November 28, 2022

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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.

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.

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.

Overcoming The Personal Trough Of Sorrow

One of the reason why I’ve decided to 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.

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 the fear of not wanting to feel guilt. I am burdened by a low threshold for feeling guilty if I don’t try my best 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.

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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 more 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 do just enough. Once the just 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 until both kids are in school full-time will I consider going back to work. We have enough money to live a middle-class lifestyle. Therefore, choosing to make more money feels bad.

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 30 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 looked 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 your best isn’t good enough.

And 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 20 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.

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After a while, she asked if she could join me and I welcomed her in. Her father decided to push 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. But I invited her 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.

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 as they returned to the skies.

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. You’re the only one they can be with. I’ve found this strategy to work very well. Further, it enables my wife 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.

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 true.

Thankfully, my daughter has shown a 7-day winning streak of love and kindness. I’ll cherish these days until she turns sour once again.

Doing Enough With My Passion Project

Buy This, Not That is a passion project that took two years to write. 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 soul into something, it can feel like a big let down once the project is done. Suddenly, there is a void of time to fill. When there is no longer this specific goal to achieve, a sadness may fill one’s 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.

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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 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 was like getting all the way to the quarter-finals and losing a 5-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 too.

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, which is tiring. 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 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 18 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 once 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!

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!

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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