rating my top 3 difficult conversations

Jun 18, 2025 6:58 am

Dear ,


I honour of my next event coming right up next Thursday "let's talk: Difficult Conversations"...


I'm gonna be rating ranking my top 3 difficult conversations and rating them from 0 - 5 pull-my-hair difficulty scale šŸ˜‚


Let's begin...



1. Getting fired from my dream job OVER THE PHONE

7 years ago, I had a particular dream job. 


There’s basically only 1 major company in SG that offers this job, so when I got the opportunity to fill in for a role in that company for a few months, I jumped on it.


They didn’t have time to train me because I was an urgent contract-role hire. I vowed that I’ll do my absolute best because I thought— this is it! This is my chance to chase my dream!


I did the best I could with the little I was taught. But for some reason, there was a technical mistake I made.


I was scolded over the phone and I simply couldn’t hold back my tears.


21 year old Rae was simply not equipped to speak up for herself. She didn’t consider that in order to do the job well, she should have requested proper training. She was given no chances. 


Looking back, I wish I could tell little rae that the right employer will value a relationship with her. She’s human. She’s not a machine.


Two weeks later, I was fired over the phone while seated at a Starbucks.


I was given no explanation nor email closure. 


Scary meter 😰😰😰😰😰

Shock factor 🫨🫨🫨🫨🫨

Fulfilment level - 0


(Zero fulfilment because I wasn’t even given a chance to share my perspective. It wasn’t even a conversation. I was discarded like a faulty machine, as fast as I was hired.)



2. First time I ā€œstood upā€ to my parents about the work and business I am doing outside uni (I was 21!) 

For years I was hiding my 90% of my life from my parents — I told them I was late night studying when I was attending sales trainings and meeting my mentors.


I was taking emceeing and training gigs, and I was selling products door to door.


I automatically thought they’ll nag at me to focus on my studies so I rather not have the conversation with them.


Overtime my r/s with my parents felt very shallow and empty… we weren’t having meaningful conversations because I just wanted to avoid them asking me about my studies or work or anything that’ll reveal what I’m doing outside of school.


It reached a time where there was an overseas conference I wanted to attend (it was in Malaysia). I sighed, and just told my mentor ā€œmy parents aren’t agreeable to me goingā€ — actually, I didn’t even ask them. I just assumed they’ll disagree.


A good friend of mine knew this and told me ā€œRae, if you can’t stand up for your business decisions to your parents… how can you run a business— this, or any other?ā€ 


Deep down, I knew— I didn't stand up for my business because I don’t know if I’ll succeed. I didn’t even trust myself to make it work. 


As an avoidant person in relationships, difficult conversations are extremely hard for me. But I knew that if I don’t have this conversation, I’ll forever be PLAYING SMALL. 


So I did. 


Nothing was ā€œsolvedā€ in a single conversation, but I did feel a surge of self-respect, and could see my parents were open to listen.


My relationship with my parents has improved tremendously over the years. 


My dad has helped me distribute flyers door to door. My mom has happily invited her friends to my product launch (tho she says she doesn’t like sales) 


And tho I’ve started and stopped many mini projects/ ventures over the years, they’ve (tried their best) to be supportive of me.


It’s still challenging, no doubt, because they have a certain fixed idea of how a successful business look like— they often make comments that make me sigh, or subconsciously dismiss my wins to highlight their practical concerns. 


It’s an evolving relationship. One of the challenges of entrepreneurship and designing a life that’s uniquely yours is that people can't visualise your vision. They won’t understand, because it's not their dreams, it is yours.


But remember— their need for certainty should never limit the infinite possibility waiting for you in the unknown.


Scary meter 😰😰😰😰

Shock factor 🫨🫨

Fulfilment level 🄰🄰🄰



3. Breaking up with the person I seriously considered moving halfway across the world for 

3 years ago I entered a relationship that was very very uncomfortable for the asian-crave-for-certainty part of me. It was a bit of a whirlwind romance, we met on the plane to Bali and he was in Asia for 6 months only. 


I was confronted with a decision: To try and see if this is a relationship worth fighting for, or let it go. Well, we decided to try. 


