Hey everyone, I’m Jeff and thanks for reading Second Generation — a newsletter where I share my evolving thoughts on wealth from the perspective of a first-generation college graduate.

Join the Second Generation

TL;DR

• Way back when, on Second Generation: Money Flows

• I bought an apartment! It was stressful, exciting, humbling and a big part of why I didn’t have time to write these newsletter issues.

• I took a short hiatus, but I’m back to writing these issues (and things will be a little different). Achievement is a tricky subject and I want writing these to be fun as opposed to some to-do list item; it’s just me and my thoughts.

I told you all that I would finally get consistent about writing newsletter issues — last time, even outlining what I think are the core components of building Financial Security — and ... I failed spectacularly.

But, as strange as it may sound, I'm glad I did. The past few months have been a bit of a rollercoaster for me, and I've been thinking about how to revamp this newsletter, so I just wanted to drop a note here on how I've been and what to expect from me moving forward.

Living The American Dream

First off, I bought an apartment! I got a real estate agent, applied for a mortgage, hired expensive lawyers who just told me where to sign stuff and now have a place I can call my home. I had been dreaming of the day for what feels like forever, and the more I think about it, the less I believe it.

In the spirit of transparency and honesty though, this achievement was bitter-sweet. In addition to the financial discipline it took to live with my parents to save and invest my money, the constant emotional battle of balancing my needs and the expectations of others was increasingly weighing me down to say the least.

I was already a full-time software engineer, an involved son taking care of my aging parents and an aspiring entrepreneur trying to make every new habit and side hustle a reality. To top it all off, it turns out that looking for a home I'm willing to stay in for years, taking out a ton of debt, risking a ton of my savings, proving years worth of my finances and furnishing the place without breaking the bank was kind of stressful? Go figure 😅

Taking a Step Back

Soon after starting the home-buying process, I realized I wasn't really doing anything well anymore — I was neglecting my health, half-assing my day job (don't tell my manager), and writing each newsletter issue with barely any mental energy left in the tank.

So I took a step back.

I let the aspirations for this newsletter take a back seat because I made the decision that everything else was more important for once. I pride myself as a "high-achiever" that has to do everything right or not do it at all, but that's just not sustainable — what's the point of achievement if you forget to live afterwards?

The excitement of chasing a dream, building new skills and putting out new issues was still there, but I accepted that it didn't need to happen all at once. The goals that I set out to achieve didn't have to go anywhere just because it didn't happen when I thought it would.

I knew that when I was in a better place, I could pick up where I left off — restart this conversation, continue learning with you all, and (hopefully) help anyone that stumbles on these issues with my learnings.

Second Gen

So, here we go again — except this time, I'll be a lot more honest: I have no plan.

I'll write when I have time on my hands and about the topics that I think are most helpful first — not some perfectly curated series, and not scheduled to send every two weeks on Monday mornings.

I’ll still want to talk financial security, building wealth — heck even cryptocurrency — so if you’re still interested in listening, I’m looking to make writing these a lot more fun. It’ll just be me and my thoughts (feat. some funky diagrams).

See you at some later point ✌🏼

— Jeff

Hey everyone, I’m Jeff and thanks for reading Second Generation — a bi-weekly1 newsletter where I share my evolving thoughts on wealth from the perspective of a first-generation college graduate.

I hope you enjoy the content 🙏🏼

Join the Second Generation

TL;DR

• Previously, on Second Generation: Wealth From the Ground Up 👈🏼

• All of us were passed down some form of the American dream, but achieving the things on our lists won’t always make us happy. Oftentimes, what we really want is financial security.

• Money is part of everyday lives and flows through our socioeconomic system. Wealth is about having stake in the financial infrastructure by supporting what already exists, creating new value channels or making the system better as a whole.

• Choose your own adventure — invest in what works today, create what could be better, and/or rearchitect what wealth looks like.

• Next steps: Betterment for passive investing, Wealth shown to scale, Chamath Palihapitiya on Money and Business Models Aren’t Just For Business.

Our Origin Story ⬅️

When I was growing up, my parents never talked about wealth — it was always about money.

