2023 Financial Samurai Year In Review: More Fails Than Wins


I’ve been writing year-in-review posts for over a decade now. It’s a rewarding way to document what went well and where I can improve. While 2023 brought more failures than wins, being alive and healthy fills me with gratitude.

My theme for 2023 was “Back To Easy Living.” After an exhausting pandemic period, I aimed to relax more this year. However, especially in the last quarter, 2023 was anything but calm. I felt more stressed than I would have preferred.

For the first time since 2011, it seems like I aged twice as fast. The skin on my face feels like it’s running away.

Let’s break the details down into my annual categories – Health, Wealth, Family, Financial Samurai, and X-Factor. I hope you will share some of your wins and losses for the year as well.

2023 Year In Review: Health

I’ll highlight my 2023 goals and put them in quotes, for clarity. Then I’ll comment on what happened.

Even though I’m just quoting myself, I don’t want to be accused of plagiarism like a certain Ivy League president. As a Financial Samurai, I want to uphold the highest standards. If I don’t, I may bring dishonor to my family.

1) Stay the same weight

“I will stay the same weight of between 167-168 pounds all of 2023. The ideal weight chart says I should be between 151 – 163 pounds at 5’10”. But screw that! I’m not a teenager any longer.”

2023 result: I gained about four pounds up to 172 pounds, then went back down to 167-168 pounds after deciding to eat less in 3Q. Now I’m back to about 170 pounds. Therefore, I failed my goal. For reference, I’m 5′ 10″ tall.

I blame my failure on my decumulation experiment with food! For three months, I was a glutton. Then I got sick of eating calorie-dense foods so I went the other way. But then the holidays got to me.

Although I can no longer grace the cover of Men’s Fitness magazine with my shirt off, at least I haven’t gained too much weight from 2022. Nothing like a good sweat and long bathroom session can’t fix.

2) Stay injury-free

“At 45, my mind is often stronger than my body. I think I can play five days a week but I really can’t without pain or a heightened risk of injury. Everything from my heels to my hips to my shoulders aches after playing sports.

I will stretch for five minutes before and after every match. A foam roller will be my new best friend. Every off day I will soak in the hot tub. Finally, I will use elastic bands to strengthen my shoulders four times a week.

Getting injured would also prevent me from playing with my children and I can’t let that happen at their current ages of 3 and 5.”

2023 result: I injured my back twice. As a result, I failed.

The first time was when I was sitting cross-legged on the floor signing books for over an hour. For my newsletter, I did a 280-book Buy This Not That fundraiser for the residents of the devastating Maui fire. I signed and mailed a book to every subscriber who donated $65 or more to the Maui Strong Fund or a similar charity. Overall, we raised over $46,000. Great job y’all!

After an hour, my lower back just gave out and I could not get up. I had to call my wife to carry me to the couch. I attribute this freak accident to the tremendous sadness I felt for the fire victims while I wrote little notes and signed each book.

The second time I injured my back was at 8:15 pm on a cold night playing pickleball. On the very first point, I ran forward to get a dink and jammed a nerve between my lower vertebrae. I couldn’t walk the very next day. Warming up is important! I have not been consistently stretching or using my foam roller at all.

2023 Year In Review: Wealth

1) Follow the first rule of financial independence: never lose money

“I think we’ll be lucky (~40% chance) if the S&P 500 closes the year in the 4,000 – 4,250 range. With ~30% of my net worth in public equities, a 10% decline will drag down my net worth by 3%.

I expect the national median home price to decline by about 8% in 2023. This will result in a 4% drag on my net worth given real estate counts for about 50% of my net worth. However, I’ve already priced my real estate portfolio about 10% below market prices.

Based on the above expectations, my realistic downside scenario is a 7% decline in net worth.

A realistic upside scenario is that stocks close up 10% to 4,235, resulting in a net worth increase of 3%. Meanwhile, I think the realistic best-case scenario is for housing prices to stay flat. As a result, my best-case realistic upside scenario is a 3% increase in net worth.

2023 result: Surpassed expectations. The real estate that I own is likely down around 5% in 2023, dragging down my net worth by about 2.5%. Meanwhile, the S&P 500 is up over 24%, which pulls my net worth up by about 7%, for a net gain of 4.5%. Add on savings from active and passive income sources, and my net worth is up around 8.5% after a flat 2022.

Given I was expecting my net worth to be down 3% in 2023, I feel like a 8.5% gain is a big win. I’m just glad we didn’t go down the abyss once SVB and First Republic started going under in March 2023. That time period reminded me of when Lehman Brothers, Washington Mutual, and Salomon Brothers went under in 2008. That was traumatic!

My goal after fake retiring in 2012 has been to increase my net worth by 5% – 10% a year with minimal volatility. Therefore, I’m within the target for 2023.

