What a Former Intelligence Agent Taught Me About How to Think

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Shane Parrish - Clear Thinking

After leaving the Canadian version of the CIA, Shane Parrish has become a leading expert on decision making. He interviews some of the most interesting people in the world on his podcast, The Knowledge Project, and he sends a newsletter to over 600,000 people each week about mastering what other people have already figured out.

I first learned about Shane back in 2021 when my buddy Cam sent me an episode of the podcast. Not only did I enjoy this episode with Kat Cole, I noticed that Shane asks incredibly thoughtful and unique questions that typical business podcast didn’t.

I still have notes in my phone with takeaways from that episode that range from perspective on mindset to business best practices to relationship advice. Shane allows the audience to get a glimpse into how these successful business leaders, industry experts, and thought leaders really think.

Shane recently published a book called Clear Thinking, and I listened to the audiobook while I was in New Zealand. Usually I listen to audiobooks when I’m working out or on a long drive in the car. However, I couldn’t do that with this book. There were so many thought provoking ideas that I only listened while walking so that I could have my notes app open to jot down takeaways and apply the concepts in real time.

Biggest Takeaways on How to Improve Decision Making

There is so much to learn from Shane and this book, but I want to highlight a few of my biggest takeaways with some reflections and applications to my own life. This is definitely a book I plan on revisiting multiple times.

1. There are four major instinctual defaults that are ingrained biological tendencies. They can't be removed but can be managed

Emotion: “We tend to respond to feelings rather than reasons and facts … When we respond emotionally, we often don’t even realize that we’re in a position that calls for thinking at all. When you are possessed by the moment, all the reasoning tools in the world won’t help you.”

Interesting enough, my default is the opposite of this, rational and logical thinking. So in my case, I’ve had to practice becoming more aware of my emotions and let myself feel these emotions in the moment. Then, I can turn to my rationale brain on how to move forward. Going to therapy over the past 5 years and learning about the many types of emotions has helped me tremendously here.

Ego: “We tend to react to anything that threatens our sense of self-worth or our position in a group hierarchy … Most people go through life assuming that they’re right . . . and that people who don’t see things their way are wrong. We mistake how we want the world to be with how it actually is.”

I’m fortunate that my natural inclination is modesty. I’m not afraid to ask questions, admit when there is something I don’t know, and own up to my mistakes. But this is a good reminder as its very easy to get caught comparing myself to others.

After my first year at EY, I was not selected for an early promotion when two of my peers were. There was an initial urge of envy and “why not me”, but I was able to take a step back and realize we had a very long career ahead. It allowed me to reflect and ask “what did they do to get this result that I didn’t, and how can I improve for next time”?

Social: “We tend to conform to the norms of our larger social group …The social default inspires conformity. It coaxes us to fall in line with an idea or behavior simply because other people do. It embodies what the term ‘social pressure’ refers to: wanting to belong to the crowd, fear of being an outsider, fear of being scorned, fear of disappointing other people.”

This is one I get caught up in all the time. Its easy to “go with the crowd” whether its small decisions like ordering a beer because everyone else is drinking or pursuing a high paying corporate job after college because that’s just what I was taught success looks like. Being an outsider is difficult in the moment. But if being different is true to my authentic self then it will be easier over the long run than pretending to be what I’m not or choosing to do things I don’t believe in.

Inertia: “We’re habit forming and comfort seeking. We tend to resist change, and to prefer ideas, processes, and environments that are familiar … The inertia default pushes us to maintain the status quo. Starting something is hard but so too is stopping something. We resist change even when change is for the best.

This is the big one that hits home for me. Starting something new is definitely hard, but that is expected. I have found that stopping something that is already in motion is extremely difficult. I experienced this in my past relationship. Things were going well in my mind, so it was my natural inclination to stay with the status quo and stick with what was working, instead of digging in and asking the difficult questions or putting in work to make the relationship better.

I learned from this experience and applied it to my career. I was in a very comfortable routine with my corporate job at EY. I had a good reputation among my bosses, I knew the subject matter well, and was making a nice salary. However, I started to ask myself the deeper questions of did I really enjoy this, was I getting fulfilment from it, is this where I want to be?

