A secret to winning

We all want to win in our relationships, investments, love. But winning is often counterintuitive. And we can sum it up like this.

To win, you must be willing to lose.

You see, in relationships, we want to be right or argue our point or make people see our way, our hurts, our pain, our truths. But if you’ve been around the block and have some experience, you know that doesn’t work. In fact, it only poisons relationships. Making people see what you see isn’t a way to create intimacy. To go deeper with people, you have to lose that need to be known first and, instead, try to understand others before being understood, empathize with them, feel their pain. When you do that, you will likely deepen your relationships. Of course, you want to find people where this “losing” is mutual. They are willing to “lose” for you and you for them. But sometimes, it takes someone to initiate it. And if you do, you will not find yourself without friends and loved ones.

Who doesn’t want more money? Of course, we all do. I’m just keeping it real here. But, what we aren’t real about is how to win in this area. In investing, winning is also about losing. Maybe you’ve lost money trying to invest, and you don’t want to touch the stock market. But I think there’s a reason for that. It’s the fact that you’re trying too hard to win. I know that sounds confusing. But let me explain. When I lost money in the market, often it happened because I was too afraid to lose money: anytime my stock or investment started losing money, I would sell. Then that investment would recover and appreciate, and I would feel terrible because I felt like I was missing out. So then I would buy back into that stock when the price was higher. Then it would go down again, and I would sell again because I was losing money. And that cycle kept happening. In short, I would try so hard to win that, at any moment when I was losing, I would try to save myself by getting out of the market out of fear of losing more money. Maybe you can relate. After reading books and reflecting on my countless mistakes, I realized that I needed to just buy and hold. But to do that, I had to get my head right. I had to be willing to lose my money, all of it if necessary, if I had a high conviction about a company. That’s when I started making money. To make money, you have to be willing to lose it.

Love is complex. And I don’t want to say that to make romantic relationships work, you just have to lose, because that’s not necessarily true. But it does help. I’ve seen it in my marriage. When I’m willing to die to myself for my wife, our relationship goes better. And, when I say “die to myself,” what I mean is that I’m willing to set my agenda, preferences, desires, etc. aside and let hers be higher, more important. That’s losing. And if you do that, you will win. Your love will grow. Now, I don’t mean for you to get abused. No, marriage or romantic relationship is a two-way street. So you need to tell the other person to treat you better if they are treating you like crap. But often, to engender love, love will feel like a one-way street. And you might be the roadkill sometimes. But your relationship will likely flourish.

And, in general, too many of us care too much. We live like we have something to lose. We strive to upgrade our cars, houses, jobs. And we are terrified of getting them taken away from us. But what we don’t see is that this race robs us of joy. When we care so much about our stuff and titles and money, keeping up with the Jones, we just end up living poorer lives. We lose.

It’s when we stop caring so much that we begin to live more richly. When we stop trying to make another buck, sacrificing time with loved ones, and start making sure they feel loved, we are richer. I mean, have you ever seen someone who seems to live so effortlessly, who doesn’t seem to have a care in the world? I don’t mean that they are careless. They just are not that burdened. They may not be the wealthiest person, but they have something money can’t buy. They are free. I’m not saying we should all become homeless people. But we all burden ourselves with things that just don’t matter that much. If that’s you, stop worrying about winning. In fact, be more willing to lose.

If you do, you’ll become a real winner.


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When I made one of the biggest bets in my life

Sometimes you need to abandon plan b and go all in.

I recently read this 2013 article on Steve Job’s presentation of a lifetime. It was for the first iPhone. It was monumental, legendary, historic. Yet the article outlines all of the things that could have gone wrong (how the multitouch, making a call and surfing the web, messaging, etc. wasn’t working well). They had to get specialized cell service just for the presentation. It really shouldn’t have succeeded. It should have failed.

And usually, Jobs had a plan b for these types of presentations, having an out for himself. But not for this one. No. There was only plan a.

I think life is a lot like that, especially when it comes to decision making. Life is a bet. I don’t mean you’re going to the horse tracks and making wagers all of the time. What I mean is that we are all deciding on various opportunities and decisions. And each one is a wager. You can try to get a new job or make a change in your life, and each decision has risks and rewards, and they’re on a spectrum. And often, one option seems safer than the other. And choosing one over the other is betting. That is especially true when it comes to the big decisions in life. So, we are all making bets, more often than we may realize.

And, even playing it safe is a bet. If you don’t take risks and play everything in life safely is still betting. You’re playing the conservative hand, sure. But you’re also losing out on the possibilities or opportunities that only higher risks afford. There are possibly fewer bumps or losses or failures, yes. But, the safe bet is still a bet.

