About a year and a half ago, I emailed my parents (who are first-generation Korean Americans) announcing that I’d decided to leave my PM job at Microsoft. Without very concrete skills, and without another job lined up.

I had tried my best to think rationally about my situation, and I concluded that opportunity costs of staying at a job where I didn’t feel I was learning the right things were too high. Of course, if I were being purely rational, I could have waited until securing another job or getting funding for my own company/project, but I felt the urgent need to test myself and create an identity around taking calculated risks, to convince myself that I was not afraid.

The truth is, I had been hoping to leave a lot earlier, but due to family and financial circumstances I didn’t feel that I could afford to. After biding my time for several months, and spending all of my spare time learning web development, I felt I had earned the right to put myself first and invest in my personal development and my career.

Initially, my parents were concerned and not convinced that it was a good idea. Over months of phone calls, though, they came to understand why this was important to me (even as they tried to talk me out of it on several occasions). When the time came, I harbored doubts myself about whether this was the right move, but I needed to quiet those fears and make the final sell to my parents.

The approach I used was to anticipate my parents’ fears and to address each one separately to show I’d thought through the decision and had a concrete plan for problems that might arise.

Here’s the email, lightly edited to remove some overly arrogant parts (like a male bird puffing its chest during mating season, I was trying my hardest to convince them that I was competent, heh) and to remove specific names.

If you find it helpful, please feel free to recycle and customize it to break the news to your own parents.

Email to my parents about quitting my job

Hi Mom and Dad,

I’m resigning from my job today (at my 1:1 with my manager at 1pm, in fact). I’ll stay on until the end of the month.

I haven’t heard back from Khan Academy yet [NOTE: I had only just done my first interview/phone screen and hadn’t heard back], but I’m hard at work writing a blog post explaining how to code an exercise for their website. This might help my chances. Either way, I’m not afraid of being jobless for two reasons:

1. I can learn more, faster

I am really looking forward to having a few months off to engage in some really focused, fast-paced learning. Having the full-time job slows down this process at least 3-fold [NOTE: Yes, this is a completely made-up statistic], due to limited attention and motivation resources during the day. I will be learning how to build a product from the beginning to the end, and to get real users. I will keep building relationships with people in the startup community who can help me reach my goals. I might even try to start raising money for a startup.

This is invaluable education. Think of this time off as an investment, similar to how you pay to go to medical, law, and business school expecting that you will make more money to recoup the losses afterward. Only, I won’t be paying tuition. Living expenses will be my real-world tuition, which is a pretty fair discount. I believe my value coming out of this period will be much higher than going in, and the skills I learn will be attractive to big companies and small companies alike.

2. I can find another job

Following point 1, I’m a pretty competent person and think can find another job without too much trouble. I spoke with my coworker and friend X, who is super sweet, about my plans to move on. She said to me (and exclaimed that she is explicitly not trying to flatter me) that I am one of the most exceptional people she’s encountered at Microsoft and that I am really mature and operate like a person at the Principal PM level or higher. She has worked with interns from top schools, and she felt that they weren’t as effective.

This was a huge ego boost and a real surprise for me, because I feel that I haven’t been performing at my best (except for doing a few things lately). She also said that big corporations will drain the passion out of motivated, passionate people, and so she supports me in my decision to pursue my real passion. Finally, she said she is pretty sure that if things don’t work out, I will have no trouble getting back into another big company.

Of course, I should acknowledge that there are some risks:

1. Running out of money / It may be harder to find a job than I thought

This is possible. However, I am almost certain that part-time or contract work (e.g., making basic websites for non-technical companies like restaurants) won’t be too hard to find. I can easily build a website for a company, and I have other skills that I can pitch to companies when I diagnose a pain point for them. Finding a lower-tier job will almost certainly be no problem.

In terms of finances, I have about $13k or so in savings (I put $12k in my Fidelity 401(k) and $5k in a Roth IRA last year). I estimate my run-rate at about $2k a month, including food, gas, miscellaneous expenses. So ~5 months of run-way.

2. Being unemployed when many of my close friends all work for big companies could be psychologically difficult when things are hard.

I’m trying to surround myself with like-minded startup people in similar situations. I have already taken good steps towards this by following up with a friend, Y, who I met at a startup event. She was also a PM at Microsoft and has been really helpful in introducing me to startup people in the area.

3. Physical health & health insurance

I’m using all the medical benefits I can to take care of any existing conditions before I leave. After that, I will need to use your health insurance, Mom. Thank you for supporting me this way.

4. Emotional and mental health

I’m taking weekly free meditation classes at a local Buddhist temple with my good friend Z. They are very helpful. Socially, I will be scheduling time with friends so that I interact with people every day. I have realized that good one-on-one face time with friends is really important to my well-being. Finally, I am looking into resuming therapy because it’s more targeted to me than meditation and can help me overcome personal disappointments. This is an investment in my long-term stability and strength, which I will need as a successful startup founder.

On the whole, I’ve thought this through for a long time (past 5 months, practically), and feel confident with my decision. I’m very excited about being freed to learn things that are really going to help me propel my career.

Thanks and love you, Stephanie


Not everyone has the luxury of quitting their job, and quitting your job can sometimes be a red herring, when putting in more hours of hard work is the more critical issue at hand. In my case, I did have that luxury, though, so I needed to make myself aware of it and make the best decision given that option. My justification for quitting was to buy myself time and energy to do deliberate practice on the coding skills I needed for my next pursuit. I was behind and needed all the time I could get. After quitting I found that my assumptions held - I was more productive and learned much more and faster with the time I had bought myself.

Also, Microsoft is not a bad place to work. I feel fortunate to have worked with some really stellar people there, but ultimately it wasn’t a great fit for me culture-wise. I craved a level of ownership that wasn’t accessible to a junior PM at a 100,000-person behemoth of a company.

Finally, I’m lucky that my parents are reasonable and (for the most part) trust me to make good decisions/tolerate my strongheaded-ness. Unfortunately, not all parents are as understanding and convince-able.