Long Term vs Short Term Games

I want to explore the idea of thinking long term vs short term. My hypothesis is that both are critical and if we can harness the advantages of each based on the situation we are facing, it will lead to incredible results.

Lets start with long term thinking

I heard Sahil Bloom talk about playing the long game on a podcast with Danny Miranda. He summarizes it here below while quoting Naval Ravikant.

Compound Effect

Everyone has heard of compounding interest when it comes to investing and your bank account. If you consistently invest a small amount of money every month, over time its grows exponentially.

But I love the idea of expanding this concept to other areas of your life like relationships, career / business decisions, and health.

Its so easy to get caught comparing yourself to where you “should be” in this world of LinkedIn status updates, Instagram photos, and even just seeing the progress your friends are making. Everyone announces their big promotion at the PE company on LinkedIn, they share pictures of their baby shower, or post their new marathon PR on Strava.

There are so many external expectations around being at a certain place by a certain age. Vice President at the PE shop, Senior Manager in Consulting, married by 28, kids by 30, etc. When you get caught up in that thinking, most tend to default to short term thinking. I’m behind so I need to do whatever it takes to get that next promotion the fastest or I’m getting old and still single so I need to find my partner.

However, maybe long term thinking would be more beneficial in these scenarios. Do you really want to rush into choosing the person you are going to spend the next 50+ years with? Do you need to kill yourself and go run a marathon next month or can you build it up a race that suits your health goals?

In Think and Grow Rich Napoleon Hill states “For the average person the greatest capacity to create is between 40 and 60” and when you look at Warren Buffet’s net worth over the years, it doesn’t really take off until his 60s.

Sure the promotions and pay raises in your 20s are great and getting married in your mid 20s to the person you love is incredible. I’m not saying there is anything wrong with it. But my thought is that is not the only way. We aren’t screwed if we are “behind” and aren’t the first to achieve those things because we are playing a long term game.

If you do a poll of a bunch of 40-50 years old, I bet that the people who were promoted the most early on and who got married first aren’t necessarily the happiest in their work and marriage. Now if these “early achievers” are asking the difficult questions and doing work they enjoy then they are certainly on a fast track to success and I fully support them doubling down on it.

But if not…That span of 20-25 years is a long time for the people are who putting in daily, weekly, monthly consistent action into finding work that they love, into becoming a better person, and into improving their relationships to let the compounding effect take place.

One more cool example of this that I came across yesterday is from James Clear, author of Atomic Habits (one of the best books I’ve read).

Talk about compounding effect. It took 7 years to get to 500k subscribers, then only 2 more years to get 1M, and another 2 years to get 3M. I don’t know what James’ goals are but over the course of 10 years he created an audience that will enable him to pursue pretty much any kind of venture he wants.

Play with Long Term People

The other part of the quote from Naval is playing these long term games with long term people. The power of associating with long term people is trust builds over time. By consistently showing up day in and day out in your business, for your friends, for your partner, the trust will continuously compound to the point where certain decisions and life situations become a lot easier.

When you get to know someone consistently over many years, you get to know their strengths, their weaknesses, and what you can depend on them for.

A simple example but take a barber. I went to the same lady (shoutout Lee!) to cut my hair from age 5 until I was 23. I knew I could trust her to give me a great haircut, I knew how much it would cost, how long it would take, and would just show up every 6-8 weeks without thinking about it. But now that I moved back to Austin, I don’t have a barber I like here yet. So I had to ask around to my friends for recommendations, compare prices and online reviews, and will probably try out a few different shops until I find one I like. A lot more work, time and effort. I

Its important to surround yourself with other people that are also thinking long term so that your intentions are aligned. Great partnerships are grounded on common values, trust, and playing the same game. Going back to the barber example, I don’t want to choose someone that is playing a short term game and is planning to move to Dallas in 6 months because I will put all that work in establishing the relationship then will start over.

This same idea can apply to someone you want to invest in real estate with, be friends with, partner on a startup with, choose to date/marry, or hire as an employee.

Believe in the end of the story

One challenge I have come across in thinking long term besides just comparing myself to others, is staying motivated and believing in myself that its going to work out. How do we keep ourselves going in tough times?

James Clear wrote his newsletter for 6 years (at least two articles per week for six years straight) before he released his book and became the best seller author he is today. That is ALOT of time, energy, and effort without seeing tangible results.

Something Jesse Itzler says which has stuck with me is “Believe in the end of the story”.

When I was on that 5th straight first date and couldn’t seem to get to a second date with someone, I thought of that saying. I know my person is out there so I need to just stick to the process, continue to learn, continue to put myself out there.

Even in the past few weeks, I’ve had thoughts of what am I doing? I spent hours looking for businesses to acquire but nothing seems to fit my criteria. I’ve reached out to 50+ people to network and only a small subset have responded. Wouldn’t it be a lot easier just to go back to EY, have the pay checks come in, and progress up the corporate ladder? But that’s not my story. I want to live my life on my terms and there’s no easy path to get there. I know I can and will get there. Its going to take some trial and error, some uncomfortable weeks, but that’s what will make it so much sweeter once I get there.

Lets shift over to Short Term Games

A few concepts come to mind when I think playing short term games:

1. Jesse Itzler’s motto Live Life with Urgency

2. Stoic philosophy of Memento Mori “Remember you will die”

Live Life with Urgency

I mentioned in my last newsletter this talk Jesse gave that totally changed my life. It was watching this talk where he not only explained the concept of Living Life with Urgency but was actively living it. I still get the chills thinking about it and can’t imagine what it was like being in the room, but Jesse’s sister had suddenly passed away just a few days prior to the event. You just don’t know how much time you have left on this Earth so its about being intentional and doing stuff now, not later. Its doing what you love, its saying yes to things, its hopping on that flight to see your loved ones, taking that risk even if there’s a high probability of failure, its about having FUN.