Now, I don’t think we should be making bets just to make one. No, that’s stupid. Risk in and of itself isn’t the point. That’s like dancing on the edge of a cliff just for the fun of it. Risk without respecting the risks, and not caring for the reward is just being dangerous. I don’t think you or anyone should do that.

Instead, there must be a goal and aim for the risks you take. You need to know the purpose of the bet and the risk involved. They need to be worth it. If you gamble something important, it must be for something better, greater, worth the ante. And if you’re betting, you might not have a plan b, but you should at least have a plan a.

For Jobs, he was, in a way, betting the future of his company. Apple hadn’t delivered anything new in an extended period, and people had been calling for a phone after the iPod’s iconic launch. Jobs was also announcing the launch of the AppleTV, but he believed he needed more. He needed the iPhone, which he was determined to deliver. And he did.

Over thirteen years later, Apple’s flagship product is still the iPhone, netting billions and billions of dollars and is arguably the most successful product ever. Yet, it started with a handful of partially working, glitchy prototypes in the hands of a man with a dream of making one of the greatest bets in his life. He went all in.

I think the biggest bet in my life was getting married. I was in my early thirties, and my future in-laws weren’t exactly my biggest fans during our engagement, and my fiancé was having doubts. We had even broken up during our engagement for a few days. I was terrified to tell you the truth. I had already experienced a broken engagement with another girl in my early twenties, and coming back from that took me about five years. And I wasn’t sure if I had the emotional resilience to recover from this engagement breaking. The likelihood of things working out between us at the time was uncertain. But after some prayer, I continued to feel the conviction to be with her. In fact, it grew. So I went all in. I wooed her with a romantic trip to Chicago and, afterwards, convinced her to meet with a therapist together. She was my plan a. And we made it to the altar.

Now, over ten years and two kids later, we’re stronger than we’ve ever been. We won.

What about you? What’s your plan a? If you don’t have one, form one. Dream a dream that you think is a stretch, might even consider silly, foolish. If the goal is about happiness, a healthy family, lifestyle, financial success, whatever, why not go for it? Why not abandon plan b? Make that bet. And who knows? You might win. Of course it’s not guaranteed.

But, if anything, you won’t just be alive.

You’ll have lived.


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How you can survive the pandemic

In this pandemic, our best medicine is to face reality.

Reality is being true to the situation at hand, you know, that we are in the middle of a pandemic and being with people is highly risky, especially indoors, mask-less. “Facing reality” means more than intellectual ascent, but actually practicing what you know to be true.

And, that might sound too obvious, but today I was at the grocery store and I saw a guy walking around the store with his mask dangling from one ear while he talked on the phone, flapping his bare lips. I wanted to say, “Hey, wearing a mask off of one ear doesn’t mean you’re wearing a mask.” Or, yesterday I heard about some family members of mine who are going out and even attending house parties.

I’m sure these aren’t stupid people. The ones I know are quite intelligent, well educated, “normal” people. Yet, they are still taking, in my opinion, outrageously dangerous risks for an unbalanced reward. I mean, why couldn’t that guy keep his mask on while talking?

You might be tempted to take the same kinds of risks. That’s probably especially true as you’re thinking about the holidays. I get it. I miss casseroles and pie. I want to hang out with family members, even that awkward uncle.

But, we are terrible at gauging risk for ourselves. We’re much better at it for others. We can see when something someone else is doing is too dangerous; but when it comes to measuring our own risks, we’re awful at it (read this article to find out more). I think that’s what causes that guy I saw on the phone and my partying family members to take bigger risks than what seems reasonable.

You see, right now, and for the foreseeable future, being true to reality is our best preventive measure to keep our loved ones and us healthy. Yes, there has been good news about Pfizer’s vaccine, but it’s not fully vetted yet. In other words, it’s still not real.

It can feel like the pandemic is close to ending. I feel it, too.

But it hasn’t ended yet. Just because we are close doesn’t mean we are there.

The last leg of a race is often the hardest one, and most treacherous.

When you think you’re winning is often when you can slack and let an opponent win. This mindset is why most accidents happen close to your home. We relax because we feel like we’re home when we’re still driving.

The reality is, we haven’t won; and we’re not home. Not yet.

But we can be. I think we will be.

And my hope is this, that as many of us as possible will get there, together—alive and well.


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Failing as a father

One of my greatest fears is to ruin my kids with my parenting.

You don’t have to be a parent to understand that fear. But when you are one, it just makes it more visceral, possible—real.

I’ve got two sons. They’re great. They love to play, roughhouse, laugh—all the good stuff kids typically do.

There are times when they misbehave. But that’s not the worst part.

