614 | Getting Personal with Personal Finance: Oz Chen

24 Aug 2026 · 1 h 3 min · 30 chapters

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Oz Chen’s journey to being financially independent (FI) and, more importantly, learning to be okay with FI psychologically—especially the fear of leaving a high-paying tech job and drawing down income.

Guest background

Oz, 37, studied economics, works in UX design (apps/websites). He’s an FI adherent introduced via Tim Ferriss and writes the newsletter Money for Humans.

Key claims

FI isn’t just math; it’s acceptance, inquiry, and experimentation. He crossed FI milestones years earlier but hedged due to fear of no paycheck and “golden handcuffs.” He used writing exercises to break down fears, then practiced acceptance by listing what he accepts (e.g., scarcity feelings, weirdness without a paycheck). He also defines “work” as directed autonomous effort with output (writing, creating music), not corporate meetings.

Notable examples

He planned a “quit if” list (micromanagement, loss of autonomy, manager/culture changes after an acquisition). He took FMLA in March 2026 (12 weeks) for burnout/anxiety, slept/rested, and by weeks 2–3 felt work thoughts fade. During the leave, he received a layoff notice and ended up with ~4 months not working (garden leave/severance). He’s now exploring community college classes and trade/arts interests (music, trades) while planning for kids in 2–3 years.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Exploring the Financial Independence Journey

1:15 to 1:49

Discussion about the concept of financial independence and its psychological aspects.

“Before we get started, I keep this podcast entirely ad-free for two reasons.”

Oz's Background and Education

1:49 to 2:04

Oz shares his educational background and entry into the UX design field.

“I'm really jazzed to be here and to be talking about this topic.”

Understanding Financial Independence

2:04 to 3:35

Oz explains his perspective on financial independence and its acceptance.

“And I studied economics in college and didn't use that for most of my career.”

The Transition from Employment to Financial Independence

3:35 to 4:34

Oz discusses the transition from a stable job to exploring financial independence.

“And it took me a long time to accept that, to deal with all the fears.”

Dealing with Job Layoffs and Financial Security

4:34 to 5:56

Oz recounts his experience with layoffs and grappling with financial security.

“I first was introduced to it through 4-Hour Workweek by Tim Ferriss.”

Preparing for Change in Career

5:56 to 7:11

Oz talks about recognizing the need for change in his professional life.

“So can you back us up a little bit about how you moved into this psychological space you're in now?”

The Emotional Impact of Job Satisfaction

7:11 to 8:17

Discussion on the emotional aspects of job satisfaction and its effect on decisions.

“And it was just like a blip on the paper, like on the screen rather.”

Creating a Personal Policy Statement

8:17 to 12:39

Oz shares how he crafted a personal policy statement regarding his career.

“And so why not just kind of keep doing it?”

Taking a Break with FMLA

12:39 to 14:01

Oz discusses the benefits of taking a Family Medical Leave for self-discovery.

“So you were like, I got to move up this timeline.”

Exploring FMLA for Personal Insight

14:01 to 14:49

Learn how Oz Chen viewed his FMLA leave as a test for his career and mental health.

“why don't I take a mini experiment before that?”
Show all 30 chapters

The Impact of Burnout on Decision-Making

14:49 to 15:18

Discuss the connection between burnout symptoms and the decision to take a break from work.

“You did have anxiety that was severe enough to qualify for that.”

Navigating Career Fears and Risks

15:18 to 17:44

Understand the fears associated with leaving a job and the strategies to address them.

“So when you were thinking, okay, I'm going to leave in August or maybe December, were you thinking I'm going to leave this job?”

Tactical Approaches to Overcoming Fear

17:44 to 20:01

Discover practical tactics for dealing with fears about career changes through writing and analysis.

“And writing is a tool that works really well for me.”

Acceptance as a Tool for Managing Fear

20:01 to 22:45

Learn the importance of acceptance in working through fears and uncertainties related to career transitions.

“So you started writing down what am I really actually afraid of?”

Lessons from a FMLA Sabbatical

22:45 to 25:04

Explore the lessons learned before, during, and after Oz's FMLA sabbatical, emphasizing rest and recovery.

“I accept that not having a paycheck coming in will feel weird and scary.”

The Shift in Perspective After Time Off

25:04 to 28:00

Examine how a longer break can change perspectives on work and productivity.

“I was really excited to take that time off.”

The Impact of Extended Time Off

28:00 to 29:50

Exploring the transformative effects of taking an extended break from work.

“I was just like, I readily had things to fill up my time that were enjoyable.”

Surprise Layoff and Its Timing

29:50 to 33:15

Discussing the unexpected layoff notice received during a sabbatical.

“In literally the last week of my medical leave slash sabbatical, I received the layoff notice.”

Future Aspirations and Parenthood

33:15 to 36:47

Reflecting on the next decade and plans for parenthood amidst financial independence.

“So then my initial 12 week time off sabbatical medical leave just turned into like what it is now.”

Exploration and Personal Growth

36:47 to 41:04

Discussing the importance of exploration and experimentation in this new life phase.

“I love this answer because it's personally something I've been thinking about because Brad Ed and I are trying to work on our time buckets from we're doing the die with zero activity.”

Defining Work and Creativity

41:04 to 42:00

Exploring the relationship between work, creativity, and personal fulfillment.

“It's like that sat in the background of my mind for years and years.”

The Nature of Work and Creativity

42:00 to 44:21

Explore how work can be defined beyond traditional jobs, focusing on creativity and autonomy.

“Work to me could look like writing a blog post or having this conversation with you because there's going to be this lovely conversation and then output like, oh, something is living on in the world.”

Finding Contrast in Work and Life

44:21 to 46:37

Discuss the significance of contrast in work experiences and how it enriches personal time.

“because if we don't, like people are really at risk of like, oh, I have all this open time before me and I know that work is bad.”

The Impact of AI on Creativity and Work

46:37 to 49:09

Analyze the effects of AI on creativity and the expectations in corporate environments.

“I feel like you're saying you can still have that contrast, but it just feels so much better because it's work that you are directing, that you are choosing.”

Navigating Identity Beyond Work

49:09 to 52:56

Examine social perceptions and personal identity when stepping away from traditional employment.

“There aren't company goals I have to hit.”

Practical Strategies for Financial Independence

52:56 to 56:00

Learn practical steps to manage finances and overcome the challenges of transitioning to financial independence.

“structure that is nice because I have this class that I go to Monday through Thursday for like four hours and it gives my day some structure and I like learning it I'm not sure if I answered your question.”

Decumulation Strategies for Financial Freedom

56:00 to 57:04

Learn how to manage withdrawals from investments while finding alternatives to funding your lifestyle.

“But in my 20s, I bought a bunch of random stuff in Robin Hood and I have like all these random stocks, right?”

