Conversations with Courage – Rachel Jacqueline

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Continuing on the 2017 theme of “living bravely”, this month we hear from ex-Hong Kong resident and journalist Rachel Jacqueline in our “Conversations with Courage” series. Here, Rachel shares her experience of “daring greatly” and what courage has meant for her in her life. 


Long before I came across Brené Brown and her important work in encouraging others to “dare greatly”, “step into the arena” and “rise strong” through Justine Campbell at Mindquest Group, I stepped into the arena in my own life. Or, more accurately, I stepped into the ring.

In 2012 I became one of the first two women to raise money for charity in Hong Kong by fighting in an amateur boxing match in the annual Hedge Fund Fight Night. The whole experience was utterly terrifying, and consuming. I spent six months, at least five times a week, throwing (and copping) punches and training like a maniac. But nothing prepares you for the fear you feel when in the ring: It begins in your stomach, sending a fluttering sensation through your whole body, and settles somewhere in your throat. Teetering on the balls of your feet, fists raised, facing your opponent, your mind searches for hints of their next move while summonsing the courage to step out from your defence and throw a punch yourself. It’s exhilarating, exhausting and petrifying, all at once.

I didn’t win. I didn’t lose spectacularly however; it was a fair fight. But in the scope of Roosevelt’s quote, “I failed”. Yet I stepped out of the ring that a winner: I knew that I had failed while daring greatly, and could hold my head high in the company of other brave men and women.  Ever since, I have made it my mission to step into the arena in every aspect of my life. And boy have I stayed true to that vision.

Later that year, I stepped away from full-time employment as a corporate lawyer to pursue my passion to be a writer. When I handed in my notice, I only had a little bit of steady work to rely on, from which I knew I could pay the rent (just!).  I also had a little pot of savings, if things went pear-shaped. On the other hand, I had a big pot of uncertainty: I had no “formal” training as a journalist, editor, or creative writer. But I did have a dream: I wanted to be a writer. I wanted to tell stories, and help others write their stories.

So I did, what Brené Brown refers to, as “choosing courage over comfort”. I closed my eyes and threw myself into the big, scary world of writing. Many days I felt like a fraud. I worried how I was going to pay the bills. But I remained steadfast (and stubborn) on my vision. Did my face get marred by dust, and sweat, and blood? Did I fall short? Did the critics throw their harsh words on me? And did I fail? Yes, yes, yes and yes. There were many nights when I cried into pages of redline edits from frustrated editors. There were many times when I felt the sting of rejected pitches, or simply received no response at all. And that was just the beginning of the struggles of starting a new career and a new business in a foreign country, all on my own.

But I didn’t give up. I chose not to let my “failures” hold me back. Instead, I got up, dusted myself off, and went at it again, learning from my mistakes. I “strived valiantly”, showed “great enthusiasm” and “devotion”, as Roosevelt’s quote demands. Slowly, steadily, and surely, that scary arena became my comfort zone. A space where I eventually became known, and dare I say it, even sought after for my skills.

Was the transition hard? Absolutely. But it was worth it. Every tear, every foregone social occasion, every sleepless night. I’d do it all again in a heartbeat.

Apart from hard work, a huge part of my evolution as a writer came from the self-belief I acquired through the sport of ultra running – running distances more than a marathon. Yup: As I was stepping into the arena in my career, I was also stepping into the arena physically, running insane distances that I previously thought was impossible! It all seemed like madness, but as the distances I ran increased from 50 kilometres, to 70 kilometres and eventually 100 kilometres, all in a day, so did my mindset. With every new distance accomplished I was reminded that the only limits I faced lay in my own mind. The physically stronger I became, the more mentally resilient I became, and more hardened to deal with setbacks that came with stepping into the arena.

I am a firm believer of the magical powers that achieving physical challenges have on our mind. So when I moved to a new city (New York) last year after living in Hong Kong for almost 7 years and I was asked by an old friend to join a team to play “Touch Football” (a.k.a. “Touch Footy” or simply “Touch”), I did the one thing I knew how to do: I said “yes”, even when what I really wanted to do was run away in fear.

