March 1, 2024

Financial Samurai
Slicing Through Money's Mysteries
Published: by 23 Comments
Here in the San Francisco tech startup scene, we have a term called “the trough of sorrow.” The trough of sorrow refers to the sadness that comes after a setback or a big win.
After a setback, you’re tasked with finding product-market fit to survive given your company has a limited runway of cash. You may feel a combination of dread and emptiness. Instead of getting back up for the tenth time, it’s tempting to just accept defeat.
On the other hand, after experiencing the joy of a big win, there is often a question of what’s next? Sorrow can form because everything that comes next may never be as good. You may feel a combination of emptiness and disappointment.
What I’ve discovered is there is also a trough of sorrow that relates to one’s personal endeavors. Instead of experiencing incremental upticks in happiness, we go through these peaks and valleys due to our insatiable desire for more. Further, emotion is difficult to regulate.
The more effort you put into something, the more you set yourself up for disappointment. Therefore, to avoid the trough of sorrow, it may be wise to manage not only your expectations, but your commitment.
With everybody away on holiday, let me use this post to reflect on a funk I felt a couple of weeks ago.
One of the reason why I embrace the quiet quitting movement is because I’m burned out. After two-and-a-half years of pandemic life, it sure would be nice to take a break. But as a stay at home parent to two young children, there is seldom ever a break.
My biggest goal for 2022 was to “have more fun!” However, so far, I’m failing in this endeavor because I’ve been working too much.
Once the bear market hit, I felt like I had to work harder to just run in place. After all, the first rule of financial independence is to never lose money. When you’ve got family depending on you, the pressure to provide goes up.
Although it’s been enjoyable talking to some interesting new people during the marketing process of my new book, the process was also sometimes stressful and anxiety-inducing. Being on a schedule again felt foreign. And tackling live TV is not for the faint of heart.
I haven’t had this many meetings and back-and-forth emails with so many people since I fake retired in 2012!
But now I finally have some breathing room. While on vacation at Lake Tahoe, my first in over a year, I was able to identify the core reason why I haven’t been able to relax more.
My work ethic is built mainly on not wanting to feel guilt. I am burdened by a low threshold for feeling guilty if I don’t try hard because I don’t want let my friend Mark down. When I was 13, Mark died at age 15 and never got his chance.
Eventually, if we want to be happy or at least be less miserable, we all need to discover how much is good enough. Good enough can include money, titles, material things, children, awards, and accolades.
My blogging buddy Joe from Retire By 40 left a comment in my 10-year fake retirement anniversary post. Joe also retired in 2012 and has a son. We found our enough, but we are on somewhat different ends of the good-enough spectrum after leaving our day jobs.
He writes,
“It really depends on your personality. For me, I have no desire to work more or make more money at all. We have one kid and we have enough to send him to college. That’s plenty, IMO. I’m just not very driven.”
I love his attitude and I wish I had the same outlook when it comes to building wealth at this stage in life. Seriously, there’s no point sacrificing to make more money if you already have enough passive income to cover your living expenses.
Luckily, I enjoy writing and connecting with others online. It’s cathartic. If I didn’t enjoy writing, I would have quit a decade ago.
One of the reasons why Joe may be more relaxed is because his wife has continued to work for 10 years after he left his job. My wife, on the other hand, negotiated a severance when she turned 35 in 2015. Therefore, the pressure for me to provide may be higher. We also have two kids and live in San Francisco, a higher-cost city.
That said, even if Joe’s wife had also retired early, I’m not sure Joe would be as focused as me in building more wealth. He simply feels like he has enough, which makes him a very wealthy man.
Because I feel guilt more easily, I tend to work beyond my happiness zone. I also worry that one day I will no longer have my health and energy. Without an income-earning spouse, I should make the most of my energy while I still can.
However, I don’t want to feel miserable. Therefore, I’ve devised a solution for those of us who have achieved our net worth targets to be OK with letting go.
To minimize guilt, you must find the point where you feel like you’ve done enough. Once the enough target is reached, you must appreciate your effort and let go. Take stock of all the things you’ve done up until now. Show gratitude for your struggles instead of taking them for granted.
I’m not talking about doing the bare minimum to get by. I’m talking about finding the crossover point where nobody will fault you if you decide to take things down a notch or walk away completely.
Some of us are far too hard on ourselves, despite having done way more than average. Don’t lose perspective. If you’re feeling fatigued it’s probably because you’ve being working your hardest for an extended period of time.
Unfortunately, the harder we try, the greater our expectations. And when things don’t go our way, we tend to suffer.
Let me explain with two recent examples on how I experienced the trough of sorrow. Maybe you can share some of your personal experiences as well.
Dad guilt is a problem that is not discussed enough. Sadly, men are unable to share their feelings without being ridiculed for being too sensitive. But here goes nothing.