They were focused on paying the bills and putting food on the table. They didn’t have the time or energy to sit down, and just think about “what wealth means” like I have the privilege of doing today. All they had was a dream.

The American Dream

It was the dream all our parents passed down to us at one point or another. They told us that even though succeeding was hard, success was just a matter of following a few simple steps:

1. Graduate college ✅

2. Get a “good” job ✅

3. Buy a house ✅

4. Live happily ever after 🎉

In essence, it’s the reason we call ourselves “first-generation college graduates” to begin with. This dream was our guiding light and, at least for me, a big part of why I am where I am today.

But it's far from perfect. College challenges our ideals when we realize just how much we don’t know and now, two years out of college myself, I can attest to the fact that even getting that good job or buying a house doesn’t always make us happy.

Now What?

Over the coming weeks, I want to kick off the Pillars of Wealth by talking about financial security — the peace of mind that we’re often looking for when we think about wealth (spoiler alert: it was never really about the money).

For today’s issue, we’ll start with understanding how money works and why we need to differentiate it from wealth in order to obtain financial security.

Building Wealth 💸

Having money is pretty transparent — we can just check our wallets or pull out our phones and log into our bank accounts — but wealth is harder to see. It’s systemic, cultural and a reflection of our financial infrastructure.

In actuality, wealth is about consistently influencing money flows.

Money Flows

Money is part of our everyday lives. We earn it from our jobs, spend it on the things we want and save some of it to spend later.

In this sense, money’s value is clear (we give X dollars in exchange for Y) and transient, (once we give it in exchange for something else, it’s value to us is gone).

But the purpose of money extends beyond our own, isolated financial decisions.

Money we earn is someone else’s expense, money we spend is probably going to Amazon and the money we put in our bank accounts doesn’t actually just sit there. It constantly moves between people, businesses and governments at scale and effectively serves as a common language to communicate value.

In other words, every financial decision sets off a chain reaction of socioeconomic activity where money inevitably leaves our immediate control and becomes subject to the invisible forces of our existing financial infrastructure.

Wealth is about having stake in this financial infrastructure — whether that’s in the form of financially supporting what already exists, creating new value channels that others can benefit from or doing the work that’s necessary to make the system better as a whole.

Wealth Influences The Current

If the ebb and flow of money is like water, then building wealth is analogous to its current — shaping the volume and direction of money throughout our socioeconomic system.

The way I see it, there are three broad paths we can take to turn our money into wealth that are all equally valuable and depend on each other:

1. Invest in what works today: Whether you want to support your community or just get a piece of the profit pie yourself, every financial decision is your chance to influence the money flow (no matter how slight). Like the plumbing that guides the running water in our homes, existing financial organizations are rigid, but effective.

2. Create what could be better: We can create what we know will be valuable — i.e. start something people are willing to pay for. If we notice the plumbing is broken, we can take the high-risk, high-reward path and try fixing it ourselves. It’ll be messy, but some of us will just prefer to create these things ourselves and, if it works, we gain wealth from capitalizing on an opportunity to create.

3. Rearchitect what wealth looks like: Now, there comes a time when the system itself is part of the problem — and that’s to be expected! Our financial system is far from perfect, but it’s important to remember that people are ultimately what legitimize value. If new systems are imagined, created, and adopted by everyone else, then those who were there to lay the groundwork of these new systems2 would be, by definition, wealthy.

So as to not go on a separate tangent here, I’ll unpack these a little more in a later issue.

Next Steps 🛠️

Our system is, without a doubt, an imperfect one, but change starts small. Below is a shortlist of resources that I’ve found particularly helpful in my journey so far; I hope they prove useful to you too:

Practical Resources

• Betterment: Investing on auto-pilot — Betterment is a “robo-advisor” that I personally use to regularly invest in things like my Roth IRA.

• Robinhood: The technology-first investment platform — Robinhood helped ease me into the world of investing in stocks and I consider it an essential (and easy) tool for every newbie.

• Coinbase: Crypto is the future, but damn is it complicated — Coinbase may not be a perfect final destination for cryptocurrency investing, but it’s the best first step into this new world.

Further Reading

• Wealth, shown to scale: An incredible visualization of wealth that not only provides countless research-driven insights about the concentration of wealth, but does so in a way that speaks volumes.

