Hey Travel Family,

Today I’m back home after spending a week soaking up the humidity in Singapore. I gotta tell you, going from cool winter evenings to long, hot days where your makeup sweats off as soon as you put it on was quite the shock to the system! Coming back to the cold again was even more shocking but made better thanks to warm, baggy jumpers and bowls of lentil stew. Most of my travel nowadays comes about from work but this trip was different.

Many years ago, when I was still in school, my family and I lived in Singapore. My mum, sister and I moved back to Brisbane for my high school years but they moved back again a few years ago and last week, my beautiful little sister graduated from high school. Excited for such a big life moment, she asked me to come to Singapore to celebrate. So, I packed a bag, boarded a flight and spent the week with my family, drenched in sweat and full of joy. But, a funny thing happens when you find yourself at a high school graduation because, for the first time in a very long time, you find yourself thinking back on your own.

When you’re 17 and preparing to walk out of your high school for the very last time, you get asked a lot of questions about your plans for the future. Some people are lucky because they actually have a plan and it’s one they’ve been working on for a very long time. I know people who, even when we were in primary school, knew what career they wanted to go after and planned their entire high school years, extra-curricular activities and life choices around it. Then there’s people who had a rough idea of what they thought was a good plan, got through high school and sort of ambled after their career hoping it was the right one. A long way behind those people are the one’s like me who had no idea whatsoever what they wanted to do and no clue how to work it out.

At that point in your life, the pressure feels like the most intense you’ve ever experienced. It’s an overwhelming feeling of expectation, a need to plan your whole life and decide what you want to do with it then commit to years upon years of going after it. For most of us, we don’t have a clue who we are as individuals or even what our genuine passions, interests, dreams and desires are because we haven’t really led our own lives yet. Up until this point, they’ve really been led by our school schedules, friends, certain pressures and a desire to fit in. Simply put, we haven’t had the chance to live from our hearts yet.

I left high school an absolute mess. I was insecure, had very little self-belief, had low self-esteem and felt incredibly stupid. That kind of place isn’t exactly the best one to be making important life path decisions from. I started out at University studying a course I thought would be a good fit for me but with no real career outcomes in mind or bigger dreams to keep me motivated. After a few months, I deferred and got a job instead, figuring I may as well be working full-time and earning good money, rather than wasting my time doing something I didn’t enjoy. That’s how I ended up in my pre-Little Grey Box office job for 7 years.

Speaking to my sister last week, her headspace sounded similar to mine. With no real idea what she truly wants to go after in this life, she was finding it difficult to make these big life decisions and commit to years upon years of study for a career she isn’t even sure she wants. In these situations, it seems like fear takes over and we start making decisions based on what we think we should be doing, rather than based on what we know we truly want to do. It’s been around 15 years since I walked out the doors of my high school and you would think, with that much time having passed, those ghosts would be long gone. But, stepping through the doors of my sisters high school, it suddenly became clear to me they weren’t.

I’ve always envied Matt’s ability to forget things. Sometimes, I watch him fall asleep at night and the second his head hits the pillow and he takes a few deep breaths, he’s out like a light. For me, I know I’ve got about two hours of deep self-assessment to get through before I’m anywhere near sleep. My mind loves to take me through live action replays of my greatest hits, ‘Mistakes Reel,’ edition. This involves me, mentally, dragging myself through the emotional mud. It’s a guilt road trip past famous sites such as, ‘Remember-The-Time-You-Did-That-Stupid-Thing Boulevard,’ and, ‘You-Were-So-Embarassing Lane.’ I re-live old conversations, interactions and mistakes over and over, thinking about what I did wrong and cringing, wishing I was better.

While many of these late night self-roast sessions are based on current events, many are still centred around things I did when I was 17. As we all remember, we aren’t exactly our best versions of ourselves at 17 so my mind has no shortage of awful moments to recall. A psychologist has diagnosed this as clinical anxiety with a generous helping of social anxiety. I’ve self diagnosed it as extremely bloody annoying.

Sitting in the crowd at my sisters graduation, day-dreaming through speeches, I can’t stop my mind wandering back to this exact time in my life and the person I wish I was. The 15-odd years since I graduated have been a tapestry of emotions and life experiences, good and bad. I’ve made a huge number of mistakes, embarrassed myself countless times, said and done things I regret and worn some truly heinous outfits. But I’ve also met some incredible people, made life-changing decisions, learned valuable lessons and become a person I’m very proud of.

As I watch my beautiful, vibrant little sister stroll across stage nervously and hold up her high school diploma for the cameras, I realise I can’t change my past mistakes but I can share them with her and offer all the love and support I have. I guess that’s exactly what my parents felt 15 years ago as they watched me graduate too. While it would be amazing to travel back in time with all the life experience and knowledge I have now, re-do my high school years and graduate knowing I want to pursue the career I have, I think it sounds better than it is. Somehow, I’m not sure the extra years to work on my dreams would feel as good because the years I spent miserable, fighting my way out of it, have made these past five even more valuable to me.

There’s simply no way to avoid mistakes in life and, truthfully, each one makes us a better person if we just take the time to look for the lesson. Though, I don’t recommend spending hours at night raking yourself over the coals over them. Instead, it’s best to accept who you were in that moment and treat yourself with the same love, compassion and understanding you’d show your 17-year-old baby sister. All that life experience we’ve been gathering has to come in handy at some point and a little perspective and self-love seems like the perfect moment to put it all to good use.

Rather than wishing I could change the last 15 years, I’m focused on what I can achieve in the next 15. There’s really no other way but forward and I’ve no doubt there are more mistakes, failures and lessons to come. But with them comes a better version of myself, someone stronger and wiser who will look back on this time and smile kindly at all the things I didn’t yet know. Just like my parents all those years ago and us, together, watching my sister graduate last week, all I can offer myself and others is unconditional love and support and the knowledge past mistakes cannot be changed.

Have a great weekend and I’ll talk to you next Friday.

Love, Phoebe x

Question of the week:

“What advice would you give your 17-year-old/high-school-graduating self and why?”

Share your answer in the comments… 

P.S The Week That Was (a.k.a TW) is evolving! To help me get my passion back for my writing I’m going to be doing my best to make each week’s post have a more focused feel. If you’re on O.G Little Grey Box supporter, you may remember my personal posts from ‘Phoebe’s Column.’

My plan is to bring those back, here. I’ll be reflecting on the week that was, looking for a key theme, thought, lesson or idea and turning it into a post here. Each post will have its own title that’s specific to the piece while still retaining the TW vibe! I’ll also be posing questions to you guys, giving you a chance to share your thoughts and experiences better too. Thanks, as always, for allowing me to grow and evolve – your support means the world! P x 


  1. “What advice would you give your 17-year-old/high-school-graduating self and why?” Journey along and enjoy the adventure! I settled into school in High School. I went to five different schools and was home schooled before I ended up in high school. It was a shock and then trying to make friends at that age oh boy! I attended four different higher education institutions and have made two cross country moves in my adult life. Quite the journey and oh so many adventures along the way 🙂 Great Post – appreciate your sharing your experiences. Happy Weekend – Enjoy

  2. Fantastic article phoebe. It is articles like these that uplift and empower fellow humans to achieve more irrespective of our imperfections. I could soo relate to you and especially with the 2 hour nightly self roast sessions 😉 😉 guilty AF there.
    But anyways thanks for sharing this and we need to see more such articles on social media.

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