One of the reasons why my book marketing efforts lowered my happiness level was because it took away time I could have spent with my children. Instead of taking them on adventures at 10:30 am, like I often did, I sometimes couldn’t because I had to be home by 11 am or 12 noon for a podcast or TV interview.
As an old dad, it felt bad choosing book marketing over playing with my children. As a result, only until both kids are in school full-time will I consider going back to work. We have enough passive income to live a middle-class lifestyle. Therefore, choosing to make more money feels off.
The average amount of time a college-educated mother spends with their children is about 120 minutes a day. Hence, to feel like an OK father, I needed to spend at least two hours a day with my kids. But most of us want to be better than average, so I shot for spending more time with them.
One Saturday, I decided to drive both kids to a new playground 26 minutes away. I dropped my wife and kids off and went to find parking in Russian Hill. When I met up with them 15 minutes later I saw them happily playing on the new structures. I was excited to play with them!
When I asked my daughter whether I could help lift her up a rope ladder, she shook her head and said “no.” She wanted mommy.
Then I walked over to my son who was sitting stationary in a spinning cup chair. He actually looked a little glum. So I asked him whether I could spin him and he also said “no.” He also wanted mommy.
My children constantly vie for their mother’s attention. After I tried so hard to be present, this was my parental trough of sorrow. I felt like chopped tuna guts. One of the worst feelings is when you feel your best isn’t good enough.
At this point, I felt like a useless father. Was evolution telling me I should go back to work to make more money and spend less time being a caregiver? It would be the more efficient thing to do. Had I not spent enough time with my children for them to show me some love? Seems like it.
With two daggers to the heart I decided to go for a walk along the edge of Francisco Park. I found a spot and took in the views of the bay. After about 15 minutes of sulking I went back to try again. My son apologized and I responded with a “that’s OK,” even though I still felt bummed since my daughter was still not being very open.
For about five minutes, I sat in a basket swing while they swung in regular swings next to me. I just rocked back and forth, looking at the sky.
Suddenly, a little girl came up to me and decided to push the swing I was in. After a while, she asked if she could join me and I welcomed her in. Her father pushed us.
When I told her it was time for me to take my family to the slide part of the playground, she grabbed my hand and gave me a hug! She wanted to come with me, which made things awkward since her father was right there. I didn’t want him to feel like I was feeling. But I invited them to join us and we walked hand in hand to the slides.
No matter where I went, there she was. A 3.5-year-old who seemed to love me more than any other person at this humungous playground. Why did she single me out of from over a hundred other people? I felt like she was an angel sent from heaven to cheer me up and make me feel like I was a good-enough dad.
Thirty minutes later when I told her we had to go, she and her dad followed us all the way down the hill. She gave me a hug and we said our goodbyes. I was imagining both she and her dad disappearing in front of my eyes, leaving behind puffs of smoke as they returned to heaven.
On the drive back, I began to feel an inner peace. This little girl made me feel like I had been doing enough. She also made me feel less guilty about not spending as much time with my children during the book marketing process. The emptiness inside started to fade.
If you are a parent struggling to balance work and childcare, please tell yourself, I am doing the best I can with the time I have. Through the tantrums, the whining, the rejections, and the screaming, eventually, your kids will come around if you keep showing up.
Strategically, if you are a father, you may want to take your children out to play on your own. This way, there is no vying for attention. Further, it enables your partner to unwind.
And if your children rebuff you for another parent or caregiver, utilize the time to do whatever you want guilt-free. One day, I walked out of my room and greeted my daughter with a big smile. I was excited to take her to the zoo, but for some reason she started crying. So instead of sulking, I went to work out, chatted with friends at the tennis club, and then picked up my son from school. It felt natural.
Finally, if you don’t want to feel the deep lows of parenting, you may not want to spend too much time with your children beyond the average. By putting in average effort, you’ll rationally expect average responses from your children. It sounds sad, but it’s logical.
Thankfully, my daughter has recently shown a 7-day streak of love and kindness. I’ll deposit these days for when the difficult times eventually return.
Buy This, Not That is a passion project that took two years to finish and six months to market. I didn’t write the book to get rich. I wrote the book because it had to be written. The market lacked a personal finance book written by an early retirement practitioner with a finance background.
One of the people I enjoyed speaking with on my book marketing tour was Srini Rao, the host of The Unmistakable Creative podcast (Apple). Srini and I go way back since 2009. Back then, he was a digital nomad who surfed around the world. I, on the other hand, was grinding miserably away at my finance job I wanted to escape.
His life was what I had wanted.
