Probability as a Heuristic

Hi, 

In these newsletters, I talk a lot about my heuristics a lot. I find them to be super helpful and quick ways to get to my decision and move forward. 

This week, we are going to talk about how to make decisions that will play out over a long time, that you have to make without sufficient data. 

The goal: give yourself the best probability you will end where you want to. 

If you want the best version of this idea, go read Thinking in Bets by Annie Duke.

Okay, let’s jump in. 

As I finished college, I didn’t have a clear picture of what I wanted to do. More precisely, I didn’t know what I wanted to do for my first role. I knew that I wanted to be a product manager of some sort at a big tech company. 

The issue: I didn’t know how I could get there.

*Caveat, it is totally okay, to not know how you are going to get where you want to get to. It is probably the most normal thing to experience as a human. 

So what did I do? 

I created three scenarios that made sense to me for getting my dream job: 

• Scenario 1: Get a job in my dream industry… any job. 

• Scenario 2: Get my dream job… anywhere. 

• Scenario 3: Get a job at any company, in a geographic area where I felt I could grow into the person who would get my dream job. 

I looked at these three, and I figured that just doing one wasn’t enough. The job I choose will need to have at least 2 of the 3 options. 

My logic: if each one of these gives me a 33% chance of getting to where I want to go, then if I do 2 I will have a 66% chance. 

My goal was only to be better than a coin flip. 

The thing about probability is that there will always be circumstances where you lose. That’s the game, but if you can give yourself a better than a coin flip chance, you know that more times than not you will end up ahead. 

Here is why this heuristic worked so well for me because what you want to happen will usually pale in comparison to what actually happens when you follow your interest, not the location. 

You are probably thinking, “this guy… isn’t a product manager or working in tech.” 

You would be correct, as it pertains to my original goal, I would at this juncture be a complete failure. But let’s look at what I did for the past 7 years at The Hero’s Journal: 

• Built a product.

• Identified an audience

• Oversaw all marketing budgets, KPIs, and product margins. 

• Managed the P&L 

• Oversaw manufacturing timelines 

• Managed the support function for the product

• Ran team meetings for company-wide alignment

I asked ChatGPT to make a simple list of what a product manager does: 

• Identifies customer needs through research, interviews, and data, then translates them into clear product requirements.

• Prioritizes and plans the roadmap, deciding what gets built, when, and why based on impact, effort, and business goals.

• Guides cross-functional teams (engineering, design, marketing, support) to build and launch products on time.

• Measures product performance using analytics, KPIs, and customer feedback, then iterates to improve outcomes.

• Communicates decisions and progress to stakeholders, managing expectations and ensuring alignment across the company.

If you ask me, those are pretty similar. 

Although I have never been a product manager at a tech company, I have had similar responsibilities to a product manager during my time at The Hero’s Journal. 

When I was finishing college, I didn’t have any opportunities that offered me a direct line to the job that I wanted. So, I had to make decisions without certainty. Using my heuristic, I was able to create direction that helped me do something in the midst of uncertainty. 

I moved forward with 66% of what I thought would get me where I wanted, and I ended up getting about 80% of my goal. 

I would say that is a win. 

The lesson here: create parameters that allow you to move forward, not because they offer you certainty, but because they offer you a high enough level of clarity that you are able to navigate your way. 

If you do this well, you will find something that will probably be better than what you originally wanted. 

Bye,

Kyle