5 Lessons from my gap year that I'll guard with my life
Learned a lot, failed a lot, tried a lot, did a lot, and here we are.
In 1 month I will no longer be the gal on the gap year. I’ll have to change my LinkedIn bio and the way I introduce myself. Perhaps the people who follow me for my gap year content will unfollow me. Perhaps I will no longer be relevant on LinkedIn since I’d have a big girl job.
I could go on and on about my uncertainties, but I decided to jot down some things that I have become certain about through my past gap year. This is inspired by a substack I recently discovered, Jenny’s Career Break(through).
also did a full-year sabbatical from her career as a tech PM.So here it is. My 5 lessons from my gap year.
#1 Don’t seek. Attract.
I started out this gap year in Singapore, with no friends and one freelance gig. I wanted two things; friends and work that I felt passionate about doing. But I had neither. I naturally started seeking out for both of these.
For friends (I admit that I felt like a loser) I cold DMed a bunch of people on LinkedIn, from mutual friends to alumni to just random people in Singapore. I met a ton of really interesting folks through this process, but the hit rate (finding individuals whom I actually clicked with) was so darn low. There were many times when I just stayed through the coffee even though I was not interested in hearing what they had to say.
Why? Because I was desperate for friends.
For meaningful work, I spam applied for internships and gigs that I had absolutely no interest in. I thought unrelatable work was better than no work, so I applied to everything I could on LinkedIn jobs, from localization, translation, tutoring, recruiting, etc. I got rejected mostly because I would need work visa sponsorship, but I think my ingenuine interest (rather, desperation) showed in the interviews. Bottom line, I didn’t get really far.
I can’t remember what it was but around October, halfway into my gap year, I decided that I would stop being pathetic and desperate and letting the world and peer pressure govern my path. I think I realized how stupid it was that while I decided to take a gap year to “figure out my true passion” I was still taking steps in ways that I felt like I was supposed to, rather than what I wanted to. What the heck was I doing?
I went back to first-principles-esque thinking, and thought to myself, what do I actually enjoy? What is something that I do, where I viscerally feel joy from doing it?
And the answer was two things. 1. Talking to people, and 2. Writing.
The time I spent desperately looking for friends and work was then rechanneled into committing myself to doing those two things. Just allowing myself to fully pursue that visceral experience of joy. It very slowly gained traction here and there, but what really sparked it all was Jeshua’s startup pitch event (he’s an incredible character so you must follow his substack here:). Since then, it’s been through meeting people through LinkedIn and my writing where I’ve met my current crowd of driven, passionate, caring, intelligent individuals that I am so proud to call my friends. Moreover, through their support on LinkedIn, my exposure and reach has increased significantly that I’ve received so many requests to lead marketing, communications, brandings for companies. Still not sure what they see in me, but it’s kind of ironic how desperate I was to find a single role that I could do what I enjoy doing all those months ago, and now I’m getting all these offers that I didn’t ask for.
The point is, as much as it is a cliche contemporarily used in the dating scene, things come when you least expect it. And if you desperately seek for friends, jobs, boyfriends, whatever, that mindset of scarcity and depletion might actually be what’s stopping people from approaching you. Rather, focus on doing whatever makes you happy first, work on yoself! And then you will find yourself getting offers left and right. Don’t seek! Attract!!
#2 Brute force works.
Okay now I’m realizing that this post might be a lot longer than I intended it to be but I’m on a roll. Ah! Brute force!!
In a very unintentional way, I think I experienced the founder/entrepreneur lifestyle this year. Everything just kind of depends on you, no boss will tell you when or what to do, and if you don’t work, you will be broke and unproductive. You learn to establish systems and environments that provoke your productivity and creativity, but you also learn to handle your unproductive poopy self.
This was one thing that I had not anticipated to face this year. Facing that ugly, gluttonous, undisciplined self is a tedious and annoying process. At a certain point, you just get sick of yourself for procrastinating and ignoring important tasks, and you just have to sit down at your desk and ask the important question,
What are you afraid of?
You just have to bring yourself to the desk and brute force ask yourself this important question. No one else is going to ask it for you.
I had many many potato days (sorry to everyone who I had to reschedule meetings with), but what I noticed is that those potato days always end with some sort of task that I start doing out of brute force. And why does it work? I think it’s because oftentimes my answer is in my head.
What am I afraid of? Not writing a good enough LinkedIn post. Not being interesting enough for the interviewee. Not having good enough questions to entertain the person. Failure. Rejection. Judgement.
These are things that won’t be solved just by potato-ing around even more, like the great
said, you need to get the reps in. Sometimes you just gotta brute force it. AND it always always helps to perceive whatever failure comes your way as a step to becoming better (oh my goodness I am starting to sound like a bumper sticker but I hope this serves as a reminder to you too). For those of us who are recovering perfectionists, starting anything new can feel daunting, but just knowing that this is a step in the path anyways of becoming better, always helps easen that pressure.So just brute force it first! I am certainly brute-forcing this substack piece.
