What I Learned About Risk While Building My First Investment Portfolio

Three simple checks that turned my anxiety-inducing portfolio into one I can hold through anything.

I built my first portfolio back in 1990's. Like most beginners, I had a collection of “good picks” with no real plan. Heavy on growth, light on diversification, and absolutely no exit strategy.

I did well at times, but I also carried a quiet anxiety: what happens if the market really turns ugly?

That question hit me hard during the 2000 dot-com crash.

The 2000 Wake-Up Call

My $30,000 Reality Check
When the market collapsed in 2000, my portfolio fell nearly 35% while the S&P dropped about 20%.
That extra 15% wasn’t bad luck — it was bad design.

I’d built a portfolio that could only thrive in one environment: endless tech growth.
When that bubble burst, my portfolio exposed just how fragile it was.

Instead of panic-selling (my first instinct), I forced myself to treat it as a learning opportunity.

The 3 Questions That Fixed Everything

1. “If this dropped 40%, would I buy more or sell?”
This question cuts through all the noise.
If you can’t honestly say you’d buy more during a major decline, you probably shouldn’t own it.
It forced me to hold only companies and funds I truly understood and believed in long-term.

2. “Do I have at least 3 different ways to make money?”
I learned this the hard way. My portfolio back then was basically “tech goes up forever.”
When tech cracked, everything cracked.

Now I make sure I’m spread across sectors, geographies, and asset classes. Not because I’m scared — because I’m smart.

3. “Could I ignore this for 6 months?”
If your portfolio requires constant babysitting, it’s not a portfolio — it’s a hobby.
I rebuilt mine so I could walk away for months and still sleep well. That’s when I knew I had something sustainable.

What Changed

• My returns stabilized (less second-guessing = better decisions)
• I stopped obsessively checking daily (now maybe twice a month)
• I barely blinked during later corrections
• I finally had a plan that worked in more than one kind of market

The Real Win

The biggest reward isn’t the returns — it’s the peace of mind.

I don’t wake up worried about headlines.
I don’t second-guess every position.
I’ve built a portfolio I can trust, so I can focus on building wealth in other ways — career, skills, business.

💬 Your Turn
Ask yourself these three questions about your portfolio:

• Would you buy more if it dropped 40%?
• Do you have at least 3 different ways to make money?
• Could you ignore it for 6 months?

If any answer is “no,” that’s your starting point.