Life’s Unwritten Rules

“I am free, no matter what rules surround me. If I find them tolerable, I tolerate them; if I find them too obnoxious, I break them.”

– Robert A. Heinlein


In August 2020, one of Major League Baseball’s emerging superstars, Fernando Tatis Jr., did something that every young baseball player dreams of: he hit a monster grand slam to help his team win. As you’d expect, there was quite a bit of excitement after the game. Unfortunately, it wasn’t all praise. No, Tatis Jr. broke one of baseball’s unwritten rules and some people weren’t happy about it. 

“I didn’t like it, personally. You’re up by seven in the eighth inning, it’s typically not a good time to swing 3-0. It’s kind of the way we were all raised in the game.”, complained opposing manager Chris Woodward in the post game press conference. 

Baseball is full of unwritten rules meant to uphold order, tradition, and prevent players from straying too far away from the norm.  Break one of them and corrective action is typically swift to follow. I think these rules discourage creativity, slow the evolution of the sport, and just plain make everything less fun. Quite frankly, they’re bullshit. 

Just like many of life’s unwritten rules. 

Like baseball, our lives are guided by countless unwritten rules that exist to uphold order, tradition, and prevent people from straying too far away from the norm. And like baseball, some of them are outdated, stifle creativity, and make everything less fun. 

Here’s my list of life’s unwritten rules that are complete nonsense:

  • You can’t leave the office until your boss does. This breeds a toxic company culture that values activity over productivity. 
  • It’s considered rude if you don’t respond to an email or text message immediately after it’s received. Don’t get sucked into other people’s schedule or demands. If something is truly an emergency, they can pick up the phone and call. 
  • Talking about your salary is faux pas. This can be done in a way that’s not braggadocios or overly prying. Maybe more transparency on this front could help alleviate persistent income disparities
  • You’re more successful if you have more money. I believe this unwritten rule is a key reason why Americans chase endlessly after more money. Instead of defining your own success, the size of a salary or bank account is used as a proxy. 
  • Never leave a good job. I’ve never met anyone who took a risk on a new job, career, or endeavor and regretted the experience. Even if it doesn’t work out perfectly, tremendous personal growth will occur.
  • Don’t start a business without the right experience. This rule is usually promoted by Wantrepreneurs — people that love to talk about starting a business but never actually do anything. 
  • Start a business with no experience. This is the opposing rule to the above that asserts you must start a business with no experience. I think the middle ground is more reasonable. 
  • Never give up. Most of us probably give up on things too early, but the maxim of never giving up takes it too far. I prefer an objective analysis of your situation to guide the decision to press on or not. 
  • No elbows on the table. This feels like an ancient rule from the Elizabethan era to look down upon people who didn’t display certain manners. Who cares.
  • You need to give someone a gift on their birthday. I like the approach my friend Francis takes. When he comes across something that he knows you’ll love, he buys it and gives it to you immediately. It doesn’t matter if it falls on a specific day of the year. 
  • You need to get married before the age of x, or you’ll never find love. So much energy in youth is spent trying to find that “right person” — because if we don’t, there’s no hope. It’s a bogus claim. It doesn’t matter how old you are. 
  • Your family/friends/company always come first. This is a bad decision shortcut, usually encouraged by the group in question. 
  • You need children to have a family. This old-school rule turns a blind eye on the countless other ways someone could build their own family. 
  • If a man can’t deal with something on his own, he’s weak. This macho attitude is slowly fading away but is still pretty prevalent. Imagine what could be accomplished once this rule is broken?
  • Conversational silence is uncomfortable and should be avoided. I’d argue that the best relationships have plenty of silence and neither person feels awkward. Maybe the feeling of comfort in that silence is a sign that the relationship has evolved. 
  • When someone asks “how are you”, the only acceptable answers are some variation of “OK” or “Good”. Everyone is dealing with challenges yet they’re glossed over and pushed down until it’s too late. What if we could actually share how we feel without worrying about breaking an unwritten social norm?

