The Game of Investing (hard vs easy)
Feb 27, 2026Read time - 4 minutes / Disclosure
Knowing the difference between hard and easy investing can:
- Save you time.
- Save you money.
- Help you avoid stress.
Unfortunately, there's a lot of options.
The Many Choices
Many people wanting to invest are overwhelmed by the numerous options, like:
- Day trading.
- Stock funds.
- Cryptocurrency.
- Individual stocks.
- Getting loans to buy real estate.
The different options can be mind-boggling.
Not knowing what to do.
Or fear of doing the wrong thing.
Can lead to doing nothing at all.
And as the years pass — 5 years, 10 years, 15 years...
Not investing can lead to a lifetime of needing to work a 9-5 job.
"Never get so busy making a living that you forget to make a life."
— Dolly Parton
The thought of needing to work a 9-5 job until I was 60 scared the heck out of me.
Watching my dad pass away from cancer at age 48.
And watching my mom pass in her early 60s unexpectedly.
Was a stark reminder —
There's no guarantees in life.
I knew investing was one thing I did have control of.
To build up enough assets to leave 9-5 life early.
To do my own thing.
To create a freer life.
But there's so many different things to invest in.
The Investing Scale
Here's 5 different ways I've invested over the past 15+ years while going from $0 to $1M+ in investments (ranked from hardest to easiest).
Hope it's useful.
Let's dive in.
Day Trading: 1/5
Making money buying and selling stocks every day may sound appealing.
But many studies show up to 97% of day traders lose money in the long run.
Deciding:
- What to buy.
- When to buy.
- How much to buy.
And:
- What to sell.
- When to sell.
- How much to sell.
...is a lot of work.
Famed investor Warren Buffett has compared day trading to casual hookups—exciting in the moment but destructive over time.
Individual Stocks: 2/5
Owning individual stocks is less work than day trading.
But still requires you to decide:
- What to buy.
- When to buy.
- How much to buy.
And:
- What to sell.
- When to sell.
- How much to sell.
There's many educators out there like Brian that help investors learn these things. But it takes a lot of patience and a lot of time.
Valuation Cheat Sheet pic.twitter.com/Ue8kbO9ejB
— Brian Feroldi (@BrianFeroldi) February 22, 2026
"Know what you own, and know why you own it." — Peter Lynch
Buying and selling stocks without doing research on each company isn't much different than gambling.
Cryptocurrency: 3/5
Owning cryptocurrency like Bitcoin has become easier.
Buying it on Coinbase, a cryptocurrency exchange.
Or inside investment accounts through one of the largest funds like IBIT (iShares Bitcoin Trust).
But it's still a new asset, with an unknown future.
And can drip in price by 50%+ in a matter of weeks.
Bitcoin price history
Although Bitcoin has grown tremendously, sitting through 50% price drops can be hard unless you're a true believer in the technology.
Real Estate: 4/5
Getting a loan to buy a home or rental property takes a lot of effort.
But I've found after getting past that point.
It's not as much work to maintain the home as most people make it out to be (depending on the type of property you own).
For example:
I got a loan to buy a little condo in this building in 2008.
Back when I didn't know much about home loans.
Tiny seattle condo
Since 2008 there's only been 4 renters.
And I've had to replace:
- The fridge.
- The carpet.
- The dish washer.
- The washing machine.
- The the hot water heater.
That sounds like a lot.
But not really over 10+ years.
Same story with this place:
Tiny seattle condo #2
I've owned this little condo for 15+ years and there's only been 4 renters as well.
(my free playbook for getting money to buy a home)
People that don't own a rental property often talk about how much work it is.
But that's not always true.
I've found it to be less work then I initially expected.
Some types of real estate are easier to own and maintain (and cost less) than others.
Stock Fund: 5/5
Buying a stock fund has been my easiest investment.
For example:
VOO (The Vanguard S&P500 ETF) is one of the largest stock funds.
It includes 500 of the largest companies in America.
$100 invested in an S&P500 stock fund today means owning:
$7.83 of NVIDIA stock
$6.46 of Apple stock
$5.39 of Microsoft stock
$3.92 of Amazon stock
$3.31 of Google stock
+ 495 other companies
Over the past 30 years the stock market has been growing 10% per year on average:
Stock market history: s&p500
"The goal of non-professionals shouldn't be to pick winners, rather to own businesses bound to do well, a low-cost S&P500 fund will achieve this goal" —Investor Warren Buffett.
The bottom line
There's many options with investing.
The first 10 years of my investing journey.
I was so dang busy with work and life.
That investing in an S&P500 Fund (#5) and figuring out how to get loans to buy real estate (#4) were the only 2 things I focused on.
After those first 10 years I started tinkering with:
- Day trading.
- Buying crypto.
- Buying individual stocks.
And day trading was one of my biggest mistakes.
Lost quite a bit of money.
Simply buying an S&P500 fund remains my favorite, low stress way to invest.
I hope sharing my experiences and mistakes is helpful. Feel free to take what you find useful, and discard the rest.
That's all for today.
See you next Saturday.
