Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside

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.

Trough of sorrow
By Paul Graham of Y Combinator

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. This post visits Pity City and then leaves.

Overcoming The Personal Trough Of Sorrow

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.

Getting Right With Good Enough

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.

Different Income Situations

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.

Overcome The Trough Of Sorrow By Doing Enough

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.

The Struggle To Do Enough As A Father

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 when 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.

An Angel Found Me

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. In the moment I felt all alone.

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.

Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside - Francisco Park when an angel found me
Francisco Park

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 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.

Overcoming The Trough Of Sorrow As A Parent

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. Work all day and night! By putting in average effort, you'll rationally expect average responses from your children. It sounds sad, but it's logical.

If you’re a stay-at-home dad, you should consider going back to work after two years. You’ll better protect your family and your heart!

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.

Related: The Joy Of Low Expectations

Doing Enough With My Passion Project

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.

Striving To Make A National Bestseller List

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. It is also the most meritocratic list based on sales, not an editorial committee.

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 through their marketing dollars, 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 semifinals and losing a 4-set match.

Buy This Not That Wall Street Journal Bestseller

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.

Letting Go Of The Marketing Grind

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 two 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.

Defeat Emptiness With Time And Effort

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 your own well-being and happiness.

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.

Related posts:

The Source Of All Stress: Giving A Giant Crap

For A Better Life, Be The One Percent In Something, Anything

The Negatives Of Early Retirement Nobody Likes Talking About – Felt the trough of sorrow after leaving my 13-year career as well! Even though I had enough money to be free, there was a really downer moment initially as well.

Paying Off Your Home Early May Not Provide The Joy You Expect – If you are hyper-focused on paying off debt over a long period of time, I'm sorry to say you will also feel disappointed once you've achieved your goal.

Reader Questions And Recommendations

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?

Pick up a copy of Buy This, Not That, my instant Wall Street Journal bestseller. The book helps you make more optimal investment decisions so you can live a better, more fulfilling life. 

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites today. 

About The Author

50 thoughts on “Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside”

  1. Thanks for this, a really cathartic read! I set out on my journey for financial independence 8 years ago after making every bad financial decision there was and finding myself in heaps of debt. My sole aim at that time was to create an income stream outside of my 9-5 job that would some day allow me to quit and do as I pleased. That time was May of this year. My expectation upon achieving this was for a deep sense of calm and fulfilment. This lasted for all of one month until I began to experience so many of the emotions of guilt and feeling despondent at my lack of purpose or goal that got me out of bed each morning that you described. Reading this has reassured me that what I am experiencing is a well trodden path!! Thanks, some real food for thought. Keep up the great work!! ( 3/4 of the way through your book, Congrats , a great read!)

    1. You’re welcome and congrats on achieving financial independence! One month is about right. Then it’s wondering, “what’s next?” Or “Is that it?”

      I hope you find greater purpose with your free time. And so good to hear you are reading my book.

      Best, Sam

  2. I’ve been thinking a lot about the phrase you used about work ethic driven by guilt. I think that describes mine as well but it didn’t really click until I saw this.

  3. Thank you for your vulnerability to share your personal troughs and, in particular, those in relationship with your children. I want to affirm your decision to be present with them during these formative years. I missed those with our three who are now adults by earning lifetime platinum status traveling for business. I followed the curve you showed struggling through a startup that was successfully acquired and a host of other things. All the way, I rationalized this as providing for my family. Modelling from my family of origin influenced me much more than I realized.

    I quit my job when our kids were in their teens to catch up only to learn that our relation”ship” had sailed. Challenges of their addiction and mental illness followed which are troughs that simply do not negotiate. They are what they are. During this period, I lost a late career follow on corporate job and was crushed by the empty returns of a life spent chasing success. That crushing trough paved the way for a new relationship with my adult children – as adults – not a patched version of the old one.

    My definition of success has since changed as a person, father, husband and businessman. A mutual adult friendship with my adult children has not only covered past guilt, it has become one of the greatest blessings I could have ever imagined. Unlike our other friends, they really know who we were and are. Now, we listen and speak freely into each other’s lives. This is miracle since my son was asked just before a breakthrough in rehab to chose something he thought impossible. His choice? His and my relationship.