And now, a small challenge. The next time you’re face to face with an unwritten rule you don’t agree with, take a page out of Fernando Tatis Jr.’s book, and break it

What’s one of life’s unwritten rules that you disagree with?


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The Transactional Trap

After a few minutes of riding the shopping cart around like a nine-year-old, I skidded my way over to the carpet section at Home Depot. I was a man on a mission. My new area rug was sliding uncontrollably on my apartment floor and I needed one of those anti-slip pads.  I searched up and down the aisles to no avail and decided to get some help. 

“Excuse me, I’m looking for those pads you put under a carpet to prevent it from slipping, Where can I find them?” I asked the orange-clad associate. 

He thought about it for a few seconds and replied, “Hmm, we don’t have any of those. Sorry about that.” 

Dejected, I dragged my cart away to find the remaining few items on my shopping list. Not one to give up easily, I made one final pass through the carpets section before checking out. Halfway down the aisle, at eye level, I stumbled upon “carpet tape” for securing rugs to slippery surfaces. Success! 

Now that I’m home, I’ve been thinking about the experience. The employee technically answered my question correctly — Home Depot didn’t have the anti-slip pads I asked for. But I wasn’t there to buy a particular product — I was there to stop a rug from drifting around like a deck chair on the Titanic. I was there to solve a problem. 

Unfortunately, I think this type of communication is extremely common. Especially in the business world. We’re busy and feel pressure to treat each interaction as a transaction instead of an opportunity to uncover and solve an underlying problem. It’s a two-way street and I’ve been trying to keep this in mind during recent exchanges. 

How can I ask better questions? Instead of asking for specific “anti-slip pads”, I need to focus on the root problem and ask for help fixing a sliding rug. 

On the flip side, how can I dig deeper to become more consultative in my problem solving? The question I’m being asked probably isn’t the true problem — but just the tip of the iceberg. 

Where have you seen this in action? How have you overcome the transactional trap?


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Timeless Personal Finance Wisdom (or, “The Money Lessons I Wish I Learned Sooner”)

Photo by NeONBRAND

Thinking back on my high school days, there was only one class where I remember what was taught. In this class, we learned practical skills like how to create a budget, balance a checkbook, and invest in the stock market. Balancing a checkbook has since become an old fashioned activity but that Intro to Business class fueled my interest in the power of personal finance. I consider it one of life’s essential skills — right up there with reading, writing, and how to drive a manual transmission.

These are the money lessons I wish I learned sooner.


💸 Consider tracking your spending for a few months. I once did it for an entire year and learned a ton. Most importantly, it forced me to understand the full picture of my personal finances. I witnessed (sometimes painfully) where money was going, how much to save, and what was left over for fun stuff. 

💸 Even if you don’t track your income/spending, take the time to determine which spending categories are most important. Happily spend money on the things you care about and ruthlessly cut spending in the areas that don’t matter. For example, I gladly spend money on travel and eating out for lunch — both things I love to do. But I am extremely frugal when it comes to furniture and brand name clothing  — because I don’t value them. What’s your list? 

💸 Cutting costs is important but you will eventually reach a point of diminishing returns. If expenses are cut ad infinitum, you’ll run out of costs to cut. Don’t overlook the value in growing your income and future earning potential. Invest in your education, negotiate a higher salary, or start a side hustle (or all three). Cutting costs has a limit, but increasing income has no ceiling.

💸 Build up an emergency fund to cover 6 months of living expenses. Keep it in a low risk, liquid account that you can easily access when an emergency arises. Hopefully it’s never needed but it will ease your mind knowing it’s there — just in case.   

💸 Time plays a tremendous part in the success of retirement savings. Start saving for retirement beginning with your first job after school. It doesn’t matter if you’re only able to sock away $5 per month, save anything. Retirement might be 40 years away but it’s critical to get in the savings habit. The amount saved each month can be ramped up as your earnings grow.

💸 Don’t drive yourself crazy trying to build the perfect retirement portfolio. Most 401ks have an overwhelming choice of mutual funds, ETFs, or stocks at your fingertips. Don’t fiddle with the investment choices every month — it’s a waste of time and you’ll most likely end up doing more harm than good. I use a “target retirement fund” that automatically adjusts as I get older. This lets me set it and (almost) forget it, so I can review my account every 6 months instead of every 6 days.

