Financial Review 2022: Losing Money, Portfolio Changes, and Financial Therapy


written by oz chen

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The following, just like anything I write on this blog, is only information and education, and not to be confused with advice of any sort.

It’s cringe-worthy to read last year’s financial review because all of 2021’s gains have been wiped out over the course of 2022.

Top line: My portfolio was crushed by crypto implosions. And high growth tech stocks funded by free money (near 0% interest rates) got demolished in 2022 when rates got cranked up.

I’m haunted by what Morgan Housel said in Psychology of Money: “The correct lesson to learn from surprises is that the world is surprising.”

In this year’s financial review, I’ll start with a big teaching moment, then do a deep dive into my portfolio + investing lessons for the nerds, and end with financial reflections. Jump links to each section here:

The psychology of losing money

In May 2022, a massive crypto project called Terra started to fail. A bunch of people had their money invested, directly or indirectly, in Terra’s stablecoin called UST. This coin was supposed to be backed 1:1 to the dollar, but it lost its peg.

That was the first wave of losses. Then Voyager and Celsius, two companies where I also held crypto, were exposed to the Terra failure. In the first wave I lost money. The second wave is being sorted out in bankruptcy courts, but my funds (and millions of other customers’) are held up and may end up in complete loss.

Tl;dr? I should have diversified more and earlier. But I’m glad this didn’t sink my whole portfolio and I’m glad I’m learning this lesson now at 33 instead of near retirement age.

I detail more in this post: what I learned losing more than six figures worth of money.

This event sets the context for my current portfolio allocation and the tone for the rest of this post.

Money coaching and financial therapy

Against this backdrop of financial loss and volatility, I’ve developed an appreciation for financial therapy. How’s that, exactly?

My clients fill out a coaching form that includes a question about their biggest money worry. Within the first 10 minutes of coaching, I quickly uncover that the issue is always deeper. What starts as a simple face value question (about investing or how much debt to pay) is actually a mix of emotions, limiting beliefs and financial baggage that deeply affect how my clients think about money.

I help them get unstuck and the result is feeling much better about money.

I’m also getting a picture of the type of ideal client I want to serve. These are people who value spirituality, self improvement, and philosophy. Basically, clients who are open-minded to the softer side of money that often gets overlooked, but actually makes the most meaningful difference.

If this is you, check out my coaching page here.

When I was writing down goals for 2023, I asked myself: “Are there any 30 day challenges I’d like to take on?”

The idea of creating a course/workshop every month for the entire year really stirred me. Look out world!

How my portfolio changed + investing lessons learned

Here’s a quick look at my current allocation. I intentionally exclude the value of my primary residence because 1) I aim to hold onto the house forever and 2) It doesn’t factor that much into how I make investments going forward.

Assets% of Net worth: No Real Estate% of Net worth w/Primary Residence
All stocks61%38%
Company Equity27%16%
Alts + Crypto29%18%
Cash & cash equivalents10%6%

Most of my wealth are in stocks, particularly retirement accounts and company stock. Overall, crypto decreased from over 61% of my net worth to ~24% today.

Given these massive portfolio changes, here are the investing lessons I learned in 2022:

Macroeconomics lessons: what happens when money is free
When interest rates are nearly 0, the cost to borrow money becomes free. That incentivizes a few things: more borrowing, more risk-chasing, and less desire to put money in savings/bonds that barely pay interest.

Super low interest rates incentivize investment in higher beta (risk) investments like growth stocks and crypto, which can quickly inflate as we saw in 2020-2021.

This environment makes it hard to determine the intrinsic value of assets. Is this stock a truly good business, or has it inflated because it’s become funded by free money? To cloud the picture even more, rising asset prices attract attention and create a sensationalist investing environment. No one wants to be the “dumb one” in their friend group who doesn’t get in on the next shiny stock.

Eventually, the market balanced out this dynamic.

Image credit: Polen Capital

“In the short run, the market is a voting machine but in the long run, it is a weighing machine.” —Warren Buffett

My personal lesson? I’ve become more aware of interest rates and how they change my money behavior. With low interest rates, I saw myself incentivized to buy individual stocks (vs index investing), and now with higher rates I’ve been incentivized to buy bonds and save money.