    We decided to do a podcast together to talk about the story of our improbable friendship. At his age of 35 and my 62 years, it’s amazing to see the healing that still comes from sharing our stories in conversation. Now that I am also writing a book, I can see the trough ahead that you’ve shared. Only this time, my son and my family are an encouragement from a place of deep connection.

    When asked by others who know our story, I tell them to be willing to give up their primary relationship as parents for something much better. Those early troughs are not to be treated as problems to solve, but a path to unfold toward much more than we can see. I’m grateful for the path and hope you will also become friends with your children as adults. When they have the choice, that’s when you know it’s real.

    1. Wonderful you and your son reconnected and have created a best friendship today. I would assume many, maybe most aren’t able to have this type of relationship.

      And it does take two to make a great relationship. It’s why I want to visit my parents more bc they do not visit or call often. But for those of us who want to make the relationship happen, it’s worth trying!

      Thanks for reminding us about what’s important in your podcast. How would you figure out the right balance if you were to rewind time by 32 years? It seems hard to control the happiness and outcome of our children. I’m also assuming that because you worked hard you have built a lot of wealth and optionality. So that’s good.

      Perhaps kids up to a certain age don’t really care at all about how much money their parents have if they have the basics, just that they are available?

      I’m listening to your second episode right now about turning points. Again, great idea and awesome stuff that you guys are reconnecting. Part of the reason why I decided to consistently record on my podcast is so that my children have a huge archive to listen to when they are adults. I leave little hints here and there to them that I love them.

  4. FS, thank you for keeping it real and being brave enough to share these difficult feelings with the world. I love your story of playground despair followed by redemption at the swings. One silver lining to the trough of sorrow is the beauty in even the small acts of kindness that heal you. Sometimes even reading a blog post that you relate to can have a healing impact :-)

    I have also had the bewildering experience of accomplishing a big goal and feeling empty and lost afterwards. It is such an odd facet of the human experience that achieving what you think you were striving for ends up falling short. It’s oddly comforting to read and be reminded that we’re not alone in this. My own experience centered around professional success and the type of project assignments I worked on. After working on several dream international project assignments, I experienced a similar sense of concern and disappointment at the cost these “dream” assignments had incurred on my personal life (or lack thereof at the time).

    Thanks for your work and particularly for modeling how to learn from even (and especially!) the difficult experiences and transform them into gifts.

  5. Hello, I’ve been having a really hard time lately and it is parenting related so I thought I would share. It was inevitable though… my youngest just started 6th grade this year and OVERNIGHT became a teen. Doors are closed, I’m not even allowed to smooth a hair on her head etc.
    So… I’m over here adjusting to my new role and feeling very lonely. Sigh

  6. Just read the follow-up Financial Samurai post wondering why more people weren’t experiencing the “trough of sorrow.”

    I’ve certainly gone through those troughs in the past, but the phrase isn’t resonating with me at my current stage of life, for a few reasons:

    1. I’m 68, in good health, still earning a good income, on solid footing financially and in my relationships. My years of intense striving are behind me, and so the peaks and valleys have evened out.
    2. I think the “troughs” in part have a biochemical explanation related to dopamine levels. High achievements result in a dopamine rush, followed by a dopamine deficit. Stanford’s Andrew Huberman has explored this topic in his podcasts. There are ways to modulate your dopamine levels – personally, I’m a fan of cold plunges.
    3. My past periods of sorrow have usually been tied to regrets – not having tried harder, having offended or let down people I care about, making mistakes in judgment. I’ve come around to a view that free will is an illusion, and so ideas that “I could have done better” are false: if I rewound the clock, I would inevitably do the same things and make the same mistakes. So best to just move on without looking backwards.

  7. Thomas Storrs

    Everybody’s situation is different but what I have found helpful during life’s changes and challenges over 71 years is the famous book Meditations and the principles of stoicism.

