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My Financial 20s

Financial 20s

My Financial 20s

I got a question from one of my readers about how young people can take control of their money and their lives and she wondered about what I did successfully and what I would have changed about my twenties. It’s an excellent question!

My Financial 20s: What I did right

Paying off Student Loans

I did quite well in my 20s financially speaking because I paid off my student loan debt as quickly as possible and I was smart enough not to have any consumer debt in the first place. This involved frugal living to the extreme, which wasn’t that fun at the time but I truly have no regrets about it now because it set me up for where I’m at today. Of course, I’m from Canada so I didn’t have the crushing amounts of student debt that most Americans have.

Better Jobs

The other thing I did right was move up in the world of ESL teaching to better and better jobs. I found jobs that paid more, had more vacation time and best of all, had plenty of overtime opportunities so that I was able to double my salary in many months and at some points, even make $5000-6000 per month (a LOT for an ESL teacher). I continued to live reasonably frugally and put away at least $2000/month for most of my mid-late twenties. For more advice about advancing your career as an ESL teacher, check out: The Wealthy English Teacher

Investing in Dividend Paying Stocks

By the time I was around 30, I had a large pool of money and fortunately the stock market had just crashed, so I went on a spending spree (after researching and reading compulsively for about 2 years before that) buying lots of dividend paying stocks. I was smart enough to hold onto them until now to amass some huge gains.


Finally, something that I did was travel, a lot. I had the money and vacation time so I just did it-traveling to something like 20+ countries from the time I was 24-30. It was kind of expensive but totally worth it. Of course you should travel responsibly and if you have debt, it’s unwise to be jet-setting around the world.

My Financial 20s: What I did wrong

Wasting Time

Something that I regret doing was wasting so much time. Like I used to sit in my house during vacation and binge-watch TV programs, or I would go out drinking. I could have been doing a million and one more productive things like furthering my education, getting in great shape or expanding my internet empire.

An Expensive Hobby

The other thing I really regret was getting so into scuba diving. Like I bought all my own equipment and eventually became an instructor. I thought I would be able to work and make a bit of money doing it, but the truth is that it’s really hard to even break even, no matter what country you work in. Insurance, Padi fees and gear is just too expensive and the pay too low.

These days, it’s all about the cheap hobbies like hiking, biking or stand-up paddleboarding. If you have your own board or bike, which I do, it’s free! With scuba diving, each and every single time you go out diving you have to pay, a lot in most cases! It’s not my style anymore.

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