The other day, I realized it’s been 10 years since I came to California.

The San Francisco Bay Area is now the second longest place I have ever lived besides my childhood hometown of Houston, Texas.

It got me thinking about how much has changed since I arrived in California.

I wanted to share a snapshot of what my world looked like when I first got here vs. what it looks like now.

2009

I came to California single, early in my career, ever optimistic about the future, and feeling like I had reached the promised land.

The world was in the grips of a huge recession, but I was determined to make things work no matter what because I felt the Bay Area was going to be my permanent home.

I was moving here for good.

Career:

I had just quit management consulting at McKinsey in New York, my first real job after grad school.

I worked there for two years and learned a ton of functional skills (I started that job with no business experience).

By 2009, the financial crisis had hit the firm hard and many projects dried up.

But I felt optimistic about the future because I was moving to California to take a private equity investing job at a firm in Palo Alto.

I also studied nights and weekends for the CFA program (had already passed 2 levels, just started level 3) because I wanted to increase my finance/investing knowledge and open up new career options down the road.

I spent that summer actually enjoying New York (for a change), compared to the long consulting hours I had been working which didn’t allow much time to enjoy the city, build relationships outside of work, etc.

I remember spending that summer getting off work at a reasonable hour, going to free plays and concerts with friends in Central Park, checking out new neighborhoods and restaurants, and even taking a July 4 road trip to Maine with some buddies.

It was one of the best summers ever.

Finances:

The financial crisis had wiped out one-third of my meager savings just a few months earlier.

That stung badly and taught me how hard it is to invest profitably…especially when the markets are gyrating severely.

I didn’t know how to manage my portfolio back then; I had bought into several oil mutual funds which got hosed during the market meltdown.

When all the dust settled, I had a couple thousand left in a checking account and (I think) ~$22k or so still left in my Roth IRA. I had an employer 401k which I had maxed out for a couple years, but that took a severe beating during the financial crisis.

My net worth was still negative because I had 6-figure student loans.

Health:

I had no notion of how to live/eat a healthy lifestyle. Ironically, though, I recall feeling actually pretty fit.

For one, I was still young.

Two, it was New York City, and unless it was raining, I walked everywhere – both out of enjoyment and because I was too cheap to pay for a subway ride (and way too cheap to take a taxi; no Uber back then).

I remember working really hard at the firm until early summer and, other than walking around the city a lot, I didn’t get much exercise (I regret this now).

At work, I often ate expensive but not healthy takeout dinners on the firm’s dime after working long hours.

Family & Happiness:

I didn’t have my own family in 2009, or even a significant other.

I dated someone that summer and it felt like it *could* become a thing, but she was heading back to school far away and I was heading to the West Coast.

It wasn’t pragmatic and it didn’t work out.

Overall, I had spent the prior couple years mostly working at the office and traveling for work.

I didn’t invest nearly enough time back then meeting new friends or dating.

I regret this now because I must admit I don’t have a great deal of warm friendship memories from that time in New York.

I was very career focused back then and didn’t appreciate enough how spending a lot of time to build and maintain strong friendships is so critical to your fulfillment and overall happiness.

My best memories are from that summer just before I left, hanging out with friends old and new.

All these years later, those are the memories I carry most fondly. I remember far less about the long days in the office.

I wish I had chosen a better balance of priorities and spent more time just enjoying my late 20s in New York, building more/stronger connections and friendships and stressing less about the “next career move.”

2019

A decade later, I now have my own family and baby girl (and multiple mortgages). I would say I have changed a lot and become a lot more pragmatic.

California also changed greatly over the last decade.

It’s still a terrific place to live but I no longer feel it is necessarily the promised land.

We could live here for good, but we don’t have to…and, given our priorities in life, it’s likely we won’t.

Career:

I am definitely not early in my career anymore. Over the last 10 years, I worked in several industries (consulting, private equity, tech), but I have been in tech for most of that time working as a product manager.

I’ve learned some things….

Even though the demand for tech knowledge workers is strong and well-paying jobs seem stably plentiful in the industry as a whole, tech is a very challenging industry to thrive in.

My transition from finance to tech was the most challenging transition I’ve done. I came in with a business and legal background, and I can tell you that technologists don’t much like MBAs or lawyers.

Silicon Valley is also very “hits” driven and luck plays a gigantic role: being in the right place at the right time and meeting the right people.

If you joined companies like Facebook, Twitter, Dropbox, Pinterest, Airbnb, Snap, etc, just at the right time when they were in their infancy and obscure, boy did you make it.

You didn’t have to be stellar and you still hit the jackpot, even if you only stayed a couple years.

Luck drives a very wide range of outcomes in tech, yet most folks don’t get lucky.

At the same time, there’s a LOT of “churn” at companies…all of them. Despite what you may think about the industry, individual tech companies are anything but stable.

Roles and functions are so fluid with Brownian motion that you have to constantly be adapting and adjusting. You can never rest on your laurels…until you’re truly FI and never need to work again.

Age and gender discrimination are prevalant; you’ve probably heard about it in the news.

When you’re young, there are lots of potential paths and folks are more open to taking a bet on you. As you get older (and by that I mean, your late 20s and 30s), the tech industry becomes rapidly less welcoming.

The best way to keep career doors open in tech is to continually invest in upleveling your skills/capabilities, relationships and network, and industry insight/knowledge.

I’ll admit my own career has not gone as far as I hoped. Now, half a dozen jobs later, I’ve become far more pragmatic about my capabilities and limitations and what is still possible in my career.