  8. Frugal Bazooka

    I’m gonna call my response to your post “tough love” so you already know where this is going. For context here are a few things about me: I am one generation before you by age, but not in the same universe by how we were taught to interact with reality. This is because my generation’s parents went thru the world wide depression – actual starvation and poverty, hot and cold wars vs. Hitler, Stalin, Mao and incredible social and economic change from the 30s to the 80s. They survived a crazy unsafe world and they wanted us to survive as best we could. We were taught from the get go that life was unfair, difficult, without guarantees and if you aren’t mentally and physically tough skinned, don’t come crying to them for relief. It sounds harsh right? It was harsh. No safe spaces, no restorative justice, none of the nanny state BS that many in the West believe they are entitled. If we failed in school we got an F, if we broke the law we went to jail. Where I live now that doesn’t happen anymore. The state has outlawed these normal lessons and consequences for bad behavior.
    More to your point about troughs of sorrow, who has time for such things? Life is about living…to paraphrase Conrad Birdie “we’ve got a lot of living to do” !
    Somewhere in the world someone is starving, being throw in jail for defying their govt or being born into unimaginable poverty. Meanwhile many of the working poor in the west live good lives compared to 90% of the rest of the world. Anyone who’s travelled the 3rd world countries understands troughs of sorrow that cannot ever be overcome because they are too deep and wide. Always see the bigger picture…for us, right now at this moment in time, life is a Cabaret or if you prefer Auntie Mame life is a banquet and most poor suckers are just too foolish to know it!
    I don’t mean to diminish your sad feelings or anyone else who feels depressed. I would just say to anyone who feels unexplainable sorrow, stop reading our lying perverse media that sells doom and gloom for a quick click for profit. Get outside and breath the air and run a few laps.
    Open your eyes and see how amazingly lucky we all are to have, by pure luck, landed in a country that has made our short time on earth the absolute best it can possibly be if we work hard, follow the rules and act as good citizens. I should be very poor right now, but I am not. If you see the truth and beauty and potential of the world around you – you will never be poor no matter how much or how little money you have.
    And most importantly make sure your kids understand that mostly this is the greatest most prosperous time in the history of mankind. More people have more material comfort than anytime since the beginning of time. I am not a Pollyanna, I have experienced many things that have caused me grief…but when I step back and do the cost benefit it’s easy to never allow the bad things in life to overshadow the good.

    1. Sounds good. So my main question is, are you happy? And how are your children and your relationship with them?

      I think if you feel that you should be poor but you are not, then you will naturally feel very rich.

      1. Frugal Bazooka

        I should probably feel less happy than I do, but in all honesty I am very happy in my life. I have not achieved most of my biggest and most cherished goals in life which were related to the music and film business…and yet I thank God daily for what I do have. For most of my young life I was in sports or the music business and I was selfish, self centered and a dog eat dog jerk. I put myself and my goals above everything. Then one day my first daughter was born and my entire life changed in a flash. She was the most beautiful and creative thing I had ever done. Then my 2nd daughter was born and the focus of my life was no longer narcissistic and shallow. I had no other goal but to make sure they had the best life possible. I had a lot to learn (and change) and living that truth was no picnic but it was a joy and I credit my daughters with motivating me to achieve impressive financial goals. I had no business achieving those goals considering how half assed I had typically dealt w financial issues, but for them I would do anything to give them a better life.
        Now my daughters are grown and married and we still have great relationships. Life was not perfect, it never is…but I thank my parents every day for teaching me and my brothers to always appreciate and show gratitude for what we in this country have been given…opportunity, freedom and hope.

  9. When I was a 5, the old cat I didn’t like very much ran away to go up to kitty heaven. I told my mom, “Good. I want a dog now.” I’ve apologized many times since then and every time she laughs it off. As she says, I was 5 and 5 year olds do ridiculous and thoughtless things sometimes.

    Appreciate how hard you’re trying – and succeeding – to be a good dad, Sam. But you’re being too hard on yourself. Kids do weird things, like not wanting to hang out with you sometimes at a playground, because they’re kids. Really. It’s them, not you. You’re doing great.

  10. Hi Sam,

    Single parent here. I’ve been working like crazy for the past year, and especially during the past 2 months —-> At the point of a burnout. I desire to spend more time with my child and do want to take some time to find myself. I have tried hard enough. And like you mentioned in your article, some of us are way too hard on ourselves, even though we do more than the average. I am always guilty of being too harsh on myself. I always think that I could’ve should’ve done better and feel regret or guilt, or I should not have done this or done that.