Leveraging Low Income Years

57:04 to 58:16

Discover the benefits of optimizing tax advantages and government programs during low income periods.

“You know, it's sort of like they say in writing, oh, you don't want to, the night before, you don't want to finish your full thought or whatever.”

Creating Space in Your Life

58:16 to 1:00:43

Explore how to utilize time off and personal breaks for better mental health and clarity.

“Do you have any other tips for us before we wrap this up?”

Breaking Down Challenges

1:00:43 to 1:02:06

Understand the importance of breaking large goals into manageable steps to reduce fear and increase action.

“And so you said, when I said, hey, what's the next 10 years look like?”
Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00When I first sat down to write this introduction for Oz, I wrote, I met Oz at Economy this year. Whoops, nope, I did not. But I feel like I did, and I bet everyone else at Economy feels that way too. Oz has this magnetic combination of confidence and vulnerability, warmth and wisdom, and makes him someone you want to be around, and someone, I imagine, with enormous social capital. I don't know. I'll ask him today if he has 500 friends and a book deal yet with Penguin. I've been reading Oz's newsletter, Money for Humans, since I got back from Cincinnati. It's the kind of financial content I really like to consume, personal and insightful.

0:43Oz always makes me question something in my own life, rethink some idea of mine that probably needs rethinking. And that's where I'm hoping to go with our conversation today, to discuss something rather counterintuitive how to become okay with FI. I think I spend too much time thinking about how to be okay with not being FI. Anyway, the tools are maybe the same. Acceptance, soulful inquiry, experimentation. Maybe? Let's explore together with Oz. Welcome to Choose FI.

1:19Jonathan Mendonsa:Before we get started, I keep this podcast entirely ad-free for two reasons. First, First, this is a five podcast and I don't want to promote products that I don't want you to buy in the first place. And second, I really like the clean listening experience of a show where you don't have to fast forward ads. To keep it ad free, all I ask of you as a listener is the next time you open a travel rewards credit card, go to choosefi.com slash cards. And with that, on to the show.

1:48Welcome Oz. Thank you so much. I'm really jazzed to be here and to be talking about this topic. Okay, so let's start out with some basic information. How about your age, your education, your job? Let's start with that. Sure. At the time of recording, I am 37, squarely in my late 30s. And I studied economics in college and didn't use that for most of my career. So I am in the UX design field, user experience, where a lot of it is designing apps and websites to be easier to use. So that's the industry I've been in for most of my career and how I really built my way towards FI. Don't you have to have like a really specific education for that?

2:39How do you get into that with an economics degree? Yeah. So I found myself to be very lucky because at that time, user experience was a very new field. And so I even was in interviews where the interviewer would ask me, so like, what exactly

2:57Jonathan Mendonsa:is user experience design? Like they knew that they needed it, but they weren't quite sure. The field hasn't really formalized yet. So I did take a couple like certificates here and there. There was like extension classes, but now there are full on degrees around this thing. And I felt like I was able to get into the field with a lower barrier of entry all the way back then. Yeah. Okay. Well, tell us where you're at in your financial journey. Are you financially independent right now? Is that a complicated question? You know, I want to say on the Choose the Five podcast, yes. Yes, I am financially independent.

3:40And it took me a long time to accept that, to deal with all the fears. And I would always hedge, like, yes, I'm pretty comfortable, but, and the laundry list of hedges and excuses and what ifs and buts, which really dovetail into all the psychology around money we're going to get into today. Yeah, I really hope that we can place some fireworks in the background there for your big announcement that you're officially FI. So what does that mean to you in terms of, and I don't even mean philosophically. I mean, does that mean, okay, I know that without ever bringing in any more money, I can have my basic needs plus a little bit more covered for the rest of my life.

4:28Is that what that means to you? Yeah. So there's the classic FI approach. I've been a FI adherent for many years. I first was introduced to it through 4-Hour Workweek by Tim Ferriss. And he didn't talk about it directly, but listening to his podcast and materials, I got exposed to Fi, funny enough, through Tim Ferriss. So yes, I think from an early age, I had, ever since I entered my career, I did have this sense of I could use my money to buy my freedom. I could use my income to invest and then live off the 4 % rule and all of that. But the living off the 4 % rule part, that gave me so much heartburn, even though I listened to all the Choose FI podcasts, because accumulating and investing in VTI and all the index funds, really easy.

5:22You know, it's like a really well-flexed muscle. But the other side of it, drawing down, looking at a long period of time of no active income, that's the scary part for me. And have you started doing that? Yes-ish. I've recently got laid off. So I am still on payroll until the final severance gets finalized. And then I'll have this severance that helps build the runway even more. But after that, no other income coming in. Well, let's back up a little because that's in fact why I reached out to you because in your newsletter, you had talked about getting laid off and what a experience that was in terms of that wasn't exactly your plan, but that you had had sort of an interesting buildup to that stopping point.

6:12So can you back us up a little bit about how you moved into this psychological space you're in now? Yes. So for listeners, I think people in the ChooseFI community can really identify with a question that often gets posted to ChooseFI, which is here are my stats. I'm so-and-so. Am I ready to FI? Can I FI now? And I even saw iterations of that when I went to Camp FI and Economy where people went up and offered themselves as case studies. Like, here's my stuff, but can I do it? And so I want to share with you my journey to getting okay with that, getting okay with my own FI journey and FI status and getting comfortable leaving a corporate job, not jumping into another job and just taking a extended career break.

7:05So sometimes instead of saying early retired, I would tell people I'm on extended career break. And so I think that this is a very common experience is that I had actually crossed some five milestones years ago. And it was just like a blip on the paper, like on the screen rather. Oh, okay. Like I could do it, but I think I need more. And I like my job enough anyway. So why change anything? And very soon, like a couple of years after, basically leading up to present day, I would say the last year and a half were very formative for me where my job became unsustainable for personal reasons, like my level of engagement in the job, my level of burnout, some mental health issues, like a lot of anxiety.

7:54And I work a white collar office job. And even with that, I really started to have this seed of an idea that I should leave. Really comfortable job that I've been in for the last seven years, which means I spent my entire 30s in this job, which is kind of wild for me to say out loud and hear for myself. Yeah, I wanted to just pause on that because I think it's so important what you said of like, oh, I really like my job. And so why not just kind of keep doing it? And a year and a half later, to know how much that changed. And that can be for any of us, you know, so often you hear people say, well, I don't really need to make this big plan, or I don't really need to put away a bunch of money because I really like my job.

8:41And so I'm happy to go until 65. I'm like, man, that is 22 years away or whatever, right? Like there's so many things that can happen in between then. And I think having that freedom to say, if that were to change, I'm not going to feel trapped is huge. It's one of the biggest benefits of kind of doing this. So you found yourself in a position where you said, hey, this is no longer fun. This is in fact extremely stressful. Exactly. Exactly. Before I got to that point, I had done an exercise. I like to write a lot to process my feelings. And so when some of my friends would ask me, hey, would you consider retiring early?