After speaking to him for an hour on his podcast, we talked for another hour as he gave me some advice. During this time, he told me many authors he spoke to felt an emptiness inside after their books were published. As a fellow Portfolio Penguin author, he felt the same trough of sorrow.
After spending so much time putting your heart into something, it can feel like a big let down once the project is done. Suddenly, there is a void of time to fill. What’s next? When there is no longer this specific goal to achieve, a sadness may fill your soul.
I told Srini I didn’t feel the emptiness yet. We recorded a week before my book’s launch date on July 19, 2022.
Given I was spending so much time marketing my book, I decided I might as well try to shoot for the Wall Street Journal bestseller list. I had written a personal finance book, so the Wall Street Journal bestseller list was the most relevant and coveted list.
But the reality is, first-time authors like me with black hair don’t make it very far. The publishing industry is extremely competitive and homogenous. Only people who work for enormous platforms, are annointed by the publisher to back, or who are already famous tend to get on a major bestseller list.
The odds of an author getting on the Wall Street Journal bestseller list is less than 0.5%. After all, there are over 100,000 nonfiction books published a year. And only between 100 – 300 books get on the list a year.
However, with tremendous support from the Financial Samurai community, Buy This, Not That, made it! As a tennis player, making the WSJ bestseller list is like making it to the main draw of the U.S. Open. And reaching #5 on the list is like getting all the way to the quarterfinals and losing a 5-set match.
I was thrilled…. for about a week.
Then I began to feel that emptiness Srini had mentioned. After all the struggles, breaking the status quo for that moment was probably as good as it was going to get. With likely no more upside, the excitement (and anxiety) disappeared.
Ideally, my publisher would like me to market the book with as much vigor as possible, forever.
If enough people read the book and spread the word, Buy This, Not That could go on to be a personal finance book classic. That would be nice. But I have other things I want to do.
Mainly, I want to make up for lost time with my children and wife. More date nights for starters. Because unlike my children, my wife will love me back 100% of the time if I make the effort. I also want to spend more time with my parents, who are in their mid-70s.
I promised my publisher I would try hard for four months before my book launched and for one-and-a-half months after. After Labor Day Weekend, I will take things easier for the rest of the year.
Making it as a professional writer is brutally hard. It is a grind that is full of rejections and self-doubt. We’re always bracing for criticism as well. However, knowing I can succeed as a professional writer if I want to is satisfying.
I’ve overcome my trough of sorrow as an author because I have done enough to get the word out. Now it’s up to people to support the book through a purchase, a share, or positive review or not. I’ve let go of the rope and it is incredibly freeing!
If you don’t want to feel the expansive emptiness after a professional win, don’t give it everything you’ve got. Instead, follow the middle path by doing enough to hedge against the highs and lows.
Be careful about the money or success you wish for. Once you get it, any happiness you experience will likely be fleeting. The key to feeling content is knowing you tried your best within a reasonable time period.
For raising children, your best might be for the first 20 years of their lives. After that, you’ve got to let them go and trust they will make good decisions based on your tutelage. Constantly worrying about your kids after they leave the house won’t do you any good.
For marketing a product, your best might be for three months before and after the product is launched. After that, you’ve got to let your customers decide for themselves. Trying to squeeze water from a stone will only burn you out quicker and make you bitter.
I wish all of you the best in achieving your goals. Just remember to enjoy the process! Don’t forget yourself.
When you’re feeling down, take a step back and appreciate how far you’ve already come. And if you are still experiencing emptiness, put in that one last final effort so you can finally move on.
Eventually, the emptiness inside will fade as you revert back to your steady state of being. Hang on! Once you have returned to normal, with a clear head, you can then decide whether to take on another great challenge or not.
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For A Better Life, Be The One Percent In Something, Anything
Readers, have you ever had an angel find you during a low moment? What was that experience like? How are you overcoming the pull of always working? How can you can take things easier and find more happiness?
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Filed Under: Entrepreneurship, Family Finances, Motivation
Author Bio: I started Financial Samurai in 2009 to help people achieve financial freedom sooner. Financial Samurai is now one of the largest independently run personal finance sites with about one million visitors a month.
I spent 13 years working at Goldman Sachs and Credit Suisse. In 1999, I earned my BA from William & Mary and in 2006, I received my MBA from UC Berkeley.
In 2012, I left banking after negotiating a severance package worth over five years of living expenses. Today, I enjoy being a stay-at-home dad to two young children, playing tennis, and writing.
Order a hardcopy of my new WSJ bestselling book, Buy This, Not That: How To Spend Your Way To Wealth And Freedom. Not only will you build more wealth by reading my book, you’ll also make better choices when faced with some of life’s biggest decisions.
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Abby says

