Introducing The Embossed Way - a new series!

With first-ever special guest Jordana Weiss

Introducing The Embossed Way – a new series here on CEOverthinker featuring conversations with women who are making their mark, paving their own way, and embodying what it means to be the boss of your own life.

The name comes from embossing, which – as defined by the Oxford Dictionary – is the act of stamping a design onto something, say a piece of stationery, “so that it stands out.” In other words, it adds a little something different to what would otherwise be a plain piece of paper. It’s also, of course, a play on words between “embodying” and “boss,” alluding to the concept of being a boss/being the boss.

My hope and goal for the series is to lift up female voices, showcase how they’re doing things differently (i.e. not taking the traditional path society tells them they have to, whether in work or in life in general), and inspire others to do the same.

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I’m honored to have my friend and fellow freelancer Jordana Weiss as our first guest. I met Jordana through a contract writing assignment for a Seattle-based tech company. We were originally only connected via the company’s Slack channel and had never met in person. But after I reached out on LinkedIn to ask about pricing for another project of mine (a constant tough spot for me as a freelancer), we soon exchanged numbers, met for coffee – and walks, and lunches, and more coffee – and became fast friends.

Jordana is originally from Canada but calls Seattle home. Her story of moving to the States and working for herself is one that inspires me – I hope it does the same for you.

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Lauren Scott: What did you want to be when you grew up and why?

Jordana Weiss: I actually had to call my mom and ask her about this because I don’t really remember having anything specific in my head as I was growing up. There was a week in third grade when I wanted to be a pilot. I liked to immerse myself in different topics and ideas, so my mom suggested that ‘researcher’ might be the closest match.

When I was in grade school, being a pioneer was also pretty up there. I'm not sure how that would be feasible, but that’s what I was most interested in for my career path. I did apply to work at a historical re-enactment center in my hometown when I was a teenager, but was not given an interview. Good thing too, since churning butter in 85° weather in a full-length dress doesn’t sound like a great time.

LS: How does that compare to where you are now?

JW: I’ve never churned my own butter, but I think the ‘researcher’ idea has stuck with me for a lot of my career. I really enjoy delving into different topics for my writing work, and find it a pleasant challenge to learn about new ideas and figure out how to explain them in my own words. I’ve had to do a lot of research on different topics since my writing work has been really varied, and as a result I think I have a good baseline knowledge of a lot of different industries and subjects.

LS: Tell us how you got to where you are now as a freelance writer. What was the journey like? What bumps did you hit along the way?

​​JW: Within two years of graduating university, I started my career working in theater stage management. I was privileged to be able to do this full-time, since the arts are a notoriously non-lucrative career path. My entry into the arts world was through a paid conservatory, which at the time was the first of its kind in Canada – a two-year, full-time paid training program. I was able to work with incredible mentors and was almost immediately brought on to professional productions as an apprentice.

I stayed in theater for another 6 years, but quickly realized that cobbling together a regular wage in Canadian theater was hard. In 2015, I was put on a show where I was essentially asked to do almost nothing for 3+ hours a day, but was still required to be at the theater. I decided to use that time to explore another option for supplementing my income. I joined some freelancing sites and started applying for jobs as a writer. I’d always enjoyed writing and thought that doing it in my free time would be appealing. I quickly found a few gigs I enjoyed and started to build my client list and portfolio. Soon, I was able to take on only the theater jobs that I wanted to take and use the rest of my time for writing.

In 2016, I met my now-husband, who lived in Seattle, which was almost 2,500 miles from my home in Toronto. As we dated long-distance, writing allowed me to flex my schedule to visit him often. We married in December 2019, and in February 2020 I arrived in Seattle to have the conversation of where we were going to live permanently. I arrived about three weeks before the pandemic shut down air travel, which accelerated my move to Seattle. Since moving here, I’ve been able to grow my writing business and work on it largely full-time. Being a freelancer definitely has its ebbs and flows, but it’s nice to be able to rely on my own skills to get work, even as the market changes and evolves.

LS: Tell us something you still dream about (something you still want to do/experience/accomplish).

JW: I think working on projects with more responsibility is something I would love to experience. I’ve worked closely with clients on some interesting longer-term writing projects like websites, but being able to design strategy, create an ongoing series of resources, or collaborate with clients to determine brand voice is something I want to continue to work toward in my career.

LS: Knowing what you know now, what is something you would tell your younger self?

JW: I’ve always struggled with anxiety and worry, and I think as I get older, I’ve gotten better at naming those feelings and emotions. This has helped me get a better handle on managing them, which I definitely didn’t have when I was younger. Because of that, I think I’d tell my younger self that it’s ok to be anxious, and having those feelings is a natural part of life.

LS: What does “being the boss of your own life” mean to you?

JW: I think being the boss of my own life essentially just means having the agency and autonomy to make my own decisions. Not being beholden to a certain career path or idea of how life needs to go to be meaningful.

Being able to identify what gives my life value and purpose and using that knowledge to support myself and my family is something that is important to me. For freelancers, this isn’t always straightforward. The marketplace is continually changing and navigating it can often feel fraught. Being the boss of my own life is both empowering and a huge amount of responsibility.

LS: The cover image for this article is features a photo of something that inspires you. Tell us more about it. What does it mean to you?

JW: It’s a picture of some sweet peas that I grew last year. They’re beautiful, and the result of a lot of time and effort over months to cultivate. It wasn’t necessarily difficult, but required ongoing attention, love, and care. Knowing that the result of hard work and effort can be something this beautiful is something that inspires me.

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Thank you for reading this inaugural edition of The Embossed Way series! I plan to release a new interview on a regular cadence, alternating with my usual essays. I hope you stick around for more – and if you have thoughts on how often you’d like to see an interview like this, I’d love to hear them.

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If this post inspired you – or if the series and/or entire CEOverthinker publication inspires you – consider sharing it with someone so they can be inspired too. 🤍