Wynn-ing Ways: How to Make Choices to Achieve Reliable Results

Evaluating choices

On a Saturday morning, I heard Suze talking with my oldest son. He wanted to get his ears pierced.

He is sixteen.

She then came into the office and asked me if I knew he wanted to get his ears pierced.

I didn’t.

We had a conversation over breakfast. I suggested what I’m working with you to build: a process to evaluate decisions.

Guess what I said?

I told him to start a decision-making journal and make this the first decision he thought through.

I told him I was okay with him getting his ears pierced if that was his decision once he did the process.

Now, you may think that’s a dirty trick. I said no by giving him a homework assignment he would likely never complete.


Or is it a learning moment—a time for him to get a skill that would give him an advantage throughout his life?

How would your life be different if you had a decision-making process that early in life?

If I can get him to evaluate choices and have confidence, he’ll have more opportunities in life, along with a significant competitive advantage.

At the time of this writing, his ears still aren’t pierced. Nor did he write out that list.

Maybe the urge to pierce his ears just passed. Perhaps he thought it through and decided that it wasn’t something he wanted to do.

I didn’t force him to do the work.

He may never adopt what I offer. Only time will tell.

I’m banking that through the example, he sees that being deliberate and using a decision journal will help him make better decisions.

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What does that mean?

That he will find some mythical process that makes everything go the way he expects.

That’s a fantasy.

We will always face choices where we can’t see all the critical information, resulting in unintentional consequences.

But the next time…

Like Lefty, you adapt and improve your process to become better at assessing a situation. You’ll consider a bunch of potential probabilities before making a choice.

Lefty and Annie Duke are good at this kind of thing. They can do the math in their heads and quickly assess a problem. In the Deal or No Deal problem, Lefty would know the odds, the premium, and take the offer.

If you’ve ever watched the show, few ever take what the banker offers.

Along with friends, family, and the audience, the contestant gets caught up in emotion and wants to stick it to the bank and not push the deal button.

That all feels real at the moment, but the odds are the odds.

We think we know the outcomes or worse, that our enthusiasm has some type of influence on the outcome.

There are also the Think and Grow Rich manifestation ideas that say you can manifest the future. That if you desire something so much, you’ll adopt probability planning to gain an advantage. In doing so, you become luckier.

Where I fall is that I’ll do my best to create the life I want and make the most of what life sends my way. With that mindset, I have fewer regrets and can see what opportunities are in front of me.

Here’s a thought experiment:

Imagine where you would like to be in twenty years. Can you picture what it will be like?

Now, think back to where you were twenty years ago.

Could you have imagined the life you have right now from where you were twenty years ago?

Yet you can connect those dots easily in hindsight.

Look at some of the big decisions you’ve made and their impact on the course of your life.

In my case, one colossal decision was to go to Australia.

When I was in my early twenties, I was working in a business. The company was looking to open a division in Australia. The guy they hired quit before he even got started.

I offered to go to Australia and manage the new business. I had no expertise, and the totality of my evaluation was this was a great way to see Australia on the company’s dime.

My decision set in motion a new array of choices while also closing down other opportunities.

 Yet, not much went into such a big decision. While I have no regrets, it’s only now, in reflection, that I understand that every decision has follow-on consequences.

Looking back, if I had this system at that young age, I would have been able to capture how I’d missed things that ended up being important cues to how things would turn out.

What original decision got you to where reading these emails was important?

Was it just writing a book that was in you? Was it a childhood dream of writing full-time? Whatever it was, you’re at a point in the present where you can reevaluate and be conscious of the choices you make.

When we apply your decision process to building your business system, one of the critical ingredients will determine what you want out of the business and what is possible.

One decision you make each week is to read these articles.

Your belief that your attention is worth the value in this material is a small choice, but an important one just the same.

Even if you disagree with my hypothesis, you’re exposing yourself to a countervailing thought.

I commend you for being willing to expose yourself to unconventional ideas in an effort to grow.

 Of course, I believe that adopting these practices will tip the scales in favor of those willing to embrace the systems I outline.

From my experience, I know that sometimes I’m just not ready to hear the message. As the adage goes, “When the student is ready, the master will appear.”

If you’re not ready, then you’re not ready.

I’ve had some folks say that I repeat some things over and over in these articles. I do because, just like a marketing message needs multiple contacts to take hold, so do these ideas.

It’s not the easier, softer path.

But it may be the path that gets you to where you want to be.

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In short, the more you take responsibility for thinking through your choices or at least resisting the thrill of a snap decision, the better your chance of getting to where you want to be.


P.S. Here’s one of the replies to last week’s email. When I read it I had already written this week’s email so I thought it was fitting to share it, since it spoke about younger people learning ways to make better decisions.

BTW I get a lot of replies to my emails. with IOS 15 and other privacy protection coming into play the email reply will be a certain way to gauge newsletter engagement.

Hi Joe

I was excited when your email today was about making decisions. 

I write and publish You Say Which Way, a middle-grade interactive fiction series. So I think about decisions all the time. My role as a writer is to present delicious and intriguing alternative choices to the reader. I want the choices to be equally tempting and, once a pathway is chosen I’m wanting a lingering ‘what if I’d chosen differently?’ to haunt the reader and have them start over and choose differently. 

Writing fiction with choices also involves the traditional story telling tools such as delivering wicked problems and amping up the stakes, risks and likelihood of success. It’s a very fun genre to write. 

What has ten years writing about fictional problems and choices taught me? 

1. There is almost never one single response to any problem. You usually have options.

2. Brainstorming options is a great way to get unstuck. 

3. It helps to get creative.

4. And ask for help and more information. 

5. Few modern day problems require an immediate response 

and 6. There’s often the chance for a do-over.

When I visit schools to talk about You Say Which Way stories we almost always get talking about decisions. I think it helps reduce pressure for young people to realize that their lives can be seen as a series of interconnected branching paths where their problems will be accompanied by their choices. 

Thanks for sending out your decision template. 

kind regards

Deb Potter

Deb Potter writes You Say Which Way middle grade interactive fiction. 

I love Deb’s six points.

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