Real Estate Spending

5 Financial Mistakes I Made in my 20’s

“Error” by Nick J Webb is licensed under CC BY 2.0 (image above)

I’m now a FiftySomething accountant and I think that I’ve learned a few things over the years. I now have a certain amount of wisdom when it comes to money but I’m definitely not rich. Much of my current wisdom, though, was gained at the expense of my younger self.


Like everyone else, I did silly (and maybe even crazy) things when I was young.

Here are five financial mistakes I made in my 20’s

1. I Bought a Condo (Too Young).

It was the 90’s and the real estate market was on fire in Vancouver. I hopped on the bandwagon and bought my first place when I really couldn’t afford it. I was mortgage-poor for 7 years and was not able to travel or do much of anything. I believe that your are supposed to have certain experiences in your 20’s, and I think I partially missed out. I eventually sold when I was in my 30’s and made some money, but not before I was hit with a large assessment for water damage. (Btw, I paid $119K for my first place in 1997 and its now worth about $500K)

2. I Cashed in My Retirement Fund.

I was broke in my 20’s. I was still paying off a student loan and wasn’t making very much. At the time, I was living in Toronto and the company I worked for had a group RRSP (401K for you Americans) that they matched. After 3 years, I moved back to Vancouver but ended up cashing in my RRSP because I was strapped and needed the money. I should have worked extra jobs or side hustles and done more to make more money. The fund was around $4,000 at the time – imagine what the value would be today!

3. I Hung Out With the Wrong People.

There’s a saying – you are the sum of the 5 people you hang out with the most. I hung out with partiers and other folks who didn’t have long-term goals. I ended up blowing money at the bars when I should have been hanging out with entrepreneurs, hustlers and other fitness-minded individuals.

4. I Worked for Cheap.

I’ve always been introverted. I never used to have the courage to ask for a raise or find another job that compensated me what I was worth. Unfortunately, I worked for less than I should have been paid for years (see #1) and suffered the financial price. It was tough watching other colleagues earn much more than me.

5. Not Saying ‘No’ More Often.

I was a people-pleaser in my 20’s. If someone asked for something, I would have a difficult time saying no. If we went out for dinner, I would grab the bill. If they dumped extra tasks on me at work, I would just say ‘yes’ even if someone else was supposed to do the work. I used to run around in a dazed confusion trying to keep up with the many time commitments I used to make.


I’d like to think I’m older and wiser now. I am careful who I spend time with, and now ‘No’ is one of my favorite words. I eventually bought a condo again in my 40’s, but this time-around, I made sure I could afford it. I also now make what I am worth!

I am still not ready to retire but I hope to in the coming years, although retirement (and socking money away) really isn’t my main focus anymore. I’m now all about experiences and learning new things.