Imagine I hand you a token that allows you to go back in time and change one decision that you made. Then pick up life at the age you are now. Would you actually do it? What would you have changed about the past? Now imagine you stay locked on the same moment you would have changed and I offer you the option of a second token. This token unveils all the obvious and hidden good things that happened as a result of that moment in the past. Which token do you want? How confident are you that the potential good outweighs the known good?
1. Everything we know for certain is about the past. And every decision we have to make is about the future.
Steve Jobs’s infamous commencement speech centered on the main idea: You cannot connect the dots going forward, only going backwards. The life you currently have is the result of thousands of decisions you’ve already made. Future you will be cursing or celebrating current you. But there is no way of knowing what is a good or bad decision in the moment.
I’ve realized that there’s two primary paths when it comes to internalizing decisions: learn to be more at peace with the decisions i’ve made or continue to seek out ways to obsess over optimizing every decision. In the end, I will always make non optimal choices. All of us will make decisions that don’t pan out the way we hoped. But the current versions of ourselves doesn’t need to keep punishing the past versions of us. I’ve chosen the former path. To make peace more easily with my decisions. Even the ones that turned out to be completely wrong in the end.
I would pair this idea with a philosophy I picked up from Matthew Hussey’s “Love Life”. Imagine that you are taking part in a relay race and are the anchor. The second leg messes up badly. You’ve been handed a baton and you must run your race from that point forward. Now consider every day that you wake up as being handed a baton from a previous relay runner. You cannot change what happened in their leg of the race. The only thing you can do is run your race from this point forward. So run your race.
2. You were lied to from the day you were born. If you optimized your productivity. You could fit all of life into the jar that is your existence. When what you needed is to find is as much joy in the rocks you leave out of your jar as the ones you choose to put in it.
Four Thousand Weeks by Oliver Burkeman is a must read. I referenced it in my last post and will reference it in this post. A lesson early in the book is the debunking of the infamous anecdote of a professor who brings a jar to class only to fill it with rocks, gravel, sand, and sometimes water. The moral of the story, if you prioritize the big things in life, you’ll be able to fit all the small stuff in around it. But what if there are multiple big rocks in your life that you are passionate about? What if you’re passionate about becoming the foremost expert on humpback whales AND the CEO of a Fortune 500 company. Well there’s not enough life to put both rocks in. So are you able to cope with the rocks you leave out? Can you be happy with the potential life you DIDN’T live?
Here are some of the massive rocks I plan to put in my jar:
Trying to scale a business
Starting a family with kid(s)
Buying a house that I can do dozens of DIY projects on
Here are some of the rocks I find joy in leaving out of my jar:
Turning into a famous person
Traveling to every continent
Becoming a billionaire
There is not enough life to live all the lives. Decide which one you plan to live. Don’t let the resulting outcome(s) taint your view on the decision you made.
3. If I could not tell anyone about it. Would I still want this? If yes, then it’s something that I’m doing for me. If no, then it’s something I’m doing because I think it will bring me some status from others.
We’re wired to want to look the best, be the most interesting, make the most money, own the nicest things, or brag about how our significant other is better than your significant other. One of the most impactful changes to my frame is being able to identify what I place intrinsic value on versus societal value.
I spent a few days at the end of 2025 going through almost every expense I had. Then I asked questions about them:
Did this/these purchase(s) bring me the joy I hoped it/they would?
Knowing what I know now, would I spend that money the same way again?
Was there anything I didn’t spend money on that going forward I will?
How did this money spent further my relationships and deepen my connections?
This was a more extreme and time intensive exercise that I don’t think everyone needs to do. But money in the end transforms into something. It’s a scoreboard to some. For others it turns into a way to feel special. In my mind, it’s the tool by which I use to craft a life. Here are a few categories that I spend money on and never regret it for a minute: gifts for others, once in a lifetime experiences for myself, connecting moments like group dinners, and books to expand my knowledge. If nobody, not directly involved in those transactions, ever found out how I spent that money. I’d still spend it the same.
4. “Be grateful that on this raging sea you have a mind to guide you.” - Marcus Aurelius
I try to have a mantra for each year. Toward the end of 2024, I would say “There are no silver bullets, only lead ones.” by Andrew Horowitz. Which was tied to the idea that in order to tackle big problems. You need to make slow and steady progress. There are a number of massive problems we will all encounter in our lives. Back in 2024, I had the most stressful year I’ve had in my professional life. I openly voiced my desire to quit my job without a back up plan at the time.
