Most personal finance creators give you the same miserable advice when your income climbs: hoard every spare dollar, drink cheap office coffee, and dump everything into index funds until you turn sixty-five. On the other end of the internet, hustle gurus insist you should lease an exotic sports car so the crushing monthly payments force you to work eighteen hours a day. Both camps are wrong.
When you start making real money, keeping your spending frozen at a student budget isn’t discipline. It’s fear. But spending that cash on shiny status symbols to impress strangers online is plain stupidity. The trick is knowing which upgrades give you compounding returns on your energy, and which ones are just expensive traps designed to drain your bank balance.
Entrepreneur and investor Dan Martell recently shared the seven investments high earners make once their cash flow stabilizes. Some of his points are pure gold for anyone looking for smart things to upgrade when you make money. Others, especially his take on using half-million-dollar watches as motivational tools, deserve serious pushback. Here is the realistic breakdown of what works, what falls flat, and where your money actually belongs.
1. A “Useless” Weekly Hobby (Buy Back Joy Before You Burn Out)
The first thing almost every frugal blogger tells you to cut is the exact thing you should fund first. When Dan was twenty-two, he worked a hundred hours a week until his body broke down with severe adrenal exhaustion and shingles. He only recovered his health when he forced himself to pick up mountain biking, snowboarding, and wake surfing.
Running on empty turns simple tasks into agonizing chores. In fact, a landmark cross-national study published in Nature Medicine analyzed over 93,000 adults across sixteen countries and found that having an active hobby is directly linked to fewer depressive symptoms, higher life satisfaction, and better self-reported health.
In his book Die with Zero, author Bill Perkins talks about “memory dividends.” Money is just stored energy. If you never convert that cash into experiences while your joints still work, the money goes to waste. Dan recommends the 3F filter: pick an activity that is Fun, that you can do Frequently, and that you can share with Friends.
Don’t drop five grand on carbon-fiber golf clubs if you haven’t played a round in three years. Rent first. If you stick with it for twelve weeks, then buy the solid model.
2. Eliminate Daily Decision Fatigue (Buy Laziness on Purpose)
Willpower is a finite battery. Every small choice you make before noon drains that battery before you touch the work that pays your bills.
A widely cited 2011 study in the Proceedings of the National Academy of Sciences (PNAS) examined judicial rulings over ten months. Researchers found that judges approved parole in roughly sixty-five percent of cases early in the morning. As the session dragged on and mental fatigue set in, approvals plummeted toward zero right before lunch. Once the judges ate and rested, the rate jumped straight back up. When your brain gets tired, it defaults to the easiest, lowest-risk answer, which is almost always “no.”
High earners don’t have superhuman discipline. They just build systems that make good choices automatic. Dan sets his nutrition on autopilot: a trainer designs his macros, sends the spreadsheet to a local meal prep service, and pre-portioned containers show up in his fridge twice a week. He doesn’t think about lunch. He just opens the door and eats.
You don’t need a private chef to pull this off:
- Sign up for a weekly meal prep delivery so dinner is settled on busy weekdays.
- Hire a home cleaner twice a month to take chores off your weekend plate. (If your living space constantly feels cluttered, our guide to low-effort home organization systems shows how simple tweaks keep rooms clean without constant tidying).
- Set staple groceries on recurring subscription.
- Pick a simple daily wardrobe so you aren’t staring blankly into your closet at seven in the morning.
3. The “Forcing Function” Trap: Why You Shouldn’t Buy a Luxury Watch or Sports Car
Here is where Dan and I strongly disagree.
In the video, Dan talks about wearing a half-million-dollar Richard Mille watch. He claims it isn’t an ego flex, but a daily physical symbol reminding him to build a billion-dollar enterprise. He also shares a story about encouraging a team member to buy a Porsche he could barely afford so the fear of payments would push him to earn more.
That is reckless logic for ninety-nine percent of readers.
Calling an expensive toy a “forcing function” is how ambitious professionals justify standard lifestyle inflation. Taking on heavy debt doesn’t make you sharper. It makes you stressed. When you have huge overhead breathing down your neck, you take desperate gigs, accept bad clients, and compromise your long-term judgment just to make next month’s payment.
If you want a real forcing function that doesn’t blow up your balance sheet, book an unforgiving physical challenge like a half-marathon, hire a strict coach, or lock yourself into a public launch date. Keep your rewards tied to realized milestones, not unearned optimism.
4. An Environmental Reset (Buy Yourself a Clean Slate)
Your physical environment quietly dictates who you are allowed to be. Friends from high school remember who you were at eighteen. Coworkers expect you to react the same way you reacted three years ago. Without realizing it, you keep playing that assigned role.
When Dan turned twenty-two, he dumped his savings into a backpacking trip across Australia. Nobody in Sydney knew his background, his insecurities, or his past mistakes. That clean slate allowed him to adopt new habits without anyone rolling their eyes. He picked up road cycling, spoke up in crowds, and shed old assumptions.