• Chamath Palihapitiya on Money: One of my favorite talks on the topic of money and wealth. Chamath Palihapitiya speaks to how we can understand money as an instrument of change and Silicon Valley’s failure to cultivate meaningful value.

• Business Models Aren’t Just For Business: Why don’t we talk about business models outside of the workplace? If you want to sustainably help the people you care about, you need to figure out how you’re going to systematically deliver value to them. That’s what a business model is for.

Moving Forward ➡️

While the American dream is both inspiring and comforting, its’s also limiting to those of us that are may not quite fit within each checkbox. Maybe we’re struggling through our college classes, still figuring out what career we want to pursue or aren’t ready to settle down and buy a house.

Building wealth is about more than just having money. We use money within a living, breathing financial system where people are the ones that decide what’s valuable and wealth comes from being intentional with our money and facilitating how value is created and re-distributed.

Reframing our rigid set of goals into a flexible understanding of financial security will serve as a bridge between generational ideals around success — and I hope you’ll join me on that journey.

Coming Up

1. Choose Your Own Adventure: the different ways to build wealth

2. When Have We “Made It”: the limits of delayed gratification

3. Having a Flexible Roadmap: creating a personal financial system

4. The Meritocracy Trap: why hard work alone isn’t always enough

5. Wealthy But Guilty: a short note on ethical wealth creation

Stay tuned!

— Jeff

Hey everyone, I’m Jeff and thanks for reading Second Generation — a (roughly) bi-weekly newsletter where I share my evolving thoughts on wealth from the perspective of a first-generation college graduate.

If you’re new to these, let me be the first to say welcome and thank you so much for subscribing! 🎉 I hope you enjoy the content, but if you don’t (or you just get too many emails) that’s cool too; feel free to unsubscribe at any point at the bottom of this email.

TL;DR

• Talking about wealth in the abstract is a luxury that most of us can’t afford. Let’s ground ourselves a bit and talk about financial literacy.

• Chances are, our schools or parents didn’t teach us this stuff. If you want to get a grasp of some financial literacy basics or learn more about the personal finance journeys of others, check out: NYT Post-Grad Survival Guide, Andrei Jikh and The Mad Fientist.

• We all need to treat ourselves from time to time, but make sure you’re being intentional with your money. Get a birds-eye view of you finances using YouNeedABudget, The Personal Finance Flowchart, and Personal Capital.

• Successful change won’t happen right away. All that matters is that you try to be better today than you were tomorrow. Try simplifying the process by recognizing the power of doing nothing and making the good decisions the easy ones.

• Wealth, like financial literacy, can be thought of with respect to the past, present and future. Stay tuned for more issues on the Pillars of Wealth.

Wealth is Too Abstract 💭

The truth is, wealth is a hard concept to define. But even if we factor out the all the sociological complexities of class and the emotional difficulties of being a first-generation college graduate, the little things are harder than they have to be.

I can sit here comfortably in front of my computer and just pontificate about wealth — talk about what it means, why we need it to enact social change, or the tech industry's shortcomings in addressing inequality, but let’s be honest. These ideas alone don’t really help us get past the first step of managing our own finances.

So, today I want to ground ourselves a bit and talk about financial literacy. I want to focus on the here-and-now and start a conversation about how we can develop the skills that will enable us to make informed and effective decisions with our money.

Hit the Books 📚

To start, let’s acknowledge that we just aren’t taught this stuff.

Public schools barely include personal finance in their curriculums. Our parents usually don’t make enough money, or really have the time, to teach us about saving and investing.

Based on recent student data, by the age of 15, we fall behind our peers in financial literacy based on factors like our parent’s education level, socioeconomic status or even just the number of books we had around growing up.

But, if I’ve learned anything from my fellow first-gen grads, it’s that succeeding with the cards stacked against us is kind of our thing. We had the guts to break away and drive to push through the so-called “hidden curriculum” in college. In a way, we’re now faced with a similar challenge.

We succeeded once, and we can do it again. Only this time, we can learn from, and support, each other.

