Do You Want to Make Your Life Easier?

Once Poor, Always Poor

Despite my profession, some people are shocked to learn that I’m not always a shining example of what to do when it comes to spending money. “Come on Mr. Finance. Aren’t you supposed to be the ‘money guy’?”

Don’t get me wrong, I enjoy saving just as much as the next guy. But who doesn’t like nice stuff? Now, five-figure watches don’t conjure up anything for me. I’ll take three hot, crispy, messy Birria tacos with a side of consommé over a dollop of caviar at a 5-star restaurant. But all that goes out the door when it comes to shoes.

Let me explain.

When I was younger, we didn’t have much money. Hell, most days, we didn’t have any money. My grandmother was 72. Long retired by now, living off social security, disability checks, and money from Connecticut’s DCF program. All while responsible for raising two growing boys. One who, go figure, had a liking for the finer things in life. 

One of my first memories of money was when I learned how much money she made a month. ~$900. Almost a $1,000! I couldn’t believe it. We were rich! I was damn near salivating, thinking about everything I could do with all that money in one place. That was until I discovered a more important fact of life. The things I never thought twice about weren’t free. 

I later found out our rent alone was $750/m. 

So much for being part of the 1%. 

There were a lot of emotions that stemmed from that pivotal moment. Guilt for always asking to go to McDonald’s every time we drove past one. Shame for feeling so greedy, knowing Grandma was doing the best she could.

My brother and I were long accustomed to hand-me-downs. But every year before school started, my cousin (I guess he took pity on us) would take my brother and me to the mall to get new shoes. 

Looking back at all this taught me a couple of things. First, I need to take care of my things—especially my shoes—and if I want something, I have to get it myself.

I firmly believe that if you want to get better at saving money, you have something you can unapologetically spend money on that makes you happy, then focus all your efforts on your current and future well-being.


Do You Want To Make Your Life Easier? 

Know where you need to be. Know what you’re going to wear. Know what you’re going to do and have an idea of what you’re going to say.

Do yourself a favor, make decisions ahead of time, and then get out of your own way.

But if it were that simple, wouldn’t everyone do it? 

The truth is, our habits often hold us back. We are habit-forming machines. You know the old phrase, creatures of habit. What did you do as soon as you woke up today? What did you do before you went to bed last night? How did you decide what to wear today? 

Chances are, based on your answer, I could have a pretty good guess at what you’ll do in these same scenarios in two weeks. 

As Charles Duhigg put it, “The brain is constantly looking for ways to save energy.” This drive for efficiency is why we lean so heavily on automatic routines—they’re easy, familiar, and take less mental effort.

While habits can be helpful, they can also become our biggest hurdles. 

Duhigg writes, “The brain’s dependence on automatic routines can be dangerous. Habits are often as much a curse as a benefit.” As much as habits help retirees save during their working years, the same routines can make it painfully difficult for them to spend money later in life. 

On the flip side, It’s hard to get into the habit of saving money if you have to do mental gymnastics at every decision point. 

As it relates to finances, I call these habits systems because they should be less physical actions—moving money here to there—and more of a structured set of processes designed to achieve a specific goal.

By building systems that prioritize saving and investing, you’ll free up mental energy, eliminate financial stress, and create a lifestyle that works for you.

At its core, we are simply a reflection of our habits and systems. 


The Problem Isn’t You. It’s Your System

Most people struggle with saving more money. That’s not earth-shattering news. 

However, as Desiderius Erasmus once said: “A nail is driven out by another nail. A habit is overcome by another habit.”

Start by tackling the low-hanging fruit: non-housing debt. According to the 2024 Annual Retirement Study from Allianz Life Insurance Company, non-housing debt is limiting retirement savings for 56% of Millennials, 50% of Gen Xers, and 35% of Boomers. 

But let’s be clear—big debts like mortgages and car payments aren’t the problem. Now, a 5%+ interest rate on a multi-year-long debt doesn’t help. But owning a house or a car alone isn’t what’s stopping you from growing your savings; it’s the smaller, recurring debts that drag you down.

Once those liabilities are moderated or even reconciled, you need to replace unproductive financial systems with better ones. And luckily, in this interconnected, digital world, you don’t even have to do the heavy lifting. 

For me, the game changer was automation.

Here’s how I approach it on payday:

  • 401(k) (auto-deducted from paycheck)
  • Automate savings to a basic savings account (one month’s rent)
  • Anything above that goes to a High-Yield Savings Account (HYSA) 
  • Contribute to my Roth IRA
  • “Travel and Vacation” account

What works for you could be totally different. But the goal should be to let the machines do the work.

By automating my savings and investments every time I get paid, I’ve been able to save more consistently and focus my energy on the things that matter most. 

 My colleague, Nick Maggiulli talks about this in his post about perceived pain

“Instead of increasing your audience’s current pain you can lower their perceived pain. The Automatic Millionaire by David Bach is one example of this. Bach’s idea to automate your finances through automated transfers is one way to lower your perceived pain when it comes to saving money. Since you don’t notice the money automatically coming out of your paycheck, this method makes it much easier to accumulate wealth.”

That’s why I use Liftoff. Liftoff takes the guesswork out of investing. Let us handle the boring but necessary tasks so you can focus on what’s important. 

Investing gets tricky because we tend to overcomplicate it. The more you try to tinker with your investments, the worse you’ll likely perform. The trick is to find the right allocation for you and determine how long you plan to invest. Invest according to that plan, and resist the urge to meddle. 

Anything beyond that is speculation, which isn’t inherently bad—but it’s not investing, and you should size it appropriately.

The bottom line: Automate your saving and investing, then spend the rest however you please. 


My perspective on money is constantly evolving. 

Now that I’m an adult with higher priorities—bills, responsibilities, and long-term goals—I don’t buy shoes often. But if I happen to spot a pair of Jordans—specifically 1-14s—that I don’t already have, or a retro colorway that I like, and I have the discretionary funds, you better believe I’m buying them. It simply reminds me of all the times I couldn’t do that, and that brings me a certain kind of appreciation for how fortunate I am. Although I’m positive if my grandma was still here, she’d be shaking her head, saying, who the hell needs that many shoes?! 

For most of you, it’s probably not shoes. Maybe it’s clothes. Maybe it’s wine. Maybe it’s traveling. Whatever it is, there’s probably something you’re passionate about, something that brings you joy and makes the effort of saving worthwhile.

I recognize that my view on this is a simplified and perhaps selfish one—especially compared to someone with kids. But regardless of your circumstances, the key to changing your habits (and your life) lies in understanding how habits work: cue, routine, reward.

Charles Duhigg puts it best: “The brain is constantly looking for ways to save energy.” Once you understand your cue—the trigger for your habit—you can rewrite the routine and build a reward system that motivates you. 

It’s about making decisions ahead of time and getting out of your own way.

By designing better systems, you can simplify your life and free up energy for what truly matters. For me, that means having room to enjoy what I love without guilt. 

Whether it’s saving for the future, splurging on something meaningful, or finding a balance between the two, we are a reflection of the habits and systems we fall back on.

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