Boring Strategies That Actually Work (and Why)
In the past, we’ve talked about what isn’t worth your time or money due to a low return on hassle. Today, I want to flip the script and share something I’ve seen consistently across thousands of entrepreneurs and investors: what delivers the highest return on hassle.
The Wealthy Think Differently About ROI
After a certain point, the wealthy stop obsessing over traditional ROI. Instead, they focus on a simple but powerful framework that I call "Return on Hassle":
Return on Hassle = Money saved or earned / (Time + Energy + Brain damage)
The wealthy delegate or eliminate complexity. They recognize that every financial optimization carries hidden costs in the denominator that most people never calculate.
Once you've made more money than you'll ever spend, there are only 3 reasons to do anything:
- You genuinely enjoy it
- It serves a mission bigger than yourself
- It measurably improves your quality of life
Everything else? Just noise.
A Simple Decision Framework That Changes Everything
To put this into practical terms, I use what my friend Ayman Abdul calls the "Ease vs. Effect" framework:
Ease (1-5) × Effect (1-5) = Score
Only implement strategies that score 15 or higher. This instantly eliminates about 90% of the "optimization" advice you'll encounter.
Where You Should Focus: Scores 15+
401(k) Match: Ease 5 × Effect 5 = 25
This is the ultimate no-brainer. It takes minutes to set up, requires zero ongoing maintenance, and delivers an immediate 100% return on your money. No complex strategy will ever beat this.
Simple Index Fund Portfolio: Ease 5 × Effect 4 = 20
This strategy consistently outperforms 90% of complex portfolios with a fraction of the hassle. I've seen people with eight-figure portfolios who spend less than an hour per year on investment management.
Term Life Insurance: Ease 4 × Effect 5 = 20
Easy to set up and provides enormous peace of mind for minimal cost. Once established, it requires virtually no maintenance.
One Bank Account: Ease 5 × Effect 4 = 20
Maintain a single business account, a personal account, and perhaps one investment account. The mental bandwidth saved is worth more than the marginal interest gained through complexity.
Focus on Earning More: Ease 5 × Effect 5 = 25
Your earning potential typically has a much higher ceiling than your ability to optimize expenses. Focus your energy on high-leverage activities that grow their income rather than squeezing pennies from existing resources.
The Hidden Costs of Over-Optimization
Everybody says, "HSA takes 3 seconds!" But the reality is different:
- Switch to high deductible plan
- Kid needs ear tubes = $8,000 (ask me how I know)
- Tax savings = $2,500
- Net loss = $5,500
Ease 2 × Effect 1 = 2. We use the PPO in our house.
This is what I call the "Optimization Death Spiral." It starts innocently enough:
- You begin with a simple financial life
- You add one "optimization hack" at a time (HSA, backdoor Roth, 529s, REITs...)
- Before you know it, you're managing 15+ accounts
- You're saving perhaps $10K per year through these optimizations
- Meanwhile, you're missing $100K opportunities because your mental bandwidth is buried in administrative tasks
Remember: Your genius work has an effect of 1000×, while tax optimization typically has an effect of maybe 1.5×. Every hour spent on the 1.5× steals from your potential 1000× activities.
The $100K Phone Call
One of my clients, a successful creative professional, was offered a specialized investment strategy by JP Morgan that would generate approximately 1% in additional returns, about $100K per year for his portfolio size.
The catch? It required four quarterly calls.
His calculation: Ease 1 × Effect 1 = 1
He walked away from 100K annually to avoid four phone calls. He understood the true cost of complexity on his creative output, which was worth far more.
The Power of Financial Simplicity
Charlie Munger famously said the best way to get rich is to have $10M lying around. He wasn't just being glib—he was talking about Return on Hassle.
I witnessed this firsthand when a client with a streamlined financial life spotted a competitor up for sale. Because he had cash ready and mental bandwidth available, he purchased the business for $2M and ultimately 10× his own business as a result. A more complex financial situation would have killed the deal.
The Bottom Line
- Your financial life should fit on the back of a napkin. If you need spreadsheets to track it all, you've likely over-optimized.
- Calculate your ROH. Use Ease x Effect. Be ruthless about eliminating anything that scores below 15.
Remember: sometimes the highest return comes from doing nothing. Boring wins.
Until next time,