Career Side Hustles Spending

Side Hustles I’ve Done

I’m more or less an employee now, but in my 30’s, I used to be quite the hustler. I was self employed for a number of years and did anything I could think of to make money. Now, that I am in my early 50’s, I look back at that period with a certain amount of fondness.


Here area few of the side-hustles I used to do (and maybe you could too) with a brief description of my experience with each:

  1. Selling stuff on eBay – I used to search around and look for cool small items or collectables. I couldn’t find enough things and I got tired of the time it took to process orders (tracking bids, postage, etc)
  2. Bartender – The hours were long and the tips weren’t much. To be honest, I’m an introvert, and this probably wasn’t the best choice for me
  3. Security – At special events and bars. Again, the hours were long and the money wasn’t great.
  4. Multi-Level Marketing – I sold vitamins. Ultimately, I didn’t like the recruiting aspect and the expectation to consume so many of the products.
  5. Accountant – This was my main gig – I was self-employed for 5 years. I realized that, after a while, I did not like doing taxes and bookkeeping – most small-business owners are so dis-organized and I found it challenging to charge decent rates for any length of time.
  6. Talent contests – I did a few singing contests! Ok – this was mostly for fun! I did make some money, but not a long-term plan and very competitive.
  7. Film/TV Extra – this was more recent. I had fun and learned a ton about the film-making process, but the hours were long and the pay low.


There was a common theme in many of these hustles – they were location-dependent and took too much of my time, while not paying me enough in return.

I am also very independent and don’t like to be told what to do. In some of the jobs above, I was at the mercy of some unreasonable bosses which took the fun out of the work. I was so busy back then and the last thing I wanted was some fool making my life hell.

Some hustles just weren’t the best use of my time.


As I mentioned, I am now mostly an employee … something happened to me in my 40’s.

I bought another condo. Real Estate is one of the best long-term investments you can make, but it comes with short-term costs. In my case, I kind of lost my hustle. Because, I had a mortgage, I became more risk-averse, and stayed in a high-paying job probably longer than I should have.

I still hung out with some of the wrong people. I look back and think I still partied a bit too much and went out for drinks at the pub more than I should have. I should have been hanging with other like-minded folks.


Nowadays, I really try to spend as much time as I can around entrepreneurial/hustler types. I am in the best shape of my life and no longer hang out in the bars (and shop) like I used to.

I feel I am slowly getting my ‘hustle’ back. Here are my current side-hustles:

  1. YouTube – a small channel doing covers of various songs.
  2. This blog – just started it about a month ago.
  3. Acting – I’ve been auditioning occasionally for TV. Yes, I’m an introvert, but I’ve decided to push myself.

1 and 2 are location-independent but 3 is not. That’s ok – regardless of what happens, I am picking up new skills that I never would have learned by doing one ‘day job’

I think I’d eventually like to be a Digital Nomad and travel the world!