I feel somewhat constant existential dread that I’m not spending my time well. I recently left my job and feel much better about the amount of time I spend with my kids, but rarely step back to appreciate it and just find other things to feel badly about. I’m working on it!
I once took off the day to spend with my child and he told me he didn’t want to play with me and instead ran over to the neighbor’s house. I was crushed.
Financial Samurai says

I feel you on the existential dread. There is like this constant low level baseline stress we feel as parents. And I’m sure people who are parents who also have work issues they are dealing with.
I would be crushed too if I took time off of work I only have my son or daughter not want to play with me. We’re going to try to set expectations as much as possible where we say what we will be doing the next day. That seems to help.
Happy Asian Woman says

Hi Sam, I am a long time reader and first time commenter as well. Thank you for sharing so openly about your struggles. I too am a parent of young kids and I have to say, they are fickle. Today they want your wife, tomorrow they want you. Their mood depends on the time of day I’m glad the little angel found you and brightened your day.
Also, now my youngest just went to school so I have time on my hands for the first time in a decade. Thank you for the reminder about keeping my values straight. My first inclination was to jump into work but I really need to think about why I’m doing things… I discovered when I jumped into much more work, I had no energy when my kids came home. So now I am guarding my schedule more carefully, working less when they are in school, so I still have time to engage with them when they come home.
When I had very little child care, I built a consulting business that required very little time. Because it’s one-to-one coaching it’s difficult to scale so I’ve decided even though I have a lot more time, I don’t need to work more to scale the business because it was already doing really well with the limited time I invested.
Thank you for reminding me of what is important, and not to always be chasing the next financial goal. I appreciate your sharing your wisdom. Enjoy this time of life with your young children, wife and good health. It goes quickly so savor it (a reminder for myself as well!)
Financial Samurai says

“ I discovered when I jumped into much more work, I had no energy when my kids came home. So now I am guarding my schedule more carefully, working less when they are in school, so I still have time to engage with them when they come home.”
Good plan! I really admire working parents who are able to work hard all day and THEN have the energy to play for a couple hours with their kids, feed them, bathe, and put them to bed. Where is talking 13 to 15 hour days dude so easy to get burned out after a while.
Congrats on the Asian Hustle Network award. I think I reached out to the podcast hosts a month ago, but no response. Not sure if it’s worth following up. I feel so at peace now that all the marketing is done.
Bill says

