What Is Enough? Tiffany Chen on Walking Away From the Dream Job

At 21, Tiffany Chen turned down a six figure Wall Street offer on the spot, with no plan for what came next. Six years later, deep inside a fast moving AI startup that looked perfect on paper, she found herself asking the same quiet question: what are we all actually doing here?

In this Soul Sessions, Tiffany walks Damon through two leaps of faith that shaped her life and the inner compass that made both possible. They get into the golden handcuffs that keep high performers stuck, the immigrant household where security came first, the role her Christian faith plays as a compass, and the ten year journaling practice she uses to check in with herself every six months.

This is a conversation about the difference between climbing a ladder and choosing your own direction, and about answering the one question most people in privileged positions never stop to ask: how much is enough?

No bow on the end. Just an honest look at what it costs to bet on yourself.

Transcript

SPEAKER_00 0:03

Alright, well, we're back again with another soul session. I'm excited about this um episode, and I'll turn it over to our guests to just introduce herself. Um, I'd love for you to share with the folks who is Tiffany.

SPEAKER_02 0:15

Thank you so much for having me on the show, Domin, and I'm excited to share a bit of my stories. My background is I am someone who has always been in very pressure cooker environments, but I'm fundamentally a very mission-driven uh per mission-driven person. I am deeply Christian and I have always spent my life striving for excellence, but wanting to stay grounded throughout that all. And so I would say that my journey um through Princeton, through working in startups and high-growth marketing environments is wanting to stay true to myself and true to my roots of giving back to community, giving back to the world around me.

SPEAKER_00 1:01

Uh thank you. I I didn't the the Christian part kind of for good or for bad, like it's interesting that we we talk about this. I did not know that. Um I don't know how much you know about my background, too. I almost was a pastor at one point. Um but I'm sure somewhere along in our stories we'll talk about how does being Christian be in I was thinking about this verse of like listener of the meek, and like how does that work in a high growth capitalist society? Um so is there a lot of high there?

SPEAKER_02 1:38

I didn't know. Yeah, that's super cool.

SPEAKER_00 1:42

Yeah, I I had one of the things I wrestled with while working in tech in San Francisco was like being deeply Christian and feeling like a part of my mission was to um share the gospel, and what does that look like to share the gospel and my faith? Um, or a lot of the people I work with were going for bike rides on a Sunday morning while I was trying to go to church and was just trying to wrap our head around like it's just so different, and what does that mean to stay true? And yeah, I I'd be curious as well, like, how did you hold on to that faith in college? This is also just not on the script, but just yeah.

SPEAKER_02 2:19

Um in college and in San Francisco, it's definitely been a challenge, and I would say it's been I would say that my Christian faith is what has helped me keep my compass strong over the years and not just doing what everyone accepts to be the cool or prestigious or right thing to be doing uh with my life and my time and my resources. I think in college it was very much difficult to prioritize faith when um there's a lot of things calling for your attention being a student athlete at Princeton, you just don't have that much time, but it's counterproductive to think that setting aside time for something that doesn't feel like it's actively moving you forward in whatever your goals are, but renews your soul and renews your spirit can actually help you so much more in living a meaningful life, which is what we're all trying to do at the end of the day, um, rather than always progressing toward goals.

SPEAKER_00 3:29

Yeah, I love that, and it's um I'm sure we'll be able to tie it back because this makes so much more sense now of um how you've been able to do some of the things that you were doing. Uh, one of the first stories that we want to talk about is the first transition you were thinking about coming out of college. I'd love for you to share a little bit about that.

SPEAKER_02 3:50

So I studied economics, did all the right things, applied to the right internships, and ended up working for a bank on Wall Street one summer. And that was a particularly challenging time because I it was on paper everything I could have wanted, and any it was everything that anyone in my shoes could have wanted. Studying economics, you always want to go and work for a big bank and then have that return offer post-grad and not have to worry about it and have your path set. Um, but the reality was when I worked that internship over the summer, it was miserable. Um, I spent 12 hours a day in a windowless room. I the happiest part of my day was when I could go get coffee for the associates because I could actually leave and breathe air and walk around. And I felt very much like a cog in a machine as well. And when I got the return offer, the big question was: do I take it? And I have such privilege to be able to have this kind of opportunity and not worry about what I'm doing after grad. But on the other hand, it just felt very um, it did not feel true to myself and the kind of work that I wanted to be doing for a long time. And I've always been in pursuit of work that feels genuine and meaningful to me, and that's because work is what you will spend the majority of your waking hours doing, it's not just a way of providing sustenance for you and your family, but it's also that kind of impact you have on this world. And so I weighed these kinds of questions, and I realized that even though I felt like there was a lot of sunk cost of okay, I studied this major, I acquired these kinds of experiences and skill sets for this world of finance, it wasn't quite what I wanted, and I knew that choosing to continue down this path would be choosing someone else's dream and choosing what other people think is good when deep down I know it's not what I want.