I don’t think I’ll stay in tech forever but product management, which is really just general management + product design, is a really good skill and highly transferable.

Finances:

The last 10 years were an amazing bull run. You made money if you bought pretty much anything in 2009 and held it through 2019.

One thing I kick myself in the pants for is not buying as much real estate as I could afford from 2009-2013. There were some amazing deals back then which are now long gone.

If I had a do over, I would have bought either 2 more rental properties in the Bay Area or 8-10 in Phoenix, Austin, or Atlanta. Had I done that, retirement would have come a lot sooner.

While the numbers say I am already financially independent, I still feel compelled to make our margin of safety bigger…that’s why I haven’t totally thrown in the towel yet.

After 2008, I don’t take anything for granted: if another black swan event occurs, we need to be able to weather it without panic selling anything. Finding a fulfilling and lucrative career path after years of early retirement is not a realistic option. We need to build enough cushion now.

Unlike in 2008 when my wealth got sliced by a third, these days my finances are more diversified (and intentional). A decade of compounding + frugality + lack of material desire helped my assets grow very materially.

What helped: Articulating a clear framework and checklist process that I now follow methodically once or twice a year when managing my portfolio brought far stronger discipline and confidence and has taken the emotion/guesswork out of the equation.

Even just thinking and writing down in advance “if X happens, I will do Y with my portfolio” for as many scenarios as you can forecast is tremendously clarifying.

When X eventually happens, you’re not then making shit up on the fly while you’re emotional and not thinking clearly. Rather, you’re simply executing a playbook that you already rigorously considered at a time when you were thinking calmly and strategically.

Recently, I rebalanced heavily toward cash, since all indicators suggest a high likelihood of recession in the near future, and I want to be able to go shopping if things start dipping.

One important thing, really important, is that I found a spouse who is pretty aligned with me in terms of financial values.

That makes it easier to work together toward shared financial goals. It’s much harder to do this if you’re pulling in opposite directions.

We’re on the right path together and building passive income to diversify away from our jobs and reach early retirement, and that goal is within line of sight…

Health:

As I’ve gotten older, I’ve really come to appreciate that health is really the most important thing. It makes everything else possible.

There’s no point to working hard and achieving early retirement if you have to trade your health for it.

Taking care of yourself from a young age and staying fit and healthy is a LOT easier than trying to undo years or decades of bad habits and chronic aches after you’re older. Take it from someone who’s starting to feel those aches in the neck and back now!

Despite these small discomforts, I give most of the credit for my current personal health to my wife. She’s a lot more disciplined about diet than I am.

Before I met her, I ate poorly and didn’t take good care of myself. I still don’t do a great job, but she insists on better nutrition in our diet which probably adds years to my life!

She’s also more OCD about health (as a healthcare professional), and that’s good for our kid’s survival since I’m definitely less on top of this than she is!

My big wish is that we had more discipline and joint accountability about getting regular physical exercise…. This is an area we are both not good at, yet we know is critical.

It’s really challenging to carve out time to exercise when you’re both intensely busy professionals, and landlords, and side business hustlers…with a toddler at home.

One struggle I always have is that exercise is so boring. Whether you’re running or swimming or playing tennis, you’re not able to get stuff done even though your mind is constantly scanning through your task list.

At the same time, exercise time doesn’t allow enough mental tranquility and space to think strategically about anything that can move your business/life. You’re focusing on not running into things, staying in your swimlane, or hitting the ball, after all.

It’s kind of a mental dead zone where you’re constantly scanning your task list (if you’re able to think at all), yet not actually getting anything done…while at the same time not able to think and focus on anything strategic.

You could listen to podcasts but only if you’re jogging/walking.

Poll to readers: If you are insanely busy yet still able to successfully make time to exercise consistently:

1. what exercise do you do?
2. how do you reinforce the right mindset to yourself to prioritize exercise highly even when you’re tired and have little free time?
3. how do you handle the “mental dead zone” problem?

Family & Happiness:

I feel more content now than I did a decade ago.

I also feel really lucky about the important people in my life. In particular, I’m really thankful I met a terrific spouse. I feel we’re a good team together. We support each other as companions and best friends.

We both got very good educations and are generally healthy. We have good work habits, strong professional skills, and an aligned save/invest mindset.

Even though we were not born into families of means, we got a fair number of lucky breaks in life.

Many years ago, my wife said this thing which I remember vividly. I was talking to her about how, when you’re born into wealth, it’s so much easier to build wealth. You don’t need to depend nearly as much on working hard, lucky breaks, being scrappy, etc, because you can just use old money to make new money.

My wife clasped my hands in hers and said, “…We have each other. And we’ll build wealth with our own hands.”

It was a simple statement but its clarity and tenderness and truth really moved me. I still remember that moment all these years later.

She was saying: “We are together and that’s what matters. We’ll be fine no matter what. We won’t worry for money because we’re not afraid of hard work. We have strong values. And our definition of wealth is more than money – it’s us as companions.”

Well, we did build wealth with our own hands. With several million in assets now, a beautiful baby girl, and companionship and silliness between us…we are content and happy.

Isn’t that what it’s all for in the end?

What’s your story over the last 10 years?

Now I’d like to hear from you….

What did your career, finances, health, family, or happiness look like a decade ago?

What about now?

What were the big lessons you learned, the most satisfying triumphs, the major setbacks?

What would you have done differently? What would you have told your younger self if you could go back in time?

Leave a comment below and let me know.

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