You don’t have to flee to the other side of the planet to get this benefit. A four-day solo retreat to a rented cabin three hours away works just as well. Leave your regular laptop at home, shut off group chats, and give your thoughts room to breathe (I still refuse to spend more than eight dollars on airport water, no matter what my account balance looks like, but booking a quiet cabin once a year has paid for itself ten times over). It gives you space to decide what habits you want to carry forward.
5. Curate Your Circle (Pay to Build Genuine Relationships)
Keith Ferrazzi laid this out years ago in his book Never Eat Alone: your professional trajectory rarely rises above the average standards of your closest five friends. The trouble is that as you grow, finding people with similar drive and integrity gets harder.
Dan uses what he calls the 5×5 rule. Every day, reach out to five people you respect, and offer five times more value than you ask for in return. More importantly, use your capital to host gatherings. Pay for a private dinner room at a quiet bistro. Cover the tab, invite six or eight interesting people, and make one rule clear: nobody is there to sell anything. You are just bringing good people together around a meal.
Spending five hundred bucks on a great dinner with sharp minds yields more long-term opportunities than ten thousand dollars dropped on generic online courses.
6. Capital Allocation Over Cash Hoarding
Leaving tens of thousands of dollars idling in a standard commercial checking account feels safe, but it is a guaranteed loss. According to historical tracking from the U.S. Bureau of Labor Statistics, inflation steadily chews through cash purchasing power year after year. Money that sits still quietly dies.
When Dan sold his first technology company, Sphere, a mentor gave him straightforward advice: take half for your next venture, and put the rest into assets that work while you sleep. If you are exploring different ways to build sustainable income streams, reading through our framework on twenty-five proven ways to make money will help you spot which models match your background.
For most households, the hierarchy of investing is simple:
- High-earning personal skills: Learning sales, copywriting, or technical workflows often returns fifty to one hundred percent annually on your earning power.
- Low-cost index funds: Broad market funds that track the total market with minimal management fees.
- Cash buffer: Three to six months of lean living expenses in a liquid high-yield account, and not a penny more rotting in checking.
7. Targeted Local Giving (Build Your Giving Muscle Early)
Dan’s final upgrade sounds strange at first glance: he calls it “buying love.” At age eleven, he was put on heavy prescription medication for ADHD, which eventually sent him down a dark spiral into juvenile detention and rehab. An adult named Brian took time to mentor him when nobody else would.
Today, Dan and his wife run personal giving initiatives for troubled youth and detention centers. He doesn’t just mail a generic check to a giant non-profit foundation; he shows up in person with his time and resources.
If you wait until you feel wealthy before you give back, you will never start. Giving isn’t about the size of the check. It’s about building empathy and reminding yourself why you work so hard in the first place. Pick a specific issue you lived through, find a local grassroots group doing honest work on that front, and help them out directly.
High-ROI Upgrades vs. Expensive Traps
Before spending a single extra dollar this month, run your potential purchase through this filter:
| Category | High-ROI Upgrade | What to Skip | Real Payoff |
|---|---|---|---|
| Health & Energy | A weekly hobby with friends (biking, climbing) | High-end home gym equipment that gathers dust | Proven drop in depressive symptoms; sustainable energy |
| Daily Bandwidth | Meal prep delivery, bi-weekly house cleaning | Complex gadget subscriptions that require maintenance | 5–10 hours of clean focus recovered each week |
| Motivation | Tough athletic goals, public launch deadlines | Leased luxury sports cars and expensive watches | Genuine self-respect without dangerous overhead |
| Relationships | Hosting quiet dinners for people you respect | VIP club tables and superficial networking galas | Authentic friendships that bring compounding goodwill |
| Capital | Skill training and low-cost index funds | Speculative meme trading and idle checking balances | Defends against inflation while growing your earning ceiling |
Frequently Asked Questions
How much money should I save before making lifestyle upgrades?
Keep a strict minimum of three months of essential living expenses parked in a separate high-yield savings account. Do not spend a dime on lifestyle upgrades until your high-interest credit card debt sits at absolute zero.
What is the very first thing I should upgrade?
Upgrade whatever daily task causes you the most chronic irritation. For most people working long hours, that means grocery delivery or bi-weekly home cleaning. Removing daily chores instantly pays dividends in mental clarity.
How do I know if an upgrade is worth the money?
Ask yourself one question: will this purchase give me back energy, or will it demand more of my attention to manage and maintain? If an item requires constant care, insurance, and worry, it isn’t an upgrade. It is an anchor.
The Verdict: What to Do This Week
Don’t try to overhaul seven parts of your routine at once. That just creates another messy to-do list.
Pick one daily chore that regularly drains your patience on Thursday night. Pay to eliminate it this week. Once your schedule feels lighter and your head is clear, put whatever surplus remains into an index fund and get outside on Saturday morning.
Spend money to make your days quieter, not louder.