SPEAKER_00 6:04

Yeah. Before we go on, were there people looking at you weird? Um, how did your parents take this?

SPEAKER_02 6:14

Yeah. So I am I come from a Chinese immigrant household where security is number one. And I obviously worked very hard to get into Princeton, which is emblematic of security, right? And so they very much wanted me to choose a career path that would provide as much stability as possible. So it was very hard for me to explain why I would turn down this very candidly lucrative uh position in pursuit of a very vague unknown mission to do work that I really enjoy.

SPEAKER_00 7:01

And the the part of I'm I'm there's there's you you talk about wrestling with this question of being mission driven, you talk about you know there is a safe path. And I'd imagine you were what 20, 21? Even younger.

SPEAKER_02 7:22

2020, yeah.

SPEAKER_00 7:24

Yeah, how how does someone at that age have the just the boldness to say I'm in tune? Because I'd I'd imagine my myself, I thought I was like being true to myself, but looking back, I was like nowhere close. Like, how does someone get there at that age?

SPEAKER_02 7:43

I think it's I think my career journey has been a process of elimination, and I think it's very hard when you look at a sea of options and you're like, I have to find one path that's amazing. The odds of that happening are very low when it's infinite options. The reality is you actually just try different paths, and you have to be very honest with yourself do I really like this? Can I see myself doing this for the next not just like a couple of years, but next 10, 15, 40 years? And I think I have gradually landed where I am by elimination of trying something for a little bit, or even talking to people, learning about their path, deciding like, does that sound like something that feels in my wheelhouse and something I would that wouldn't even feel like work or something that I would be excited to do every day? Because the last thing I wanted was to have Sunday scaries and dread going to work on Monday. I was like, I have a lot of Mondays ahead of me for the rest of my life, and part of it is betting on yourself as well that you can find that because I think a lot of people just are afraid to dream big enough that they can't find that, and so they don't even let themselves try. And I think that that is also what holds a lot of people back is not even allowing themselves the dreams of is there more? Like, can I can I have more? Do I deserve more?

unknown 9:13

Yeah.

SPEAKER_00 9:14

That's I love that. And so I'd imagine set it up for me. You got this offer letter. Um, I'd imagine there was an email back to the I'd manage the recruiter ton know, and then walk me through that day, and then what what next?

SPEAKER_02 9:32

So I actually went into this beautiful corner office. So the entire internship was in this windowless floor, and uh when we actually got the offers, it was in obviously the managing director's conference room, and it's quite the cell, and it's like this could be your life ahead of you. Um I actually think I might have turned it down on the spot. I think either I turned it down on the spot or they could tell from the way that I was not excited when they said I had it that I was not going to accept it. Um and that was truly a leap of faith because I wasn't sure what I wanted to do next.

SPEAKER_00 10:13

Um do you remember how much? I don't know if you can share what that salary was.

SPEAKER_02 10:20

It was it was probably around 100k um for a college student in your life who has never made money, right? And you're like, wow, that is so yeah, that's yeah, very exciting. And I'm like, I'm turning this down for I don't even know what I'm going to be doing differently. Um and for that it was knowing that I absolutely did not want to be doing this type of work, nor living this type of lifestyle, um combined with a lot of reflection about what is it that I dislike the most in some ways. Again, going back to the process of elimination, and why do I feel why did I feel so at odds with this type of work? And for me, that came back to I wanted to feel like the work that I was doing had very direct impact on the company. Um, and so that's also why when I looked back on the bank life, I didn't want to just go and work for a big tech company, honestly. Um, and just go like work for Google, for example, with no shade to Google. I love the company, I have a lot of friends who work there, but um, I think in my head, the math I was doing was okay, I just don't really want to work at a big company, to be honest. I like I want to feel like me showing up every day being there makes a big difference on how we're doing as a company, and that was what the that was the conclusion that eventually brought me to the world of startups because I was like, I want to be able to have an idea that will create impact and just just be able to run with it with no red tape and have impact in that way.

SPEAKER_00 12:07

Yeah. One of the things I often think about is decisions like that, um, they don't happen a lot, but they do build a muscle of the more you flow into like this feels aligned with me, the easier it is to choose yourself moving forward. Um, looking back on that, um I'm curious, like, how would you say that you've continually built that muscle, or how did that decision help to shape um follow decisions in the future?