I ultimately made the difficult decision to leave that comfort for a totally new job, new city, and new people. By making that change, I exposed myself to the exciting world of entrepreneurship. Now, I’m on the flip side of the inertia equation trying to start my next venture from scratch and get it moving. Again, its not easy, but as long as I stay consistent and get 1% better each day, I will succeed.

2. Must be clear on what’s the most important thing when making a decision

At the time of listening to this section of the book, I was deciding between two options for where to sublet an apartment in Austin, so I completed the following exercise Shane discusses.

How to determine the most important thing:

1. Write down all the criteria you can think of that goes into the decision (get sticky notes and put one criteria on each)

2. Select the first one you think might be the most important and put on the wall. Then one by one compare it against each other criteria without thinking about the others. Select the winner and repeat.

3. If you are having trouble deciding, add quantities to each criteria as they battle to provide boundaries (ex. cost, amount of time, distance)

4. Make sure that you have relevant and accurate info about the options

Here is how this went down for my subletting decision:

Criteria

• Location

  • Must be within 15 minute walk of the lake front trail

  • ~10 minute drive to bars, restaurants, gym, and grocery store downtown

• Roommate likability

  • Must be clean and respectful

  • Bonus if they have common interests and we could be friends

  • 8+ on scale of 1 - 10

• Price

  • Max rent: $1,100 / month

• Availability of the sublet

  • Want to move in by Jan 10

  • Only want to commit to 3 months in case I want to move elsewhere

Comparison

Location vs Roommate Likability: I could always drive to the lake for a run, but its tough to avoid the people I live with

Price vs Roommate Likability: I set a quantitative boundary that I would be willing to pay up to $200 more per month if I preferred the roommates as long as the price still fell under my max rent

Availability of sublet vs Roommate Likeability: I set another quantitative boundary around being flexible with my move in by 1 week and my move out by 1 month if I preferred the roommates

Decision

I gathered as much relevant and accurate information about the decision as possible. I knew the locations of each spot. I gathered the cost of rent, utilities, and furniture. I got specific dates when the apartments were available. I spoke on the phone to both potential roommates to get a general feeling of likability.

I ultimately landed on Roommate Likability as the most important thing. One of my core values is relationships. Who I surround myself with influences my life and a great roommate can have a huge positive impact (shoutout Josh and 18K!).

This process made my decision easy. I connected much better with my current roommate Max than the other guy I turned down. Max stressed that he cares about keeping the kitchen and house clean. And the big kicker was actually when he mentioned playing lots of pickup basketball. I’ve been wanting to play for a while now and never did. By surrounding myself with people pursuing my goals, I made it easier on myself to achieve them. We played for 2 hours my first week back in Austin and I absolutely loved it (minus my broken rib ☹️)

I sacrificed a little bit on price and location but in the end I’m happy with both my decision making process and the outcome.

3. Shoot Bullets before Cannonballs

The premise is to test on a small scale and preserve as many options as possible before committing all resources on one thing.

Shane tells this story of two ships in battle. Its better to start with shooting bullets at the opposing ship to gauge the correct trajectory. You most likely will miss on the first few shots, but you are able to adjust. Then, once you figure out the perfect launch angle, you load up the massive cannonball and fire it to sink the other ship. If you start with the massive cannonball and miss, then you are screwed being stuck with nothing left but tiny bullets.

I don’t know exactly what my next business venture will be, but I’m testing a lot of small projects to keep my options open. I’m excited about the idea of starting an adventure travel company. So instead of pouring my life savings into launching a company with trips all over the world, I’m going to start small and plan a local retreat in Austin or one domestic adventure for people in my network. I’m enjoying the process of writing these newsletters so I am going to practice writing every day. I signed up for a $97 course that is teaching me the foundations of copywriting before I commit to applying for full time writing jobs. I will tweak and adjust as I discover what I enjoy and what I’m good at, then once I find that I will go all in.

Final Thoughts

These three concepts barely scratch the surface on the golden nuggets from this book, but I enjoyed going in depth on each of them and reflecting on how I can apply them to my life.

There is so much great content out there between books, podcasts, Youtube videos, and more. But at the end of the day, its useless unless we take digest the information and take action on what we’ve learned.

Thank you for reading! As always please reply and let me know what resonated with you, what you disagree with, or what this made you question. I love chatting about this stuff!

Cheers,

Andrew