💸 Remove the thinking from your savings, spending, and investing by automating as much as possible. I feed all my money to a single checking account and schedule monthly transfers to my savings and investment accounts. Everything continually grows over time, slow and steady, without the need for one-off decisions or manually moving money. It defaults my behavior to saving and investing, freeing up time to do more interesting things than constantly worrying about whether my checking account needs more money.

💸 Don’t try to time the market. You might get lucky, but you won’t realistically be good at it. The vast majority of financial professionals who dedicate their entire lives to this endeavor cannot consistently beat the market. What makes you different than them? The S&P 500 has outperformed most actively managed funds for the past 10 years running. 

💸 Low fees are your best friend and index funds usually have the lowest fees. The lion’s share of my investments are in an S&P 500 index fund that has a .04% expense ratio (I pay 40 cents annually for every $1,000 invested). Investment fees, even if they appear small, can wreak havoc on an otherwise sound investment strategy. Jack Bogle, inventor of the index fund and founder of Vanguard, said it best. “Where returns are concerned, time is your friend. But where costs are concerned, time is your enemy.” 

💸 With that said, it can still be fun to play Wolf of Wall Street and invest in individual stocks and invest more aggressively. Jack Bogle calls this his “Funny Money” account and I follow his recommendations: “Life is short. If you want to enjoy the fun, enjoy! But not with one penny more than 5 percent of your investment assets. That can be your Funny Money account. But at least 95 percent of your investments should be in your Serious Money account.“ 

💸 Contrary to what you read, building wealth is boring. It’s not about a million dollar idea, a million dollar stock pick, or a million dollar lotto ticket. Save consistently, invest consistently, and reap the rewards of compound interest


Recommended Reading

The below books have helped me tremendously during my lifelong personal finance journey. 

📚 I Will Teach You to Be Rich by Ramit Sethi – a must read for any recent college grad (and everyone else, really). A lot of the above advice is from Ramit’s book. 

📚 The Little Book of Common Sense Investing by Jack Bogle – my specific investing strategy is heavily guided by this book. 

📚 Berkshire Hathaway annual reports by Warren Buffet – I never thought I’d spend my free time reading corporate annual reports but these are a master class in making complex financial topics seem simple. 

📚 The Choose Yourself Guide to Wealth by James Altucher – a unique book on finances and life that inspires you to think outside of the box. 

📚 What I Learned Losing a Million Dollars by Jim Paul & Brendan Moynihan – tells the story of Paul’s disastrous fall from investing grace and delves into the psychological aspect of investing. 

📚 Where Are the Customers’ Yachts? by Fred Schwed – originally published in 1940, this book hilariously pulls back the curtain on Wall Street and the lessons still hold true today. 

📚 Enough: True Measures of Money, Business and Life by Jack Bogle – when talking about finances it’s easy to lose track of what really matters (hint: it’s not money). This book focuses on the important things in life through a financial lens. 


Bonus Advice!

In writing this post, I was wondering how other people think about their personal finances and what lessons they’ve learned. To answer that question, I asked a few trusted friends “If you could pass along only one piece of financial advice, what would it be?”

Judging by their replies, I regret not asking the question sooner. 

💡 “Figure out how much risk you are willing to accept, which will most likely change as one gets older. Then get advice and information from lots of sources (e.g. books, financial experts, friends). This will help you make good decisions that align with your goals.”
-My Dad

💡 “Live below your means.”
-Aunt Joyce

💡 Make building your credit your priority. If you don’t have credit or it’s poor, go to your local credit union and ask if they offer “secured loans”. These are small loans taken against the balance of a savings account. This is the fastest, safest way to build credit, especially for people who don’t have a lot of income or have issues controlling credit card spending. If you do want to go the credit card route, many companies offer student cards with low limits.”
Johanna Silfa 


I’d love to hear your answer to the same question: If you could pass along only one piece of financial advice, what would it be?


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