One reason many people shy away from competition is that they dislike losing. With often only one winner, the sting of defeat can feel too humiliating. When people stop competing, they can become more fragile over time, to the point where even small setbacks can disrupt their well being.
Ironically, the best path to victory often involves losing repeatedly. After enough losses, you build resilience, learning to handle failure and keep moving forward. Every loss is a chance to learn from your mistakes, sharpening your skills and improving your odds of winning the next time.
If you’re someone who has lost, I commend you. A person who loses is still far ahead of the one who never tries at all.
Note: I wrote this post partly in response to some newsletter readers who were upset I wasn’t more upset about Harris losing. After all, I'm a minority who lives in deep-blue San Francisco. For as long as I can remember, I’ve tried to look at the positives of every situation. Perseverance is also a core value I’m trying to instill in my kids, especially since life won’t always be comfortable.
Let's look at some case studies on how losing can eventually lead to winning. Nothing is permanent.
Losing to Win: The Presidential Election
With Trump’s victory, roughly half the country faces disappointment over Harris's loss, while the other half celebrates. Women, in particular, have voiced frustration to me, largely due to concerns about potential threats to reproductive rights.
Despite a decisive defeat—even in the popular vote—there are key lessons here for Democrats as they look to shift momentum in the next election.
First, Democrats may recognize the importance of a robust primary election rather than selecting a candidate at the eleventh hour. A full primary process enables voters to feel more involved in choosing their candidate and to gain a deeper understanding of who they’re supporting.
Harris's loss also underscores the need to connect more broadly with the American public. Democrats must expand their appeal, especially to working-class Americans who feel the daily pain of inflation the hardest. Avoiding candidates with a reputation for elitism, like California Governor Gavin Newsom, could be helpful. Although Newsom is a slick communicator, dining at the exclusive French Laundry during COVID restrictions damaged his standing with middle-class voters.
Additionally, the perception of insufficient attention to border security has been a sticking point. When Harris was asked on The View what she might have done differently, she couldn’t identify anything specific. There's also the perception that DEI initiatives took priority over other concerns like the economy, while making a large swath of the population feel excluded. Democrats now have an opportunity to reflect on these election results and recalibrate for the future.
Those most disappointed by Harris’s loss may even feel inspired to take meaningful action: donating more, changing careers, or actively supporting their cause—moving beyond virtue signaling or harboring resentment toward those with opposing views.
The pendulum always swings.
Losing to Win: Finding Love in All the Wrong Places
Finding love is both serendipity and a numbers game. The more people you put yourself out there with, the better your odds of finding a life partner.
Years ago, I spoke to a 34-year-old man, whom I'll call Biff. He was 6'4″, a bit overweight, jovial, and seemed unsure about his direction in life. Despite owning a townhouse and holding a stable job, he was unhappy.
When I asked why, he said, “I’m living the American dream, but I have no one to share it with. I can’t seem to find a girlfriend. I go to conferences hoping to meet someone, but nothing ever comes of it. I’m always in the friend zone.”
I then asked him how many women he had asked out in the past year. He admitted that he hadn’t asked out anyone. When I asked why, he shrugged, saying, “Maybe I’m just afraid of being rejected.”
“Welcome to the club!” I replied. “But that’s actually a strength we have as men. By asking, we grow stronger.” I encouraged Biff to approach at least 10 women for coffee or lunch at his next conference.
Seven women gave him the time of day, and one became his future wife.
Losing to Win: From Day Trading to Long-Term Investing
In my 20s, I was a day trader, riding high after one stock skyrocketed 50x in 2020. Emboldened, I even asked my managing director, Michele, if I could trade Worldcom options. She reluctantly agreed, but I sensed her unease.
18 months later, I wasn’t invited back for a third-year analyst position. I was too preoccupied with my own trades, losing sight of my role and alienating my senior colleagues at Goldman Sachs. Thankfully, I secured a position at Credit Suisse, where I continued to trade heavily, though with little success.
One year, the head of International flew in to question my habits. He gave me an ultimatum to stop trading or face termination. It was a wake-up call, and I realized I was hurting my career due to what had essentially become a trading addiction.