    On another note, I was talking about your blog with my spin instructor. She was already a fan of yours along with other personal finance bloggers. She debated about buying your book. Of course I gave her my 2cents and she decided to purchase. Anyway, the point is, you’re already very popular, have tons of fans, and you might not realize. You’ve tried hard for the past many years. Give yourself a break as well! :)

    1. Being a single parent has got to be the toughest occupation! You got this!

      I’ve found it’s very hard to convince the average person to buy a personal finance book, even if the book can help them build the most wealth and make the best decisions.

      But everything is rational in the end. We decide to spend and do what we really want. And there’s nobody that can force another to do otherwise.

      Thanks for being an evangelist of Buy This, Not That! I appreciate it.

  11. 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.

    1. 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 feel it.

      I would be crushed, too, if I took time off of work only to 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.

  12. 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!)

    1. “ 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. After 13 to 15 hour days, it’s 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.

      1. I just looked up this network you mentioned. Wow what a small world. My brother and one of the host dated back when they were in high school or college. Haha. Glad to see her hustling or doing well.

  13. 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

    1. 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.

      1. 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.

  14. 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?

    1. 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.


    2. Here you go JC. If you are a minority, the odds of getting published, let alone making a bestseller list is bleak.



      We guessed that most of the authors would be white, but we were shocked by the extent of the inequality once we analyzed the data. Of the 7,124 books for which we identified the author’s race, 95 percent were written by white people.

      Author diversity at major publishing houses has increased in recent years, but white writers still dominate. Non-Hispanic white people account for 60 percent of the U.S. population; in 2018, they wrote 89 percent of the books in our sample.

  15. 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!

  16. 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.

    1. 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

      1. 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.

  17. 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?

    1. 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

      1. 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.

  18. 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.

    1. 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.

      1. Paper Tiger

        One thing I’ve also realized about kids as they become adults. They remember a lot more than you realize as they were growing up. Even when you don’t feel wanted by them as they go through various growth stages, somehow it comes back to you down the road. My daughter turns 24 tomorrow and has always been the light of my life. She actually calls me her best friend which feels incredible even if a bit exaggerated.

        What I have learned about raising a daughter from child to adult is that while she was given a lot of advantages and appreciated those, what she remembers most is not what I gave her but how I made her feel. Spending time with her and all the sacrifices you have made for your kids may not seem all that appreciated now but you are building “compound interest” that will one day have you waking up and realizing how much of an impact you really had and how much it really was appreciated.

        1. “what she remembers most is not what I gave her but how I made her feel” wonderful wisdom!

          As parents, we just try our best and cross our fingers for the outcome. We don’t know whether we are making a great impact until much later. So yes, it’s like investing for the long-run and hoping for a strong outcome years down the road. That is the constant low-level anxiety many parents, including myself face. We think to ourself, will our efforts be worth it? B/c we see so many terrible stories in the news about people doing bad things. Surely, their parents gave them love, time, and tutelage as well? Maybe, maybe not.

          Just hard to know the future. So we’ve got to just do our best and go with the present!

          1. Paper Tiger

            You and they will also find out very quickly how well they have it once they become school-age. They will meet and see many kids from broken homes and less fortunate circumstances that will have an impact and make them even more fully appreciate the life they get to enjoy with two loving parents who really care about them and only want what is best for them.

            Our daughter attended and worked at our local Boys and Girls Club from elementary school through high school and even a couple of summers in college and she witnessed firsthand the variability of how people live and grow up and the difference a loving environment really makes.

            1. “They will meet and see many kids from broken homes and less fortunate circumstances that will have an impact and make them even more fully appreciate the life they get to enjoy with two loving parents who really care about them and only want what is best for them.”

              This is my fear. They might not, as I did attending school in Malaysia and then going to public school for high school. If they continue to attend the language immersion school, they swill be surrounded by kids who have highly involved parents who love and care for them.