#3 You are a scarce resource, learn to say no.
Like I mentioned in #1, it was around the end of 2023 that I started to live the dream that I never knew I had, where I no longer needed to cold DM random people on Linkedin for friends and opportunities, and people who already knew who I am and what I do were actively seeking for my attention (I know I’m tooting my own horn here, but there’s a point).
But then I rang in the new year in 2024 feeling even more disillusioned and mentally exhausted. “Virtual coffees” no longer excited me, and just looking at the notification number on top of the LinkedIn app made my heart pound, in a bad way. I was accepting offers left and right to start projects, have chats, and help out in hustles. An hour-long period of not talking to anyone was a luxury, and it was very few and far between.
After escaping for a few days in the countryside of Taiwan (as you can read here), I realized that those hour-long (or more) periods of not talking to anyone were just as deliberate of a choice as choosing to have a virtual coffee with someone. Blanks in our calendar are not abysses of nothingness but necessary windows of recharge and filling up your cup.
A “no” to someone is a “yes” to yourself.
It’s a discussion of a forgotten opportunity cost that comes with taking too many opportunities. Perhaps taking on too many shifts for the restaurant job means more opportunities to earn $$, but the cost is less time spent with family during dinnertime. Or perhaps helping friends with their side hustles means getting an opportunity to help grow something that you care about, but the cost is less time spent working on your self-growth.
It’s a concept that I realized I learned when training for running, but rest days are part of the training plan too. And if you don’t properly take the rest days, you become more prone to injuries and burnout.
Seeing yourself as a scarce resource and protecting the amount of yesses you give out to people is crucial. A simple “no” is so underrated, and we gotta learn how to be better at saying it.
#4 When in doubt, journal.
This one’s simple. When gap year is all about discovering your childlike curiosity and keeping an open mind to everything that comes your way, taking the time to SLOW DOWN has been monumental in keeping my enthusiasm going while staying intentional. There’s probably some magic in the delay your penmanship or typing has compared to your brain that slows down thought processes. I know good friends (and incredible writers)
and swear by it too.#5 Give give give.
This year was the year that I learned the power of just giving. And it’s come in many forms. I’ll share three.
First is through LinkedIn cold DMing. Out of all the methods that I tried and tested, the most effective way to get someone completely out of your reach on linkedin to respond to your message and land you a virtual coffee is the following:
Follow their LinkedIn content
Engage by liking and commenting (but comment meaningfully by 1. Showing interest, and 2. Offering your own two cents)
Repeat
Direct message them
Why does this work? Linkedin cold DMing and asking straight up for a coffee or chat is a very high hurdle to pass because from the get-go, you are asking them to give you something. And why on earth would you give a 10 dollar bill to a random person who approached you on the street?
Instead, by engaging and commenting, you spark that connection by giving them something first. Offer support and encouragement to show that you actually care, and then they’ll be more willing to talk to you, perhaps because you’ve piqued their interest or because they now feel indebted to you.
This is a method that I unintentionally started doing, but good friend Lily explained to me why this worked on her!! Thanks Lily!
Second is through my friends, in particular, Natasha, Tahreem, and Jay. If these three individuals ever came together to start something of their own, they could conquer the world. Growing up in Japanese environments where everything is meant to be kept private, it was so foreign and refreshing to me how these three would ALWAYS be willing to share their resources with me.
Natasha, the minute I voiced a desire to purchase property she showed me her full-fledged excel sheet on how she calculated her property mortgages and value.
Tahreem, whenever I said I was feeling a lack of some kind of information or instruction, she would whatsapp me a bunch of pdfs or links that she found helpful.
Jay, everywhere I go, he’s introducing me to his powerful friends and network that are somehow related to what I’m brewing.
These three friends are mavericks and connectors in their own ways, and I rarely do find people who speak poorly of them. And their common thread? They never gatekeep. Always so willing to help, share, and teach, I have a feeling that this is what makes people attracted to them. I can see with my own eyes that this trait of theirs has served them well, grown their networks, and brought them opportunities.
I’ve learned to adopt this in my philosophy too, and I try to be as open and generous with my resources, and if I can’t do it myself (like mentioned in advice #3), I will connect them to someone else who can help. The point is, generosity usually has a compound positive effect.
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Phew this piece turned out to be way way longer than expected but I hope that it resonates with some of y’all. The gap year has brought me a whole lot more clarity to how I feel about myself and who I want to be, and if time and money permits, I would prescribe all adults to a gap year of trying things out. No one is going to make that decision other than yourself!!
See ya next week!!