In 2025, I wouldn’t even be able to recognize the 2024 version of me. I spent the last five months of 2024 building a version of me that was a bomb shelter, fortified in the ground, ready for a nuclear blast. There were hard conversations, lots of reflection, and most importantly a mountain of evidence that the person I am is capable of getting through big problems. Give yourself more credit. Whatever it is you’re facing. Your mind will be able to navigate those choppy waters. Even if you are adrift in the middle of the ocean right now. A shoreline exists. And you will reach it in time.
5. If someone were to observe you for a week, what would they say your priorities are versus what you state they are? - Sahil Bloom
If I followed through with all the potentialities that I’ve talked about in the past. I think I’d be a top 10% athlete, international coach, well known business owner, and climbed Everest. There are the things we say are important to us. But if your calendar is not filled with supporting evidence. Then you need to reevaluate those priorities.
My calendar is largely filled with rugby, social events, webinars, people’s birthdays, and adventures. These are the things I prioritize. I also want to be more focused on working toward long term goals and my health. There are once a week meetings on my calendar related to those. But if I were to think of my minutes in the day as a budget. I would say I don’t spend nearly the amount that a person who says long term goals and health are important would. Which means I need to rebalance my time ledger.
If you said saving for a house is important. And found out your largest expense is eating out but you don’t want to cook food at home. Then saving for a house isn’t actually that important. In the same way, I need to say no to more things that burn my time bank. Some of those “no”s will be a literal decline to a specified event. Others will be me saying no to watching YouTube or doing something other than the things I want to be making progress on. If it’s a priority, then any spectator of my life will see it’s important.
6. Bet Sizing
Texas Hold Em is an incredibly educational tool when thinking about decision making. At the National Rugby Coaching Summit in 2024, I heard one of the coaches say that preparing for a game is more poker than chess. The only thing you know for certain is the cards in your hand. Which perfectly sums up decision making in life. I don’t know if the person across from me has or is willing to do the things they say. There’s plenty of people who are going to actively deceive me and others who unintentionally harm me. In poker those would be bluffs. The only thing I know for certain are the cards I hold.
This brings me to bet sizing. In poker, you have multiple rounds where more information is uncovered and then your corresponding decision to raise the stakes or hold the current bet you have. I have been mulling over the idea of bet sizing a lot. I’ve been right about some things and wrong about others. But I’ve never been great at figuring out what the appropriate bet size is for the things I believe to be true.
Here are two bets that I’m putting money behind in 2026:
Sales skills become MORE valuable in the age of AI
Consumer empowerment has been on the rise since the rise of the internet. As consumers, we have more information about any product/service than ever before. Yet there’s a downside to all that data: analysis paralysis. I currently think of sales as the generous act of letting the right person know you might have a solution to their problem. So I think salespeople who find the right ways to educate and empower their buyers will win. Buyers need honest and good sales people to help them make better decisions. I plan to be one of those educators.Analog Life
We are too digitally connected. There’s too many apps. Our phones are addicting by design. I’m already not on social media. Eventually I think our brains will push us hard to go outdoors. Find places without cell signals. And have good old fashioned analog fun. So this is my calling to go skip rocks in a lake and explore the outdoors. I’ve been on the analog fun wagon for a few years. Why not find ways to invest in the things I already do.
With the two bets above. There’s the question of how much of a bet size do I make. The answer? You’ll find out soon enough.
7. Learning only occurs in the application of knowledge and not the acquisition of it
I heard someone say there is no amount of reading that can teach you how to swim. Which is beautifully simple way of summarizing this section. I’m incredibly guilty of learning for the sake of learning. Or filling silence and any sort of void with learning. But how many DIY home projects, furniture flipping, and business building knowledge will I actually use. Likely a fraction of what i’ve consumed.
What I really needed all along was to learn something —> Attempt to apply it —> Fail —> Keep going and try again.
Time for me and us to:
Make mistakes.
Look silly.
Skin your knee.
In the end, the only person who is able to live your life is you. That life is not supposed to be neat and perfect. It’s supposed to be yours. Whatever you do, don’t trade the life you’re meant to live for the one that someone else thinks is right for you. Decide. Then make peace with whatever happens after.
From the version of Jeremy Boco that existed on January 11, 2026.
All ideas and opinions in these newsletters are expressly my own. If I use AI to aid in the assistance of my writing, i will disclose it. I did not use AI in the writing of this piece.