You might be reading this because you know your parents want what’s best for you, but why does “what’s best for you” feel so wrong?

Most parents want you to choose the safer path. Some parents believe in it so much, they’ll imply there’s no other way…and to even consider otherwise would be a mistake. I didn’t really understand why, until I read this in one of Paul Graham’s essays:

All parents tend to be more conservative for their kids than they would for themselves, simply because, as parents, they share risks more than rewards. If your eight year old son decides to climb a tall tree, or your teenage daughter decides to date the local bad boy, you won’t get a share in the excitement, but if your son falls, or your daughter gets pregnant, you’ll have to deal with the consequences.

Paul Graham, How to Do What You Love

Once I read that, I was like, Oooooooooooohh. This is why I will never be able to convince them, and why they’re on a life-long campaign to ensure I’ll have a pension. To be fair, they were refugees who landed in America with nothing. They don’t want that to happen to me. I get it.

But it’s one thing to be empathetic, and another to let their views dictate what you do.

“Should I?” needs to be answered by you, and only you. Part of raising a child requires instilling family values, but as you grow into adulthood, your parents must respect the fact that you will ultimately create values for yourself.

The second part (“my parents keep telling me to”) comes from a fear of being wrong. It could come from your fear of failing or your fear of ignoring the wisdom of parents you respect, or it could come from your parents’ fear of you failing, projected onto you—their hearts unable to handle seeing you struggle.

Regardless, if you what to pursue what you love, you must do it on your own.

Managing your parents’ feelings is not your job, but if you are burdened by their opinion, these techniques may worth a shot. You can give them assurance that you are independent (i.e., won’t crash on their couch and eat their food to “do you what you love”), and proof of success (any results from side hustles, or stats on the industry based on your job search).

Or, if this is an option for you, you can keep all pursuits private until you’ve “made it.” Then their hearts are unburdened by worry (again, not your job, but if this is easier for you I’m all for it) and if you fail, they’ll never know the difference.

You may not want to keep them in the dark, but if you’re hoping for their approval, you may never receive it.

Whose approval do you want: theirs or yours? In the long run, I hope you choose you.

With love,
Mariam

At the height of my indecision, I asked this question nearly every day. If you’re analytical like me, you want a pros and cons chart, or ideally, an equation that takes all the variables and spits out an answer you can get behind. With all the responsibilities I had outside of work, on really trying days, I would take the day off, excel my finances, and put my thoughts on paper. It didn’t spit out an answer, but it helped me get out of my head. One day, I knew it was time; with the support of my significant other, I filed my resignation and quit. Two weeks later, I clocked into my home office and got to work — on myself.

Should you quit your job or stay? Instead of asking should, let’s ask, when?