In hopes of helping you avoid the trials and errors I went through to learn this stuff, here’s a short list of resources that helped me get started:

• NYT Post-Grad Survival Guide: This corner of the New York Times is a great place to not only get easy-to-understand definitions for financial literacy basics, but also explain just how weird life is after college.

• Andrei Jikh: If YouTube is more your vibe then I highly recommend watching Andrei Jikh. Andrei talks bout all things personal finance and (dividend growth) investing while still being pretty entertaining. Check out his videos on why he invests, what a Roth IRA is or his recent thoughts on cancelling student loan debt.

• The Mad Fientist: Though this veers off a little bit from our focus on financial literacy, the Mad Fientist is definitely my go-to personal finance podcast. The podcast gets its name from “financial independence” (FI), but the interviews often provide some great perspective as you hear about other people’s personal finance journeys. My personal favorites are From Broke to Millionaire in 5 Years and The Psychology of Money.

Take a Closer Look 🔎

The next order of business requires that we each take a good, hard look at where our money actually goes.

I know I’ve definitely been guilty of buying stuff I don’t need on Amazon just because or paying some ridiculous fees on Uber Eats for some late-night boba. And I stand by most, but not all, of those decisions because sometimes we just gotta treat ourselves.

But, unless you’re actually rich and just reading this newsletter about money for fun, you probably can’t (or at least shouldn’t) live that life every day.

Most of the time, finding the balance between our impulses and long-term goals is just a matter taking a step back and paying attention.

How much do you really spend on stuff you don’t need? On ordering food when you’re with friends? Or on all of your subscriptions that always seem to charge you on different days of the month? It’s one thing to justify ordering in after a rough day; it’s another to see that ordering in costs you $300 a month that you’d rather spend paying down some debt.

Fortunately, you don’t have to really answer those questions because we can get technology to do it for us:

•  YNAB: YouNeedABudget is by far the best budgeting app, I’ve used. They’re easy to use, honest about wanting you to be intentional with every dollar and it’s free for college students.

  • Disclaimer: I’m not huge on budgets as a lifestyle because they always just sort of feel like diets — you box yourself into a plan and when things don’t go according to that plan (and they never do), everything blows up. Instead, I see budgeting more as an exercise that gets me thinking about how I want to spending my money — and this has proved invaluable to me.

• The Personal Finance Flowchart: Now this Reddit post is the kind of content that nobody really asked for, but everyone deserves to see. Even though personal finance is not a “one-size-fits-all” deal, this flowchart is a great starting point if you want to quickly get a sense of where your money should more or less be going.

• Personal Capital: Personal Capital is the Swiss Army knife of personal finance platforms — offering free financial advice based on your savings/investing goals all in one simple dashboard. It’s super easy to use and I don’t leave home without it.

Choose a Little Differently 🤔

Ok so, that was a lot.

By no stretch of the imagination do I expect any of you reading right now to go through all of the resources I shared, learn all there is to know about financial literacy and change you financial habits by tomorrow. Successful change is a slow and sometimes painful process.

Which brings me to my last point: making better, more effective financial decisions is as much a consequence of accumulating knowledge as it is being willing to act on your learnings over and over again.

I could go on forever about how we’re creatures of habit that are resistant to change, afraid of stress and constantly motivated by what we already believe, but I’ll leave that up to the real psychologists. For now, just remember that we do stuff like this all the time:

And to avoid overwhelming you with even more information and maximizing your chances of success, all that matters is that you try to be better today than you were tomorrow. That you make one choice a little differently.

So feel free to start small:

• Recognize the power of doing nothing

  • Sometimes the only thing we need to avoid overspending is to slow down. Technology is designed to make our lives easier, and usually we love that about it. But it also means giving up some control and mistaking a company’s desire for you to buy things, for real urgency or importance.

  • Wait before you checkout. Let it sit in the cart for a day or two. Sometimes you’ll come back to it and still want to buy it, and other times you’ll save yourself from an emotional purchase that might not have been worth it.

• Make your good decisions the “easy” ones

  • Building a new habit will inevitably come with some resistance, but try setting your environment up in a way that makes it easier to make that better choice.