The 2008 financial crisis was another turning point, wiping out 35–40% of my net worth in just six months. Desperate to make sense of all the chaos, I launched Financial Samurai in 2009 as a type of personal therapy. It was then that I resolved to focus on long-term investing.
In 2011, I promised to leave the industry if I could recover my crisis-era losses. The fear of financial ruin forced me to reevaluate my life goals, similar to how someone might gain new clarity after surviving a near-fatal accident.
Since then, holding the S&P 500 rather than day trading has worked out well over the long haul. The experience taught me that sometimes losing is exactly what you need to find the right path. If there was no financial crisis, I probably would be much poorer and stressed today.
Losing to Win: When Others Force Their Desires on You
Here’s an interesting local example called Proposition K. Below is a map showing who voted “NO” (purple) to close a two-mile stretch of road along the beach on the west side, and who voted “YES” (green). Most residents on the west side, especially those in the northwest (deep purple), opposed the closure due to the inconvenience it would cause to their commute south.
However, residents on the east side, who wouldn’t be affected by the increased traffic, overwhelmingly voted “YES.” The west side Supervisor, Joel Engardio, placed the measure on a citywide ballot, knowing the majority would support the idea of a new park since they wouldn’t bear the impact.
As a result, residents on the west side are upset—not only about longer commutes but also about increased traffic and potential injuries in their neighborhoods as ~20,000 cars are rerouted through the Sunset district daily. Engardio’s political career is now at risk for going against the people he is supposed to represent. I would not be surprised if Joel Engardio gets recalled for lying to his constituency and losing their trust.
What are the wins here? Oceanfront property owners may see a boost in property values. Some residents have a stronger case for working from home and getting their requests accepted. The west side of San Francisco may overall become more desirable given it already has the most amount of parks per square mile in the city.
Meanwhile, this vote demonstrates how certain issues can be strategically placed on a citywide ballot for a favorable outcome. I suspect roads like the Marina Boulevard and the Embarcadero could be put on the next citywide ballot to be shut down as revenge from west siders.
Feeling Like You Have No Authority Can Give You Great Motivation
For those feeling most outraged, this setback might ignite a drive to build significant wealth, empowering them to one day influence decisions in their favor. Without this loss, they might never have felt motivated to pursue such ambitious financial goals. It’s tough when others impose their will on you—no one likes to feel powerless.
For white residents on San Francisco’s west side opposed to the highway shutdown, this could offer a glimpse into what it feels like to be in the minority on a daily basis. Growing up in Virginia, I encountered racial conflicts that gave me tremendous motivation to achieve financial independence as soon as possible.
The desire to never be beholden to anyone fueled my willingness to work 60+ hours a week and sacrifice leisure to save more. Today, having the freedom to stand up for myself without fear of financial ruin is an empowering feeling.
Being a Loser Might Be the Best Thing That Ever Happened
Imagine you’re part of a minority group that’s rarely represented and often overlooked. Losing is familiar, and with identity politics at play, getting ahead can feel nearly impossible.
Now, let’s say you’re part of the 60% majority, running against a candidate from a 7% minority group. Technically, you’d only need 12% of the majority vote to win against a minority candidate with full support from their group. The odds are in your favor—numbers and resources back you.
But here’s the twist: what if, even with these advantages, you still lose? Despite being the frontrunner, despite the support and resources, you come up short. Such a defeat can be crushing, especially when the expectation to win was so high.
On the other hand, for those used to losing, the sting of failure fades quicker. And if you do manage to secure a victory, it feels monumental—a rare achievement against the odds. If you come from modest means, that victory is even sweeter, giving you a sense of resilience and a hunger for more.
This hypothetical isn’t just about elections; it applies across every type of competition:
- Competing with colleagues for a promotion
- Growing a business, website, YouTube channel, or podcast
- Securing a book deal, grant, or award
- Getting into college or a private organization like a club
- Getting picked to be on a team
In any of these scenarios, overcoming the odds brings a sense of triumph that’s hard to replicate when the odds were already in your favor.
