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 š
Let's begin...
1. Getting fired from my dream job OVER THE PHONE
7 years ago, I had a particular dream job.
Thereās 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 didnāt have time to train me because I was an urgent contract-role hire. I vowed that Iāll do my absolute best because I thoughtā 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 couldnāt hold back my tears.
21 year old Rae was simply not equipped to speak up for herself. She didnāt 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. Sheās human. Sheās 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 š°š°š°š°š°
Shock factor š«Øš«Øš«Øš«Øš«Ø
Fulfilment level - 0
(Zero fulfilment because I wasnāt even given a chance to share my perspective. It wasnāt even a conversation. I was discarded like a faulty machine, as fast as I was hired.)
2. First time I āstood 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 ā 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 theyāll 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 werenāt having meaningful conversations because I just wanted to avoid them asking me about my studies or work or anything thatāll reveal what Iām 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 āmy parents arenāt agreeable to me goingā ā actually, I didnāt even ask them. I just assumed theyāll disagree.
A good friend of mine knew this and told me āRae, if you canāt stand up for your business decisions to your parents⦠how can you run a businessā this, or any other?ā
Deep down, I knewā I didn't stand up for my business because I donāt know if Iāll succeed. I didnāt 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 donāt have this conversation, Iāll forever be PLAYING SMALL.
So I did.
Nothing was āsolvedā 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 doesnāt like sales)
And tho Iāve started and stopped many mini projects/ ventures over the years, theyāve (tried their best) to be supportive of me.
Itās still challenging, no doubt, because they have a certain fixed idea of how a successful business look likeā they often make comments that make me sigh, or subconsciously dismiss my wins to highlight their practical concerns.
Itās an evolving relationship. One of the challenges of entrepreneurship and designing a life thatās uniquely yours is that people can't visualise your vision. They wonāt understand, because it's not their dreams, it is yours.
But rememberā their need for certainty should never limit the infinite possibility waiting for you in the unknown.
Scary meter š°š°š°š°
Shock factor š«Øš«Ø
Fulfilment level š„°š„°š„°
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 markā¦
> we had those tough āwhat 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 wasnāt an easy conversationā¦)
> 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:
š¬ with myselfā am I ready to leave my family/ social circle/ in-person communities and relationships Iāve built over the years, to start a new life somewhere else
š¬ with my parentsā *ok I wouldnāt recommend having the parent conversation so early in the r/s when youāre 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
š¬ with himā 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 Iāve already started building relationships with his family, some of his friends, and we have mutual friends as wellā¦
Breakups are always hard because you think back about the āwhat 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 mirrorsā 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 š°š°
Shock factor š«Øš«Øš«Øš«Ø
Fulfilment level š„°š„°š„°
How to make decisions you don't regret
Difficult Conversations are tough because:
- We have to confront our emotions and make space for the other party's emotions
- 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:
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 ā professionally and personally.
If this speaks to you, join us in our upcoming gatheringā "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 wayā 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 š©
We'll be doing something a lil bit different ā 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) š„ŗ
Thereāll 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!
If youād like to join us, do catch the EARLY BIRD TICKETS
(ENDING in 12 hours)šš¼
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 š„ŗ
All you need is ONE shift in perspective, ONE conversation, ONE decision ā it can completely change your life.
āØš 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)šš¼
bring a friend you like! hehe
In your corner,
Rae xx