How to tell your Asian parents anything in 3 simple steps (and in my case, that you’re quitting your Fortune 50 corporate job)

My dad came to America with $500 & a suitcase, and he lost $200 of it when he left his suitcase unattended on a Greyhound bus. And somehow, he managed to raise 3 daughters in suburban Long Island, NY, sending us to weekly music lessons and paying for three expensive colleges. #OGhustle #financialaid

Suffice it to say, financial stability & security are really important to him. So I knew, when I wanted to leave my cushy, stable, high-prestige job at a Fortune 50 company a few years ago, I’d need to prepare my dad.*

This is how to prepare your Asian parent for any major life change or decision you’re making, in three easy steps.

Step 1: Plant the seed AKA “Speak your reality”| 6–9 months ahead

Call them and instead of saying that everything is fine, explain how you’re regularly sleeping 4–5 hours a night, having terrible migraines that only resolve when you throw up (or when you finally sleep), and that you feel like you’re climbing a ladder that you didn’t mean to get on.

Just kidding, I didn’t do this. (I come from a conflict-avoidant family and culture where admitting you’re struggling is frowned upon)

I maybe admitted I wasn’t sleeping enough and that I was feeling a little bit stressed.

The key, however, is to express that you aren’t happy** and/or that you’re not doing well — however much you are able — before you actually make a change.

The good news is that you can do this today, even before you know what change you’re going to make. This can be scary. And it’s the first step.

Step 2: Water the seed AKA “The Gentle Warning” | 6 months ahead

Call your parents, likely out of the blue for them, and give them this gentle warning:

“Dad, I want you to know that I’ve been thinking about things and next year, I’m planning on leaving my job.” (or whatever is your big decision)

When your parent immediately barks, “No!”, don’t take it personally or argue your case. This is purely step 2: The Gentle Warning. Simply hear his or her “no”, listen to the reasons, and then change the subject.

And when they immediately text you after you hang up, “Work for FLAAG. (Facebook, LinkedIn, Apple, Amazon, Google)”, just laugh. Who comes up with these acronyms?!

Again, do not take it personally or hold it against him: remind yourself that they probably learned “FLAAG” from some website that Asian parents read, practice gratitude that they’re keeping themselves mentally sharp, and that they have your best interests at heart.

Step 3: Fertilize the seed AKA “In-person Reinforcement” | 3 months ahead

When you see them for a major holiday, like Thanksgiving or Christmas, wait until you have a moment with just them, like a quiet breakfast the day after or a drive in the car. (DO NOT BRING THIS UP DURING THE FAMILY DINNER #pastexperience).

“Dad, remember how I told you a few months ago that I was going to leave my job next year?

I’m still planning on doing that. I might change my mind, but I’m still planning on doing it.”

FULL STOP. You don’t need to explain or defend; this is simply the same Gentle Warning, but done in-person so that they can see that you’re serious. And you can add the qualifier that you might change your mind because — you might! But again, you don’t have to argue or defend your case.

Obviously, if they ask why, this is the moment to be vulnerable and explain that you think there’s more to life than this specific job or company, that while you’re thriving professionally, you’re struggling internally, and that you’d like to see what else is out there.

Don’t expect them to affirm this or even get it — if they do, awesome! But it’s enough that you’ve said it.

And that’s the key: You deliver the same message, gently and thoughtfully, over a period of time both verbally and in-person, so that your parent understands (1) you’ve given this thought, (2), you’re serious about it, and (3) they have time to get adjusted to this.

(Optional) Step 4: Get over your own fears about leaving | 1 month to 3+ years

This is next week’s article, but the key is that there are two parallel processes: (A) preparing your parents and (B) preparing yourself, and that step B will happen right up til the month before you make your decision.

Preparing myself to leave took 3 years, applying to 2 Master’s programs (and leaving one, another story for another day), and even after you’ve decided you’re going to leave, the last month will STILL present fears.

One month before I resigned, I spoke with my dad again, to deliver the same message, and here was his response:

“Y’know Tiffany, I still wish you’d stay at <company name> but you’ve made good decisions to this point —

And I (pause) HOPE (pause again) that this (pause) is also a good choice for you.”

It wasn’t the most glowing affirmation I’ve ever gotten, but I took it for what it was: acceptance.

(Optional) Step 5: Actually Resign.

Congrats! It’s not easy.

So what did I do next? I got a Masters in Management at Stanford Graduate School of Business, one of the best experiences and decisions in my life.

Was my dad thrilled? HELL TO THE YES.

Did I know this was going to happen when I first warned him 9 months earlier? No. In fact, I didn’t even know this at the 1 month mark before resigning.

The point isn’t to know the destination — it’s to bring your parents along with you on the journey.

Try these 3 steps with other major life decisions and let me know how it goes! You can reach me at hello@tiffanyteng.com

Disclaimers/Notes

• * I remember my friends who came from individualist family cultures asking why my parents’ approval mattered and why I even needed to prepare them. This is a whole other essay, but suffice it to say that in collectivist cultures, your individual decisions reflect on the collective and as the youngest of three daughters and still unmarried, my dad still sees me as his responsibility.
• **unhappy : If you’re just starting to feel “unhappy” at work/in life, ask yourself if there are things in your control that can make your job/life better. Do those things. And see if you’re still unhappy. I was.
• All of these conversations would’ve been easier (maybe) if I’d know what I was doing next or had another job lined up.
• This isn’t going to work for every parent. Some of you have parents whose identity is deeply tied up in your success or who subconsciously want to influence your life decisions. Get support from your friends, siblings or from a therapist.