  • Have a problem buying stuff online? Make it inconvenient to buy stuff by not saving your passwords or credit card info for those sites. Have trouble sticking to a budget? Set up automatic deposits that pay your bills and move money into your savings as soon as you get your paycheck.

No matter what you choose, it’s worth mentioning that you don’t have to change it all at once. That if you mess up along the way you still have a chance to be better again tomorrow.

Pillars of Wealth 🏛️

Financial literacy understood as a learning process — where we acknowledge the past, look at our present circumstances and slowly work towards a better future — actually gives us a clue to understanding the more elusive concept of wealth.

As weird as it sounds, I like to think our present lives are like dots on a larger timeline that just keeps going. Each moment is briefly experienced until the next one.

As time goes on, and we’ve experienced a bunch of moments, good stuff and bad stuff happens — both to us by the circumstances we can’t control and because of us.

If we decide to take as much control as possible and accept what what’s beyond our sphere of influence, we eventually get more and more say on the direction we‘re traveling in. We don’t really stop traveling, but (hopefully) we experience the moments we were looking forward to and better stuff happens in our lives.

Building wealth works the same way and the next few issues will dive into what I’m calling the Pillars of Wealth (cheesy, I know, but bear with me):

• Debt

• Personal Finance

• Investing

This time around I focused on a small part of personal finance and I hope something I said resonated with helps out no matter where you currently are.

— Jeff

Thank you so much for reading to Second Generation! If you found this post helpful, have a question or just want to share your thoughts, leave a comment — my digital door is always open!

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Sometimes, growth implies loss. While many first-generation college graduates like myself are taught to cherish higher education for the opportunity that it is, we often feel as if we're leaving behind a part of ourselves in the process. Take Lorena Aguillas, participant of a case study on first-generation college students, talking through what it felt like to be stuck choosing between her father and her future:

The thing that gets to me a lot when I go home is that my father continually, every day, tells me that he needs me to come home. He just tells me, "It's so silly for you to still be there. You should come home and go to [the local college]" ... It makes me feel kind of in the middle with what I want and what he wants, because I do respect a lot at times what he wants and I would like to help him. But I don't think it's really fair of him to ask this of me, for me to stop. Because this is really what I want to do with my life now. It's awfully hard because it makes me feel like I've been a bad daughter.

Like Lorena, I've felt that same frustration — what some call breakaway guilt — of wanting to help my family, but at the expense of my own ambitions and desires; of being told to "fly" and "make the most of my American education" but still having to explain to my parents why I'd want to move out of my childhood home, or take a lower-paying job.

Yet, I still believe our stories are a source of strength. At one point they empowered us to take a leap of faith towards higher education and can now act as a guiding light on this untravelled path as we graduate into the "real world". While Second Generation aims to document my journey and give practical advice on money, I think our stories are what actually help us answer some of the underlying questions that we sometimes forget to ask: what does wealth even mean? what do I value?

The way I see it, our stories are our superpower. Our lived experiences give us an intimate understanding of multiple cultures, value systems and perspectives on what constitutes a "good life". They allow us to take a step back from our pre-existing beliefs, question the underlying assumptions, and ultimately empower us to make the hard choice of breaking away and standing our ground for what we believe is right.

Cutting Through The Noise

As a starting point, I think we develop our existing values from two places — ourselves (our ideas, personal goals, and reflections on the past) and the people around us (family, friends, social media, or some random guy on the internet who writes newsletters).

The problem nowadays is that there's just too much information. The people around us and notifications on our phones all actively try to tell us what we should care about, why we should care about it, and that we should care about it right now. As a result, I imagine our brains are just big, tangled messes most of the time — trying to learn as much as we can, incorporate everything we hear into our lives and expecting others to do the same.

I think, it's also especially difficult to cut through the noise as first-generation college graduates. In many ways, we internalize the voices of our families through our stories, sometimes mistaking them for our own, and choose to navigate our lives as delegates of the American dream. While honorable, the “long leash of loyalty” oftentimes doesn’t give us the opportunity to distinguish our voice from those of our parents’ and we find ourselves perpetually conflicted.

To untangle ourselves a bit, and accurately judge what it is we value, you have to decide who you think is worth listening to. In the words of international religious leader and moral philosopher, Jonathan Sacks:

Win the respect of people you respect, and you can forget the rest.