I do, too. I get angry at them, and it’s wrong.

I’m not saying all anger is wrong. It’s not. Sometimes it’s right to be angry when your child disobeys you or does something bad for themselves or others.

And it must be dealt with, disciplined. But it needn’t be done angrily.

That’s where I fail. Instead of responding, sometimes I react. Instead of talking, sometimes I yell. Instead of instructing, sometimes I scold.

Yeah, I know. I’m failing.

But it’s not all of the time. I’m getting better. I do all of that reacting less and less, or, at least, I hope so.

And, there are some things that my kids and I do that are gloriously good.

These days, my firstborn and I go for bike rides. We ride all over the neighborhood. He leads the way. He’s trying new things like riding and taking his hand off of the handlebar or going with no feet on the pedals or pedaling while standing up. And I applaud him and celebrate his accomplishments. I shower him with encouragement.

Those are the best days.

I know that no father is perfect. But I want to improve my imperfections as each day passes. I want my son to have more happy days than sad. And when I must discipline him, I want to do it in a manner that is loving and true and good.

If you’re a parent and feel like you are failing your child, remember this.

All of our parents failed us in some form or fashion. I don’t know anyone who grew up with perfect parents, with a leave-it-to-beaver family, whatever that is. I certainly didn’t grow up that way.

And, really, who said parenthood was about perfection. Being perfect doesn’t work; life’s too messy for that. That’s why we should change the way we think about parenting.

It’s in the depths of imperfection and failings that we have the opportunity to choose to grow. It’s where we get to realize we were wrong and course-correct. It’s where we learn to become better fathers, mothers—parents.

To be a better father isn’t about always being right or good. I find it’s often about knowing when you’re wrong and admitting to it—and even being willing to ask your kid to forgive you for being an ass, temperamental, wrong.

It’s in the wrongness where we can be the most right. It’s in our worst where we can be our best. It’s when we fail as parents that we have the opportunity to succeed in parenting.

No, it’s not about being perfect. It’s about being perfected. It’s about being humble enough to realize we are all in process.

And if you do that, you may not be the “perfect” parent, but you will be a good one. You will bring out of the best in your child by admitting to your worst.

Because, really, parenting is less about failing or succeeding, and more about this.

Love.

If you do that, you won’t ruin your kids. Even with all of your failings, you’ll raise them well.

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The greatest reward for pandemic risk

Assessing risk is hard anytime, but, in a pandemic, it’s even harder. But it’s paramount.

People should think “The coronavirus kills and is unpredictable, so I should wear a mask, especially indoors, and socially distance so I don’t transmit or get infected and become a transmitter.” But many don’t.

Especially in the US.

People aren’t socially distancing. People aren’t wearing masks.

And I think it has a lot to do with how people assess risk. Yes, it’s not the only reason the virus is rampant in our country. Sure, people are selfish. And true, people think the pandemic is a hoax. But there’s also this critical mental exercise that so many of us fail to practice that often harms us. We don’t think realistically about the downside of our actions.

And, to be honest, that’s the wonderful thing about Americans: we are optimists. We attempt the impossible because we refuse to see the impossibilities. That’s what makes us scrappy, entrepreneurial, rugged, dogged, where many of us have an I-can’t-let-some-stupid-virus-stop-me-from-living-my-best-life mindset. That’s an attribute—in a pre-pandemic world.

My mother. I love her. She’s an octogenarian. She’s old. And last week she went to a store with my sister and picked up legos for my first born son. And I scolded her for it. Because, to me, going to the store with my sister to pick up legos for my son isn’t worth the risk of putting herself in danger of getting a virus that would likely kill her. But she scoffed at me.

The virus turns optimism against us. It seizes that which is usually a strength in a non-pandemic world and turns it into, not only a weakness, but a weapon. See, my mother’s ventures into a toy store can lead to her getting herself, or me, or my son, or others, sick.

Often we don’t even know what the stakes are. We’re completely unaware. That’s especially true now. I think it’s because the virus can’t be seen and anyone who’s sick is behind hospital walls and you can’t really see what is going on with them. All we have are some stories people tell us in the media or social media. And we lack the imagination and awareness (maybe even the humility) to apply those horrific accounts to ourselves.

Till it’s too late.

The pandemic is a long view problem. Short term desires and actions only threaten and kill more people. There are no quick fixes. It needs to be handled with creating new habits, patterns, thinking that affect our lives. But too many refuse to think that way, and, instead, they do what they want when they want because that’s what they’ve always done.