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2) Increase passive income by 5% to $400,000

“I expect CPI to go below 5% by year-end, if not by July. Hence, my real passive income goal is to beat the average inflation rate for 2023.

The rise in interest rates helped boost our passive income by 10% to ~$380,000 in 2022. As interest rates come down and my Treasury bonds mature in 2023, I’ll need to find new ways to generate more passive income.

My hope is that by mid-2023, there will be more private real estate deals at lower valuations and higher yields. If so, I will roll hundreds of thousands of dollars into private real estate funds and deals from my expiring short-term Treasury bonds.

In addition to boosting investment yields through real estate, my plan is to reinvest 80%+ of all online income into stocks, real estate, and private investments.”

2023: Fail. Things were going in the right direction, especially thanks to higher Treasury bond yields. I kept dollar-cost averaging into private real estate funds and public real state ETFs like VNQ.

However, I decided to buy a forever home in 4Q 2023, which used up a lot of my capital. As a result, I’ve lost years of passive income progress. I’ll write about this situation in more detail in an upcoming post.

3) Boost spending by 20%

“We spent about $240,000 a year after taxes in 2022, which is equivalent to about $320,000 a year in gross passive income. Therefore, we plan to boost spending by $48,000 to $288,000. $288,000 equals $384,000 in gross passive income. In other words, we plan to spend all of our annual passive income in 2023.

Although we are happy with our current spending, I’ve started my decumulation phase given I’ll be 46 in mid-2023. Losing lots of money in the stock market in 2022 has made spending more money in 2023 easier. Given I expect another difficult year, I’d much rather spend my money than lose it.”

2023 result: Fail. I spent about $18,000 more, compared to my target of $48,000. I’ve found it very difficult to spend more money than I’m used to. For example, I tried my best to spend more money on food, but only ended up spending about $3,000 more compared to the $12,000 target. We also haven’t taken family vacations that required spending $12,000 more. I kept up my donations at a similar rate.

4) Beat back real estate FOMO

‘If my expectations are correct, there will be more housing deals by mid-2023. By then, prices could be down 10% and mortgage rates could be back down to 5% for the average 30-year fixed. The temptation to upgrade to a nicer home will be great!

But just like how eating a fifth slice of key lime pie is bad for your physique, buying a fifth property in San Francisco is bad for my sanity. Being a landlord decreases the quality of my life. Something always comes up. Plus, my wife doesn’t want to move and I need to appreciate what we have.”

2023 result: Fail. My expectations were indeed correct for home price declines, not so much the mortgage rate. A dream property I had been eyeing in May 2022 came back off market at a lower price. The agent just contacted me directly. After months of negotiations and 75 days in escrow, I finally closed in 4Q2023. I feel good knowing that at least we lived in our other property for 18 more months.

Ever since I was in middle school in Kuala Lumpur, visiting a rich friend with a mansion in the hills, I’ve loved real estate. To be able to live well and provide for my family are two of my favorite things. Alas, now I’m paying the price with more expenses.

2023 Year In Review: Family

1) Give as much attention to my daughter as I did to my son

“My intensity towards childcare has waned. Part of the reason is that I’ve already read all the books, watched all the videos, and know what to expect. Another reason is due to an increase in laziness after being a stay-at-home dad for five and a half years already.

Now that our daughter is three, it’s time to focus again! Her memories will form and I’ve noticed, just like our son, she now wants to spend more time with me. As a result, I’m going to do just that.

To be specific, my goal is to spend two hours in the morning with her, two hours in the afternoon, and 30 minutes in the evening. She will be attending preschool two days a week.”

2023 result: Success! I stepped up caring for my daughter to the point where I no longer feel any dad guilt.

One of my wins was convincing my wife it was time for our daughter to learn how to swim. Given her sensitivity to chlorine, prior trips to the pool would result in her waking up itchy with rashes in the middle of the night, disrupting everyone’s sleep. We took a break for many months and then decided to try again using Aquafor, an ointment-like substance, beforehand as a barrier to protect her skin.

Other frequent trips with my daughter included taking her to the carousel in Golden Gate Park, Stowe Lake hikes, endless playground, the zoo to ride the steam train, acrobatics, beach on warm days, and painting. Every trip was between 2-4.5 hours long, which gave my wife much needed time to do her own thing.

2) See my parents twice

“It sounds kind of sad to have a goal of seeing my parents only twice a year. But they live in Honolulu and I live in San Francisco. They made a big effort to visit us in 2022. I hope to convince them to visit for a week again in 2023.

I will also fly out to visit them for a week at least once this year, either by myself or with family. We still haven’t taken the kids on an airplane yet. But maybe we will this summer!”

