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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Bumper Cars

If you peeked at my YouTube video suggestions, you’d be confused. I don’t know what led Google to think I’d enjoy videos of chiropractors cracking their patients backs, necks, and hips — but they clearly know more about my interests than I do. I’ve discovered three things from watching these videos: First, there’s something oddly addicting in witnessing the realignment of a skeletal system. Second, there’s a high correlation between the decibel level of the crack and the number of views

And third: my body and mind could use a realignment. 

Before the COVID pandemic, my “normal” life was dependent on activity. Wake up and sleepily hustle to the gym. Bounce from client meeting to meeting. Drinks and dinner with a friend. A quick weekend getaway. Filling my time with movement, productivity, and entertainment was a nonstop pursuit.

As long as my life was filled with activity, I was happy. That activity has faded away, and so has my happiness. 

The gym is closed. My friends can’t leave their homes. Trips are out of the question. 

As I reread those observations, I feel embarrassed because my concerns seem pretty insignificant. With all the serious problems going on in the world, my life should feel great. My family is healthy, I have a job, and I don’t worry about my next meal. Relatively, my life should be full of happiness. But the reality is that I’m still struggling to consistently find it.

I believe the culprit to be a disconnect between my body and mind. 

For my entire life, I’ve trained to ruthlessly hunt for activity — and I became pretty damn good at it. This training has shaped my mind’s reward system into a bumper car, constantly racing in search of something to crash into. This approach served me well for many years because there was always something I could aim the bumper car towards and smash on the accelerator.

But now the game has changed. My mind is still racing around, but my body is at home. Put a bumper car inside a 2 bedroom apartment and things are bound to break.

I’ve been contemplating a quote from Ryan Holiday, where he suggests, “there are two types of time in our lives: dead time, when people are passive and waiting, and alive time, when people are learning and acting and utilizing every second. Every moment of failure, every moment or situation that we did not deliberately choose or control, presents this choice: Alive time. Dead time. Which will it be?”

I like Ryan’s definition and distinction between dead time and alive time. Before the pandemic, I sought out activity because it fit my flawed definition of “alive time”. As long as I was doing something, it felt like I was making the most of life. But now that activity is limited, everything just feels like dead time. When I reflect on these difficult months, my happiness was stripped away not because of objective suffering, but because of my faulty definitions. A misalignment.

Just because life is different doesn’t mean the time is wasted or that I’m any less alive. In fact, I’d argue that most of my pre-pandemic, full-of-action-time, actually fit Ryan’s definition of dead time. I was busy, but I wasn’t always learning or consciously utilizing every moment. 

Like those addictive YouTube videos, I think a realignment is in order. And like an old John Wayne movie, I need to let the bumper cars out of their corral to ride off into the sunset. The world has changed but I can still find ways to make it Alive Time by enjoying what’s at hand and utilizing every second to the fullest.