But the pandemic isn’t about losing money or failure or losing a job or getting broken up with—no. It’s about death. It’s about forfeiting your life, or, worse, your actions costing the lives of your loved ones. When we are cavalier and careless, trying to live on as if the pandemic didn’t exist, we aren’t endangering just ourselves; we are risking the lives of everyone we love, too.

See, the world has changed; and in order to survive, even thrive in it, we must also change. We must adapt. What once was safe is now dangerous, no matter how optimistic we feel. And with each interaction with the physical world, we must measure it against this new reality.

And if you do, there is reward.

It’s life.


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Savoring life

Life is short; enjoy today.

This week an old friend’s wife died. It was sudden—tragic. She was young, around my age, too young to die. They likely had dreams of growing gray together, wrinkled, swinging on a creaky porch swing, talking about their grown kids and grandkids. Now that’s gone.

See, life can sucker punch you in the face. It can knock the wind out of you, and make you feel like you’re dying.

But that’s not my point. The point is to enjoy—no, savor—each day.

And I don’t mean to party hard and do something thrilling. I mean sip and take in the moments and the mundane things like embracing your spouse, telling your loved ones that you love them, eating a home cooked meal with family—the things we get to do everyday, but often take for granted because they are so normal. When placed against the finality of death, those are the things that matter most.

So let your palate of life absorb each and every flavor. Relish them. Feel satiated.

For life’s a delicious gift.

Give thanks.


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Things got weirder

These past few days things just got weirder.

An image of a married couple brandishing firearms and pointing them at people who were peacefully protesting shocked me.

They live in my city. They’re not far from me, which only added to the weirdness.

These people, who are basically my neighbors, looked like some strange mash up of Rambo and James Bond. And I couldn’t help but wonder, ‘What would cause someone to do something like that?’

And the only thing I could think of was this.

Fear—naked and unadulterated terror.

It distorts reality, dements our thinking, bends our minds away from facts into a terrible fiction. It makes peaceful protestors into “terrorists.” It can make something uncomfortable into a nightmarish scene that came from a movie like The Ring.

But the fact is that we all live with fear. They just lived it in public, captured on video, shared on public media.

Now don’t get me wrong. I’m not defending them. What they did was absolutely wrong. They could have killed someone. Their actions were reckless, foolish, and terrible.

But, I am trying to understand why someone in my city would do something so outrageous. What would cause someone to think, “You know what? I’m going to grab my semiautomatic rifle and take it out to the lawn and hold the line,” and then I say, “Hey, Honey! Grab your pistol and meet me out there!” I mean, you don’t do that unless you thought it’s a good idea, or felt compelled somehow.

And that’s the issue isn’t it? What made them think it was a good idea?

Any rational human would have known it would get filmed and splashed on social media. Anyone who would have taken a second and breathed in and out and asked themselves, “Is pulling out firearms in public the right move?” would have realized how idiotic it was.

Yet they didn’t. And they stood their ground, holding the line, imagining they were defending their hill to the death even though death never came for them.

St. Louis is one of my favorite places in the world. I’ve live in other parts of the country (New York City and San Diego). I’ve traveled. But St. Louis is great. It has amazing amenities, it has rolling hills, lakes and rivers, bursts with color with the autumnal foliage, and the nicest people. (They usually don’t wave their guns around.) Really.

They will smile and wave at you. That’s right. Complete strangers look at you in the eyes, acknowledge your humanity and then greet you warmly. Let me tell you something, that didn’t happen in NYC. I love that place but it isn’t known for its friendliness. But St. Louis is friendly, exceedingly so.

Now you juxtapose that with these two gun slingers. It’s strange. But in a way it’s not.

St. Louis has some of the loosest gun laws in the nation for a reason. We love our 2nd amendment here in Missouri. And it doesn’t take much to see it. When I scroll down my Facebook feed, I’ll see friends holding their AR15 or a family member talking about this new “easy conceal and carry” that they bought for the missus.

And the city’s love for guns is largely due to the fact that we are a very conservative (I’m not using the term in the political sense, although that’s true, too) city. We love safety, comfort, ease of living. I mean, there’s a reason why this is one of the most affordable cities to live in and pays some of the highest wages. We love to be fat and happy here, quietly living in our fiefdoms in fly-over country, unbothered, unmolested, eating pasta, toasted ravioli, custard, and thin crust pizza until we are rub-your-belly full.

But then you have barbarians “breaking down” the gate terrorizing a private street, invading their land, penetrating their border and ransacking their village of a city block.

That broke up the tranquility of this couple’s existence and disturbed their daily life, the safety they felt. It’s likely they’ve been feeling uneasy for months, not just from the pandemic but the “riots.” Tensions within in their home might have been high, as it has been for many of us.