I have a little different take on this. Guilt is a feeling that derives itself when you do something immoral, illegal or simply wrong by design. I understand the emptiness or sadness you feel about your friends death but you did nothing to feel guilty about. When you currently spend more time with your kids than 90 percent of men how can you feel guilty when you need to take a break? Your constant desire to do more, make more or care more is just how your built. Toning that done doesn’t make you guilty of anything. It makes you human.
I sound like my therapist here but for myself recognizing what emotion I’m truly feeling rather than lumping everything into the guilt category has made it easier for me to deal with highs and lows.
Thanks, Bill
Financial Samurai says

Indeed. Have you experienced this trough of sorrow before? If so, why did you experience it? And how did you get out of it?
I’m hoping more readers can share their stories. So far, nobody has. Not sure why.
Bill says

Absolutely, the biggest sorrow that’s not too personal was paying off my business. I could tell you exactly how many years, months and days I had till it was paid off anytime anyone asked. Once I finally did, you talk about a let down. I looked forward to this day for 15 years. My realization was that the journey was far more important than the destination. I know that’s cliché, but for me it truly was.
JC says

I guess you proved your own perception wrong with your book’s success. Well done.
“But the reality is, first-time authors like me with black hair don’t make it very far. The publishing industry is extremely competitive and homogenous. Only people who work for enormous platforms, are annointed by the publisher to back, or who are already famous tend to get on a major bestseller list.”
Can we conclude that the publishing industry isn’t systemically prejudiced against folk with black hair?
Financial Samurai says

It still is unfortunately. Maybe if there is a sustainable trend. But not yet. Minorities make up about 17% of authors who get book deals, yet we account for about 40% of the population.
It is extremely hard to get a literary agent, let alone a book deal. But that’s just the way it goes in every homogenous environment. Everything is a struggle, including getting book blurbs.
You gotta keep on fighting. No complaining. Don’t let the gatekeepers hold you back.
If you have written a book, I’d love to hear about your experience. Some people think things are much easier than they really are. So providing first-hand experience is always great.
Untemplater says

It’s easy to forget to celebrate our wins, enjoy the journey, and savor the moments when we get so overwhelmed or tied up with various things. The older I get the more and more I have to deal with the unexpected. Something always comes up because there’s only so much that we can control. That’s why we gotta enjoy the ups as much as we can when they happen before something else distracts us.
Enjoy that WSJ win every chance you get – that is an unbelievable achievement! Congrats!
Liam says

I’m curious why the WSJ bestseller list is the preferable one? It always seemed that the NYT one was the one most media paid attention to.
Financial Samurai says

Sure. The WSJ bestseller list is more meritocratic. It’s based on the number of book sales. The NYT list is editorial and not just based on the number of sales. In other words, you can sell a lot of copies to make the list, but you might not make the list if their editorial board doesn’t approve. You might have written something politically they don’t like, be the wrong minority, offended someone on their editorial team etc. Conversely, if you work at The NY Times, the chances of you getting on their list is much higher.
As a finance writer, I wanted to focus on a finance publication list. NYT is a great bestseller list. But it is similar to how elite private schools will pick and choose its candidates, whether they have the best grades, test scores, and experience or not. Think of NYT list like Harvard and WSJ list like MIT or Cal Tech.
You thinking of writing a book? If not, I encourage you to give it a go. It’s a good eye-opening experience.
Have you experienced any troughs of sorrow? If so, how did you overcome it? thx
Liam says

Didn’t know that about the NYT list. It’s always the touted one on the book covers, but that would make sense, wouldn’t it?
I have written a book – a text for my field, and like most texts it didn’t sell much. The marketing was non-existent from the publisher, but that is another story… I donated the royalties to an outreach fund for my field.
As for the trough of sorrow, I think mine would be getting a negative result from a biopsy (no cancer), then realizing that I only dodged the bullet this time. Cancer sucks and it’s caused the majority of deaths in my family.
Kevin says

Launching your book and getting on the Bestseller’s list is a phenomenal achievement! You should definitely work that as long as it has momentum. But it should be a stepping stone, not a plateau like the publisher wants it to be. I noticed Dave Ramsey is still on the list with a book that’s nearly 20 years old. Imagine if he stopped listening to the needs of his crowd after publishing that book.
Did you have a moment of inspiration during the writing of this book that you could pursue now that it’s published?
Financial Samurai says