Though having what feels like an infinite number of resources seems great, looking closer into the paradox of choice urges us to question that assumption. We all-too-often find ourselves needing ways to simplify our lives after the technology-induced decision fatigue and then (ironically) paying tech companies for convenience we now feel we need.

And while some may argue that not staying informed about everything is irresponsible, that we’re burying our heads in the sand, I’d argue that it’s better to care deeply about a few things than trying to play catch-up as new important issues in the world inevitably become known. Instead, we should focus our efforts on thoroughly understanding the nuances of issues we’re willing to fight for and eventually humbling ourselves to those that care more about issues we’re unaware of, know something we don’t, or offer a perspective we’re blind to.

There’s no need for us to expect ourselves and others to care about every issue, every fact and every opinion searchable on Google; doing so will just leave us paralyzed and powerless without the energy or expertise we need to actually listen.

Aligning Ourselves

Once we’ve untangled what we listen to a bit — picked a handful of YouTubers, bloggers, close friends and family members — we can actually start defining our values, right? Realistically, there are tons of different ways we can go about achieving this: drafting ourselves a personal mission statement, trying to find our Ikigai, starting with “why”; but I think at the heart of all of these, and the hardest part, is actually committing to the decision.

While I could sell you on those existing frameworks or tangentially add onto them claiming I’ve unveiled a “novel” or profound idea, I’m not. I think no matter which framework makes the most sense to you, it ultimately comes down to what you do when the time comes to make a choice: do you say to yourself “I value my physical health”, but choose to put in an extra hour or two of work instead of exercising? Do you say to others “mental health and homelessness are serious issues we should all care about”, but refuse to make eye contact with that homeless woman you’ve seen every so often on the subway?

I’ll be honest, I’ve definitely done those things myself and recognize that nobody’s consistent 100% of the time. I’m not trying to be one of those guys on the internet that tries to hypocritically judge others for doing what we all do, or neatly package nuanced issues into easy-to-digest headlines:

But I am going to be one of those guys that says even though learning about the issues and framing our values is great, I think following through on those promises to ourselves, especially when it would make us uncomfortable is crucial for actual change. Underrated-philosopher Mike Tyson said it best:

Everybody has a plan until they get punched in the mouth.

Part of the reason its taken me so long to write up this first issue is that I found myself searching for the answer ✨, like some all-encompassing diagram or insight that sort of explains all of it: the paradoxical nature of breaking away and why it is so damn hard to define our own values. I think we just need to come to terms with the fact that there is no “answer”. That changing ourselves is more of a byproduct of the micro-decisions we make everyday and the stories we tell ourselves about what they mean as we look back.

Moving Forward

Because this issue is already getting pretty long, I'll leave anyone that's made it this far with one big idea about wealth that captures why I think it’s such an important thing to understand: wealth is an instrument of change.

For better or worse, money is deeply entrenched into the fabric of our society. Those that criticize wealth both underestimate the effects of the negative feedback loop and fail to realize that money is needed to do good things to begin with. While not the only avenue for change, wealth is what enables us to have our stories heard, not just told, and to have a lasting influence on the social systems we know could be better.

I’m by no means, anymore knowledgeable than the next guy willing to read a bunch of psychology papers and write a newsletter. That said, I hope some of the insight that I came across, shared and will continue to share over the coming weeks here will prove useful — with a more in-depth look into what motivates us to stick to our values, deep dives into the different pillars of wealth (debt, personal finance, investing), and a vision for re-defining how wealth is created.

— Jeff

The Problem

First-generation college students all over the country graduate into the real world and face a new set of problem that revolve around one concept: wealth.

How do I manage my finances? What if I don't love my "good job"? How do I support my parents financially and emotionally? I truly believe that understanding wealth — in every meaning of the word — is a crucial piece to that puzzle.

A Solution

Second Generation aims to capture my evolving thoughts on wealth with first-generation college graduates in mind — from developing healthy personal finance habits to understanding the tech industry’s role in shaping the wealth-knowledge gap.

This newsletter will always be a work in progress, but I hope you’ll join me on this journey.

Stay Tuned!

— Jeff

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