Step by Step: How We Retired in Our 30s

Free at 40? We Did It by 33 — The numbers, timeline and story of how we made it work.

Feb 11, 2025

It was the title of a random finance book shoved into the stacks of our local library that snagged my husband’s attention.

Titled Free at 45, it promised to illuminate the world of early retirement.

Retire early? That wasn’t even in our awareness when we borrowed this book from the library in early 2021.

Forty-five, hey? Something about it stuck.

But it wasn’t until this idea collided with the concept of investing for cash flow in Spring of 2021 that our first, big, BIG vision was born.

We wanted to be free at 40.

It was the whisper of an idea that turned into a movement within our household that flipped everything we envisioned for our future on its head.

As two “kids” in our early 30s, we set the goal: we wanted to be completely financially independent by the age of 40 and have the option not to work.

Now (spoiler!), if you’ve followed The Freedom Diaries for long, you’ll know we hit it by 33 years old and have scaled up our vision since.

But today, I want to share with you the timeline, the numbers and our story of how we made it work.

Sometimes hearing the end result of a story like ours can feel out of reach or unrealistic, but the goal of this diary is to break it all down so you can see how many baby steps we took to reach early retirement in our mid 30s.

We Decided to Make Money in 2017

This is where we’ll start our story.

Flynn and I had been dating for 2 years and we were getting ready to move in together that Fall.

I lived in a townhouse I bought in 2015 on my own in a fast developing neighbourhood and had about $30,000 in mutual funds at the bank.

Flynn had just finished wiping out his $15,000 line of credit of consumer debt and we were ready to make some money.

In July 2017, we attended a Tony Robbins event and this was the epicentre of our first big money move.

Phil Town was a guest speaker at the event and had this whole program that was all about stock investing.

We had already been exploring the idea of owning rental units, but it was this day we made the decision.

Would we make money in the stock market? Or with real estate investments?

With practically zero knowledge of how the stock market worked, we decided rental properties were our ticket to freedom.

That winter, we went to work learning as much as we could about owning investment properties and cash flowing them.

On May 4, 2018, we bought our first “door”for $315,000 with a $60,000 down payment.

It was a cute, studio apartment that we repainted, cleaned and readied for a renter.

We each put in $15,000 from our savings and borrowed the remaining $30,000 from my parents at a 2% interest rate.

I remember this felt like a HUGE amount of money.

By June 1, we had our first tenants in place, a lovely couple arriving on a Visa from Australia.

We rented our first place for $1,249 per month and were in business.

Our original goal was to accumulate enough rental properties to gross $10,000 per month.

With that as the goal, we went to work over the next 2 years to build our cash to buy more properties.

Going forward, I’m going to present to you a simplified but accurate timeline of how our dream evolved.

2020: A Jump into the Market

FEBRUARY

We welcomed our first baby to the world only weeks before everything shut down.

MARCH

We watched the world unravel, and more importantly, the stock market crash hard.

It looked like an opportunity to us, so we spent the month understanding what the market was, how it worked and how we could take advantage of it.

APRIL

Flynn and I (nervously!) put our first dollars into the stock market together.

We deposited $1059.40 into our TFSA and bought 2 bank stocks - Bank of Nova Scotia (BNS.TO) and CIBC (CM.TO).

This felt terrifying and we spent the following weeks watching our money fluctuate up and down.

Over the next few months, we bought into almost 30 individual stocks primarily focussed on growth with a small quarterly dividend payment.

Our goal was to ride the market recovery after the covid crash and make enough money to buy another rental property.

MAY

Our very first month of dividends rolled in from purchasing stocks the previous month.

We made $22.29.

It was the first time we saw what true passive income was all about and we were hooked.

If we could make this work, we wouldn’t have to pursue our rental property business and could instead cash flow monthly without all of the headache of finding tenants, collecting rent, maintenance and all of the work that comes with being a landlord.

The light bulb had turned on.