I’ve also learned that I’m really wired to invest for the long term. That’s a nice way of saying I’m terrible at getting out of investments on time.

Bad timing and learning the right lesson

I’m bad at getting out on time and even less so on a dime. When Terra started stumbling, I didn’t react quickly enough pull funds out of Stablegains. Even after losing money in Stablegains via the Luna collapse, I thought Luna’s failure was as an isolated event.

This Bankless podcast (Nov 18, 2022) details how the crypto house of cards got built and how it imploded. It is a crazy web of firms passing risk onto other firms in a sick incestuous cycle.

I couldn’t have seen that this was a systemic issue with crypto, and consequently didn’t pull out funds in Celsius or Voyager on time. I nearly did not withdraw funds from Gemini’s Earn program (powered by Genesis) in time, which I consider a lucky break. So I’m 1 for 4 🤣

The pull game out: bad for contraception, bad for investing.

So I’m left with the question: “What are the right lessons to learn from this?”

  • Do not trust things that offer insane APY: even if the interest rate is “real” for a time, I should not expect it to last, and I should not expect myself to withdraw funds in time if the investment is a sham. I learned firsthand the phrase “if it sounds too good to be true, then it is.”
  • Risky things are actually doubly risky: at face value, alternative investments like crypto are already risky compared to boring bonds and index funds. The hidden danger is that when the market goes south, risky assets are the first place where people want to pull money out of. When this happens, those already-risky assets fall even further. This isn’t just crypto—plenty of tech stocks are down 75%+ from the year before.
  • Diversification is key: While I’ve lost money, I’m glad that I diversified in 2 ways: I held my crypto across different accounts, and crypto was never my entire portfolio. I could lose it all and still make my mortgage payments. Part of my new diversification strategy is to self custody most of crypto in wallets.

Counterintuitively, I can’t imagine a better time to invest.

This is a common misunderstanding: people see all the scandals and blame it on crypto, but assets like Bitcoin and Ethereum weren’t the scam. It’s the centralized crypto organizations like FTX that posed as overly confident while they were actually mismanaging user funds. Business in the front, ponzi in the back.

Similarly, when firms like Lehman Brothers led 2008’s financial crash, it’s important to realize that THOSE companies were the problem—not the entire stock market.

Consequently, right after 2008 (the low) was the best time to buy into the stock market.
Consequently, I still buy index funds and crypto (50/50 Bitcoin Ethereum) every week.

A simple portfolio is a strong portfolio

As part of my year-end financial checklist, I logged in brokerage accounts to do some tax loss harvesting. I was shocked to see the names of several companies I had bought in 2020 and 2021 – and forgot I own.

I sold these stocks. My logic: “If I didn’t remember to sell these when they were down, I’m not likely to remember to sell these when they’re up either. Plus, even if these stocks make an unlikely 10x gain, the amount of shares I hold wouldn’t make a material difference. Better to put it in something I believe in, like indexes.” And might as well capture a loss on names I no longer care about.

A simple portfolio is easier to manage and reduces risk. A complicated portfolio reflects FOMO, is hard to manage, and requires better timing (which I already proved I’m bad at).

It’s no surprise that I’ve developed a deeper appreciation for retirement accounts. The 401K is a mind hack – due to the natural restrictions in most 401Ks (only index funds), they discourage trading and stop investors from otherwise riskier, bad investments. The 401K is a hedge against bad risk. The 401K is like a pantry that only has healthy food in it. Long live the 401K! Ok…I’ll stop.

New investments

As a result of rates going up and the stock market going down, my money has flowed a lot more into bonds and buying indexes at a discount.

  • Series I Bonds: I will most likely continue to allocate $10K a year into these high yielding, government backed bonds. Read my article about it.
  • Treasury Bonds: Buying 26 week bonds earning 4.5%+ interest. I pick this time horizon because I may need those funds for a housing project, and the rates are purported to hold over the next year.
  • Fidelity Zero Cost Funds: These are index funds that charge ZERO expenses. I’m parking a lot more of my money in FNILX, which is Fidelity’s S&P 500 equivalent.

Three new investment learnings

Asset allocation: where you hold your investments matter because of taxes. When investments held inside retirement accounts produce income you don’t have tax consequences from how your investments perform in retirement accounts, it’s more “tax efficient” to hold investments that tend to produce regular income inside 401Ks and IRAs.

