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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Resolutions are good, legacies better

Don’t just make resolutions; leave a legacy.

Over the break, I, like many of you, reflected on the past year and casted hopes for the next. It was a mixture of memories and dreams, sadness and joy, grief and gratitude. There wasn’t much clarity that came from that exercise for me. But there was one question that rang clearly.

And it was this: What legacy will you leave?

When I say “legacy,” I don’t just mean an inheritance of money or property or things that you leave behind to your inheritors. I certainly don’t mean getting your name on a big building with Roman columns, no.

I mean less conspicuous things that leave a greater impact, like shaping your children to make them more loving, unselfish, and honorable human beings. I mean giving the hopeless hope and beauty and truth. I mean the immaterial things that make the world materially better. A legacy is more than the items we leave behind; they are the impressions, even imprints, we make on a person’s soul and the world’s spirit.

Isn’t this a question that we should all ask ourselves? So, What legacy will you leave?

For me, as I let that question slap me across the face, and I feel the reverberations of its meaning pulse through me, I think of my children. I am far from a perfect parent. In fact, often, I think, “I’m a terrible father.” But that doesn’t mean I don’t try to improve. I do. But I fail often. And when I do, I ask for forgiveness, from God, from my wife—from my children.

The question also compels me to write more, better. I don’t just want to write on this blog, although I do love it. I want to create art by writing a novel. I want to tell stories that shape not only this generation but generations to come. I don’t know if I can or will. But I must try.

Maybe you don’t want to have children, or you’re not a writer, or whatever. That’s fine. There are other ways to leave a legacy. You can create something else. You affect your neighbors, coworkers, friends, etc. We all have an impact on the people around us. And it’s not just about what you do, but how you do it. Do you respect others even when you disagree with them? Do you treat people who have less than you with more dignity? Do you love people as you want to be loved? Those are legacy leaving questions.

Don’t get me wrong; I’m not perfect at this. I’m awful at it, really. But that doesn’t mean I shouldn’t continue fighting to carve out a better world. If anything, if my family and friends can say that I never gave up and continued to fight for good, that would be enough, I think.

So, in this season of making resolutions, setting goals, trying to be a better you, do that, but do more than that. Those changes are good. But let’s all find ways to create more lasting change, something that will live longer than ourselves. Let’s leave a legacy that will bear fruit beyond 2021, or the years to come, that will echo past the grave.

And, the fact is, we are all leaving a legacy whether we like it or not. The question is, What kind will it be?

That’s a question only you can answer.

It’s a choice.

So, what will you choose? It’s one you get to make every day, every moment.

Right now.

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A stronger you is often born from weakeness

Weakness often begets our greatest strength.

Most of us hate the idea of being weak. It conjures up images of being needy, helpless, desperate.

But that is one of the best ways of unleashing our greatest strengths. It’s often when we’ve hit a place where we feel the most vulnerable, exposed that something is catalyzed to take us to a place we never imaged going, somewhere better than we ever dreamed.

It happened to me.

I was fired from the only job I was qualified for in my mid-twenties. It devastated me. I lied in bed for months wallowing in depression from the loss of a dream and career and years of training. I didn’t have any idea of what I was going to do for a career moving forward; I had no idea how I was supposed to pay for rent. I was lost; I was weak.

But, at that time, what I didn’t know was that that season not only formed my character and solidified a faith in me that would help me weather future storms; it set me on a new trajectory that served me better in so many different ways.

After I got fired, I started an entry level job at a huge bank that helped me understand business and finance. That helped me land a job at a small design company that gave me a view into entrepreneurship. Marrying those experiences, I started my own company. And later, I used the cumulative learnings to begin investing.

Getting fired ended up being one of the best things that ever happened to me.

Being terminated initiated the trailheads for new successes and directions that I would have never imagined for myself all those years back. And with each step forward, I couldn’t have known where it would lead me. But, over time, when I looked back, I started to understand the beauty of how things worked out for my benefit.

And I’d be remiss to say that I wasn’t aided by incredible Divine Grace. I was. I was the object of God’s mercy and love. But that’s not my point. Nor am I saying that there aren’t deeply tragic events that happen to us that can collapse all of our hopes and darken even the brightest of days. There are.

My point is that there is almost always a way out when the terrible strikes. And if we are open to the possibilities, things tend to work out better than they were before, even when you feel like you’re at your weakest—often especially when you’re there.

See, even this pandemic that’s ravaging our world is a case study for this dynamic. The virus has brought us to our knees and halted travel, commerce, holidays—life. But, even now, in this pit of weakness, we can see the sprouts of new strength growing in our world. It’s visible in the historic innovations in science with the vaccine developments, bolstering our supply chains, and improving our healthcare protocols. It’s evident in how we appreciate our health and families and how we’re all washing our hands a thousand times a day.

Christmas also gives credence to this. Jesus, the Son of God, was born as a baby. He came into the world vulnerable, flesh and blood, killable. And he didn’t arrive with pomp or in a court or with a scepter or divine fire. No, he came swaddled and weak, suckling and shivering, lying in a manger.