9:22You seemed like you could do it. I wrote down a list of things that was going on in my life. And the scenario was, if these things change about my life and work situation, then I would seriously look at quitting. And those things were, I got a management or management changes in such a way where I feel like I'm being micromanaged. I don't have a lot of autonomy in my work. Maybe my relationship with my manager isn't that great. That would be like the biggest one. And then the second one would be that like the broader company culture, like change would change a lot because the company I worked at went through an acquisition.

10:02And so fast forward, all those things happen in a span of like a year, year and a half after that exercise where I was like, you know, I was pretty happy in my previous role, but my role changed, my team changed, my manager changed, the broader organization, just it wasn't the same company that I joined. And that's when I really started to have this internal dialogue like, oh, you need to look at leaving at some point. Like it's not no longer a five-year plan like it was before. Because before I was on a, I gave myself like a five-year clock. Now it's like next year. Yeah. Oh my gosh. I love that you had that document.

10:40Did you physically write it down if these things change? Yeah. Yeah. I love that. I've been thinking so much about sort of my past self and my future self. And hearing you say that reminded me of something that ChooseFI, in fact, inspired me to do many, many years ago because Jonathan and Brad talked about the investor, the investor statement. Oh, what is it? The investor policy statement. And the idea was, okay, when you're calm and everything is great, like you write this letter to your future self, essentially that's saying, hey, when the market drops, here's what you're going to do. And here's your plan.

11:17And here's when that plan might change. And I remember hearing that. And at the time I was like, oh, this is so smart because it takes your emotions out of it. And so I had done something similar with my client load where I was like, well, this is how many clients I want to have. But week to week, I can kind of really change how I feel about that. Like, oh, I should be taking more or I should be taking less. And so I did that statement where I was like, here's what would have to change in order for me to change that number. And it did help for me to go back to that in those moments where I was like, oh, should I change this?

11:52Well, the criteria hasn't been met yet. So it's cool to hear that you did that. And then you were able to have the wisdom to sort of listen to that version of yourself that was like, okay, here's what's going to be too much. Here's what's going to be kind of a deal breaker. Yeah, I love that you made that connection with the IPS. I think it's called investor policy statement. And for me, I guess it was kind of like a work policy statement, like if the nature of my work changes to pass these guardrails of these values that I've set, which is like how I like to work and the style of work and autonomy.

12:31If those things change drastically, then it's time to make a move or reallocation, if you will, in my life. Yeah. Okay. So you were like, I got to move up this timeline. I got maybe a year left. Okay. than what happened. So there came a point where, you know, before I thought, oh, I would leave maybe in the next five years. And then after my job changed so much and moved down to about a year or so, but I still found myself waffling. I was like, so is it like the middle of the year? Is it the end of the year? But then I work for a company that has vests at different schedules. So I was still very much operating from like golden handcuffs and all of that.

13:16And so I really thought, okay, let me make like a final, final decision. It's going to be in 2026. And I'm looking at either August or December because I had vest dates around then. But absolutely by the end of the year, I would be gone. So once that idea really settled into my brain, I really started to look at different options. And one of those was to take FMLA or medical leave. And I mean, one of the reasons why my job changed so much, there was a lot of components of like stress and burnout and anxiety and other health stuff I was going on, where I think my mindset was, if I was going to leave this place I've been at for seven years anyway, why don't I take a mini experiment before that?

14:04Why don't I create some space before that final decision? And for those who don't know, Family Medical Leave Act, FMLA, allows up to a maximum of 12 weeks, roughly three months off that protects your job such that you could return to that job. And I saw it as like a free insurance policy. You know, I saw it as, okay, if I were to leave anyway, then if I, you know, successfully was able to get this approved, then I would have the three months off to really test what does it feel like to be not working for that amount of time, which would be the longest break I've ever taken since I started work.

14:43Well, and how smart too, because, you know, the reason I imagine that you were granted that leave was because you did have symptoms of burnout. You did have anxiety that was severe enough to qualify for that. And so there is a good question of like, if I have a break, will I feel differently about going back, right? Will I feel like actually I like my job again? Or does this cement for me that I can't? Exactly. I really found that I just needed space. Like I needed space away from work to get to a healthier baseline. Yeah. So when you were thinking, okay, I'm going to leave in August or maybe December, were you thinking I'm going to leave this job?

15:30Or were you thinking I'm going to leave all jobs? Oh, this is part of what added to the golden handcuffs, or more like one more year syndrome, I should say, what added more pressure to this was I knew that in my heart, if I were to leave this job, I probably wouldn't be working another job for a long time. There was that binary fear in my head as like, you leave this, you're not going to get a job in tech again. Like who's going to hire you with when you've been out of work for so long and all those narratives. So that also may be fearful of like, yeah, if I walk away from this job, it might be walking away, quote unquote, for good.

16:09and that added more self-imposed pressure. I was just listening to this podcast. I don't even remember what it was. Every once in a while, I'll like jump into these different financial podcasts and see if there's something there for me. And the thing that I really struggle with is anything that is like really, really fear-based. And this one that I was listening to was talking about how dangerous it can be to be young, meaning before 55, I think was his definition, and to leave your high paying job because of just what you were saying. Like if you change your mind in a few years, you might not be able to get back to it.

16:47And so I hear that you were wrestling with that same thing. And I get that there is some, there is something important there, but now being on the other side of that, and we'll get back to your kind of your timeline, but just where you are now, how do you think about that now in terms of that fear of, well, you know, I walked away from this and I wouldn't be able to get back in. Does that sit with you differently? Absolutely. I like what you said about timeline just now, because even though the conversation might, I might have some takeaways that sound linear. There was a lot of zigzagging. There was like, I think I want to do this, but how do I feel about it?

17:27Let me sure know about it. Like a lot of internal going back and forth, talking to my partner. And so I think that with the fear of leaving, really looking at that fear and getting more specific, it just helps so much because I realized that my fear was a very generalized fear. And writing is a tool that works really well for me. So when I started to inquire like, okay, let's break down this fear. So, okay, the fear is like, let's say that this will be the last job that I'll have in tech and I might not be paid this much ever again. That was one narrative, right? And then just literally writing down that fear and asking like, is that true?

18:09It's like, okay, it's not 100 % true. Like this is potentially a reversible decision. And there's so much on the spectrum between like phi and then fully phi and then like fully working full time. There could be working something part time, there could be volunteer. There could be all these things that just required me to engage my imagination more. And I think that the fear, when fear is active for me, it takes away from that imagination. Yeah. This reminds me of something that Maggie Tucker said. I interviewed her, I don't know, like a year ago or so. And she was talking about fear as well. That one thing that had helped her was write down the things that she was afraid would happen and then put dollar amounts to them and have like, oh no, this, this thing happens and it costs a hundred thousand dollars and we need this new sewer system and it costs.