2023 result: Semi-fail. I flew my parents, my sister, and her boyfriend out in June. However, I could not convince my parents to fly out again. When I asked if I could come visit them in Hawaii, they declined. How sad.

At least I regularly call and e-mail my dad about four times a week on average. I’m not sure how to convince my parents to see their grandkids and me more. But I’ll keep trying. I never thought this would be one of the toughest challenges.

3) Teach my boy how to swim.

“I looked into private lessons and they cost $80 for 20 minutes! WTF. The swim school said it will take a child roughly 24-48, 20-minute lessons to learn how to swim. Hence, we’re talking $1,920 to $3,840. Actually, adding up the total cost doesn’t sound as bad as the 20-minute rate.

Given we don’t have a pool and I can’t seem to ever get a spot at the much cheaper group lessons, I may have to go this expensive route. Regardless, I will definitely give my boy lessons when we go up to Lake Tahoe.”

2023 result: Success! I skipped private lessons and taught my boy myself over multiple 1-2-hour sessions.

While in Lake Tahoe in June, my boy finally got the courage to take off his floaty. When we got back to San Francisco, I was determined to get him to swim, so I signed us up for weekly one-hour rec swim sessions at the Pomeroy Center. We went every week and on July 14, 2024, I finally let go and let him swim to me. We’ve been swimming three times a month on average for an hour each time since.

2023 Financial Samurai year in review - taught my bow how to swim
A month after he learned how to swim, he mustered up the courage to dive 10 feet down to grab some plastic octopuses at a friend’s vacation property

Emboldened by my son’s ability to swim and my teaching results, I decided to make it a goal to teach my 3.5-year-old daughter how to swim by year end too. She’s swimming now but still needs to learn how to come up for air.

4) Be better aligned on parenting styles.

“Although I think I’m nice, I’m sure my wife would say I have a more “tough love” type of parenting style. She, on the other hand, has a more gentle parenting style. I’d like for us to narrow the gap.

One of my greatest fears is raising soft kids who cannot launch as adults. If we coddle our children too much, they may become weak. If a perpetual safety net removes their fear of failure, they might end up always being dependent on us.”

2023 Result: Work in progress. I still think we’re still too soft on our kids. They have too many toys, eat too much good food, and are not as appreciative as I would like them to be. But our daughter just turned 4 and our son is 6.5, so there’s still time.

I made both of them work for two weeks with me on a laborious landscaping project. I also got both of them to help paint an outdoor hand railing, a deck, and the walls of a garage at our previous home. Hopefully, they will remember this manual labor, realize that nothing lasts, and better respect property.

2023 Year In Review Financial Samurai - Teaching daughter to paint outdoor hand railing black
Got my daughter to help me clean, sand, and paint an outdoor handrail

2023 Year In Review: Financial Samurai

1) Publish three times a week on average, not four times

“I said I’ve published three times a week on average since 2009. But in reality, I’ve averaged closer to four times a week due to my free weekly newsletter.

My newsletter usually comes out on Sunday morning, which means I often spend Friday night, Saturday morning, or Sunday morning writing it. This also means I can never fully take the weekend off. This will change in 2023.

I will either publish two posts a week and one newsletter or publish a bi-weekly newsletter going forward. I also need to update ~200 posts, so I will republish them over the years as well.

For my 14th year operating Financial Samurai, I need to take things down to rejuvenate the mind. My eyes are also getting more easily fatigued, which means less screen time.”

2023 result: Fail. I kept my three-times-a-week publishing cadence plus wrote one newsletter a week for 52 weeks in a row. Sadly, there were many days when I didn’t want to write. This is a sign that my enthusiasm for writing is fading. The decline also has to do with increased eye fatigue.

Here are my best posts and podcasts for 2023. Overall, I wrote 156 posts and updated 400+. I also updated the design of the site and the internal guts for more reliability. That cost me $2,000.

2) Write 25% shorter posts

“Thanks to social media, fewer people read great personal finance books and long-form content online. Hence, as a writer, I should evolve with the times if I want to attract a younger audience.

Writing shorter posts also reduces my workload, as well as my father’s and wife’s workloads as editors. I will get to the point quicker.”

2023 result: Fail. I didn’t shorten my posts, which probably lost readers who are accustomed to sound bites, only reading titles, and watching TikTok videos. When I write, I feel bad not going deep into financial and life topics because they are so important. I’ve also got too much money at stake to not be thorough.

3) Record at least 30 more podcast episodes

“In December 2022, I came up with the practice of recording podcast episodes in my car after dropping off my son at school. The acoustics are good enough and my thoughts are fresh. I also wanted to be productive before playing sports.

Releasing podcasts is a fun way to connect with readers and share nuanced thoughts about my latest posts. I often incorporate reader feedback, which comes in the comments section after posts are published.”