Fight On And Never Surrender
After coming to America as a high schooler, I’ve experienced my fair share of losses. From falling short in district tennis, to getting in trouble with the law right after high school, to facing college rejections, to ending my finance career after just 13 years, to family false starts, to getting rejected by six out of seven preschools, I’ve grown accustomed to losing.
Yet, all those setbacks have helped me develop a kind of short-term memory loss that keeps me going. Because of it, I’m able to keep competing. The losses and rejections no longer sting as much as they did in my 20s and 30s.
Losing helps develop resilience, a vital trait if you want to eventually succeed. The next time you lose, reflect on the loss, and then carry on. Nothing will always go your way. Accept the fact and embrace the new challenge.
Tips For Overcoming Losses So That You May Succeed
- View Losses as Learning Opportunities: Instead of seeing losses as failures, treat them as feedback. Identify what went wrong, learn from it, and adapt your approach.
- Build Resilience through Repetition: The more you expose yourself to challenging situations, the less each loss will sting. Gradually, you’ll develop the mental toughness to handle setbacks.
- Separate Ego from Outcome: Avoid tying your self-worth to winning or losing. Stay confident in your abilities, regardless of the outcome, which will help you bounce back more easily.
- Celebrate Small Wins Along the Way: Recognize small improvements, even if they don’t lead to an immediate win. This will help you stay motivated and see progress.
- Surround Yourself with Growth-Oriented People: Spend time with people who encourage you to learn from mistakes and keep pushing forward. A positive, resilient network makes it easier to stay motivated.
- Practice Self-Compassion: Be kind to yourself after a loss. Instead of beating yourself up, remind yourself that everyone experiences setbacks. Compassion can make the journey to success far more sustainable.
- Set New Goals Immediately: After a loss, quickly refocus on the next objective. This will help you keep moving forward without dwelling on the setback.
- Embrace the Process, Not Just the Outcome: Winning is great, but the journey is often more valuable. When you enjoy the process of improving, the end result matters less, making losses easier to accept.
Readers, when have you faced a loss that helped you grow? How did you learn from it and come out stronger? Do you think people who avoid competition might be less resilient and take losses harder? What are some ways we can help people see the benefits of losing so they can eventually experience the joy of winning?
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As an asian immigrant woman, I am very upset by trump’s win. He represents the deep racism and resentment of the whites to the colored people. I also don’t like the abortion ban, it just brings more traumatized human beings to the already crowded world. Women should have total control of their body which includes terminate the fetus at any stage before it could be born. However, the super left dems go too far to encourage crimes that affect average people, to jack up the legal immigration system by allowing millions of people crossing the borders without proper documents (it takes years for people who obey to the law to prepare the paperwork), to over regulate to the teeth, to superficially doing DEI by using racial quota, and to allow biologically males to crush biologically females in sports etc.
I have a doomed look for the US. No effective leaders, but a bunch of greedy f××ks that represent the powerful and the wealthy, both parties and one of which is more racist than the other. Its people are entitled and miss the good old days, but in general have no competition edge over the cheaper and more efficient global workforce that capitalism prefers. So enjoy the current days as we could, the future would be worse no matter who is elected. It only differs in how fast we go down the hill anyways.
Sorry about your loss, but what we chose to do each day, who we lend our power to locally affects 98% of our life, not who is President. The prime directive of the federal government is to preserve and defend the Bill of Rights, our rights.
Ironically the democrats are the party of racism as FDR, by executive order (unilateral), placed the Japanese-Americans into concentration camps and seized their property. They also were against the Tuskegee airmen, fought against women’s suffrage, wrote the Jim Crow laws, created the ku klux klan and defended slavery.
No Federal Abortion ban, but controlled by the state as to uphold the 10th amendment granting more control locally.
The only 2 times a President affected my life was Bush Sr expanding the RICO statutes into civil forfeiture (eliminated the 4th and 5th amendments as it relates to property rights),
and Obama, by executive order, tried to have the county health departments take keys to our vending machines so they could perform random inspections (massive push back defeated that).
Be careful, curiosity may cause cognitive dissonance and set you free of the dogma du jour you get from MSM.
https://ballotpedia.org/Abortion_regulations_by_state
USA is a Republic.
