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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