19:05Right. And she, she was talking a lot like you were, well, once you put it down, you're able to engage with it in some kind of way that when it's in your head, it has so much power and so much, I don't know, it's so diffuse that it's hard to like wrangle. And so I get the wisdom of what you're saying of like, the takeaway here, guys, is like literally write it down so that you can engage with it in a new way, right? I think that's really smart. And I've talked to Maggie before to size your problems, break them down to size. And I think this is also where the analytical brain is actually can be helpful and leveraged, which is, okay, now that I've identified this fear, let's throw in a spreadsheet, let's put a dollar amount to it.

19:52Let's like figure out different scenarios. And then it becomes more digestible versus this like kind of broad amorphous fear that's just operating in the background. Yeah. Okay. So you started writing down what am I really actually afraid of? And you started seeing some, maybe some nuance there that wasn't quite there before. So really what I hear you saying, you know, the question I asked, like, do you feel differently about that? It sounds like what you're saying is, you're not afraid now. Is that an accurate summary? Or how are you like wrestling with your fear now that you're not working? Yeah, I love that we're touching on this now because I want to share both tactical, left-brained, logical thinking that helped me and also like the right brain stuff.

20:42And so the emotional stuff for me that worked in terms of working with fear is the theme is acceptance. And I still have fear today. we were having a conversation about this where it's still the same practice of writing down things. And what I noticed for myself was that it's not so much for me just overcoming the fear and just forget about it and just like beat the fear. For me, it was recognizing that there was a resistance I had to those fears. I was resisting like, oh, like I shouldn't feel that way because I've been consuming all this fi content and writing about this stuff. Like I should know better.

21:25Right. And that created a lot of internal resistance versus like, I got to a point where it was part of the same exercise of writing things down of kind of inverting it all. And then writing down like what I accept, like I accept these fears and I'm literally reading off of a Apple note that I wrote. I'll read off some of these. I accept that I will have moments, maybe many moments of feeling scarcity. I accept that not having an active paycheck, hitting my account will feel weird and scary. I accept that aspects of my relationship with my partner may change around money. I accept that I feel the pullback, that I may feel the pullback to LinkedIn and the job market and all the hustle culture stuff.

22:11And then I just wrote, like there's probably a list of like 15 in total, like I accept, I accept, I accept. And it's a little bit more of a mantra now. And it just makes me dance with my fears more rather than kind of keep them at a distance. And there's something about writing down like, hey, I accept that I'm a human, I'm going to have all these feelings. And just because I have these feelings that come up, it doesn't mean that I can't still make progress. There it is, right? Like I can have the feeling and it doesn't have to change what I'm doing. I read the weird and scary one again, so I don't get it wrong.

22:48I accept that not having a paycheck coming in will feel weird and scary. Yes, and so like the genius of that is when that happens, like you have predicted that and so you can kind of rest in because so much of this is about uncertainty, right? Like, oh, uncertainty freaks us out. The thing that I can have certainty about is I'm a person, like I'm a human, and I'm going to feel weird about this. And so that when that happens, it can feel instead of feeling as unmoored, it can feel more like, oh, yeah, I knew this would happen and it's happening. And it's okay. Like, I can still go forward to use your language.

23:29Yeah, I find this to be a parallel for many other things in life. when I went through really hard breakups, a big part of that healing was to say like, you know, I'm human and it makes sense that I'm sad. Let me allow myself to be sad and feel these feelings. And ironically, that helps me process things quicker than like resisting and be like, I should get over it by now. I shouldn't, you know, stop being this like sad person. So I feel like there's like a universal truth there in terms of accepting one's own feelings. An equation I always share with clients that I do not know where it's from and it's not mathematically accurate, but it's helpful is this idea of pain plus resistance equals suffering.

24:18And so the reason I like this, I know it should be something other than plus, but the idea is like the pain is part of the human experience. Like you cannot change that part. The thing happened, but the resistance is the thing that you can control. And that resistance influences that suffering. So what you're saying is like, hey, I really took that resistance down. And therefore, even though the pain was still there, like the suffering wasn't as intense. Absolutely. I love that equation. You should make a shirt with that. It's not mine. I don't know where it came from. Someone wiser than me came up with that.

24:57Well, let's go back to your timeline. When did you start your FMLA break? And what was that like for you? That was March. So March, 2026. I was really excited to take that time off. And I would describe different lessons I learned like before, during and after that period. Before that period, I found myself still having a very active productivity mindset in how I was looking at my 12 weeks off. And again, I write a lot. So I was literally writing down a note of things I will do in my sabbatical and just brainstorming. I was like, oh, I should make apps with AI. Maybe I should pursue my CFP. Maybe I should look for another job.

25:45There are all these things that I wrote down. And so again, like looking at that list, I was like, oh my gosh, like this is like everything that this mindset represents everything that has created my internal burnout and anxiety. Why am I taking time off from work? It's to give myself rest and space. and especially rest in space from, for lack of better words, workism is what I call it, workism and corporatism. What I mean by that is that I felt like my anchor point in life revolved around either work or corporate. Taking vacations based on what fits with work, and my conversations will orient around work.

26:27And so looking at that again, I felt there was a lot of clarity to writing those desires down. And then I ended up going into my sabbatical saying, if all I did on this 12 weeks off was sleep more, get more rest, and play a little bit more pickleball, then that is success. Intentionally setting a low bar for myself, rather than stressing myself out in a period that should really be about recovery. So how did that go? Was that difficult for someone who was so productive to take a step back? It was hard probably in the beginning because of just the mind that keeps running. The productivity engine is something that often buzzes in the background for optimizers or people who identify as optimizers like myself.

27:22So there's always something to work on, always something to optimize. But I would say that even just after the first two weeks, I really fell into a regular rhythm that really surprised me. I was like, oh, I'm finally not really thinking about work that much. And it seems like my day is like opening up more of like possibilities. And I was shocked at how quickly that happened around the two, three week mark. Yeah. And as the rest of that 12 week period played out for me, I started to really wonder like, how did I have any time for work? I'm seeing friends and family participated in some like local pickleball competitions and I was still writing.

28:02I was just like, I readily had things to fill up my time that were enjoyable. At one point I almost thought, oh, oh no, this experiment has worked too well. I'm not really sure if I could go back to work after this. Well, you, so one thing that stuck out to me is you said, oh, it happened faster than I thought. it was about two or three weeks and I kind of had this shift. And what I thought of was, okay, well, most of us who are working full time take a vacation that's like 10 days or two weeks, you know? And like, maybe we need a little bit more than that in order to have that kind of shift, right?