I would love to know your opinion on male rights with respect to abortion. There are certainly instances where the man wants the woman to not have an abortion yet she goes ahead with it. Yet if the man wants her to have the abortion and she does not, he is often stuck with child support.
Given that it takes two to tango (excluding rape, of course) it seems to me that if a woman consents to sex, by default she is accepting that there is a remote possibility that she might get pregnant as well.
Are you worried your kids may be subjected to increased racism (ie, “poisoning the blood”)? Or do you see this as a tough but ultimately good learning experience for them? No kids myself, but I am worried about the younger folks I know.
No. We are a minority-majority here in San Francisco, where no single racial or ethnic group makes up more than 50% of the population.
But based on my upbringing in Virginia, I found being subject to racism helps build character and resilience. Racism really gave me extra motivation to work hard and find ways to independently make money.
I’m actually more concerned about them growing up too comfortable and then becoming demotivated and spoiled. This concern is partly why I decided to accept a two book deal offer after Buy This Not That. Each book takes 2 1/2 years to write, edit, produce, and market. So they will provide five years of concrete demonstration of taking academics seriously.
See:
https://www.financialsamurai.com/the-importance-of-feeling-consistently-uncomfortable-to-gain-financial-freedom/
https://www.financialsamurai.com/income-by-race-why-is-asian-income-so-high/
But racism is still terrible, but could not be eliminated at the individual level. Systematically maybe to a certain extent. The general hostility towards Chinese Americans and people of Chinese origins by Trump and his followers is the environment that creates tragedies like Vincent Chin.
How will you hold yourself and how will you react? What are some things you can do about it?
Racism in a diverse country like ours is inevitable. People will gradually favor their own. But if you can find something you enjoy doing, have a family who loves you, do something purposeful, and have financial success, then racism just becomes a nuisance.
How has racism negatively affected your life? Did you grow up in the south for high school and college as well?
A quarter of the California votes have not yet been counted which will trend more progressive. Once all the votes are counted, Trump is projected to win the popular vote by about a point and a half, hardly a “decisive” victory, especially in a high inflation environment where a candidate only had 3 months to make her case with “news” outlets like Fox acting as propaganda outlets for the Trump campaign. If about 125K total votes changed in WI, MI, and PA, Harris wins the electoral college. 125K votes out of about 150 million votes nationwide. Again, hardly decisive. I understand some people can be duped by the right wing echo chamber, but you’re a smart guy Sam. You’re buying into a narrative that’s belied by the facts.
It’s all relative. I’m just observing the facts that the election was called by 11 AM Eastern standard time the next day. And Republicans got over 70 million votes while Democrats got 65 million votes. So that spread is quite large, and then of course, there is the electoral college spread after winning all seven battleground states.
To find the next instance of a Republican winning the popular vote, you’d have to go back another 16 years to when Bush’s father, George H. W. Bush, won the 1988 election over Michael S. Dukakis.
What do you think is the benefit of arguing what a decisive victory means? Looking forward, what do you think the Democrats should’ve done differently and will do differently in four years?
Lol. The establishment got their clocks cleaned. Trump is the first republican president in about 20 years to win the popular vote. People rejected the marxist agenda with open borders, inflation, DEI, etc. Trump won every single swing state. No mention from you of the house or senate either that Reps are going to control. Even ultra liberal California turned more red.
Michael is just in denial about the Red Wave
They said it would take days until we could determine the winner. The winner was determine on election night. Red wave came and kept getting bigger. Glad people weren’t duped into electing Kamala president. All seven battleground states went to Trump in a clean sweep .
what has Gavin Newsome done that is unethical , that Trump has not done ? Whatever issues you have with Harris or Newsome pale in comparison to all the infractions of trump .
It’s about being strategic if the Democrats want to win. But they can roll the dice again if they want. Are you a big Gavin fan? If so, what are the reasons?
Definitely can’t put Gavin Newsom up for the next election. Democrats need to learn their lesson of not choosing too left progressive politicians from California.
But if Democrats don’t, they will lose again. Need a moderate Democrat.
Weird time. Very much did not want to see Trump in the WH again. However, four weeks ago I bit the bullet and bought an Audi S5 convertible. My first real toy. I have always struggled with “deaccumulation” and treating myself, although the price of the car (bought in cash) wasn’t even 1% of NW.