So, if you are feeling weak, remember; you likely won’t remain that way. And more than that, it’s often the beginning of a path to a strength you may never have believed you could possess.

It’s the begetting of a new you.

Merry Christmas and Happy New Year. See you in 2021.

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To be rich, this is the kind of hustle we all need

Often it’s not how much money you make but what you do with it that counts.

I heard this story about this Chinese woman selling these little buns, for like fifty cents or something like that, in New York City’s Chinatown many years ago. And after maybe decades of working, she bought a building in Chinatown with her earnings. Then from there, she bought others.

You see, she didn’t make much, but she made the little that she had count. Day by day, she saved every cent to maximize her efforts to reach her future goals. She didn’t let her small income hinder her from dreaming big dreams. No, she did what she had to in the short term to enrich her long term vision.

She didn’t spend her money on nice clothes, a nice house, eating out, a Lexus. No, she saved. And, she slaved away rolling those buns before dawn, then spent the rest of the day standing on her feet selling her goods and wheeling her cart back and forth to her corner. And after she saved enough money, she invested and bought an asset that could earn her income. That’s hustle.

But it’s not just any kind of hustle. It’s immigrant hustle. It’s starting small, with virtually nothing but some buns and cart, and ending up NYC landlord rich. It’s knowing that you can compound a life’s worth of work and see incredible gains if you persist and manage your resources smartly.

She knew that even though she didn’t make a lot of money, she could save and not spend. And, this is important—over time, years, even decades, she could invest. She would accumulate assets that would make her rich. That’s the equation that makes the rich rich: saving + investing.

You see, you don’t get rich by living richly. No, you do it by living poorly and investing like the rich. That’s how fortunes are made: little by little until you have more than you can count. Fortune favors the patient and diligent. You don’t have to be an immigrant to practice immigrant hustle, nah. Anyone can do that.

Most of you have a greater advantage than this woman. Imagine what you could do if you heeded her example.

Yeah, you’d be rich.

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A time to grieve

Grieving can be one of the best things we can do.

Life isn’t all rainbows and unicorns. Sometimes it sucks. Sometimes it almost kills us. Sometimes it sends a pandemic.

Those are the times we need to grieve. We need to face the terrible state of our life or the lives of others or our world, and we need to recognize it for what it is. Broken. Wrong. Sad.

Grief isn’t something that many of us like to do. We like to feel strong, capable, ok, good. But feeling bad, not ok, incapacitated—weak, no, we don’t like that. Many of us hate it, in fact.

I know I do.

But isn’t grieving what we all need these days. Isn’t it better if we just let the sadness of all that is happening in the world, in us, wash over us? And, instead of fighting it; we just feel it. We succumb to the reality of our situation.

Sometimes that’s the best thing for us.

Sometimes that’s the best act we can perform.

Sometimes being weak is the strongest thing we can be.

And, doing that is often the first step toward healing.

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This is your bet of a lifetime

We’re all betting, but there’s more to winning.

You see, how we spend our time, energy, and money requires us to decide how we want to allocate them. How much time and money do you spend on this or that, invest in the stock market, get together or not, buy expensive clothes, or not are all investment decisions. They’re all bets.

Life is a bet.

But that’s not the problem, though. It’s that many of us don’t know how to bet well.

Some of you are conservative, others aggressive. Some of you play not to lose, others to win it all.

And, really, some make better bets than others. Some tend to win far more often.

And what makes the difference? That’s the question.

There are a lot of factors. But I think it boils down to one thing. It’s this.

Short-term thinking.

We think if we cut corners, or buy that shiny thing right now, or sell that stock to get the $1000 profit instead of waiting, we will be better off.

That’s why we buy fancy cars or too much house or refuse to save our money and invest because we’re too tempted by instant gratification.

But, all the while, we don’t realize that we are undercutting ourselves from getting the things we really want: respect, wealth, flourishing, wellness, etc.

See, all of those things take, well…time.

They are goals that take a lifetime of building, doing, working.

If you want healthy relationships, you need to cultivate them with truth-telling and integrity.

If you want wealth, you need to spend less than you make and save and invest your money.

If you want respect, you need to earn it one decision at a time and pay the same respect to others.

If you want wellness, you need to practice daily practices that make it so.

By betting well, you will increase life’s quality. You’re not just betting you’re life but how you will live, not just your livelihood but the quality of your life.

Making great bets take time to play out. They aren’t quick wins.

They’re long ones, even a lifetime. Knowing that will make the difference.

You’ll win more.

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Gratitude is good, but contentment is better

Gratitude. It’s something we hear a lot about, especially this week. But, there is something that has a greater impact on our lives, like gratitude, but more richly. What is it?

It’s contentment.

