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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This is how you make better decisions

We all want to make smart decisions. And you can, by living in the tension.

Now I’m not talking about the daily decisions like eating a sandwich or salad (get the half and half, of course), or to like a photo on Instagram or not.

Let’s talk about big decisions, like looking for a new job or not, marrying this person or not, moving to a new city or not, breaking up with that person or not.

Those decisions are hard, and scary.

Because they can really change how you live, you take them seriously. You don’t want to derail your life and become a trainwreck.

But instead of trying to figure out what is the best way forward, it’s so tempting to do nothing. You decide not to make a decision. You keep on dating that person that you’re not so sure about, stay at a job that just doesn’t quite seem to be the best fit, keep doing what you’ve been doing even though you hate it.

But that is a decision. Indecision is a decision.

So you might be asking, What should I do instead? Good question.

Everyone has their practices for making decisions: prayer, meditation, journaling, walking, fighting, driving, etc. I won’t tell you which method is best. Everyone has their own style, gait, way. You do what feels right there. But I will tell you this.

To make smart decisions, you need to sit in the tension.

That means sitting in the push and pull of the possibilities, the pros and cons, the uncertainty. You have to straddle the choices and hope nothing jumps up and smacks you in the groin. And you have to stay there.

The only issue is that we hate living like that. All of us want certainty. Everything in us craves it like a stray dog slobbers after food. So we end up making stupid decisions because we want to rid ourselves of the pain of not knowing.

To do that, many of you do the opposite of indecision: You make a rash choice because sitting in the tension sucks. It’s so tense. To make the unknown known as quickly as you can, you just decide even before you really know what you’re doing.

You get engaged even though you see enough red flags to make you feel like you’re walking around Beijing, take that job even though the new manager seems like an ass, move to a city even if you’re not confident it’s the best place for you.

One of the primary mindsets that causes you to decide too quickly is that many of you idealize what something can be, telling yourselves that such and such will work out. So you jump in. But the truth is that things often don’t work out. Marriages break up fifty percent of the time, more people than not hate their jobs, and a lot of people live with regret.

Instead of being idealistic, some of us can demonize an option, not because anything is really that wrong with it. You just think that nothing works out, so why should this be any different. You tend to be a glass half broke type of person. So you turn down anything that comes your way, thinking of all of the negative things that could happen to you. But you’re likely being overly pessimistic, because things rarely go as badly as we think they could. (As much as we think the zombie apocalypse will happen, it probably won’t.)

Regardless if you’re overly optimistic or pessimistic, making rash decisions isn’t a good decision-making process. It’s gambling.

Sure, you can make a quick decision, and sometimes that works well. Life does require assessing risk and taking risks, but it shouldn’t be treated like a roulette table, where we put all of our chips on red just because it feels right. You can get lucky, but that doesn’t mean your decision-making process is good. That doesn’t mean you will consistently make a great decision.

To do that, besides straddling the options, hoping that nothing bops you in the private parts, you need to search for the truth.

To know the facts about the options before you is key. But to do that, you need to do the work. You have to pick up a shovel and start digging. Ask the hard questions to those around you that are relevant to your decision. If you’re looking at a job, look at Glassdoor and read the reviews, talk to people in your network and ask them what it’s really like to work at that company—keep digging.

If you’re thinking about getting engaged but you have your doubts, you need to look at them. Be honest with yourself. When it comes to love, we tend to have rosy glasses on. We do that because we want to spare ourselves and the other person the truth that you shouldn’t be together (knowing that is terribly inconvenient). But you’re afraid of being lonely, so you just wander into an engagement that is convenient but genuinely uncomfortable. It sucks, really. Don’t do that. Shoveling past the smelly crap you are telling yourself will force you to see that you both would be miserable if you take one more step forward in your relationship. And you will likely do the one thing you know needs doing: Breaking up.

Shoveling to find the truth is hard work. It’s painful. You get blisters when you dig long enough. But there’s gold in them hills.

You can also get callouses and feel tempted to dig forever. That’s just going back to indecision.

To mitigate against that, create a deadline. Sometimes one is given to you by a potential employer in an offer letter, or something like that. But when it’s not, make your own. Mark it in your calendar. Tell yourself that you will decide by the time you set.

Of course, make sure you have enough time to dig below your dung pile. That layer can be quite thick sometimes, you know. We can tell ourselves a lot of lies. So give yourself the time to find the truth. And then you need more space to pray, meditate, journal, walk, fight, drive, or whatever you do to make your decisions. So account for that.

While you are deliberating, know that you can’t make a perfect decision. That does not exist. Remember that you are blessed to even have such choices before you. But if you practice sitting in the tension and digging for the truth, you will have a better chance of making a great decision than a poor one.

And you won’t find your life derailed from your decisions. In fact, you’ll realize you’re not even on a train. You’re not a passenger.

You’re an explorer. You’re in a forest. And you’re blazing your own path.

So decide the best way forward for your life.

Then go onward. Life is an adventure.

Decide.