In a span of 6 months we did a whole list of things most couples would likely only do at the 2 year mark…

> we had those tough ā€œwhat are your dreams/plansā€ conversations 

> discussions about our beliefs, values, perspectives on spirituality, religion, family, lifestyle

> we travelled to multiple cities over a span of months 

> he came to sg and met my very Christian parents (and as a big amgmo with a beard, towering over me… it definitely wasn’t an easy conversation…) 

> I flew to US for 3 months to meet his parents and try living together


It was A LOT, emotionally and mentally because I needed to have Difficult Conversations:

šŸ’¬ with myself— am I ready to leave my family/ social circle/ in-person communities and relationships I’ve built over the years, to start a new life somewhere else 

šŸ’¬ with my parents— *ok I wouldn’t recommend having the parent conversation so early in the r/s when you’re still figuring compatibility yourself, but because of the incoming LDR, we kind of needed to speed things up, which is largely the reason why it was emotionally taxing

šŸ’¬ with him— actually plotting out our options, while still figuring out if all of this is worth it (I.e. getting the VISA sorted out, etc)


The difficult conversations + eventual decision to end the relationship was a very long drawn out process.


In 8 months I’ve already started building relationships with his family, some of his friends, and we have mutual friends as well…


Breakups are always hard because you think back about the ā€œwhat could have beensā€. 


That being said, the many difficult conversations I needed to have for this really allowed me to understand my needs with greater depth, and revealed some of the shadows within me.


I find that romantic partners are often my greatest mirrors— besides revealing to me the truths I needed to confront, they teach me how to embrace my softness and vulnerability, and learn how to ask for what I want (which is not intuitive for my Christian asian upbringing + being a woman in general)


Scary meter 😰😰

Shock factor 🫨🫨🫨🫨

Fulfilment level 🄰🄰🄰



How to make decisions you don't regret

Difficult Conversations are tough because:

  1. We have to confront our emotions and make space for the other party's emotions
  2. The outcome is uncertain, and it may sometimes lead to the ending of a relationship


What has helped me make peace with all of this and take on these conversations courageously are these 3 truths I've observed in my life:


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Having Difficult Conversations and Tough Reflections is a life skill.

I've learnt that the more quality relationship I have with myself, the more quality relationships I have with others — professionally and personally.

If this speaks to you, join us in our upcoming gathering— "let's talk: Difficult Conversations"

I'll be collaborating with a new friend of mine, Brian. After knowing him for just 3 months, I have witnessed his vulnerability, his strength, his passion and deep sense of purpose for the work he does.


He learnt about difficult conversations the hard way— having his (ex) girlfriend whom he thought he was gonna marry BREAK UP with him due to his unresolved issues and gambling addiction.


He needed to confront the difficult truths within himself, so much so that he jokingly calls himself a "red flag detector" because he himself was a walking red flag 🚩


We'll be doing something a lil bit different — it's a mini-workshop with guided discussions around the topic of difficult conversations.


We are gonna get real vulnerable and share personal stories of our relationships (personal/ familial) as well as difficult conversations we needed to have professionally (in our career/ biz) 🄺


There’ll be facilitated opportunities to discuss ways in which you can tackle difficult conversations with greater ease and flow.


Join us on 26 June, Thursday, 7-10pm. Location will be Central Singapore!


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If you’d like to join us, do catch the EARLY BIRD TICKETS

(ENDING in 12 hours)šŸ‘‡šŸ¼


Join us here! :)



A lil bit about Brian:


He is a is a Fitness Trainer, Positive Psychology Coach, and Mental wellness advocate whose work bridges the head, heart, and body. With a background in coaching various methodologies in fitness like Rhythm Cycling, Pilates Reformer and also Personal Strength training, he also has a deeply personal story of overcoming Anxiety, Anxious Attachments, Isolation and Gambling addiction and is rebuilding from the inside out. 

 

He empowers individuals to reconnect with their truth, strengthen their inner voice through personal dialogue and Coming home to themselves.


As for myself?


Some of you may know that I started emceeing and freelancing since I was 15 years old. As a passionate soul and multi-hyphenate, I was confronted with many difficult conversations -- with my peers, my (initially disapproving) parents, and most importantly myself. 


Over the years, I ultimately overcame insecurity, low-self worth, and the tendency to bypass my inner voice in favour of advice from people "better than me". 

 

Today, I'm a coach who guides rising leaders to Own their Voice -- reclaiming their unique voice so they can speak with power and navigate conversations with compassion and authority.


On the fence? Here are some messages I received after our last event 🄺

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All you need is ONE shift in perspective, ONE conversation, ONE decision — it can completely change your life. 


āœØšŸ‘€ I'm now in Europe till 20 June, and I'm excited to come back to SG and meet you guys!


Once again, join us on 26 June, Thursday Evening!

Do catch the EARLY BIRD TICKETS (for another 12 HOURS)šŸ‘‡šŸ¼

bring a friend you like! hehe


Ok I AM IN!!



In your corner,

Rae xx


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