Read the full transcript

28:42To be able to step away from those habits of mind. I think you're absolutely right. And so keen to call out that two week period. It's because usually when I do take my like standard American vacation, like two weeks out of the year, there's always that stress of coming back. Oh my gosh, I have so much to catch up on, like so many emails and my boss is going to throw so much on my plate the moment I get back. And so crossing over those two weeks and then be like, oh, I still have like 10 weeks left out of this. I was like, wow, this is insane. Like there's so much time to really just, you know, know, really rest and not be in a hurry all the time.

29:22Gosh, that just speaks to that feeling that so many of us have around like scarcity of time, you know, where you're saying, oh, it felt like so much time to have eight weeks more or whatever that was. I mean, that time is before us anyway, but it feels really different when part of that time belongs to someone else. Okay, so you're enjoying your sabbatical and then something unexpected happens. Yes, it was divine timing, I would say. In literally the last week of my medical leave slash sabbatical, I received the layoff notice. And so I had to really scramble to figure out what this meant. So that last week was a crazy period because three things happened.

30:12So like the next week I was supposed to return to work and I was, my mental state was like, you know what, just grind through till August. It's no longer going to be December. This time period off has really affirmed to me. I should leave earlier and later. So, okay, I'm going to pick the closer day August. Right. And then I think it was like the Wednesday that week where, because I've been logged out of all my systems, some of my coworkers texted me. They're like, Hey, I don't know if you heard, but like, you should like check your email because there's a massive layoff. I was like, Oh, wow. Okay.

30:43So, so I logged in and then I see a calendar invite with HR on my calendar, you know, like the dreaded HR 15 minute call. Zero to 10. How surprised are you about this? Nine or 10. I was pretty floored. Cause I was like, wait a minute, like this is happening now. It took time for it to settle into my system. And then probably after 10 minutes, I was like pumping my fist in the air. I was like, oh hell yeah. I was like, I can't believe this is happening because the layoff date was actually pretty much the date I was planning to leave. And so I'm like, well, I'm glad I didn't jump the gun there because then I would be paid to leave the company rather than like, my plan literally was, all right, I'm going to grind it out till August on my best date.

31:32And then I'm going to ask my manager, like, can you lay me off, please? Can you fire me? You know, so that I could collect unemployment. Like I literally wrote that down as like my plans. And then like this happened and it was like, it accelerated everything. I was like, this is exactly what I had wished for. Oh my gosh. Okay. So your dream layoff timing happened. And how much time has lapsed since then? It was like 11 and a half weeks because I saw on the last week of my medical leave and I was going to return to work the very next Monday. So that was really wild because when I first read the layoff email, it said that, hey, you're going to work until about like end of July, August, and then that'll be like your final layoff date.

32:23So in my head, I was like, oh, this is kind of the same plan, except now I have like a solid end date with severance. And then because I was late to the game in terms of being logged out and not getting all that context about the layoffs, I didn't realize that in two days, the end of that week, they said, that's technically going to be the last day you could badge into the office and logged out of all systems. And that took me a while to grok. And the term in the industry is called garden leave. There's something called the Warren Act that I guess larger companies with big layoffs, they do this to, in order to accommodate like state laws, I guess.

33:04So effectively, I was like, wait, they're going to pay me for like two months to not work. And then they're going to, you know, on that final severance date, basically pay us out. So it's very generous. I'm like very like happy about all that. So then my initial 12 week time off sabbatical medical leave just turned into like what it is now. Like so as of today, I've been not working for four months. Okay, so we have found you at a very interesting place in your FI journey. And I wonder just how you're thinking about the next 10 years. Is that a hard question? Actually, I do have something around that, but please finish your question.

33:47It's a good question. I was just going to say, you know, you had thought about this in such a different way just a few years ago. And so I imagine the future has opened up for you in a really different way. And so I wonder now at this very beginning part of this part of your life, how you're conceptualizing the next decade or how you're thinking about what's next for you. And so I think throughout this conversation, I shared some of like my building blocks of confidence, what I accept and taking this time off for 12 weeks and pushing for that space and stitching things together that cumulatively added up to like a lot more confidence with this new scenario.

34:30And so when you ask that question about the next 10 years, I do have a timeline that's a little bit closer, which is my partner and I would like to have kids in the next two to three years. And so that added like a really nice boundary for myself where I think of the next two years from now as the best time to explore, to learn, to experiment with things because I want to arrive at parenthood with as little resentment as possible. honestly. I want to arrive at that stage like, you know, like I gave myself that time. I took the opportunity to really honor that time to pursue a lot of different interests and hobbies.

35:20So just two years from now, that is something that has helped shape my timeline. I'm not sure if I have something specific for 10 years, but in the long run, I think this is one of the beauties of the Choose a Phi show is the theme of learning and experimenting and being flexible and iterating. And so for me, I think that Phi is something that I could use in seasons. I just think, hey, this is like my initial Phi season. Like, let me enjoy it. Let me act like a early retiree who's taking community college classes, which is what I'm doing and doing all those things. but there might be a time where I really want to go back to work.

36:05And I got really attuned to that during COVID when a lot of the parents I talked to, they couldn't, it was actually after COVID, all the return to office mandates. I talked to a lot of parents who are so glad to be back in the office because they were stuck at home with their kids. And I'm like, wow, that's a different level of stress and pressure that I haven't experienced. And what if I get to that point? Maybe it's a five years from now. And I'm like, I can't wait to get an office job. I can't wait to get out of the house a little bit. You know, I entertain that possibility. So I'm going to try to honor the season I am now and then be open to other seasons that change with respect to work.

36:46Okay. I love this answer because it's personally something I've been thinking about because Brad Ed and I are trying to work on our time buckets from we're doing the die with zero activity. Do you know what I'm talking about? Like when is the best like time to use your resources for life experiments? Here are all these things that I want to do. And now if I think about which of these belong in, you know, the next five years, the next 10 years, right? And you're doing a version of that in real time right now where you're like, okay, I've got this two to three years. and I really want to think about what I want, what makes most sense for this time of my life that won't make sense in five years or 10 years.

37:28So I hear you, like you've got this theme of exploration. Do you have any specific things that you want to make sure that you get done, just in case I need to add them to my list? Well, man, I feel like with one thread opens up so many threads, which is the joy of talking to you as a host. So to back up a little bit, again, I'm a list person, I'm a brainstorm person, and I write down a bunch of ideas. So I'm like, oh, now that I'm definitely not going to work, like how do I want the next three to six months, the next season or two to play out? That timeline tends to work better for me. I have a better grasp of my desires and how I want to see them through in the next two seasons or so.