And seeing strangers barging into their neighborhood was the last straw, and their frayed nerves were exposed for the world to see, witness, jeer at, and ridicule.

They are the butt end of a national joke.

And yet, they’re not. There are many in our nation who believe them right and good, righteous even. More said, “Good for them,” than I ever thought would have, as if what they were doing was their God-given right and the best idea to execute. People even seemed to envy their behavior and saw it as something to aspire to, as if waving a gun at innocent people was an act one should do.

It’s disturbing.

The most ironic part of this whole situation was that the couple said that they believed in the Black Lives Matter movement. They didn’t want people to think that they didn’t believe in it they said in an interview after the incident. That was the weirdest thing I’ve heard in a long time. And that caught me off guard the most.

And I thought, ‘How could a couple who believes in Black Lives Matter point weapons at protestors who were for Black Lives Matter?’

We humans are frail creatures. Empathy isn’t just needed for some people, but for all people. I know what these people did was completely wrong and stupid. But if I’m honest with myself, I’ve been idiotic, brash, harsh, foolish. I don’t own a firearm but I’ve thought about it.

So, in all of this weirdness, I’ll end with this weird thought.

It’s easy to point the finger and wag our heads and say what is off with those people. But I wonder if we shouldn’t be grateful that we’ve been spared from doing something like that and acknowledge that if we were in the wrong place at the wrong time, that could be us. We could be caught doing the dumbest things we’ve ever done on video.

And if we think like that, maybe, just maybe, our world could be a little kinder, and generous, and gracious, even to those who are having the worst day of their life.


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Heal your wounds

The key to healing a wound is to move toward the pain.

You know the relational or financial or emotional problems that happen in life. They hurt us.

We’re wounded.

But if you don’t face the uncomfortable, even agonizing conversations you don’t want to have with your partner, friend, mother, it only makes the relationship harder, unhealthier.

Or if you don’t look at your finances as they are and really dig into them, that will only make your financial future grimmer, darker.

Maybe something in your past is haunting you. Some act you did or was done to you sits on your mind, heart, burdening you. And you want to ignore it, but it only weighs you down, like an anchor, drowning you.

The only way to heal is to move toward our fears, what pains us.

It’s like a cut.

My son runs around and often get scrapes and bleeds. When that happens, he knows the next thing we are going to do. We bring him into the bathroom and clean off the wound with soap and water. He screams, cries, hates it—all of it. But if we didn’t do that, he would only have bigger problems later, get an infection, or worse.

Likewise you need to push into the pain. Even after you grimace, maybe scream, you must press into the difficult conversation, make the terrible spreadsheet, talk to a therapist. You need to face the things that scare you.

And it will be like a surgeon taking a scalpel to an infection, cleansing you, healing you. It will keep you from greater pain.

It cuts, but it heals.

You’ll feel whole.


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You are not an imposter

You’re not an imposter; you’re just in-process.

You might be a father learning to parent, an employee who is progressing in your career, an entrepreneur hustling to survive, or a couple trying to forge a healthy marriage. That’s good; that’s great.

Life is a process.

Anytime you try something, do something, go somewhere, you’re not going to be an expert, specialist, authority, master.

And it’s easy to feel like you don’t belong, like you’re “faking it.” But you’re not.

For anyone to become a master, you have to be a beginner. You have to muddle through, practice, attempt, fail, then try again and improve.

You’re in-process.

There’s nothing more real than that.

Even experts still need to learn and feel like imposters, because we’re all continuing to learn, grow, and become.

See, to do anything, everyone is an “imposter.” Everyone is between a beginner and expert, student and teacher, birth and death.

And that’s a great place to be. That’s where the adventure is, learnings are found, discoveries are made—life is lived.

So just because you don’t know as much as you want to or feel out of your depth or lack clarity on the future, that doesn’t make you lesser.

It just means you’re on a great journey to better things.

The key is to keep moving forward.


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Gain More Gratitude by Doing This

He asked for $50.

This week my friend told me a story that broke my heart. The man who mowed my friend’s lawn, came up after he finished his work and told him that he really needed money and asked if he could borrow some. He needed $50.

Could you imagine working up the courage, the shame inducing gumption, to ask for that? Not $100,000, $10,000, or $1,000, not even $100. It was 50.

My friend held out the money and said, “Take it, but, please, don’t worry about paying it back.”

I’m writing this not to make you feel bad. It’s just to raise the awareness of the utter pain, stress, and agony that is going on in the world (which I was barely aware of until I heard a few stories recently, including the one I just told).

If you have more than many, then you should give to those who have less.

That will not only change your mindset of thinking you don’t have enough; it will remind you of how much you really have.

Giving to others makes us grateful.


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