SPEAKER_02 12:36

So I would say that that decision confidence is built from repeatedly doing things and seeing small success from it. And I would say that I have what looks like possibly unfounded confidence sometimes in taking leaps of faith, and I think it it probably stems back to doing things like that um way back when I was 19, 20 years old, where I just knew something wasn't for me and I trusted my gut. And as I take progressively larger risks, or um yeah, as I take progressively larger swings, it really comes back to how much do I trust myself and how much do I trust my gut to lead me in the right place? And I can look back at this history of times when I feel like I made the right choice, and it was um and it paid off in the end, and it led me to um new opportunities that I wouldn't have dreamed of. And so I because I was able to say no to this world of finance and dream a little bigger, I ended up in the world of startups, which was for many years like the best place I could have asked for in my career, and to be able to learn from incredibly smart people, to learn how businesses operate, um, to be immersed in the high-tech world during the rise of AI, like all these opportunities were because I was willing to trust that my gut was leading me in a direction. So, yeah.

SPEAKER_00 14:15

We're six years past that decision, and you recently made you know another major decision. Walk me through that.

SPEAKER_02 14:24

Yeah, so for the last five and a half years, I had been working in startups in Silicon Valley, working in marketing for very high-growth startups, and it was again on paper, everything I could have asked for. The internship story is relevant because my time from startups is very similar in how perfect on paper everything was, but deep down I knew it wasn't quite the right direction I wanted to go in. So when I was in college, working in finance was a very stable and prestigious path to be following, and I knew it wasn't for me. In the past year, I have had the privilege of a dream job working very closely with AI in a super fast-moving, high-growth startup, and I had mentors and peers all telling me, what an incredible opportunity! Like you were so lucky to be here. But deep down I couldn't help but feel like this was not the path that I am meant to take for the next 40 years. Um, granted, some people might work in startups because they want to just hit jackpot with equity one time and then retire into the Bahamas and then figure out what's next. Um, but I've always taken a very long-term view on okay, work is for the rest of my life, it's impact. I'm not just trying to retire. And when I was looking at my life and how much I had worked hard and gotten to where I had been, gotten to where I was after six years, it wasn't quite what I wanted. And I realized it was someone else's dream once again. And to be working in this AI world was such a glamorous place, but it felt at odds with the kind of impact that I want to have on the world, so that became a question of what is the kind of impact I want to have. Um and I think this goes back to living in a place like San Francisco where there's a lot of it's it's a bubble where everything is very focused on tech all the time and focused on innovation and moving faster, and um AI is eating the world, etc. But yeah, I felt this. I I felt I had these moments where I would look up and think, what are we all doing here, guys? Um and I I thought that I was the crazy one, but I realized I just couldn't do this for the next 40 years of my life, even though I knew working in AI during this period of time would set me up for an incredible career in marketing for tech companies, and I could keep climbing this ladder that I didn't even know I was climbing. Um, or I could stop and ask myself, like, is this the dream that I want?

SPEAKER_00 17:47

You talk about it being a dream job. Give me some examples of like how you know, it was it the pay, the people, the happy hours, the free food, like describe the dream job to me.

SPEAKER_02 18:02

Yeah, it was a dream job of for many reasons. It was the people I worked with were very smart and moved very quickly and were very well respected in the community. So on that front, it was a great environment. Um, on the other hand, the company was growing way faster than any other companies I've been at in the past. So at previous companies, I kept telling myself, oh, if I just had this, or if I just had that, or if the company was just doing better at this one thing, then I'll be happy. And so I think that I had finally found all of those things in a company, and I realized I still wasn't that happy. Um, and I was like, is this a me problem, or is there something fundamentally at odds with this type of work or this type of industry that I need to re-examine?

SPEAKER_00 19:03

Yeah, yeah. One of the things people talk about is the golden handcuff. I don't know if you've heard that term before. Um how have you thought about that as you were thinking this may not be for me?

SPEAKER_02 19:20

Oh. I mean, the handcuffs are very real coming out of a place like Princeton, living in a place like San Francisco. You hear of people with million-dollar packages left and right, especially right now during the AI bubble. So it's very hard to shake the mentality of handcuffs. I know that people with my background are going to be okay even in a terrible downturn of the economy. And I know that that is an immense privilege that allows me to be able to take risks. With that, I would say that 90%, probably 95% of my peers who have that same privilege feel the most stuck in stable paths and the most stuck with handcuffs. Um I think this is where the Christian faith comes back into play of not always giving into what society is telling you is good or desirable. And as of right now, the answer of how much money is enough money is always more. And I'm not influenced by what other people think is enough.

