What if one of the best ways to get wealthy is to trick yourself into thinking you’re broke?
It sounds counterintuitive, even ridiculous. But after decades of saving, investing, and observing how people behave around money, I’ve realized one thing: abundance often breeds complacency.
When you feel flush, you spend more, work less, and get sloppy. When you feel broke—even artificially—you hustle harder, spend carefully, and grow wealth faster. And as we all know, the path to financial freedom comes down to one formula: save and invest as aggressively as you can, for as long as you can. The problem is sustainability.
The 5% national median saving rate simply isn’t enough. Aim for at least 20%, and if you can push yourself to hit 50% for 10 years, your future self will thank you many times over.
Feeling Lazy And Unmotivated After Summer Vacation
Ever since coming back to San Francisco from my five-plus weeks in Honolulu, I’ve been feeling more lazy than usual. I started wondering why everybody doesn’t live in a place like Hawaii, where the weather is always great and the vibes are always friendly. Grinding so hard in San Francisco seemed pointless and a surefire way to burnout.
You don’t have to be rich in Honolulu because the beaches, hikes, and sunshine are free and accessible for all. If you’re a local, you even get Kamaʻāina rates for golf and other attractions, saving you even more money. Although I spent three-and-a-half weeks helping remodel my parents’ in-law unit, I felt much more at ease doing less.
The problem with coming back to San Francisco is that the vast majority of people are hustlers. Most are trying to climb the corporate ladder or build a company for greater status and money. These actions run counter to the FIRE lifestyle of giving up money and status for freedom.
But given I’ll be stuck in San Francisco for at least the next four years, I need to be careful not to act too lazy. Because if I do, I’ll start feeling FOMO from the ongoing AI/tech boom. And feeling left behind is one of the worst feelings you can have.
A Solution to Getting Rich Is to Feel Poor
As I found myself waking up later and later, I realized I needed a way to motivate myself again. Given I’m no longer a stay-at-home dad, increasing productivity felt required.
Then one day, while checking my banking app, I noticed that my checking account was in the red by $100. Doh! I had paid my annual life insurance premium automatically and forgot to leave enough in my checking account.
Since making a terrible two-year mistake with a life insurance policy, I’ve been intentionally keeping my checking account light to avoid wasteful spending. And with a free $5,000 overdraft line of credit, being down $100 wasn’t a big deal. I topped it up from money from our joint account.
But here’s what mattered: seeing red on my account made me perk up and take notice.
To be frank, I felt poor. How could I, with multiple streams of passive income, not even have enough to cover a life insurance payment? Yet with that temporary feeling of not having enough came a renewed sense of urgency—to stay on top of my finances and grind once more.
Living on the Financial Edge Makes You Focus
A couple of weeks later, rental income and dividend income replenished my checking account. But the lesson stuck with me.
Having a checking account flush with cash earning 0.1% interest was actually demotivating. It pulled me back to the lazier state I’d fallen into after returning from Honolulu.
So I decided to transfer out nearly all my excess checking funds—keeping just enough to cover upcoming bills—into my Fidelity brokerage account. That way:
- My idle cash could earn ~4% in a money market fund.
- I could dollar-cost average into stocks or bonds during market pullbacks.
- I could allocate more into alternatives like venture funds to hedge against the AI revolution for my kids’ future.
Now, whenever I log into my banking app, I see hardly any money. And you know what? That scarcity forces me to think twice before swiping my card since I don't have enough funds to pay by debit card. If a purchase isn’t a “hell yes!”, it’s a no.
Instead of ordering takeout, I’ll cook at home or live off my insides and fast. Instead of buying new sneakers, I’ll finally wear the ones collecting dust in my closet. This artificially imposed scarcity has reactivated my discipline.
Recreating the Hunger of When You Had Nothing
The whole idea of keeping yourself financially lean is to recreate the hunger of your early days, when you had little to nothing. If you want to achieve FIRE, sacrifices must be made.
Back in 1999, fresh out of William & Mary, I shared a studio apartment with a friend to save on rent. I’d get to the office by 5:30am and stay past 7pm to connect with colleagues in Asia before heading home. It was nice to also gain access to the cafeteria for a free dinner.
I put on 15–20 pounds, developed TMJ, and dealt with plantar fasciitis, all from the stress of hustling on Wall Street. But those sacrifices laid the foundation for everything that followed.
By living frugally even after promotions, I was able to bank the difference and invest aggressively. That discipline compounded over decades, has made living far easier today.
However, as I grind toward a new passive income goal by December 31, 2027, I see the wisdom of returning to that mindset. We must find ways to save and invest more if we want to one day stop trading time for money.
The Bull Market Can Make You Weak
Bull markets are intoxicating. When your investments are compounding faster than your active income, it feels like you’ve hacked life, on cheat mode. You start to believe you can’t lose.
But complacency is dangerous. I watched it happen in 2007. People levered up, bought multiple properties with no-money-down loans, and assumed the party would never end. By 2009, many had lost everything and had to rebuild from scratch. I was one of these people who foolishly bought a vacation property I certainly didn't need in 2007. It ended up declining in value by 50%.
I don’t want to relive the trauma of seeing my net worth fall 35–40% in six months. And I don’t want that for you either.
That’s why artificially feeling poor—even in bull markets—isn’t just a motivational trick. It’s a safeguard against overconfidence and reckless behavior.
Practical Ways to “Feel Poor” Without Actually Being Poor
If you’d like to try this strategy yourself, here are some ideas:
- Keep your checking account lean. Only maintain 1 month of expenses in checking. Move the rest into higher-yielding accounts in your brokerage.
- Auto-transfer your surplus. Each payday, sweep extra funds into a brokerage, high-yield savings, or investments. Out of sight, out of mind.
- Challenge yourself with no-spend weeks. Pick two weeks a month to avoid discretionary purchases. You’ll realize how much you can cut.
- Simulate living paycheck-to-paycheck. Cap your monthly spending at a fraction of your income, and redirect the rest into investments.
- Revisit your “broke college” habits. Cook cheap meals, ride public transit, share resources, and embrace minimalism—even temporarily.
- Audit your subscriptions. Cancel what you don’t truly need. Every forgotten $10/month service adds to lifestyle creep. Did I just see Apple raising their Apple TV+ by $4 to $14/month?
- Practice gratitude daily. Remind yourself how far you’ve come, and that you can survive with less.
Artificial scarcity doesn’t mean living in fear, it means using small doses of discomfort as a tool to stay sharp, disciplined, and motivated. It's about keeping things real and humble, while you build ever more wealth.
Embrace The Paradox of Wealth
So if you want to grow rich, adopt a broke mindset. Live paycheck-to-paycheck for a while. Condition yourself to track every dollar and question every expense. If you can endure that self-imposed discipline, you’ll almost certainly end up wealthier than the average person who spends freely without intention.
In the end, wealth isn’t just about the numbers in your accounts. It’s about having the mindset to stay disciplined for decades. And sometimes, the mindset that works best is remembering what it felt like to have nothing, and making sure you never go back.
Readers, do you artificially make yourself feel poor to grow rich? In a country with so much abundance, how do we do a better job to combat laziness so that we can continue to build generational wealth?
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