Learn to be comfortable in uncomfortable conversations

For many of us, the thought of holding a difficult conversation with someone can cause anxiety.

Many choose to avoid having these conversations. We hope that by ignoring both the situation as well as our feelings, things will get better.

They will not.

Grievances left unaddressed drip hurts ourselves and the connection.

I have a friend who was > 30 minutes late twice.

The excuse he gave: He was finishing some work. I thought to myself that I also had a lot of work to do. Yet, I was on time.

For the entire year, I avoided meeting him and did not initiate any meetups.

Last week, he asked to meet again. I ignored the text as I thought it will not be a good use of my time to spend it with him.

I then reminded myself that 'A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.' (Tim Ferris).

Successful people I knew were comfortable in uncomfortable conversations. They had the courage to talk about hard things and express their needs. Assertiveness is a muscle that needs to be built.

Eventually I brought this up to him, shared how I felt and asked if we could both come on time:

If we choose to give this time with each other, shall we both respect each other by coming close to the time we agreed on? I hope you can understand where I am coming from.

It took quite a bit of courage to bring this up. Here were the three considerations I had:

1. Self-respect and time saving are more important than discomfort

If I chose to say nothing, I would have risked wasting 20-30 minutes.

Worse, I would have to experience the feeling of feeling disrespected again.

I felt that the above situations were way more painful than having a difficult conversation.

Thus, communicating how I felt and what I wanted was a necessary step.

2. The worst case scenario of setting a boundary is not that bad

He could get upset and maybe even stop talking to me.

I thought to myself, if he were to react in a way that is unpleasant like feel I am petty, then I am also willing to walk away.

Why do I need this kind of friend? It is too expensive.

I can definitely do better than having a friend who does not respect me.

Thankfully he reacted in a mature way which affirmed that I chose the right friend in the first place.

3. I have to take ownership of this situation too

If I never set a boundary, I cannot blame people for crossing it twice.

He might have thought I was ‘chill’ about it as I did not really express frustration previously.

Given the goals I want to achieve, I need to be careful about how my time and energy is spent.

Waking up to the reality here in Singapore

Singapore has a global standard of living. We have a lot more security, convenience and efficiency versus our Southeast Asian neighbours.

We have a better work culture generally versus China, Japan, Korea, Hong Kong and Taiwan.

However, we cannot have our cake and eat it too. With global standard of living, also comes global competition and higher costs. This is the same message The Woke Salaryman has been trying to convey.

I feel worried seeing many in our local workforce choosing to lie flat 躺平 and cruise.

With the rise of Southeast asia, some companies have moved their APAC teams from here to our neighours and small businesses are starting to hire more workers from Malaysia where manpower costs could be 4x lower.

Singapore has shared about tripling our AI workforce to 15,000. Can we really be sure that a sizable majority of these jobs will go to Singaporeans?

Many local companies hire their tech teams in Indonesia, Vietnam and India. Even AI engineering jobs can be done by those in Vietnam.

If you’re the top few, you compete with global talent who come to Singapore. If you’re average or at the bottom, your job can be easily outsourced or replaced by AI.

My hope is that our generation will not be complacent.

Everything we have today, is built by the hard work of the previous generation.

My Ah Kong survived opium war; world war two; doing labour work at sea and being back with family only once every two weeks.

If I compare my ‘stressful’ job - an aircon office; to work in AI SaaS; learn from the best and get regional exposure. Is this really bad compared to whatever he had to go through?

We live in a time where there are so many options available. Knowledge is freely available on the internet.

It is about whether we want to take ownership, find solutions and take action.

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I am a Singaporean tech worker and content creator. Every week, I share ideas on how we can become our best selves in our career; finance; health and relationships.

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