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.


Want life advice that helps you live better? Subscribe!

2 thoughts on “When I made one of the biggest bets in my life

  1. Great post. I am stealing from someone I wont cite here but there is a piece of mind, a clarity that comes with this sort of “all-in” commitment. To embrace the “found” and let go of the search. Like “risking” hanging out with a smart-a%#-skater and ending up with a smart-a%# friend for life.

Leave a Reply