2023 result: Success! I’m proud to have recorded 64 episodes, more than double my goal. In addition, I finally figured out how to use recording software to interview other people. You can subscribe and review my podcast on Apple or Spotify. Your reviews are appreciated.

X-Factor Goals For 2023

An X-factor is something out of the ordinary that can bring you joy, meaning, and/or income.

1) Become a 4.5-level pickleball player

“I’m addicted to pickleball. It is a sport I see myself playing through my 70s, if I live that long. After several winning years at 4.0 tennis, I got bumped up to 4.5. Then at the age of 39, I got bumped up to 5.0 and stayed there for five years until 2022. The progress was exhilarating! I’d like to do the same with pickleball by playing a tournament and getting to 4.5.

2023 result. Fail. After picking up pickleball in October 2022, my enthusiasm for the sport waned by June 2023. The public courts got too crowded and the private courts became very cliquey. I’m probably about a 4.25-level player.

When I was younger, I found satisfaction in winning league titles and tournaments. Now I find satisfaction in just knowing I’ve achieved a high-enough level to beat most players I think I should beat. My main goal is to have fun, get some exercise in, and not get injured.

2) Write another book

“Although writing a traditionally published book is extremely hard, I’d like to do it again. My first book, an ebook entitled, How To Engineer Your Layoff, has helped thousands of people negotiate a severance. Being able to walk away from a job you no longer like with money in your pocket feels like winning the lottery.

My second book, a traditionally published book entitled, Buy This, Not That, went on to become a Wall Street Journal bestseller. I think it has a good chance to become a classic personal finance book that will stand the test of time.

Publishing a physical book with a reputable publisher has given me a tremendous amount of unanticipated satisfaction. My children are proud to see my work. I realized having some status is nicer than being a nobody. Helping readers gain financial courage is gratifying. Finally, it’s always wonderful to create something from nothing.

Now I just need to hammer out a new book deal.”

2023 result: 60% of the way done. In March 2023, I ended up hammering out a two-book deal with Penguin Random House. I did my best to negotiate a good deal without an agent, but I fell 10% short of my ideal amount. Perhaps the end amount I receive will be the same since agents earn a 15% fee.

It is partially due to the responsibility of writing a second traditional book that I couldn’t relax as much as I wanted in 2023. Some people write books full-time for a living. With childcare responsibilities and writing and podcasting on FS, I’m busy enough.

Buy This Not That Book Reviews

3) Make one good new friend

“Making friends seems to get harder as an adult. However, I’d like to make at least one good new friend from my son’s school or through sports.

Pre-pandemic, I used to go to a lot of fintech and startup meetups. Pre-kids, I used to go to conferences domestically and internationally. I’m not lonely, but I would like a better social life to make up for 2020-2021.

2023 result: Semi-fail. I’ve met plenty of new friends through pickleball, probably around 15 total. However, none of them became good friends. It takes a lot of effort to create deep bonds.

Despite a lack of deep friendship, I’m happy I can go to four different pickleball locations in the city and know someone. It’s more fun playing with people you know and of a similar skill level.

4) Maybe get a job again

“Another X-factor for 2023 is getting a full-time job again. My daughter is going to school three days a week and I have more time. It’s really hard to stay retired once you retire early!”

2023 result: Fail and I’m glad! If I found a full-time job, I wouldn’t have been able to fulfill my goal of spending as much time with my daughter as I did with my son. A rebound in the stock market also decreased my anxiety about returning to work.

I tried looking for a full-time job in 2H 2023, but I couldn’t find one so I put my search on pause after a month. It’s been harder to find a new job that pays well than I had expected. For those who are thinking about retiring early, I highly recommend keeping your skills and network fresh. You never know when you’ll want or need to go back to work.

2023 Was Better Than Expected

I started writing this post feeling a bit disappointed reflecting on 2023. However, reviewing my photo journal and remembering everything that transpired this year filled me with gratitude.

The stock market performed better than expected, giving my family more quality time together. We also moved into our forever home in the fourth quarter.

Most of all, I feel thankful that my closest family members remain alive and healthy. I cherish and appreciate life more with each passing year.

I experienced more stress this year than I would have liked due to taking on new projects – writing another book, learning podcast interviews, and buying a home. These opportunities caused me to invest more time, make more mistakes, and feel more pressure.

My tendency is to take on even more whenever opportunities arise because I dislike feeling regret. However, I’m pleased with living another year with focused intention.

Next up: goals for 2024!

Here’s a podcast version of my 2023 year in review with different nuances.

Reader Questions

How did your 2023 go? What were some of your successes and failures? Did anything surprise you positive or negatively this year?

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter and posts via e-mail. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. 


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