38:11Beyond that, it's more of like a question mark. And so one of those things is really thinking about what kind of work in quotes I want to do. And I'm very pulled to things that are the opposite of the environment that I was in. A tech worker who went to the office a lot, sitting in front of the screen a lot, and had to badge in three times a week. And so I was thinking it would be really great to do something hands-on. I would love to learn a lot of trade skills and music skills. So it's both like trades and arts that I started looking into. And I would say something about trades is that when I shared this with some of my friends who are also very much wanting something more analog and wanting to do something like wood shop or how to repair things, they asked me, oh, like, have you considered trade school?

39:04And it was a great question because I immediately was like, no, I'm in the season where I don't want to be committed to anything more than like 10, maybe 20 hours max, if it's a really great thing per week. I do not want to just launch myself into something that like absorbs all my time and the portfolio of my time. I really wanted to be in buckets and diversified. And that's how I like it in my first season. So it's like, all right, if I could find something that's like five to 10 hours here, five to 10 hours there. I still have time to write. I still have time to go and work out the gym. I like that mix.

39:41And that was really informative for me to create guardrails for myself in this season, because I did look at jobs. There were really cool gigs where I could learn how to be an apprentice to install solar panels. And then I really looked at that job description. And I was like, it's 40 hours a week minimum. And during the summer, he, I was like, I think I would really regret making that decision when, and also that line of thinking about doing those jobs, it was also a little bit still steeped in fear because in the tech community, there's this fear that AI is going to replace our jobs. So you better diversify by getting some sort of like manual skill, do something in the trade.

40:24So I had to admit to myself, hey, that was an element that was still playing out in my fears.

40:30Jonathan Mendonsa:And then, you know, kind of seeing that, I was like, all right, let me throw spaghetti at the wall and just stuff that's fun for the first season. And so I've long been interested in music. I've really liked electronic music, have thought it would be great to create a track, even if it's like a silly little ditty or whatever. And so, yeah, community college has been great. I'm now in my second community college class. And in like the second day, I created like a little track, you know, that was like 30 seconds. I'm like, oh, this is amazing. Like it sucks. But I am actually doing something in this area that I've really thought about for a long time.

41:10It's like that sat in the background of my mind for years and years. I want to pick up two of the threads there and kind of and talk about both of them. Like when I think it's really interesting that when I said you said, oh, well, I'm thinking about the next two or three months. You said, I thought about what I wanted work to look like. And you used that word work. And it's something that I have been thinking about as well in terms of, like, you still obviously have thought about, I still need to be making effort in some way that's going to feed me intellectually or give me purpose. Or how did you think about that?

41:51What do you mean when you say work? Something that engages my attention for a period of time and ideally with some sort of output. Work to me could look like writing a blog post or having this conversation with you because there's going to be this lovely conversation and then output like, oh, something is living on in the world. That's one way that I define work. And that is still something that is near and dear to me, that if I go a long enough time not having something creative oriented and without some sort of output, then I'll feel kind of empty. But it doesn't mean that the work has to be in the form of a formal job, like an office job or even getting a paycheck.

42:40I know this is kind of semantics, but I think maybe it could be useful. Do you think the word work here and creativity is like the same thing? Like, are those the same things and how you're conceptualizing them? Like, I want to express this creativity. I want to express this part of me and make something. Is that sort of the same thing? I think just to make this probably even more complicated, like another word that comes to mind with creativity work is maybe the through line is like effort. There's some sort of effort that feels good. And the types of effort that, let me just contrast it with my last role, the type of work that I was doing started to feel very, very abstract.

43:24It was meetings upon meetings and coordinating amongst people to see if we could get this initiative started off. And then maybe a leader just like steps into the picture and says, oh, that initiative is off now. So there's a lot of circling type of energy, like where is this going? And so that effort didn't feel, doesn't feel like great, honestly, for me. Yeah. It wasn't directed maybe. Exactly. And as someone who values, a lot of five people value autonomy and independence, especially with work. I love the type of effort that's like, I put effort into this thing and it's of my own autonomy, of my own creativity.

44:03and there's some sort of thing that could live on, whether it's like a MP3 file or a blog post, some evidence. Directed autonomous effort. I do feel like it's really useful to like pin down what we're talking about because if we don't, like people are really at risk of like, oh, I have all this open time before me and I know that work is bad. You know, I'm using my little air quotes here. And so what is like, what is the next thing for me? And I wanted the other thread that I wanted to pick up was where you use that word contrast, where you said, okay, I thought about what work was like before, and I wanted the work going forward to really be in contrast to that.

44:49So, you know, one of those things was autonomy and you were thinking about those in contrast. And I've been thinking so much about contrast as well, kind of in a similar way, but just in terms of, hey, is part of what makes my days off so great is that I'm working on the other days. Right. And like, what do I do with that information or what will I do with that when I don't have the harder days? But maybe you're kind of answering that with if you have this other kind of directed effort, those can still be contrasted with another type of day. And that contrast is part of what gives us a kind of a rich experience.

45:30I don't know. What do you think? I feel like that's so keen. There's so many ways to take that. I do feel the same thing that you're describing, which is even when I was in a job that I didn't enjoy as much, the weekends would feel that much sweeter. There'd be a little bit of this pent up energy of like, yeah, let's go out, you know, like explore the city because there's more of that contrast. The personal signal for me when I was going through a really tough time with work was realizing that my creative capacity was greatly reduced. So I would come back from work and didn't have the energy to write.

46:12And then I went a long period without writing. And that really bothered me. I was like, I do not like this equation at all. And even when I had time to write, I was too burnt out or too disinterested that I couldn't create that energy. so I feel that that was a key part of my journey that really ticked me off to okay something's off here and that that isn't to say in the future I could be in another formal type of work environment and enjoy that and still have that nice contrast with I'm so glad I'm like so looking forward to the weekend because of the hard work that was that happened earlier in the week yeah so to use that language we've been using, is it fair to say all of that effort was being used in your job?

47:01But of course, it doesn't have to be. So we can still have that contrast. I feel like you're saying you can still have that contrast, but it just feels so much better because it's work that you are directing, that you are choosing. Exactly. I have a lot of empathy for people who are falling into that rhythm where work has kind of consumed a lot of their energy, mentally and spiritually, such that there's not as much spaciousness to consider other things, to have space to do other things. I think it's a very common experience because I think then that setup leads to just playing out the status quo more.

47:46You're going to do the thing right in front of you. If I have a stressful job, but I have all these bills, but to blow off stress, I do all these things. Some may be like less or more healthy than others. And it kind of keeps the cycle going. Like I have a lot of empathy for that. I've been through that. And it is something that really takes intention and effort to get out of. Yeah. You have to have the space to use your imagination. It's like not available to us if we're in that reactive state. I think about AI a lot because my previous job was fully focused on, half of it was focused on AI initiatives to try to get other people in the product department to use AI more.