I’ve reallocated my portfolio so that REITs, bonds and higher dividend indexes sit in retirement accounts while regular stock indexes sit in my normal brokerage accounts.

FIRE assessment: I did some back of the napkin math and realized that some of my retirement accounts as they stand would reach $2 million by the time I’m at retirement age. Assuming the morbid calculation of living up to 20 years after the traditional retirement age of 60, that’d be $100K a year to spend until I’m 80. That seems like enough, especially as I plan to continue maxing out my retirement accounts.

The realization: I want to be investing a LOT more in non-tax advantaged brokerage accounts and think more about the Roth conversion. The first reason is that I plan to “retire” much earlier before 59.5, and I’d like to withdraw that amount without a penalty. Something that’s crazy about capital gains is that you can sell ~$44K/year worth of stocks to fund your life and pay no tax.

The Roth advantage is being able to withdraw contributions penalty-free, which is useful if I need to use those funds well before 60. This might be the first year I switch from traditional 401K -> Roth 401K and consider doing some backdoor Roth conversions.

RSUs and tax loss harvesting
I was surprised by my April 2022 tax bill when it came to my vested RSUs – restricted stock units that turn into actual stock.

The lesson learned: most stock-granting companies automatically withhold taxes at the lowest bracket (22%). Come tax time, I had to account for the difference between that and my actual tax bracket, which resulted in a surprise bill. I also learned a lesson about wash sales. There are so many little lessons that I’ll put it together in a guide. #notfinancial advice

Favorite finance books and media

When I look at my favorite financial books, the majority are from bloggers who became authors and podcasters:

Just Keep Buying by Nick Maggiulli, famous for his OfDollarsAndData blog

  • This book answers most common personal finance questions but in a refreshing way—completely backed by data. Nick Maggiulli is a genius at this form of data storytelling.

Buy This, Not That by Sam Dogen, famous blogger of Financial Samurai

  • Like a personal financial planner in book form, with an orientation towards FIRE (financial independence).

Rich AF by Amanda Frances, famous money influencer

  • This book is inspiring AF. Talks about money attitudes and manifesting wealth in a surprisingly accessible—and poetic way.

Quit by Annie Duke

  • The only personal psychology book on this list, Quit is such an important book about knowing when to quit on time.

Notable podcast mentions: I Will Teach You To Be Rich podcast heavily influenced me towards money coaching and The Healthy Love and Money pod is the best I’ve found on financial therapy. Hats off to the Bankless podcast for the best reporting and helping me stay sane during the crypto crashes.

Financial reflection questions

Harvard researchers found that employees who spent 15 minutes reflecting at the end of the day performed 23% better than those who did not reflect.

So I end this year’s financial review with 5 questions:

  1. What was your favorite purchase for yourself this year? For someone else?
  2. Name your top 3 money wins of 2022.
  3. What’s the biggest money lesson you learned this year?
  4. Would you do anything different about money next year to feel more prepared?
  5. What is a big money goal you want to work on for 2023?

Here are my personal answers:

1. What was your favorite purchase for yourself this year? For someone else?
For me: Iceland + Madeira trips were BIG highlights. Joining the local rock climbing gym = so good for health.
For others: hosting cocktail parties and making donations.

2. Name your to 3 money wins of 2022
One: Moving to Long Beach
Two: Diversification helped me not lose ALL my money during market meltdowns
Three: Coaching over a dozen clients to get clarity on their money problems!

3. What’s the biggest money lesson you learned this year?
That I am not my money. After losing money in crypto + the bear market, I revisited what a rich life means to me.

My Rich Life is mostly in my control: managing stress, taking breaks, meditating, and not overthinking purchases below a certain dollar figure.

4. Would you do anything different about money next year to feel more prepared?
Work with tax & financial planner for more complicated financial situations, which includes plans for selling stocks & RSUs in a tax-efficient manner.

5. What is a big money goal you want to work on for 2023?
Fund my creativity: more time and $ spent on coaching training
Community: challenge myself to connect more frequently and invest in social events


These money reflections can help me gain clarity and a sense of direction over my financial life.

If you try out some of the questions, please DM me @ozbornready or email me at

Big high five if you read through this financial review. I hope you learned as much as I did from reflecting on the past year of money.

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