25 Lessons on Money and Meaning

Notes from everything I've learned so far about the deeper forces behind our financial lives

Hi all,

Quick bit of housekeeping: thank you to all the new subscribers and visitors. If you’re new here, I’d love to know where you’re coming from. Substack’s source data is pretty bare-bones — if someone shares an article in a newsletter, for example, I usually can’t tell where it originated. So if you discovered The Root of All through a mention somewhere, feel free to comment and let me know.

Now, onto this week. I’m working on a new post, but with the holidays being what they are, I realized I won’t get it to the standard I want in time. Still, I didn’t want to skip the week entirely.

Looking back, I noticed that many newer readers haven’t seen some of my earlier essays — and that a few themes keep surfacing across the 70+ posts I’ve written here. Chief among them: the relationship between money and meaning.

So as we close out 2025, instead of a generic “best of” list, I’ve pulled together 25 reflections — moments, lessons, or stories — that explore how money shapes our sense of purpose, freedom and fulfillment.

And this is only a small sample. If this kind of writing resonates with you, I’d encourage you to dig into the full archive.

So, in no particular order:

1. Money helps nurture the things that give you meaning. But money isn’t a requirement for living a meaningful life. Living a meaningful life though will always lead to using money meaningfully.

2. Money itself is just a story. Stories allow us to change, to create the impossible, to do more than you could ever think possible, to become greater selves. Whether true or not, only a story can convince someone they can revolutionize the world. As Daniel Kahneman put it: “No one ever made a decision because of a number. They need a story.”

3. The key to happiness or contentment is learning your craft that generates all those moments that make up a life. Which means the key to personal finance is figuring out how to use your money to create the environment for those enjoyable moments.

4. When we embark on that final, inescapable journey, we can’t take wealth with us. Ancient Egyptians buried with golden artifacts bear silent witness to this truth. You also can’t take the Eiffel Tower’s iron lacework, the thunderous roars of Africa’s proud lions, or the watchful stars over Alaska’s quiet wildness. But you’ll hold dearly the memories of such sights on your deathbed. Wherever you believe you’ll travel to after you die, if you’ve woven a tapestry of adventures with your time and resources, you can rest assured you’ll venture there unburdened by regret. Don’t wait. The world beckons.

5. As we acquire more, our expenditure grows, making us yearn for even more of both. It’s akin to expanding a highway to ease congestion, only to see it grow busier. The presumption is that more money will give us greater control and happiness, yet the cycle never ends.

6. We regret what we didn’t do more than what we did.

7. Successful and satisfied people are often those who can detach from their wins and losses. Humble yet persistent. They keep moving forward, never lost along the perilous cliff edge of greed, nor stuck in the oppressive pit of fear. Wins and losses come and go – and we may never know which is which. They won’t determine the quality of your future – in money or life – as much as the virtue in your response.

8. Put down the weight of the notion that it’s all about you. If you get lost in your own desires (wealth, retirement, success), life around you becomes undesirable. Better to appreciate what you have now, which you once desired.

9. Choosing someone based on their ability to maximize certain qualities like financial security or status will not guarantee a happy marriage. In that sense, money, though big, is just one of many things that can influence the quality of a marriage. After all, a bank account won’t be there to hold your hand on your deathbed.

10. Spending money on things (experiences and material items) that align with our personalities makes us happier. Therefore, one way to boost life satisfaction is to think of what you spend money on that is synonymous with your personality. Consider these expenses your “Costco $1.50 hot dogs.” Shamelessly sell them at a loss. That is, spend money freely on the things that matter most to you. At the same time, slash costs unrelentingly on all the things that don’t.

11. The value of anything — money, talent, time, or simple presence — is in how it’s used. Be the river, not the dam.

12. Money, as a source of purpose, is inherently flawed. It can provide opportunities, but it makes for a poor foundation for a meaningful life. Spend money on what is unnecessary but meaningful. Find what gives your life authentic purpose, and then use your money to support those things.

13. Happiness lies not in the mere act of decluttering, but in understanding what truly gives our lives deep, meaningful purpose. Material possessions may either complement this purpose or detract from it. The issue arises when possessions become our primary source of meaning. I think a good critique of our material culture isn’t necessarily that we have too much stuff, it’s that we have too little meaning.

14. When done within one’s means, splurging can be a healthy expression of personal financial management, allowing for enjoyment without compromising financial security. If you can’t spend money just for the joy of it every once in a while, then what’s the point? And if you feel hesitant, here’s a bit of advice: get yourself a margarita and forget about it.

15. The pursuit of what’s easy often leads to a life marked by dissatisfaction. We frequently deceive ourselves into believing that the easy path will lead to happiness, but experience shows us otherwise. It’s an intriguing paradox in human nature that while we often crave “easy,” we tend to value “hard” all the more. After all, we look at a paycheck and money found on the ground differently.

16. When it comes to spending money on friends or experiences with friends, consider giving yourself more freedom than you would with anything else. A hard lesson no one wants to learn: all the money you need to become financially independent means nothing, absolutely nothing, if you have no one to spend it with.

17. Self-awareness goes hand in hand with financial self-awareness. Master one and the other becomes second nature. This is because a better understanding of your situation and tendencies can translate into a better handling of your finances. As has been said countless times, money is a good servant but a bad master. All told, if you make money everything or make it nothing at all, you’ll likely get more than you’ve ever wanted.

18. The cost of children is an admission to adventure, love, pain, joy, despair, loss, fulfillment – all that life can and should be. Then one day it’s over. The ride comes to a stop – hopefully, much later than sooner – and that emptiness is a bittersweet debt. It is a debt that can never be repaid. You are left desperately wishing to repay it only to take it out again so you can relive it all over, desperately wishing to take out a second mortgage on all the spills, the cuts and bruises, the breaks, the heartaches, the tears, the smiles, the hugs, the laughs, the I love yous and the goodbyes, enough to get you angry at the unfairness of it all.

This one is costing and giving a lot… guess we’re even

19. Money is one part data and math, two parts imagination and personal awareness. The science is the data and information we gather; the art is what we decide to do with it.

20. We have the calculus all wrong. It’s our actions that shape our emotions. As endurance athlete and wellness advocate Rich Roll puts it: Mood follows action. Studies show that the actions we take with money are what ultimately shape our feelings about money.

21. It is said, every saint has a past and every sinner has a future. The actions of your past are not who you are today. But they can help you become the person you want to be in the future. Recognize the inner spirit we all have to build a host of better possibilities for ourselves.

22. Is this the last time? This is the question I try to remind myself to ask whenever I’m with others and wish to be somewhere else. Maybe I’d rather not spend the money going out with friends, but what if this is the last time? Maybe I’m too tired to play catch, but what if this is the last time my son asks? We’ll never know when the last time is.

23. We cultivate two sets of virtues: resume virtues (the skills and accomplishments that show up on LinkedIn) and eulogy virtues (the qualities people remember when we’re gone, like kindness, courage, generosity, wisdom). A simple reframing question can unlock everything:

“What do you want the people you love to remember about you — and how can your money support that version of you, starting now?”

24. A good bullshit detector can go a long way in making better financial decisions. As a creative endeavor, financial success depends on knowing what to include as well as what to exclude; being able to separate good advice from bad advice; telling the truth from the bullshit.

25. The purpose of saving anything — money, health, memories — is the people we love.