48:30Like that was like my mandate. So I'm very close to this and I use AI a ton myself. And it's really interesting, the theme of contrast, because in a work environment, it's very easy to fall in line with that framing because there is literally leadership. That's like everyone has to be using AI. Like if you're not a top AI user, you're probably going to have to leave at some point. That was kind of the messaging, very common in tech. and it kind of in quotes made sense in that environment and what I found is that AI actually just created more work I'm not saying it's bad I think there's so many things that are wonderful about this technology but because you can do more you're going to be asked and expected to do more outside of that work environment I'm able to look at that with more clarity because in my personal life and time that I spend because there aren't KPIs I have to hit.

49:33There aren't company goals I have to hit. Now all the creative arts are like, why would I want to use AI to write? I'm writing because I enjoy it. That's part of my practice. It would take away from the point of writing for me. And so without the pressure of performance and productivity that is expected in a corporate environment, there's a lot of opportunity and spaciousness outside of that line of thinking to just like do your thing, AI or not. Yeah. Okay. Thanks for going down that road with me. I want to go back to, you know, one of the things that I think is so helpful about ChooseFI and shows like ChooseFI is that we get to see these unconventional things that other people are doing and that can give us the courage to do unconventional things in our own lives.

50:21Like it's so powerful just to see someone doing something different and just to hear how they actually met some of the challenges that go along with that. So I'm going to ask you a really practical, maybe not practical, I think a practical question. You said early on, you said, oh, I haven't really been saying I'm early retired. I'm saying I'm taking an extended career break. And I wonder how that has been received by others. Does that make them worry about you? This is why it's good to have five friends because you'll at least have some people who understand. I just caught up with a former classmate from college just literally yesterday.

51:08And I was trying to catch him up on what was going on. And the natural question is like, oh, okay, so what are you going to do next? Like you're going to like find another job. Even when I was telling him some of my interests, everything was kind of anchored to work. Even when I was talking about like, yeah, I'm just exploring some like electronic music classes. Like, oh yeah, like, are you going to be a DJ? So it's, it's this very quick jump to work centeredness or having like an identity to, to hold you. And I realized that could be kind of scary to not have a defined role, especially when talking to people and saying like, this is just what I'm exploring right now.

51:48And I think sometimes I find that maybe people don't know how to respond to that. And it's okay. The conversation kind of like drifts out after that. I said that I would ask, do you have 500 friends? Definitely not. I think I know 500 people, but I think as time goes on, I do feel like the circle gets like smaller and tighter. That's a theme I've noticed with like a lot of people too, just like over time. I think as a tangent off of that is the perception of someone who isn't, doesn't have a job. With my circle of friends, they might have the perception of like, oh, so you have, you just have all this free time all the time.

52:35Like, you know, can you go do and do this and that? Oh, like you're busy. You can't make it. That's weird, but you're not working. I think that's something that I'll continue to run into and I don't have a perfect solution to it my cheat for it is take community college classes like like I do have something that is like a structure that is nice because I have this class that I go to Monday through Thursday for like four hours and it gives my day some structure and I like learning it I'm not sure if I answered your question. Yeah, you made me think I hadn't really thought about, especially for someone who's younger, the negative ways that this might influence your close friendships.

53:17Do you think that any of your friends are jealous? One of my really close friends, I love him to death because he's so open. He was like, I'm so jealous of you. You're doing what I want to do. I've only had heard that once. And it is really humbling. I try not to take that and turn it into more pressure. Like, oh, this is what my friend would do with this three times. And then I should probably think about doing something similar, almost having the guilt of options. And I do think that that person who said, I'm so jealous, like that's the safe kind of jealousy. That's just like out there and friendly, right?

53:56It's the, it's the ones who aren't saying that and who kind of is sitting underneath that can feel maybe not good. Yeah. I think earlier you mentioned the word practical and I did want to add in some practical things that are... Let's do it. So some of those practical things are on like the analytical brain that my optimizer brain like really needs. I need both that like heart and mind piece to like arrive at decisions. and I'm reading from my notes. One of the really important calculations that I made was not the 4 % rule, but more like how do I pay for literally the first month, the second month?

54:43And that exercise helped me so much because the classic problem I think for people who arrive at PHY is I have this overdeveloped muscle in just contributing, contributing, contributing, buying VTI and I see this balance grow. I like to see that balance at that level because that looking at that number makes me feel fi. So finally decumulating for me is really, it was just this like daunting thing of like, Oh my gosh, I'm going to have to sell VTI. No, like it's my favorite thing. So favorite investment, I should say. So when I like really looked at it, I was like, okay, what does this look like in practice?

55:25And I didn't realize I had this total misnomer in my head because when I thought about the 4 % rule, it's like, let's say that it's $60 ,000 a year to fund it based on 4 % rule. And so I thought, oh, I have to like literally withdraw 60K in my first year. And I was like, wait, that makes no sense. I could just do it one by one, month by month. So that already lowers the perceived barrier of like, okay, 4 ,000 this month, 5 ,000 this month. And it's not as daunting to sell tens of thousands of dollars or all of that. And another calculation off of that that helped me a lot was realizing that because I looked at my whole portfolio and all its balances and in my investing career, luckily the base of it has been relatively responsible index funds.

56:16But in my 20s, I bought a bunch of random stuff in Robin Hood and I have like all these random stocks, right? So looking at the prospect of like, how would I fund the first month, two months, the first year, an aha moment clicked for me. I was like, I could do a garage sale of my junk stuff first. I don't have to touch my VTI first. There's some random crypto, there's some single stocks. I will offload those first and like, happy to. I'm happy to do that. And that for me was just like, it felt so good to, I don't know. I don't know what it is about that. That's like, that feels so good about perhaps offloading some waste in order to fund my life.

56:59You lowered the barrier to entry. Like you made it something that you were happy to do. You know, it's sort of like they say in writing, oh, you don't want to, the night before, you don't want to finish your full thought or whatever. Like make sure that it's easy to get started the next day. That's sort of the idea, right? Like you set it up so that it would be something that would be easier to do. Yeah, exactly. And so that's like the decumulation part, like how I made decumulation feel a lot less scary for myself. Those things. Another thing that really appeals to my optimizer brain is that looking forward to the optimizations I can make in my low income years, you know, which has been talked about on the show, but it's like, oh wait, I could like get tax advantages and government programs and like get things for free.

57:48That is like, it's almost kind of like, like, like for me, I love credit card points. So I love getting a little bit of bonus as I'm like doing something and kind of reframing the low income years, which could be very scary to, Hey, there's like a little bonus you get for not having an income. That also like really jive with my optimizer brain so that it just made the prospect of like the first couple years feel a lot less scary. Those are really good. Do you have any other tips for us before we wrap this up? Putting the pressure on, but I feel like this episode has been so good in terms of just making a list of like things that are going to be helpful for people as they kind of do some of these tricky things?

