Taking the Leap... starts with taking the first step

Dear leapfrogs,

If you're looking at the year on your wall calendar in disbelief: join the club. It's March of 2026 -- two years since my last entry -- and nearly ten years since I decided to take the leap and start applying for jobs down under. Not only that; this year marks 20 years since the international trip across the pond that opened my eyes, helped me see the world... and likely started it all.

Any big changes naturally spur reflection, so it makes sense that I've been thinking about when the first time was that I really "took the leap." What do I mean by that? In hindsight, they were times that I chose a new path, ventured into the unknown, and decided to take a chance on both myself and the world -- in order to try something new and uncover new possibility. Were they extreme? Not always. Were they deemed brave or bold? Not at first. As I got older and more experienced, however, carving new paths became more trying -- and more rewarding. I realize now that each leap was a combination of knowing and growing that both built my inner trust and strengthened my courage, flexing muscles like adaptability and "growth mindset." 

Maybe my biggest leap yet. August 2025

Ever since I decided to pursue my dream of living abroad, after choosing LA-based opportunities for college and my first job, I've had a fascination toward what allows us to make a bold choice, take the "road less traveled" or even simply pivot from a common barrier to progress: the status quo. Taking the Leap was born, an idea and a platform (and a someday podcast!) that will highlight stories, codify wisdom, connect fellow leapfrogs and curate inspiration so that more of us can cultivate the courage to make bold moves. 

I realize now that each leap was a combination of knowing and growing... that both built my inner trust and strengthened my courage.

In January, I took the first step toward this goal and recorded my first "podcast" interview in years - this time with my fellow expat and Sydney soul sister Becca. I started the interview by talking about my goals for the podcast, my aims for our conversation, and the birth of my love of leaps: the road less traveled. Then i asked her all the questions I had planned, giddily surprised each instant with what unveiled itself (beyond my intentions or envisioning). I asked her when she first leapt, what she thinks "taking the leap" means, when she last leapt, and when she will again. I asked Becca how she prepared, what tools and mindsets she embodied. Finally, I asked her when she feels the most brave and what leap she'll take next in 2026. 

In February, I spent a lot of time thinking about my imminent "next play." As I embarked on a new job at a new company (for the first time in ~12 years), I swore to myself that I'd document my experience. I'd "walk the walk," be brave, and curate how I was feeling mid-leap. 

Now that it's March, I'll reignite my original platform for blogging and reflecting to the world. I'll begin by sharing my latest realizations: when I first, and next, and last took the leap. 

When do I feel brave? I know that I feel brave when i'm doing something i've never done; doing something that scares me; going after something that sounds difficult and challenging but also sounds interesting or energizing to tackle.
​
When was the first time I took a leap? The first time that comes to mind for me was in the fifth grade, when i was no more than a tiny little nugget. I was already involved in asb, our associated student body, and i remember that it was a fun space to hang out with my friends and plan fun things for the school. it was suggested that i run for student body president. i didn't know what would happen or whether i'd be cool enough for that, but i remember making posters and writing a speech about what i would do or what i would promise were i to be elected. 

What that foggy memory reminds me is that taking the leap is "going for something" -- putting your heart and your ego out on the line in order to showcase that you want something, with the incentive being the chance to DO THAT THING. Have that opportunity. Maybe it's putting ourselves in the arena. It's vulnerable because there's a risk that you miss, or fail, or flop. But what we know as adults is that there is often risk present but often no chance of "failing." The worst that might happen is that we'll learn a shit ton, maybe lose money, maybe just maybe risk rejection or embarrassment. The only thing that you can guarantee is that you'll learn. Nothing else is promised. Well, that -- and that you'll likely grow and transform in the process.

The next time i took a leap was by agreeing to a college tour and interview for a scholarship that was taking place out of state, in the rainy pacific northwest, on my birthday no less. The risk was that i wouldn't get it (though i had been accepted to the school), or that i wouldn't like it and wouldn't enjoy the people. But i loved making new friends! I had traveled abroad again the summer before and i knew that i had family there to drive me to the scholarship interview. So i took the leap. The biggest memory from that trip, aside from the birthday cake that they presented me when I first got out of the car on campus, was the moment in the interview itself when they asked me how I would feel living and studying so far from my family "when I was so close to my younger sisters" -- who I had just told them about. Little did I know that five minutes into the interview (designed to tell them whether I was a right candidate for this scholarship), I would be in tears realizing that they weren't the right candidate for my first home-away-from-home when it came time to leave for college. I'd miss home too much. 

The most recent time that I took a big leap? ​When I pursued a role overseas and interviewed for, accepted and moved for a job abroad in Sydney, Australia. I had always dreamed of moving with a company or taking a chance to teach English in another country, ever since that second trip abroad to play soccer in high school. I had loved the experience of playing sport on the other side of the world, witnessing through the process the universal nature of humanity, young adulthood and womanhood on the sports pitch (when I heard a young coach yelling at a player -- though in a foreign tongue, i knew EXACTLY what he was yelling and wrote as such in my college application essays). We're all the same, but I wanted to test my resolve and see the world in order to gain a more global perspective.

When the time came to explore such a chance, after three years at Linkedin and a point of comfort and confidence that granted the courage to apply, I knew that I wanted to try an emerging market where English would get me by in both business and client services. I interviewed any colleague who would meet me, and explored at least three roles before the right one took a chance on me. By then I KNEW I had to take the chance and take the leap before too much of life passed me by.

I don't know for sure that they would have, but I had a feeling that life's milestones such as boyfriends and mortgages, aging parents and niece/nephews all would only give me greater reason not to go. So I went for it, at the ripe age of 28, because I thought that "if I don't do it now, I might not ever have the courage!" The first time I uttered that out loud, a distant colleague at the time reminded me that that wasn't necessarily true - I could always go for it and take the leap at any time.
​
What that moment on the 16th floor of our downtown SF high-rise begged me to ask was this: What was I waiting for? I wanted it. Now was the time because my heart was yearning for it. On a nearby couch over one year prior (in 2016), my mentor and manager had asked me "Cory, what would be the ONE next role you'd kill for if I told you you only had one more in your career here at Linkedin?" I took the glaring clarity in my heart and listened to it, ran with it.... because it told me that I wanted to move abroad with the company and platform I loved. It was time to move with LinkedIn... and it was time to become a broad abroad... down under.