Back when Ben was in his late 20s, he met up with his friend, Brian, at a bar. Brian was a graduate student exploring if and how to become a philosophy professor. So, Ben created a decision tree at the bar on-the-fly.

Brian said:

"Ben this is amazing - you should just take these decision analysis concepts and work with people in their 20s who are making big decisions about their life direction!"

Well, 25 years later, Ben's finally doing this! This episode introduces one of the most practical tools from decision analysis: the decision tree.

Decision trees help you get the ideas out of your head and onto paper, so you can clearly see:

• what you control

• what you don’t

• how uncertainty affects your choices

• paths leading to each outcome

Ben starts with the cleanest decision imaginable (a simple coin flip) to show how decision trees work. Then he applies the same structure to everyday choices (like whether to go to a movie) and high-stakes real-life decisions, including a dental dilemma.

You’ll learn how decision trees:

• bring values, alternatives, and information together

• help you separate decisions from outcomes

• reveal missing information

• give you clarity of action so you can make quality decisions BEFORE the outcome happens

There’s also a hands-on exercise to help you map a real decision you’re facing right now. Plus, Ben offers a bonus section for those who want to go deeper with expected value.

This episode wraps up the core decision-making tools of the Toolkit and sets the stage for what comes next: learning how to learn, one of the most powerful skills you can build in your 20s.

Now, it’s your turn!

Set up a decision tree based on an upcoming decision in your life!

If you get an insight from this exercise, post it as a comment so others can learn too.

And if you’d like help building your decision tree or calculating expected value, send a note to Ben@20Something.tools and let’s get a conversation going!

Resources * Link to Video of Decision Tree

https://m.youtube.com/watch?v=bfMFLXssBoU

In his book Measure What Matters, John Doerr famously called OKRs (Objectives and Key Results) a “superpower.”

He was talking about companies. But what if this superpower could make an even bigger impact when applied to your life, especially in your 20s?

OKRs have driven execution inside organizations for nearly 50 years, from Intel to Google to thousands of companies and nonprofits worldwide. At their core, OKRs create clarity, focus, measurable progress, and continuous learning.

But here’s the real question: Why should structured execution be reserved for companies?

Your 20s are your defining decade. This is when habits form, skills compound, networks expand, and identity capital grows. Yet of us are never taught how to define meaningful goals and execute against them.

In this pivotal bonus episode, Ben shares a real coaching case study of “Alex,” a graduating business major who felt stuck, anxious, and unclear about his future. Rather than trying to “solve his entire life,” they designed a simple 90-day OKR experiment focused on two areas:

• Building intentional daily habits and routines

• Creating clarity about post-graduation direction

Through measurable Key Results ranging from waking earlier and improving deep work, to strengthening social connection, building discipline through triathlon training, and defining a clear post-college plan, Alex shifted from reactive to proactive.

Instead of hoping things would work out, he began running a structured experiment on his own life.

In this episode, you’ll learn:

• How OKRs can drive personal growth, not just business execution

• Why small behavioral wins create powerful identity shifts

• How the OKR structure can build momentum

• The connection between OKRs and Identity Capital (Meg Jay)

• Why execution is one of the most valuable life skills to develop in your 20s

• How to design your own simple 90-day OKR cycle

Make copy of Ben's free OKR template. Choose one meaningful area of your life to focus on improving over the next 90 days. Write a short statement explaining Why it matters and Why now. Then create 3–5 measurable Key Results that make progress visible.

When you’re ready, email your draft to Ben@OKRs.com.

Ben will personally review it and offer a complimentary 30-minute coaching session to help refine your objective, strengthen your Key Results, and clarify your execution plan.

Because clarity drives action which builds momentum, leading to confidence and identity capital!

And in your defining decade, the next 90 days matter more than you think.

Thanks for listening!

How do you know if a decision was actually good BEFORE the outcome happens?

In this episode, Ben introduces a powerful framework from decision analysis, The Decision Stool.

Most of us judge decisions by how things turn out. But outcomes involve luck and things beyond your control. Good decisions can lead to bad outcomes, and bad decisions can sometimes lead to good outcomes.

So, if outcomes don't let us know if we made a good decision, what does?

The Decision Stool gives you a way to evaluate decision quality in advance, by checking the strength of three essential legs:

• Values: What do you truly care about, and across which categories?

• Alternatives: What options do you actually have, and can you create better ones using a value-focused approach?

• Information: What do you know, what don’t you know, and is it worth learning more?

Ben walks you through how he used the decision stool framework from his own 20s when he bought his first home in Northern California. He had to balance affordability, family, location, schools, and risk.

You’ll see how a value-focused, hybrid alternative led to a creative solution that satisfied competing priorities. Yes, Ben does enter the Matrix in this episode and turns his decision to buy a house into an opportunity to become a landlord!

You’ll walk away with:

• A practical checklist for evaluating decision quality

• A way to diagnose why you feel stuck

• An exercise to design alternatives that aren’t “on the menu”

• A preview of the next tool: decision trees, which make complex choices visible

When a decision feels wobbly, don’t guess. Instead, notice which leg of the stool needs strengthening AND stabilize.

A solid decision stool translates to more confident decisions also known as "Clarity of Action" which means you evaluate your decisions based on what you can control.

Now It’s Your Turn

Think about a decision you are currently facing, big or small.

Take 5–10 minutes and evaluate it using the Decision Stool.

Values. What truly matters in this decision? What outcomes are most important to you?

Alternatives. Have you clearly defined the options? Can you create an alternative based on your values?

Information. What do you know, what don’t you know, and what assumptions are you making?

If one leg feels weak, strengthen it.

If this exercise changes your approach to a decision, share what you discovered in the comments!