You see, gratitude is something you do, an action. But contentment is a state of being. It’s not just an act; it’s who you become. What I mean is that we don’t say “practice contentment,” like you would say with “gratitude.” Rather, we say to “be content.” We do say “be grateful,” but that often means for something or a particular time, like “you should be grateful for this present, or this food, etc.” Whereas, “contentment” is what you are. And therein lies the magic.

With gratitude, we’re told to give thanks for this and that, and we have our gratitude practices, journals and yoga poses (I don’t know if the last one exists or if I just made it up). But after we’re done practicing, journaling, yoga-ing. It’s easy for us to fall right back into complaining, wanting, pining.

“But John, I practice my gratitude sessions every day,” you might be thinking, “and I hear people talking about gratitude all of the time.”

I applaud you and am sure that you are practicing it, but I think we talk too much about gratitude; and not enough about contentment.

Because, even though you have that practice, you still live with dissatisfaction and envy and a grass-is-always-greener syndrome. Deep down inside, you probably think that if you get that upgraded car, or prettier spouse, or more money, or that new job, or better home, or whatever, then you’ll be happier. And you might be for a bit. But you won’t stay that way. That happiness will fade because practicing gratitude is a start, not the fulfillment.

Just because we practice gratitude doesn’t make us live gratefully. When we are content, that’s the fulfillment of gratefulness.

A sign that someone is content is if they look at their life and sincerely say, “This is exactly where I’m supposed to be right now, and I’m glad” even with all of the crap going on, the pain, the difficulties, mixed with the joys and blessings and goodness.

“Contentment” means you’re satisfied with who you are, what you have, where you are, etc. When you look around at your life and at yourself, you’re filled with satisfaction.

It’s not that gratitude or the practice thereof is bad—far from it. Gratitude is a part of contentment. To be content, we must have a gratitude practice and that can include our spirituality.

For Christians, like me, contentment should be particularly applicable to us. God is called our “portion” in the Scriptures, and that means he is everything we could ever need or want. And if we believe in him and that he is truly God, then we should grow in our contentment. We can know that this world does not have what we really want. For what truly feeds us and gives us joy isn’t here. It’s him, the Eternal Being.

Now, don’t get me wrong. I struggle with contentment, too. Very much so. Even when I’m doing my warrior one gratitude poses on my fancy yoga mat, getting my grateful namaste on, telling myself that I’m glad to be here right now, I can still feel a twinge of envy for this or that thing I want but don’t have.

But, I am improving. If I can, so can you.

So in this great season of Thanksgiving, let’s not just give thanks. Let’s learn to be content.

For, today is a gift.

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Patience: the secret to growth

Growth is a winding, circuitous, and weird path. It’s rarely a straight line. It doesn’t go the way we expect nor want it to go. Sometimes it even means going backward before we begin moving forward.

And that’s not necessarily the problem. It’s this. The problem is we often expect our growth to progress linearly, and when it doesn’t, we get disappointed, frustrated, upset.

That can lead us to slow down our growth no matter where it is, or, sadly, some of us even give up. That’s why we need to see growth differently.

What I mean by “growth” is any activity in life like learning, gaining physical capabilities or skill or fitness or spiritual development, etc. I mean any area of life where a human can progress and get better. That bettering is growth. It’s you getting better.

And, yes, it requires hard work. We need to challenge ourselves and try to do it. We all know that. But what we may not know is that it’s more than that.

Sometimes we must realize that even after working hard, things don’t always work. Sometimes you will have setbacks that will cause depressions. Sometimes you will feel like an utter and complete failure. But you’re not.

You see, your growth isn’t linear. You’re on the winding path of growing. And as long as you are still trying and working and learning, you are still on that path, no matter how you feel in the moment. Even if you’re failing, you’re not a failure; you’re just on the circuitous route toward success.

And, this is when we need patience. It’s the secret weapon for growth. Stop looking at your progress in terms of days or, worse, hours. No, look at it in terms of years, and decades. That’s what it often takes to make real leaps of progress. When you have that mindset, you’ll be able to overcome the hiccups of the day, or the week, or the month, or even years. The mistakes you made or the shortcomings or the face-plants will be blips in the grand scheme of things.

If you’re patient, you’ll give yourself space and time to grow.

And, before you know it, you’ll see a better you.

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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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Politics and investing

No matter who’s party is in the White House, the market is in the black.

The stock market has been volatile these past several days leading up to the election. And it’s easy to want to sell our investments with a click of a button and jump in a bunker and hunker down.

I get it. I was there last week.

But that doesn’t work.

You see the market has been going up for almost a century. Yes, it goes down here or there, think 2008-2009, or this past March, or last week or so. But, usually, it goes up.

That means we need to take the longview when we invest: Check out this chart.

And that’s true, no matter who wins the election. The blue lines mean a Democrat was president, the red, you guessed it, Republican. So whoever plops themselves behind the desk in the Oval office, if you stay invested, you will likely get wealthier. It’s not optimism. It’s just reality.

So don’t liquidate your retirement fund or portfolio.

Instead, vote.