Yes, Dave has created a huge business and uses the books as a great marketing tool. For some reason, I don’t have the desire to create such a large business. I just want to be free and managing employees and always trying to grow revenue makes me feel beholden to money and other people’s schedules.
I also wanted to write the book that goes beyond personal finance basics of saving and paying off debt. This is a defensive position to building wealth. Instead, with Buy This, Not That, I focus on the offensive position of spending your way to wealth and freedom.
Yes, the moment of inspiration was about not making money the end all be all. Instead, to tackle some of life’s biggest dilemmas with optimal decision-making. Best to use money as a tool. If you read it, I think you’ll like it.
Have you experienced any troughs of sorrow? If so, how did you overcome it? I’d love to hear from readers about their experiences as well. thx
Kevin says

I’m currently halfway through reading BTNT. I can tell that the ideas were refined over many years of the FS blog.
I’m a project manager by day, and I get that sunken feeling with each project at the exact point indicated on the graph; about midway through. But a new idea never fails to come to me like a bolt of lightning, and that gives me inspiration for the next project… which is usually something I’d only be able to do upon the completion of the current project. It’s like a 1031 exchange of negative emotion, where I can parlay the success of this project indefinitely into the future and never pay the tax.
Financial Samurai says

“ a 1031 exchange of negative emotion”
Nice analogy!
Scott H says

Hang in there Sam. My daughter used to be that way when she was little i.e. she would give you affection when SHE wanted to. Now that she’s an adult, she’s like a very good friend to me. We go to football games together and she even likes to watch sports with me. Also, definitely spend more time with your parents. After 75, my parents physical decline has come rapidly.
Financial Samurai says

Will do Scott. Hanging in there is the concluding paragraph of my post. Glad you and your daughters are good friends now. I hope it will be the same for my daughter and I.
Joe says

Oh wow, thanks for the mention. My wife is on sabbatical now and I feel more pressure to make money. Our cash flow is tighter than usual due to less income and travel expenses. I need a bit more cushion. I’ll probably work on another side gig when she retires.
As for kids, I think you’re doing very well. Kids will change as they grow older. My son used to be very attached to me and my wife resented that a little bit. Now that he’s older, he likes mom better. I had to play the disciplinarian role because my wife doesn’t like to do it. Anyway, life changes and you have adapt.
Buy This, Not That is a great book. I hope it becomes a classic.
Financial Samurai says

Thanks for sharing Joe. Given your comment, maybe you would feel a little more anxiety and stress if your wife also left her day job years ago? But I think you guys would have made it work as well.
Personality differences and drive differences are natural.
Dennis says

Sam. Long time reader, first time comment. I semi-retired years ago and now almost 67. Here is a few things I learned which might be helpful.
1. Have written goals. Writing forces you to clarify what you want. Humans are goal striving machines and must have projects to work towards and must have a way of measuring progress.
2. Rank your goals. When I was building my business and a single father, I was frequently beating the crap out of myself. When I was working. I felt I should be with my kids. When I was with my kids, I felt I should be working. Solve this by ranking your goals and avoid a value conflict. My kids were my highest value and as long as I was making enough to financially provide, that was where I should put my time. I lost some business and that was ok.
3. Relax and let compounding work for you. Live below your income, have belts suspenders and another belt for those unexpected bumps in the road (they will come) and do not get caught keeping up with the Jones. Envy in the thief of joy.
Thanks for the work you do in educating people. Money is not everything but it is the tool needed to help us get there. Money can have a huge impact on health, free time for enriching opportunities, etc. Keep up the great work.
Financial Samurai says

Thanks Dennis. I think I’ve got the writing part taken care of 🙂 The ranking of goals is good. Every day, I have between 1-3 goals to accomplish and that’s it. If I can get those goals done then the rest of the day is gravy.
The “relax and let compounding work for you” is easier said than done, especially in a bear market with the Fed determined to crush the economy. So the fun part is figuring out HOW to relax. Thankfully, I’m too tired to be envious. Just trying to appreciate more of what I have.
When you were debating between working and spending time with your kids, and ultimately deciding your kids were your highest value, how did you change? For example, did you start leaving work early, cut down to part-time, take a sabbatical, or retire early while they were still at home? I’d love to know more details about figuring out this push and pull.
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