You see, it wasn’t just any old “Touch” I had been asked to play. It was for a team representing the state of New York at the USA Nationals Tournament – a competition the team had won the year before! Talk about pressure. Although I was fanatical about the sport in my 20s, I hadn’t touched a ball in years. “Touch” is a high-speed, intense sport requiring incredible fitness, concentration, skill and strategy – all the things that you lose after a long time away, and especially as you get into your 30s! Plus, I’d always battled with negative self-doubt when I’d played in the past – those little voices in my head telling me I was slower than the other girls, and wasn’t as talented – and I knew being a rookie again was going to take some solid confidence to overcome them, confidence I wasn’t sure I had.

Despite the fears bubbling under the surface, I resolved to approach the new opportunity in the same spirit as I have approached such challenges in the past: I decided it was time to face my demons – those voices in my head telling me I wasn’t “fast enough”, “fit enough” or “good enough” – and step into the arena once again.

This time around, I made sure my team were my “support crew”: I shared my worries and fears about my abilities. I sought trusted feedback. And again, I worked and trained hard. I am proud to say that, after being involved in the sport for almost 15 years, I finally overcame the negative loops in my head to play some of the best “touch footy” I’ve personally ever played (and while our team didn’t win this year – we came second!)


Despite 2017 shaping up to be a very different year – married, in a new country, far away from family and friends – I’ve resolved to tackle it, once again, with the same approach that has served me so well by stepping into that ol’ arena once again. In a strange twist, after five years focusing on my passions as a writer, I have returned to my professional career. Yup: I’m stepping back into full-time, corporate work!

I spent some time wrestling with my decision, naturally. Was I really “stepping into the arena”, or simply choosing “comfort” over courage again? Was I just settling for the “easy” route, the well-trodden path, with less growth and life rewards along the way?  Or was my decision perhaps my most courageous one yet? In any event, I acknowledged that life takes us in different directions, our priorities change, and you have to remain adaptable.

But also, after reflection, a part of me has recognised an element of the “comfort” in the courageous decision to change careers that I made many years ago. I believe, now, in hindsight, that there was also a sliver of my decision that was about stepping away from fear: To be better at my career at that point, deep down I knew I was going to have to be honest about my professional weaknesses, and work on them. I was going to have to commit to my career. Step up. Work harder than ever. I was also going to have to get professionally “tougher”. And that decision, too, was going to take “balls”, as they say. And, being honest with myself now, I simply wasn’t prepared to do that: I was scared I wasn’t “good enough”, “detailed enough” or “smart enough”. I was afraid.

While I don’t regret my decision for a second, or underestimate the courageousness of my decision and what I have achieved since, I now realise that there are many ways to choose “courage over comfort” in our own lives that don’t always require life-changing and earth-shattering decisions. Sometimes choosing the courageous path is also simply about confronting those feelings of stagnation, and the difficulties we face, and choosing a different path through it. Sometimes the courageous path is not just about doing something different, but being someone different. Looking at ourselves in the mirror and realising the stories we tell ourselves may be just that: stories. Realising there is another, perhaps even more courageous way than the path that seems the most brazen.

I don’t know. I don’t have all the answers. And I don’t know where the next five years of my life will take me. But I do know this: I will always choose the most courageous path in life. And I urge you to do the same. It is, in my humble opinion, the only way to live. Life is too short, too precious, too fleeting to be lived in any way other than being fully present, and with full ownership of the course you are charting for yourself.

But you must also take the time to evaluate your own notions of courage: Courage is not just about stepping into the ring, running ultra marathons, finding a command of a sport that once eluded you, or any sort of “jumping off cliffs into the unknown” type of practice, but also confronting the truths that led you into those positions in the first place. I don’t believe you can go “wrong” in your decision, whichever you take, as long as you approach your new path with authenticity, integrity and a good dose of bravery.

— Rachel Jacqueline, New York City

Rachel Jacqueline has summed up what it means to be Daring Greatly and we are so grateful for her willingness to have this courageous conversation with us.  As Brene says, “When we deny the story, it defines us. When we own the story, we can write a brave new ending.” So, what courageous ending will you write for your own story today?