Our 2020 Investments:

We made a small goal to contribute $1000 per month from our income to our stock portfolio.

After seeing it work, in September we ramped up our savings to $2,000 per month.

I remember this feeling like A LOT of money at the time as neither of us were making crazy money.

I was grossing around $100k in my business and Flynn was making about $60,000 per year as a mechanic.

Including a reallocation of a $6,631 mutual fund, we invested $24,220 our first year of investing.

We finished the year celebrating approximately $8,000 in capital gains from this 2020 investment and rode the rising market all the way into March 2021.

The plan was in motion.

2021: Big Money Moves

This was the year we began tracking our numbers more closely. We started the year with a portfolio value of $68,081.31.

MARCH

Part 1: We first discovered investing for monthly cash flow instead of growth on a YouTube video.

We spent the month learning everything we could, sold off 90% of our individual stocks with the exception of some of the single bank stocks, and took massive action as we flipped our entire strategy to cash flow & income investing.

We purchase stocks and funds with the intent of living off of the dividend income from those funds by the time we were 40.

This marked the birth of our Free at 40 goal as two 32 year olds who believed we could do the impossible.

Part 2: We decided to put our house up for sale and invest the profit into this cashflow style of investing. It sold in 5 days for $775,000.

You can read the math behind this decision in this article: Why We Sold Our Home to Rent.

JULY

We received the net proceeds of the house sale into our bank account, totalling $465,394.52.

We topped up our emergency funds, paid off the $31,233.42 loan from my parents for the rental property and invested $408,759.51 into cash flowing funds.

We also moved into our beautiful 4 bedroom rental home.

SEPTEMBER

Surprise! We found out we were pregnant with baby #2.

We set the goal for Flynn to quit his job as a mechanic by the birth of our second baby (read that story here: Have You Run the Numbers?).

Realizing we could make a higher return yearly and not have to deal with tenant turnover, we put our rental property for sale for $345,000 and sold it in two weeks.

NOVEMBER

We received the net proceeds of the rental apartment sale, totalling $100,547.99, and invested most of it.

Our 2021 Investments:

This was a massive year of investing, with a total of $546,461 deposited into our investment broker platform.

We continued to invest in cash flowing assets that paid us monthly.

We tracked our monthly dividends for the 2021 year and received a total of $21,899.66.

As with 2020, we reinvested (compounded) all dividends earned.

You can see on the graph above the two huge jumps from our property investments.

We ended 2021 with approximately $614,141 invested.

2022: Goal Achieved

APRIL

On one of our Sunday morning money dates, we dreamed up this vision of our family travelling 4-6 months every year outside of Canada exploring new cities and warmer climates.

The plan was set in motion: we’d spend 1-2 months in January & February 2024 in Panama, Costa Rica, or some place similar.

JUNE

Flynn’s quit date and the birth of our baby!

JULY

With an average of $5,200/month in dividends, we surpassed our monthly expenses with dividends earned.

We had reached financial independence at 33 years old and work became optional.

AUGUST

Flynn handed in his resignation letter and quit his ten year career as an automotive mechanic. I continued to run my business as a health consultant.

Our 2022 Investments:

During the first half of the year, we continued to add to our portfolio with new money earned from Flynn’s job and my business.

We added no new capital after July 2022.

In 2022, we received $61,414.59 in dividends and compounded them back into our portfolio on a monthly basis.

We ended 2022 with approximately $695,000 invested.

2023: The Year of Compounding

There isn’t much to say about 2023! I like to think of it as the “year of compounding”.

It was pretty boring, financially.

We didn’t add fresh capital, but instead re-invested every dollar we earned and continued to watch it grow.

We earned a total of $66,186.04 in dividends in 2023.

We ended the year with approximately $782,000 invested and had spent the last half of the year excitedly (and nervously) planning for our first long trip out of the country with our two little girls.

Between living on one income and paying for our upcoming trip, we kept our spending pretty streamline.

2024: A Year of Change