Tracking Every Dollar I Spent for an Entire Year

When I was 10 years old, and my sister 6, our parents took us on a trip to Disney World. While we were waiting at the airport gate for our Orlando-bound flight, our dad pulled us aside. Expecting a stern lecture about our behavior on the upcoming trip, I was shocked when, instead, he handed each of us a crisp $20 bill.

“This is your souvenir money for the vacation,” he told us. “I think you’re old enough to figure out what you want to spend it on. This is all the money you’re getting for the week, so don’t even think about asking for more.”

My sister and I looked at each other with a smile. Instead of a lesson on family-trip etiquette, we’d just received 20 bucks to spend however we pleased.

Before we knew it our plane had landed, and we were strutting down the terminal in the land of Mickey and Goofy. Before we’d made it to baggage claim, an airport shop caught my sister’s eye. She ambled over to the Disney-themed memorabilia.

I still remember my confusion when she turned to me and exclaimed, “I like this hat, and it’s only $19. I’m going to get it!”

“But…we haven’t even made it INTO Disney World yet!” I protested. ”You have to make that $20 last the entire week!”

“Eh, I don’t care,” she shrugged. “This hat is pretty, and I have enough money…so I’ll buy it.”

“I think you’re making a big mistake,” I pleaded, my last-ditch effort to impart some older-brother wisdom.

I reached into my pocket and clutched Andrew Jackson tightly as I watched her happily exchange her 3 hour-old bill for a Minnie Mouse hat.

The first several times I heard my parents recall this anecdote, I thought it was just another funny example of differences between siblings. But somewhere around the 100th retelling, I realized: This isn’t just a story of contrasting personalities — it’s a lens into differing money mindsets.

My 10-year-old self was already in the “saver” mindset, despite only earning $4 a week to take out the trash and shine my dad’s shoes. (Keep an eye out for a future post on how to spit-shine penny loafers.)

Fast forward to my first full-time job shortly after graduating college. I was finally making a salary, but I also finally had real expenses. Rent, car insurance, taxes — you know, that thing called the “real world.” After a few months, the luxury of a bi-weekly paycheck was diminished by an unfortunate realization: Despite making more money than ever before, I wasn’t actually saving any of it.

I set what seemed like a simple goal: Spend less money than I was earning, and save the remainder.  

Though the goal might’ve been simple, the execution was anything but. I started looking into personal-finance articles and books, but each offered different advice on setting and maintaining a budget. I began to feel overwhelmed.

Eventually I realized I was making X dollars and spending Y dollars per month — and that while the former number was consistent, the latter was more of a mystery. Where was all my money going?

And so I decided to track every dollar I spent for an entire year. I did this manually in an Excel spreadsheet: one tab per month, one row per day, one spending category per column. (This was back in 2008, when automated personal-finance tools like Mint were still in their fledgling stages). Before bed each night, I’d pull up the spreadsheet and manually enter in every expense from that day. Here’s a look at a full month of tracking every dollar I spent.

This exercise worked. I got my expenses under control and started to save money. But as I think back on the process, I realize that it taught me much more than simply how to save.  

Here’s what I learned:

💸 The act of manually writing down each dollar I spent helped me get a good feel for my spending (and overspending) habits. I would not have received the same level of real-time feedback if I’d used automated budget programs, which tend to slightly distance users from the nitty-gritty of the tracking process. Writing down every expense made me more conscious of each purchase I made — I knew it would all need to be accounted for each evening, so there was nowhere for anything to hide! After a few days of creeping past my normal purchasing habits, I’d notice and pump the spending brakes. This is a skill we can all develop without slogging through a year-long exercise. I recommend tracking your spending for a single month — you’ll be surprised at the insights.

💸 Identifying and writing down my monthly pay, taxes, and fixed costs gave me a number: what financial advisors call discretionary income. It’s really just the amount of money you have left to spend after bills, taxes and other necessities are paid. Knowing this number was absolutely critical in my journey toward saving. I took the extra step of breaking it  into individual categories (lunch, dinner, clothing), but that wasn’t as important as knowing my number and spending less than it each month. Do you know your number?

💸 Every college grad — and anyone else looking to strengthen their personal finances — should read Ramit Sethi’s “I Will Teach You to Be Rich.” It teaches normal people how to automate their finances by creating a system, and is written in simple, straightforward language.

💸 Making more money doesn’t correlate to increased happiness. I currently earn about 3 times what I did in 2008. But am I 3 times happier? Certainly not. It’s really easy to think, “Life would be so much better if only I made X more dollars” — but even the results of a 2018 Purdue University study show this to be a counterproductive attitude.  

