this was “it.” The Holy Grail career.

But soon after graduation, when I landed my first job in the industry, a familiar flood of feelings returned. It became glaringly obvious to me that, despite my keen interest in the field, something was still missing. And while I couldn’t put my finger on what, I could feel it in my bones.

Plus, on top of that, there was an ever-growing list of things that just weren’t workin’ for me. Like the routine 9 to 5 workdays, and spending all day stuck at a desk inside a cubicle doing what felt like mundane, meaningless tasks. But when I looked around at all of my co-workers, they seemed so content and engaged with their work. I felt like there was something wrong with me for not feeling the way they did.

So I channeled my discontent with the so-called status quo and my feeling that something was missing in my career into starting a blog. It was called A Creative Pursuit, and my mission with it was to inspire others to pursue creative and meaningful work.

Suddenly, and for the first time in my career, it felt like I had a purpose. I was sharing the lessons and learnings from my own journey, as well as resources I’d found along the way, in hopes of empowering others to leave careers they felt unhappy and stuck in to pursue work they loved.

Amazingly, the blog did just that! I was getting messages from people saying, “I feel so fired up to quit my job and break out of this cubicle, but I have no idea what the heck to do next or how to make the shift. HELP!”

Cue the “aha” moment where I realized there was a need for coaching people in the direction of unconventional career paths. And it was also when I learned that I wasn’t, in fact, alone in feeling dissatisfied with traditional office jobs.

So after several months of working in cubicle prison by day and writing on the blog by night, I handed in my resignation and jumped into career coaching with both feet. Ironically, on my last day working in corporate, as a I was saying goodbye to all of my coworkers, the same people who I’d thought were so content and engaged in their work were the first ones to ask if I could help them get out of there too (because, as it turned out, they were just as unhappy, and stuck, and lost in their careers as I was).

That was nearly four years ago, and since then I’ve developed coaching programs to guide people through not only discovering what kind of out-of-the-box work they want to do but also helping them build an Escape Plan to guide them as they make their transition from cubicle to unconventional career.

Helping others discover who they are and create unique careers that allow themselves to shine is by far the most rewarding work I’ve ever done. And while it’s not the career I ever imagined I would have, I couldn’t picture myself doing anything else.

4. What advice would you have given your younger self? Or what is the best career advice you have ever received?

  • Trust yo’self! No one knows you better than you (nope, not even your parents, teachers, friends, or significant other). The things that fire you up and float your boat are there for a reason. Don’t let anyone tell you they’re not worth pursuing.

  • Quit tryin’ to stick it out in an unfulfilling career just because it’s what you studied in school—you’re allowed to grow and change your mind. You’re not married to the career path you chose at 17 years old.

  • Feeling deeply dissatisfied in your work isn’t normal. Don’t settle for it. It’s a sign it’s not the right fit for you.

  • Quitting jobs that no longer serve you doesn’t make you a failure. It means you’re growing.

  • Don’t sacrifice your happiness out of fear of disappointing others.

  • It’s okay if your path doesn’t look like everyone else’s. It shouldn’t. Because you’re not everyone else—you’re YOU. A one in 7.7 billion original, baby.

5. In 5 years, where do you hope to be professionally and personally?

With the ongoing shift away from full-time jobs and toward gig work, my mission over the next five years (and beyond) is to bring awareness to unconventional careers as a legitimate path outside of traditional employment.

Despite the changes taking place in our economy, most people are still growin’ up with the belief that a 9 to 5 desk job is the only option they have for what work can look like. And that just isn’t true anymore. I want to help shift this mindset for as many people as I possibly can.

So, in five years, I hope I’m continuing to do this by coaching Rebels one on one, and also on a larger scale by leading group coaching, hosting a podcast, writing books, and speaking at conferences around the topic of unconventional career paths.

Personally, I hope to have learned to salsa dance and watercolor paint, be fluent in Spanish, have adopted another Frenchie into our family, and added a lot more stamps in my passport.

Stay connected with Rachel!






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