58:36Yeah, I would say that really looking at what's at your disposal to buy yourself more spaciousness in time is helpful. So not everyone will take FMLA or be eligible for that. And so I saw this crazy stat that like Americans on average get so many hours of vacation a year, but they actually don't use it. If it's like 40 hours, then maybe they use like 20 hours. So I think there's like a stepping scale of experiments that one can do, especially if they're feeling a little bit either stuck in their career or wanting to experience a life outside of work, sabbatical, career, break, whatever it is, to really try to look at like, what is at my disposal?

59:24Can I actually use up all my PTO this year? Can I challenge myself to do that? Can I go beyond that? Which is, ask my team or manager, hey, can I take one more week unpaid? Maybe some places actually offer a formal sabbatical program. And also, I think just if you're already thinking about leaving your job, then try to use that time between jobs as something that adds space to your life. I kind of liken the analogy in my head is, for a lot of five people, a lot of people in this community who are listening, leaving a job and immediately jumping to another is kind of like you just had a breakup, like a relationship breakup, and you just like jump right into another relationship.

1:00:08I think most people can grok that that's probably like not the healthiest thing to do all the time. And so it's like, hey, this is an opportunity to really take the space for yourself. And a lot of things can arise once you do have that space to meditate on your life and let things come up. Yeah. I've noticed a bit of a theme in the advice that you've given. So I'm going to try to summarize it and tell me what you think, which is that you're all about breaking big things down into littler things and that that applies to almost any challenge that we have. And so you said, when I said, hey, what's the next 10 years look like?

1:00:46You said, I can do the next three to six months, right? That feels manageable. I can figure out what I might like in three to six months. You just said, hey, we could think about take your vacation, but also could you ask for one more week, right? Like just this one tiny step towards something that could give you a little bit more spaciousness. When you talked about, oh, it's hard to think about drawing down, but then I thought, what would it look like for one month? What would it look like for the first month or the second month. All of these things seem so much more doable. And of course, that's how we live our lives is like one week and one month at a time.

1:01:24And so I can see that being really applicable to the things that you shared and also the challenges that we might be facing that we haven't discussed today. Yeah. And just to add to that, I think that it's easy to fall into a frame of expecting clarity before action. And so breaking things down into smaller components and then zooming into the specifics of like, okay, even if I broken this thing from a bigger thing to a less scary, smaller thing, how would I specifically do that small thing? Get it on my calendar or whatever. That's what for me generates clarity through action. Cause it's something that I could action on versus a big blob of scary thoughts.

1:02:10Yeah. I like that phrase, generate clarity. All right. Well, we'll end on that note. Where can people find you? How can they sign up for your newsletter? Yeah. You could just type in my name anywhere, Oz Chen. So that's O-Z-C-H-E-N. And you'll probably find my Substack right away, which is ozchen.substack.com. I've titled it money for humans, but that may change. But I tend to keep things tied to my name. So that's easy to find. Yeah, Substack is a great place to read things and not be as caught up in the fast social media stuff, if that's what you're looking for. All right. Well, thank you so much for joining us today and for putting so much thought into what you were going to share with us.

1:02:57We really appreciate it. Thank you, Ginger. I think this series, Getting Personal, is so valuable. It's definitely helped me get a lot of clarity in my own journey. So I really appreciate the conversation.

From the publisher

Most Americans never truly disconnect from work—even on vacation. After decades of tying your identity, daily rhythm, and sense of worth to a paycheck, stepping away feels less like freedom and more like freefall. Oz Chen spent years financially independent before he could accept it, wrestling with the psychological gap between having enough money and being okay with not working. Key Topics Discussed Oz's Background and FI Journey (00:02:30) Oz shares his introduction to financial independence through Tim Ferriss's Four Hour Workweek, his career as a UX designer, and the moment he officially accepted being financially independent at 37—years after crossing the actual threshold. The Job That Changed Everything (00:08:15) After seven comfortable years at one tech company, management changes, an acquisition, and mounting burnout made Oz's dream job unsustainable. He reveals the "work policy statement" he'd written that predicted exactly when he'd need to leave. Taking FMLA Leave as an Experiment (00:15:40) Rather than quitting outright, Oz used 12 weeks of FMLA medical leave to test what not working would feel like. He set a deliberately low bar for success—sleep and play pickleball—instead of maintaining his productivity mindset. The Unexpected Layoff (00:22:30) During the final week of his sabbatical, Oz received a layoff notice with severance and garden leave. What could have felt devastating instead felt like "divine timing," perfectly aligning with his planned departure. Wrestling with Fear and Acceptance (00:28:00) Oz shares his practice of writing acceptance statements for every fear—from scarcity feelings to relationship changes. By acknowledging fears without resisting them, he reduced the suffering that comes from fighting his own emotions. Practical Strategies for Decumulation (00:35:45) Breaking down the scary process of drawing down investments: think month-by-month rather than annual withdrawals, and sell "junk" investments (random stocks, crypto) first before touching beloved index funds. Life After Work and Future Plans (00:42:20) Oz describes his current life taking community college music classes, learning trades, and planning for the next 2-3 years before potentially having children. He emphasizes honoring different life seasons and remaining flexible about future work. Notable Quotes Ginger: "Pain plus resistance equals suffering. The pain is part of the human experience, but the resistance is the thing that you can control." Oz Chen: "I accept that not having a paycheck coming in will feel weird and scary. I can have the feeling and it doesn't have to change what I'm doing." Oz Chen: "Clarity through action versus expecting clarity before action. Breaking things down into smaller components generates clarity." Oz Chen: "The productivity engine is something that often buzzes in the background for optimizers. There's always something to work on, always something to optimize." Oz Chen: "I realized my fear was a very generalized fear. Writing down that fear and asking, is that true? helped me see it's potentially a reversible decision." Key Takeaways Write a work policy statement listing specific conditions under which you'd leave your job, similar to an investor policy statement for market downturns Break down your fears by writing them out specifically, then question their validity and put dollar amounts to worst-case scenarios Create acceptance statements for your financial fears to reduce internal resistance rather than trying to eliminate fears entirely Calculate your first 3-6 months of expenses in retirement month-by-month rather than thinking about annual withdrawals to make decumulation less daunting Consider using all available time-off options (PTO, unpaid leave, FMLA if eligible) to experiment with extended breaks before making permanent career changes Identify "junk" investments in your portfolio that you'd be happy to sell first before touching core index fund holdings Set a low bar for success duri…

More from ChooseFI | Financial Independence Podcast

All 189 episodes
614 | Getting Personal with Personal Finance: Oz ChenChooseFI | Financial Independence Podcast · 1 h 3 min
Listen in VO