Three Questions I Needed to Answer After Deciding to Quit My Fortune 50 Corporate Job

Tiffany Teng
6 min readJan 3, 2022

In Fall 2017, I’d finally decided I was going to leave my stable, secure & comfortable job at a Fortune 50 corporation — without a plan for what next.

I’d been feeling this way for several years (even with interesting, career-growing projects throughout!), feeling a desire for more autonomy, faster decision-making, and greater impact aligned with my values. I’d even picked a date! (Which happened to fall after bonus season — I am a pragmatist.)

However, I didn’t expect the deep fears that came up with the idea of leaving and the internal questions I would still need to answer AFTER deciding I was ready to leave.

Here were the three personal questions I needed to answer before I could leave.

Question #1: What if I ended up poor? And homeless?

As the daughter of two immigrants who still count their pennies to this day — diluting dish soap (!!) to make it last, washing and reusing single-use plastic utensils — I’ve grown up with a deep aversion to being poor.

(It probably didn’t help that growing up, my mom would regularly say things like, “See that homeless person? If you don’t work hard, you’re going to be that homeless person and I won’t take care of you.”)

Despite years of financial stability, when it came time to quit my job, that deeply ingrained fear from childhood came roaring back. I’d feel my stomach clench, and rational thoughts fled.

I struggled with this for a few days until I finally sat down and calculated exactly how many months I’d have before I ran out of money and couldn’t pay for housing. (Many thanks to my best friend, Liz, who actually sat down with me because it was too scary to do it on my own!)

Suffice it to say, I did have a runway. But I needed to know my present reality so that fear of the unknown didn’t keep me from moving forward.

Question for the reader: What are the irrational fears holding you back? Where have you heard this fear expressed before? Your fears may stem from learned lessons in childhood.

What information do you need to anchor yourself in reality? More data can help defuse irrational fears.

I’m going to caveat this right now: If you don’t have an emergency fund (ie: enough saved for at least 6 months of expenses), don’t quit your day job. THE FEAR IS THEN RATIONAL, NOT IRRATIONAL. Start saving. And if you can’t save, you need to focus on that first.

Question #2: What if I wasn’t ever this successful again?

I’d recently been promoted to Executive Director, which was a major accomplishment and recognition of the many hours and effort I was putting in. It came with a pay raise and more benefits. When it came time to leave this behind, the thought hurt!

What if I wasn’t ever this successful again, in terms of compensation, title, prestige, impact, or network?

I forget who specifically asked me this, but I was fortunate to have multiple people in my life who asked me:

“How do you define success? What does it mean for you to be successful?”

And my answers ranged the gamut from “Able to pay for food and a roof over my head” to “That AND the ability to take at least one fabulous vacation each year” to really values-driven answers like, “I’d like my life and leadership to leave the world measurably better, especially for women & girls.”

While it was helpful to re-examine my definition of success, the deep fear underlying my question was: What if I became a failure after leaving?

The most helpful antidote to being afraid of future failure is the concept of “growth mindset” — which says that failure is part of the journey. Reading Carol Dweck’s book and research was incredibly helpful for reframing failure as a necessary part of growth! And again, a lot of this came from internalized thoughts about failure and success from childhood.

Question for the reader: Where do you fall on the continuum from fearing failure to embracing failure as part of the learning journey? What did your parents teach you about failure and making mistakes?

Here’s the question I’d ask myself now: “How would my truest self define success, both now and at the end of my life?”

Question #3: What if I regretted leaving?

So, on Jan 15th, 2018, I was closer — but still not convinced — that I would be able to quit.

Some combination of FOMO and a deep fear of regretting this decision (and a lack of planning) meant I was still waffling.

The turning point came during a conversation with a friend:

Backstory: Linda is the lead singer of a rock band and is walking the walk. She’s creating in the evenings while using her day job to keep the lights on. Check out her music here!

I was telling her about waffling and she told me her story, which I’m going to share with you with her permission:

“Tiffany, when I was 32, I was the editor of an award-winning weekly journal.

I’d made it. But I was also this girl who would play her guitar in her room, with a secret dream of being the lead singer of a rock band.

I wasn’t confident that I would be successful, but I was confident that if I stayed and didn’t try pursuing it, I would regret it.”

And as she said that, the final piece for me clicked into place.

I’d been asking myself if I was confident that whatever I did next would be successful — and I wasn’t feeling confident! I honestly couldn’t reassure myself that success would be guaranteed! (Which is rational — neither is health nor security, etc.)

But I could be confident that I would regret it if I stayed and didn’t try for what I hoped for.

Pro-tip: There is power in hearing other people’s stories, especially when they’ve taken courageous steps to live life more fully, even at personal cost.

If you’re feeling stuck, ask people, “What was the most courageous decision you’ve made? How did you get there?”

So what happened?

I didn’t actually leave my job until May 2018. As part of my decision to leave that job, I’d applied to graduate school and got into the Stanford Graduate School of Business, receiving my Masters in Management, and had one of the best years of my life.

After that, I took yet another leap and moved to London for two years, building a new community of friends and gaining an international perspective on my American life. I’m now back in the Bay Area, working at a fintech startup, where I get to experience the risk and reward that comes with greater autonomy & faster decision-making.

I want to acknowledge the privilege that I have — I had an emergency fund, marketable skills, past success to build upon, and a network of supportive friends and family. Maybe the next step for you isn’t leaving but preparing to leave — what are the new skills or resources you can start building now so that you can in the future?

A final thought

One of my favorite poets, Mary Oliver, has a line that haunts me and impels whenever I get afraid and want to stick with the status quo:

“Tell me, what is it you plan to do / with your one wild and precious life?

If you don’t know what you want to do with your life, next week’s article is about my own process and journey to find what matters to me. Subscribe on Medium to follow along!

Life is short. I hope you find the courage and conviction to leave the familiar for the wide, wonderful wilderness.



Tiffany Teng

Former East Coast, now West Coast. Lover of books, baking and all things beautiful. Writing & reading about identity, growth, and leadership. Stanford ’07, ‘19.