Now with the market reaction to the election I could have bought 3 of them and still in same place.
I’m trying to find positives. Not sure how this meltup will end but I’ll take the good with the bad and roll with it. Set some stops on assets.
Buying a $60,000 – $70,000 Audi S5 Convertivble with a $6 – $7 million net worth seems reasonable. Enjoy!
You write of “newsletter readers who were upset I wasn’t more upset about Harris losing. After all, I’m a minority who lives in deep-blue San Francisco. “
That reaction is a key to why their “side” lost. Americans were reacting to a segment of the population that always assumes it is “right”, and that anyone who disagrees with their ideas is “bad”. Yes, it can be argued that there are some on the winning side who share this flaw, but the tendency to push one’s political ideology upon (and to actively castigate, cancel, and malign) those who disagree with them is decidedly more pronounced on one side.
Additionally, the tendency to put people in boxes and make assumptions about how they think based on immutable characteristics (i.e., a minority who lives in deep-blue SF simply MUST be distraught this week!) is insulting to any mature individual with agency and autonomy. The world is not black and white; variables are infinite, and the man capable of recognizing and working with nuance is wise indeed. Well done, Sam!
Thank you. Yeah, it’s risky and lazy to assume one group is all alike in thought and action. I guess that’s called stereotyping? Interesting to see the gains in the Latino and Black male votes towards Trump.
I thought the bar chart that you included was quite insightful. It really shows that “identity politics” is fundamentally flawed. I think alot of people assume the political divisions are always very sharply delineated along certain demographics like Male or Female, Young or Old…. In fact, it’s like 45% vs 55% … that’s actually very balanced…
Thanks for writing this especially in such a positive light. It’s not easy to process heated political issues and events, let alone write about them in a nonpartisan, positive way. I think you do that very well.
Those who react harshly are typically lashing out because they are highly sensitive about politics in their personal life and views and thus can’t “hear” anyone else’s voice unless it exactly mirrors their own.
Setbacks and failures are a part of every successful persons life. Businesses too. They are often very painful and sting. But with the right mentality, they are a huge ingredient to growth, greater appreciation, and future successes.
Thanks. The feedback was interesting on my November 10, 2024 newsletter, which I thought was matter of fact.
But given the size of the readership (60,000), having for negative responses, all from women is pretty light. I want to understand more about the reproductive rights issue. Trump has said he will not support a federal abortion ban and the issue is up to the states to decide. However, those without means in a state that bans abortion, will have a much more difficult time if they want or need an abortion, which is a problem. I need to go read more perspectives from women about this issue, including the prosecution of doctors who are trying to save a mother’s life from complications, such as an ectopic pregnancy and more.
Sitting here in San Francisco, California, a women’s right to choose will be protected. So I need to get out there and understand more perspectives, and from the 45% of women who voted for Trump.
Sam, you are spot-on with both dating advice and losing.
I (was) a dating commando, and my creed was ” dating is a numbers game, the more people you meet, the better your chances of meeting Ms Right.” Rejection is your friend, the more no’s you get the easier it gets to approach. The key to finding the love of your life is to define Exactly what you want, and more importantly Don’t want, and pass up everything that does not meet the criteria. I went on, seriously, 215 one-on-one, meet for a drink, internet match dates over a 20 month period. Number 216 was the one, and we have been together for 16 years now.
Also, losing is powerful. I would highly recommend reading Success Forces, by Joseph Sugarman, Contemporary Books, Chicago. This book is almost Exactly what you have experienced in life, with a main premise of Cherishing your Losses, and learn from them.
It changed my outlook on life completely years ago, and I attribute some of my success and direction to what i have learned from it. If it is out of print let me know ns i’ll send you my copy. It’s that good.
Steve from Tidewater Va
“I went on, seriously, 215 one-on-one, meet for a drink, internet match dates over a 20 month period. Number 216 was the one, and we have been together for 16 years now.”
Wow! You were indeed the dating commando! Well done!
Opportunities are everywhere. Obstacles are those things on the sidelines that we see when we are not focused directly ahead on our objectives.