              I believe the biggest variable for a quality of the school is when the parents partner with the school and believe they are partners with the teachers to be co-educators. And I believe this to be true after being a high school tennis coach and experiencing a three different schools for my kids so far.

              The diversity of socioeconomic backgrounds and the discomfort I felt as a minority attending high school and college in Virginia were instrumental in building up toughness and grit. So we plan to travel to give them perspective and have them compete in things so they can learn how to lose.

              I only know what I have experienced. And what I’ve experienced so far is that life in America is very easy compared to live growing up in Zambia, Malaysia, Taiwan, and The Philippines. I do have worry the kids will have it too good.

              Related: The Importance Of Feeling Consistently Uncomfortable For Personal Growth

              1. Paper Tiger

                I understand your point and your fear. Our daughter grew up in Scottsdale so she was surrounded by wealth and privilege and her circle of friends was most definitely the same. The great thing about her time with the Boys and Girls Club is she got to see the other side. Her mother is Hispanic and I am White so she has experienced the best and worst side of that as well in terms of how some people choose to relate to her.

                I guess the key is making sure your kids have a diverse set of experiences around a diverse set of people. As parents, we didn’t really plan it out that way but life has its own way of handling it and we were there to address any emotional fallout as it occurred.

                Also, both my wife and I worked for multi-national companies most of our careers and these companies had their own daycares and we also associated a lot with the people we worked with. As such, our daughter had many diverse friends. We lived in WI for 5 years and her best friends were from Russia, India, and China. She has always been very open-minded and loves learning about people and other cultures. Again, giving them as much situational experience as you can in the formidable years seems to make them much more well-rounded and comfortable in a variety of group settings.

            2. Finance Ronin

              I like your idea of volunteering. My kids have led an incredibly charmed life compared to my middle class Up bringing (and my childhood was pretty good). Their sense of hardship and adversity does not comport with the greater population. My daughter is starting at a $45K/year high school and most people there are another cut above in wealth. Many kids need a reality check. There are some very well off kids who are really depressed because they believe they aren’t smart enough or pretty enough or popular enough or rich enough. It’s a dangerous spiral that is not based in reality but based on perception of their sheltered worlds (which the parents created for their benefit). It is a cruel irony that I’ve spent all this effort to create a “better” life with the “best” schools only to raise children who will be less resilient than me (unless I fabricate some sort of adversity for them). I should mention that other than this school we lead a fairly middle class lifestyle despite our wealth.

        2. As a father of two young daughters, this comment made me both smile and tear up a bit. I hope they also call me their best friend when they become adults.

  19. 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.

    1. 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.

  20. 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.

    1. 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.

      1. I agree. You have the writing part down. You’re 1-3 daily goals are your short-term goals, but why are they there? In many cases, they are on the list supporting your major goal. In years of following you, I suspect your number 1 goal is family. Mine also. Much of what your short-term goals involve are supporting your major goal – your family’s financial security, their emotional support, exercise/rest (so you can be at your best), etc. When you start to feel stressed or pushed, its time to step back and see if there is a value conflict. Learning to say ‘no’ was a huge help. (time sucks, demanding customers, etc.) It did cost me money, but I’m proud to say any children’s events that were missed could be counted on one hand. It’s remarkable how much time can open up and how much stress can be reduced when you make the world bend to your schedule.

        As for the compounding, our equities are in indexes and Berkshire. Set it and forget it. A major part of our net-worth is in single-family rentals. Between inflation on both the debt and equity, plus the debt amortizing down, you have near certain compounding, working with the Fed, instead of against it. When another home is free clear, it means less risk and more cash flow. SFH do not have to be a pain in the ass! Most of tenants have been with us more than 10 years; one for 25 years. The keys to compounding are proper tax management, uninterrupted compounding, and being that ‘last man standing’ (rather than optimizing).

        Hope there is something helpful in here….keep up the great work.

        1. Thanks. I do feel more relief now that the major part of the book marketing is done. I mentioned in the post the reason why I didn’t enjoy the process as much as I would’ve liked was because it took time away from spending with family.

          So now it’s time to make up for lost time. And I’m looking forward to it!

          And to clarify, this post recapt how I felt several weeks ago. I feel back to normal now.

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