Investing With Chronic Pain: How a $20K Loss Set Me Up to Win at 35

Investing with chronic pain is messy. Nobody talks about the moment they hit rock bottom with money. But I have to. Because if I skip the part where I lost everything, this story isn’t honest and it won’t help you avoid the trap that swallowed me whole.

I was 25 when I made my first real investment. And I lost it all.

The $20K Loss: My First Lesson in Investing With Chronic Pain

I’d scraped together $20,000 painting houses, my back screaming from ladders, my knees aching from crouched days on drop cloths. Hungry for freedom, I jumped into penny stocks hyped online, gold and silver companies promising explosive returns.

Eight months later: gone. Every dollar.

The pain wasn’t just financial. It was physical. I remember icing my back after a brutal shift, staring at my Questrade account balance: $0. Feeling like a fool. Like I’d never escape the cycle of pain and broke-ness.

But I didn’t close the account. I couldn’t. Something in me refused to quit entirely.

Why Chronic Pain Changes the Way You See Money

When you live with chronic illness, money isn’t about yachts or luxury. It’s about options.

The option to rest without panicking about bills.
The option to afford a Tempur-Pedic when your back locks up.
The option to pay for physio or therapy when the system makes you wait months.

For most, money buys comfort. For us, money buys survival.

The Road Back: Building Trust After Loss

For five years, I didn’t invest. I was in survival mode.

Corporate sales at Xerox drained me. My joints ached under fluorescent lights. Fired just before Christmas at 27, I fell back into painting. My body told me it wouldn’t last.

At 28, a friend vouched for me in tech. Remote work saved me. Suddenly, I had flexibility. Mornings for stretches, afternoons for meetings, evenings for recovery.

But that empty Questrade account still stared at me. A reminder of the $20K mistake.

So I started studying. Slowly. Patiently.

Reading Investopedia basics.
Following market analysts.
Practicing in a demo account.
Journaling patterns instead of chasing hype.

It wasn’t just financial rehab. It was mental rehab.

The Turning Point: From Desperation to Strategy

In 2016, I saw an opportunity: cannabis stocks. This time, I didn’t rush.

Read financial reports.
Studied regulation trends.
Watched earnings calls.

I invested $25,000, everything I’d saved in a decade.

By mid-2017, my portfolio tripled. $75,000. Enough for a down payment. Combined with $25,000 from my RRSP (first-time buyer program), I had $100,000.

At 34, I bought my first home. Renovated it. Rented the basement. Listed the main floor on Airbnb. That property became my financial anchor.

More than money, it gave me freedom from fear.

The 5 Rules of Investing With Chronic Pain

If I could go back to 25, here’s the blueprint I’d hand myself.

1. Don’t Chase Hype

If it sounds too good to be true, it is. Penny stocks ate my savings. Stick with companies that show earnings, not just promises.

2. Use Pain-Proof Systems

Your energy will fluctuate. Automate:

Auto-transfer to savings
Dividend reinvestment plans (DRIPs)
Robo-advisors if research drains you

3. Keep the Account Open

Failure isn’t final. Don’t delete the brokerage app, keep it, even empty. It’s a placeholder for your comeback.

4. Think in Options, Not Millions

You don’t need $10M. You need enough to buy flexibility:

Cover a flare month
Fund a recovery tool
Say no to a toxic job

5. Learn Before You Risk

Use free tools:

Investopedia Simulator
Demo accounts from Questrade or Interactive Brokers
Books like The Intelligent Investor or I Will Teach You to Be Rich

If You’re Just Starting Out

Here’s what I’d tell my 25-year-old self:

Step 1: Open a demo account. Practice with $100K fake dollars.
Step 2: Read 10 minutes daily (Investopedia, Motley Fool basics).
Step 3: Build a $1,000 emergency fund.
Step 4: Start auto-investing $50–100/month into an ETF.
Step 5: Revisit your plan quarterly. Don’t chase daily trends.

Tools that helped me:

Questrade (low fees, good for Canadians)
Wealthsimple (robo-advisor, set-and-forget)
YNAB (You Need a Budget) energy-friendly budgeting

What I Know Now

Looking back, my biggest win wasn’t the $75K or the house.

It was learning how to build a life that worked with my pain instead of against it.

Today, I invest mostly in ETFs and blue-chip stocks. I’m not chasing hype anymore. I’m building stability for my 40s and beyond: family, health, longevity.

I’m still the guy who lost everything at 25. But I’m also the guy who rebuilt smarter at 35.

Final Word

If you’re in survival mode, staring at a balance that feels like a death sentence, you’re not behind.

You’re building the slow way. The sustainable way. The only way that holds up when your body doesn’t play fair.

Investing With Chronic Pain: How a $20K Loss Set Me Up to Win at 35

The $20K Loss: My First Lesson in Investing With Chronic Pain

Why Chronic Pain Changes the Way You See Money

The Road Back: Building Trust After Loss

The Turning Point: From Desperation to Strategy