SPEAKER_00 21:39

Yeah, you use that term endless, it really is, because there's always going to be more, there's always gonna be a new startup, there's always gonna be something that's not right. Um one of the things as you were saying, and it comes to me this idea of you know, five and a half, six years ago, you made a decision. I'm sure it wasn't the first time you tapped into what felt right and made a decision, and I'm sure Over the last six years, you've made multiple decisions. Is there a practice? Because you also said, hey, for the next four years, I don't want to down on this path. Is there a practice that you do to constant constantly come back to self to check in to say, is this what Tiffany wants? Am I doing the thing that makes me come alive? And what does it look like?

SPEAKER_02 22:22

Yeah. I journal every single day, and I picked up that practice in college, and it started very simple with just writing down what I did that day. And on building that habit, it became let me write down what my thoughts are, or let me write down broader observations about life, and it's built into this habit of deep reflection on a recurring basis. And since journaling for the last 10 years, straight, I've developed this practice of asking myself every six months to step back and reflect on what is the state of my life and what what are my hopes for the future. And that kind of practice is what helps me stay grounded and pull out of the rat race of every single day because days can pass by so quickly if we let them, and it we can very quickly forget how far we've come or how much further we can go if we actually point our compass in the right direction. Um not point our compass if we actually follow our compass and make progress in the direction we want. So I would say that yeah, it is with this practice of constant reflection that I can again build that confidence looking back at times when I felt pretty uncertain or unhappy in the kinds of friends I had or the kinds of work I did, and being able to see the common threads there and draw the patterns and understand myself more deeply, and understand okay, knowing that this is how I felt in the past, how do I change my life and make decisions that will change that in the future?

SPEAKER_00 24:22

Yeah. As we come to a close, I'd love for you to describe. I don't know how much you can remember, whether it's your last day and the last gig, or um, the moment you decide, I'm gonna tell the folks that, like, alright, this is coming to an end. Like, as as vivid as you could, describe that moment or that day.

SPEAKER_02 24:54

I was very nervous to tell my team because they are great, they were are great people and they are building an excellent company. But I remember feeling so grateful because they were so supportive of me following my dreams, and they explicitly told me we would not be here today if we were not trying to follow our dreams and like discover what it is that we want to do with our lives. Um, because when I had told them I'm deciding to leave the company, I shared that it is in pursuit of what feels more aligned with what I want to do for the rest of my life, and I knew that following the trajectory that I was was extremely linear, and if I kept it up and let the momentum just roll from the five, six years of experience that I had, where I would end up down the line was not what I wanted, and so I knew I had to change the trajectory by not just one or two degrees, but by 45, 60 degrees, and end up in a completely different place. So when I shared that with them, um they were able to relate a lot, and I really appreciated that because um at the end of the day I joined startups because I wanted to join people who are excited to build on a mission and excited to build a different type of world, and they could really see that vision for me as well, and they knew that I was in pursuit of something like that as well. So yeah.

SPEAKER_00 26:36

Yeah, yeah. And then usually one of our ethos here at Soul Session is that we're we're wrestling with things that are not, we don't there's not a uh a bow on anything. Um we realize that life is messy and that there's a continuation and that we we love and enjoy the process. You're about six months out of that decision. Um I'd love to hear it. Doesn't have to be a full-on, I've made the right choice and figured it all out, but just like because I think there's a bunch of people out there um want to want so much assurance before they take the leap and choose themselves. So I'd love for you to share a little bit more about like where exactly are you in this journey of exploration. Um, and it doesn't need to have a bow or an end, it's just here's where I am, here's some of the things that I'm thinking about, um, any any of that.

SPEAKER_02 27:34

I would say that when you take the leap into the unknown, your biggest enemy is going to be your internal voice, and the more that you can learn to train that and notice when it's not serving you, the more dangerous you're gonna get. Um, and I would say that for myself, my first couple months were a lot of questions around criticizing myself and being like, why couldn't I have just been happy in that type of job? Or why can't I just like do a normal thing and live the American dream that my parents wanted and keep doing XYZ? And a lot of people will also have a lot of opinions when you are trying to forge your own path, and it's very easy for those opinions to infiltrate your inner voice and for you to repeat things to yourself even if you don't believe it, but it's all you've heard, and so when you are in these when you are in an unknown period of your life, making sure that you are constantly repeating back and reflecting thoughts that serve you and push you toward a future that you want, and recognizing when you are accidentally tearing yourself down or basically feeling a lot of insecurity or doubt, you have to just put those thoughts away. And I think it's a process that I'm learning every single day to be able to focus on what actually matters and not look back and not worry about what um the critical inner Tiffany is thinking.

SPEAKER_00 29:26

Alright, I think that's a great place to end it. Thank you so much, Tiffany. This has been a joy.