When to Say Yes, and When to Say No

Hello! It’s been a while… 🤩 🥳 

I took some time off from writing as I wanted to rest and recuperate for the rest of 2024 last year. So for the first time in my life, I went up into the mountains and took a very peaceful break from all the hustle and bustle in Singapore.

When the year started, I’m sure there were all of those noise about ‘making your 2025 the best one yet', or ‘setting new year goals’, etc… I have covered those before and if you’d like to read it, you can find it here. 2025 started with the new year and Lunar New Year pretty close (Both in January). If you’re someone who celebrates both, it might have been hectic, so I decided to let the new year settle in for you and kickstart this newsletter in March instead.

There have been many conversations that I’ve had with my mentees at the end of last and beginning of this year—my mentees are usually recurring and they don’t go through the ADPList platform for their subsequent sessions, but I’m more than happy to give them my time if they were keen to learn.

One of my mentees had a question of how some people seem ‘luckier’ than others—getting what they want and so on. I’ll try to break it down for you how I explained to my mentee.

Opportunities Come and Go 🌊🏄🏻‍♂️🌊

Opportunities come like waves. They come and go. Think of yourself as the surfer. For you to ride the wave, you have to start somewhere. There’s no way you can be fully prepared for it, and you are probably going to miss some waves. With practice, you can either identify waves that are coming—a small window, if you will, that allows you to surf along.

That happens the same way when setting yourself up to take advantage of opportunities. To set yourself up, you don’t have to be fully ready—no one ever is. No one is ever fully ready to raise a child, no one fully knows how to take care of pets. We just do our best and learn as we go. That’s why parents always get tips from other parents because they want to know how to deal with situations when it comes. They might not get it right the first time, but they can always keep trying to be better.

Getting Out of Your Comfort Zone 😰

The courage to say yes to something when you’re not fully prepared is how ‘luck’ happens—not always, but a fair chance that it happens that way.

We weren’t born to know everything. Our learnings and experiences guide us, but before we can learn anything, we have to be willing to put ourselves out there to try to understand something that could seem quite daunting.

When you say yes, you are essentially setting up yourself to be in that position where opportunities could present themselves. For example, I advised an ex-colleague 2 years ago, to use ADPList to speak to someone who’s got expertise in the matter she was seeking advice in, since it’s free (they recently emailed me that I can set up a paid option now), but she didn’t use it. She didn’t grab that opportunity. Granted it might have been daunting to book a stranger’s time to speak with them, but if she took action, she could have been rewarded with some new knowledge that she could have utilised to set herself up for something better. In the end, she went back to do something she didn’t like. So, when do you say yes?

Say YES when:

🔥 It aligns with your goals – Does it move you closer to what you want to achieve?

🔥 It challenges you in a good way – Growth comes from stepping outside your comfort zone.

🔥 It’s a unique opportunity – Some chances won’t come again.

🔥 It helps you build valuable relationships – Networking can lead to unexpected opportunities.

But you can’t be saying yes all the time… right?

When to Say No

Steve Jobs was known to say no to a lot of things. Here’s a video of him addressing concerns and why he says no.

Another founder also talked about focus (saying no) that you can watch here.

So, if I want opportunities, I say yes. Saying no means turning down opportunities. But, to focus, I also need to say no. So… when should you say no?

Say NO when:

🙅🏻‍♂️ It distracts from your priorities – If it takes time away from what truly matters, decline. In essence - FOCUS.

🙅🏻‍♂️ It doesn’t excite or inspire you – If it feels like an obligation rather than an opportunity, pass.

🙅🏻‍♂️ It drains your energy – Some things take more than they give.

🙅🏻‍♂️ It’s not the right timing – Even great opportunities can be a bad fit if you're overwhelmed.

When you say no for the wrong reasons, like Yahoo, who was too proud back then to buy Google, they miss out on opportunities—as you can see in the tweet below.

A story, from WallStreetBets.

1998: Yahoo refuses to buy Google for $1 million.

2002: Yahoo tries to buy Google for $3 billion. Google says $5 billion. Yahoo says no.

2008: Yahoo refuses to be sold to Microsoft for $40 billion.

2016: Yahoo sold to Verizon for $4.6 billion.

— unusual_whales (@unusual_whales) December 16, 2023

Reflect: Here’s a practical rule of thumb—If it’s not a clear yes, it’s a no. If it’s a strategic no, it creates space for the right yes.

Mentor’s Notes

While this isn’t technically design, or anything about user experience, this is about designing your life the right way so that more opportunities can come your way. I’ve known people who’ve blocked themselves their whole lives—even today. Which is why I do what I do to help whenever I can.

My purpose for mentoring is so that people can use my knowledge to get ahead without the struggles I faced, without repeating the mistakes I made. I genuinely hope that if this article can help you, your friend, or your loved ones, please share it with them. I wish you a great 2025, and I hope this would be a great start for you for the rest of the year! 🙏🏻

P.S. Yes, as always, please share it with your friends if you think it’s useful.