What is your relationship with time? Do you make the most of your days? Are you constantly checking items off on your bucket list? Time is undefeated. Nobody beats time. But what time can’t take away is the stuff you accomplished and the memories you already created. I took the solo trips to Patagonia, Australia, and New Zealand. I completed the triathlons. I helped lead my high school basketball team to a region final. I surprised my family for Rosh Hashanah. Time can’t take that stuff away from me.

Check out this short clip from Jesse’s talk explaining 3 things he does each year to live life with urgency. I implemented these in 2023 and it helped make my life a ton of fun and create lifelong memories.

1. Add an annual Misogi (year defining event)

2. Do Kevin’s Rule (6 mini adventures each year)

3. Implement 4 winning habits (one each quarter)

This is just a framework that works for Jesse and worked for me, but the point is its important to be intentional about doing the the things you want to do in life with the people you want to do them with. It doesn’t have to always be some fun, exciting adventure.

My grandpa was recently diagnosed with Alzheimer’s and last year while I was living in Austin, just had this feeling that I wanted to go see him in person. It was getting more and more difficult to have conversations with him over the phone due to his hard of hearing and I just wanted that connection. I was already doing a ton of travel, but I had the flexibility with my job to work remote so I booked the $450 last minute flight to go back to MD for 4 days so that I could see him and my family.

It was a small decision and nothing earth shattering happened during my visit with him, but I loved seeing him. Even with the Alzheimer’s he still has his jokester personality and I could only really appreciate it being in the room with him.

Another reframe that Jesse talks about is to think about how many times a year do you see your parents or your grandparents. For most people that don’t live near them its about 3-4 times per year for holidays and special occasions, maybe 6-8 times if you are lucky and intentional about it. Then think about how old they are. My grandpa is 81 and I see him 4 times a year. He is already past the average life expectancy of 79 in the US but lets just say he only has another 10 years, that’s only 40 more times I will ever see him.

Plan the trip, book the flight and spend time with the people you care about.

Memento Mori

I used to be scared to think about death. Why think about dying? I consider myself an optimistic person and don’t want to think about bad, scary things happening. But by listening to Ryan Holiday talk about Stoicism, I learned how to reframe thinking about death. What if its not a scary thought but more just think of it in terms of fact. We are all going to die. We don’t know when but it will happen eventually. So what if instead of being scared of death, we use the fact of us dying eventually to help guide us in our decision making, our thoughts, and our daily actions.

As Ryan writes in his blog “Meditating on your mortality is only depressing if you miss the point. It is in fact a tool to create priority and meaning. It’s a tool that generations have used to create real perspective and urgency. To treat our time as a gift and not waste it on the trivial and vain.”

I’ve used this mentality to help provide perspective and urgency in my life. Its why I booked a flight to Italy 6 days before leaving. Its why I quit my $200k+ salary job to pursue an new opportunity I was interested in. Its why I quit that next opportunity only 4 months in because it wasn’t energizing me. Its why I flew from Auckland to Houston on the day of the National Championship game to see my Michigan Wolverines win it all.

Most people would consider these decisions irrational and call me crazy (which they did).

“You are flying to Italy to meet and stay with two people you met once on a trip to Patagonia?”

“You are giving up $50k+ in bonuses that you can get if you just stay at the job for another 6 months?”

“You just moved all your stuff to Dallas, took this job, and are just gonna leave?”

“You just got off the plane from where?!?”

But life is short. We don’t know when its going to end. I don’t regret any of those decisions. Yeah they were expensive decisions, yeah I was exhausted, yeah they were maybe risky..but when I look back in 10, 20, 40 years am I going to remember sticking out a job I didn’t want anymore for 6 months for more money or how I took the leap into entrepreneurship? How tired I was in the days after the game / the $2k I spent to get there or how I felt seeing my team win the Natty with some of my best friends? Pretty easy answers.

So what is the answer?

Is long term or short term better?

Should I be conservative, save my money and let it compound over time or should I spent it on trips family and last minute flights across the world?

Should I be patient in the job and see if I will start to enjoy it as time goes on or should I try a bunch of things and adjust quickly in the short term?

Do I continue to date someone and give it time to develop or should I cut ties and move on to the next relationship?

My view is that we need to do both and the key is learning when to use the long term lens and when to use the short term lens. If you only think one way or the other, that’s when we can get into trouble.

For example, being too frugal with your money that you miss out on great experiences with loved ones. On the other hand, if you just focus on short term hookups and bouncing around to as many dates as possible then you’ll never go deep enough with someone to determine if they could be your life partner.

Final Thoughts

I think it comes down to being self aware. Knowing what your values are, what your vision is of where you want to go, and want you enjoy doing can help you determine whether you should think long term or short term.

I value adventure and in person experiences with people I care about so I’m going to spend my money and time going on epic trips with people I love (at the sacrifice of my savings account at times).

I value growth so I’m willing to try different jobs, take pay cuts, and take some risks so that I put myself in a position to learn and grow as opposed to optimizing for a job where I make the most amount of money but don’t feel challenged or fulfilled.

I value authenticity so I’m going to be myself on dates and while trying to meet people even if that takes longer to find my person as opposed to forcing myself into talking to every girl at the bar or saying certain things that will give me a better chance at making a girl like me.

At the end of day we are all constantly learning from these situations and experiences. Every day we make decisions, some will work out and others won’t but the idea is to continuously be self aware and tweak our thinking and decision making. Journaling and meditating have been incredibly useful tools to help me reflect on my decision making and become more self aware. Just like anything else in life, it takes practice, it takes reps and over time we will get better at knowing when to play the short term or long term game.

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