1. Do you have a job lined up? If you don’t have a job lined up, this post is for you. If you do and aren’t sure when to quit, that’s advice for another day. If you have a side hustle ramping up and are debating the jump, you’re ahead of the game. I can’t help you there. You go girl. Or boy. 
2. Do you have the financial resources to last until your next job? Let’s be real, we need to eat. According to Maslow’s Hierarchy of Needs, we need to take care of the basics: water, food, shelter, etc. If you’re not willing to lower your standards just yet, take the time to do some math. How long can you last? What’s the chances you can land another job or build your own empire to bring in that cash flow within that time?
3. If not, are you willing to work a less stressful/less lucrative job in the meantime to keep yourself afloat? Sometimes that FU money isn’t there yet, but your mental state is at stake. What’s a job you can tolerate to make up the difference? Money coming in and keep life more tolerable, since –believe me – the stress of watching your savings account sink can paralyze you from making your next move.
4. Now that we’ve gotten money out of the way, why do you want to quit? Is it because you’re bored? You’re tired of your coworkers? You hate your boss? You hate the work? You hate the commute? You work too much? You miss the camaraderie? No job is perfect, but obviously, some combination of the above (or more) is driving you away. Jot that all down and let’s tackle each one.
5. If the issue is your job, have you tried to change it? If you hate what you do, have you tried another role? Even if you can’t formally transfer (yet), could you pick up some other work from a different division or offer to do it? If you hate your boss or coworkers, have you tried to change teams? If you hate the commute, have you tried to work hybrid? You get what I’m saying. This can be tricky because you may not want to indicate you’re unhappy. Again, this goes back to that FU money (or a job lined up); if you’ve got nothing to lose, why not give your current place a chance? You may be surprised at what happens. Once, I left a job for another offer, though unfortunately, right after my manager proposed a tempting reassignment. At the time, I was impatient and chasing money ($$ for impending baby), but part of me wonders how different my life could’ve been if I stayed. I learned from this and exhausted all my options the next time, but this time, the problem was me. Which brings me to the next question…
6. If the issue is your expectations (be honest), have you tried to change them? Some of us can go to work, get paid, and not care about much else (work-wise). Quite frankly, I envy these people. My life would be sooo much easier if I could just compartmentalize work and get on with my day. (In Ronny Chieng’s words, make that money and BOUNCE.) But alas, I’m one of those people who finds identity in their job, so my expectations are, for better for worse, higher. My expectations over time have lowered though. Whereas starting out, I wanted camaraderie and peers to bond with (which is still important, I believe), now, if I can bond with just one other person, I’m good. I used to feel like I was successful if I left a job with one friend, but now, if I leave a job with no long-lasting friends, that’s ok too. (Maybe I’m just getting more anti-social. That’s possible too .)
7. If the issue is neither your job and your expectations, and you’ve set the bar as low as you can go…congratulations! We’ve arrived at the destination. It’s clear now. You should quit. You’re just not a good fit — your employer has tried, you’ve tried, it’s time to move on. The end.

But wait, Mariam! It’s not that simple. I hear you. Let’s talk about it; what’s holding you back?

I’m going to ruin my reputation. To who? Your coworkers? Your friends? Your family? Your future employers? As someone who’s quit a place two times under a year, I can tell you that life moves on. It may be rough in the beginning, but when you die, who’s really going to think, “She quit her job earlier than she should’ve so I don’t know about her.” If someone has the time to even think that, they’re not worth yours. (Ok, maybe your parents will think that, but you have to let that go.) If you’re worried about your future employers, you can explain your employment gap in a positive way. It’s all about perception and packaging.

I can tolerate it — I survived today so it can’t be that bad. Look, I’m all about that FU money, building the reserve to give you freedom. If you can truly tolerate your job, and watching your bank account grow gives you glee that outweighs your dissatisfaction, stay. However, there’s something to be said if the money isn’t doing it for you. Maybe you think it’s not that bad now because you’re not at work (or are you? ), but what about tomorrow? Do you wake up every day with dread? Do you get so stressed that when you come home, you don’t have energy for your loved ones? What kind of life do you want to live while you’re saving for your next move? Only you can answer that, but if you have the resources and risk tolerance (see: 2 & 3 above), consider what you would gain from quitting.

I’m scared of failing / of uncertainty / of not doing the “right” thing. And you have every right to be. Quitting can be scary. Getting that money will make you less scared of being out on the streets. Getting a game plan in place will make you less scared of wasting your time. If you have the money and you have a plan, are you afraid of feeling embarrassment or regret if it doesn’t work out? Please know, that trying is a journey worth living. What kind of person would you be if you didn’t try? Do you think the experience of trying is worth the confidence you gain to try again? It was for me. The first time I quit with nothing lined up, I was terrified. The second time, I knew I could do it again. It’s not important that you made it. It’s important that every day, you took one step closer to it. And quitting is that first step.

So…should you quit your job or stay? Rather, when should you quit your job or stay?

When you have the financial resources to do so, and you’ve tried changing everything you could at work (them) or changing your expectations (you), what’s left to do? You know it’s time. Go get ’em.

With anticipation,

Mariam Le

I started writing about quitting your job — seemed fitting, as I’d just quit mine — but it became longer than I thought it would be. Turns out, I have a lot to say. Give me a few more days, and it’ll be live soon. Can’t wait to share with you.

Stay tuned,

Mariam