Looking back on my year of tracking every dollar, I also discovered a few interesting spending habits:

💸 I spent 15% more at the bar than I did on groceries. Oh, to be 22 again…

💸 I spent almost no money on going out to dinner. In fact, in July, I only spent $46 on dinners out! I guess I cooked more often — or ate more PB&J sandwiches — than I do today.

💸 I was pretty darn consistent in my monthly discretionary spending, averaging $1,025 per month — with a high of $1,204 in May and a low of $823 in December.

Oh, and if you’re wondering what happened to my $20 from that 1995 Disney trip? I stuffed it in my piggy bank — and it’s now worth $126.83.

The Invisible Gorilla


The task seemed simple enough. Watch a 40-second video and count how many times the people in white shirts pass a basketball.

Only there was a slight twist. About midway through the video a giant gorilla strolls onto frame, looks at the camera, pounds his chest, and slowly walks away.

It seems silly to even ask — but how many people failed to see the gorilla?

The results speak for themselves. Half of the participants did not report seeing the gorilla walk across the screen. It’s like the gorilla was completely invisible.

How is this possible?

The culprit is a phenomenon called inattentional blindness, where “….an individual fails to perceive an unexpected stimulus in plain sight. When it becomes impossible to attend to all the stimuli in a given situation, a temporary ‘blindness’ effect can occur…”.

The research into the root causes of inattentional blindness points to a handful of theories, but I’d like to focus on two: Mental Workload and Expectation.

The Mental Workload Theory states, “when a person focuses a lot of attention on one stimulus, he/she focuses less attention on other stimuli.” This makes sense. When we’re talking on the phone while driving, our attention is on the conversation and not the stop sign we blew through. This also helps explain why half the people didn’t see the gorilla. Their mental workload was maxed out while counting the number of passes and there wasn’t enough cognitive resources to notice anything else.

The Expectation Theory says that when we expect certain events to happen, we block out other possibilities (thus causing Inattentional Blindness). If we’re tasked with counting the number of basketball passes, the idea of a man in a gorilla suit strolling across a screen might not even register as a possible scenario (well, unless we’re at a Phoenix Suns game). Our expectation of “normal” can cause us to block out other possibilities.

Learning about Inattentional Blindness has caused me to reflect on all the things I’ve missed that have been right in front of me. For example:

🦍 I’ve walked past my neighbors front steps hundreds of times before — so I didn’t notice and enjoy the new plants decorating her stoop.

🦍 I’ve been so focused on working through a tough work problem with a specific solution that I missed an obvious (and simple) fix.

🦍 I’ve had expectations about how life was “supposed” to unfold that have limited other potential outcomes from turning into reality.

I know it’s impossible to avoid every Invisible Gorilla — but I find it helpful to know they’re out there…lurking in everyday life. When I’m narrow-mindedly focused on a single task, or thinking I know all possible outcomes, I try to take a step back and find that pesky gorilla.

Where are your Invisible Gorillas? How can you bring them into focus?

Stumbling Upon My Greatest Investment

I recently met with an old colleague, Hicham, to catch-up over coffee. Hicham and I didn’t just work together — he hired me at my first tech company when I was struggling to shift out of the finance industry.

We made our way through the normal rounds of chit-chat — reminiscing about the “good ol’ days” and sharing what we’re up to now. Nothing too out of the ordinary.

But then Hicham changed the subject and caught me off guard: “You know, I still have that thank-you letter you wrote me.”

He was referring to the handwritten note I’d sent him, along with three other interviewers, thanking each of them for their time and consideration for the position I’d interviewed for in 2010.

We eventually changed topics, caught up a bit more, and parted ways.

But as I walked back to my apartment, I couldn’t stop thinking about what Hicham had said. Our casual catch-up led me to a powerful realization: Until now, I hadn’t even been aware of the greatest investment I’ve ever made.

How long did it take me to write, address, and stamp four thank-you notes and drop them into a mailbox? 30 minutes, max.

What was the return on investment for those 30 minutes? I’m struggling to put a number on breaking into the tech industry, working alongside incredible people for five years, and ultimately learning the skills to start my own consulting company.

Admittedly, sending a handwritten note is pretty easy. At the same time, though, it’s just as easy not to do it. And I think that’s why Hicham hung onto that piece of paper. I was the only candidate who made a personable, memorable connection that set me apart from the pack.

Who do you care about? Maybe it’s an old mentor. Or a friend who helped you through a tough time. Or a new customer you met at a conference.

Write them a note — they might just remember it 9 years later.