How I Ditched the 9 to 5 Life

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This post is going to explain how I left the 9-5 lifestyle and how I am experiencing life working for myself.

One day in July of 2011, I was making the 30 minute drive from St. Thomas back in to London, ON. During this drive in particular, I felt the frustration of having to go to the same job day in day out to do the kind of work that I really had no passion doing. So many times while I was working, I felt as if I was wasting my time. I felt the yearning to do more with my life.

Since I dropped out of university in 2006, I have had a strong passion in personal development. After reading so many books and reading hundreds of blog posts, I knew that working for myself was the only way to go.

I was jumping from job to job looking for security and a better pay cheque but it wasn’t until I had been working as an electrician for 3 years that enough was enough. One of the deepest realizations I had was that no job is secure. When you are working for someone else, you are at the mercy of how they run the business. They determine your hours, when you work and if you get to work at all.

I can’t stand living at the mercy of someone else. It just doesn’t work for me.

In January of 2011, I was given a reality check. I was indefinitely laid off from my job. That is also known as being fired. At least my boss had the decency to lay me off so I could claim unemployment. The reasons for why I was fired was all too familiar to me.

Since my first job at McDonalds at the young age of 15, I have never enjoyed being told how to do my job when I think that my way is better. Call it whatever you’d like but if I feel my way is best, then I want to do it.

I’m not the kind of person who will do things inefficiently just in order to please my employer because they think it’s the best way. I’m not the type of person who fits nicely in to a cog or a well-oiled machine. I tend to stir things up and this is why the 9-5 lifestyle doesn’t work for me. Do you feel the same way?

Many businesses expect you to do things, how they want you to do them. There is not much room for creativity or innovation. This sounds awfully familiar to the indoctrinations centres most of us experience for 14+ years of our life. Schools are the perfect breeding grounds for obedient workers.

The lack of room for creativity and innovation factored with working under the terms of someone else is why I was feeling so frustrated and a lack of passion. I felt as if anyone could do my job and if I wasn’t doing it then someone else would. I didn’t feel as if I was contributing my full potential.

Setting Your Own Path

Don’t die with your music still inside you. Listen to your intuitive inner voice and find what passion stirs your soul.
– Wayne Dyer

As I mentioned at the start of this article, it was the long drives to and from work that were the catalyst for change. I had a lot of time to reflect and my plan to set my own path became real.

With another brutal Ontario winter approaching, I knew that I wanted to move. I knew that British Columbia was a viable option as the climate was milder compared to Ontario.

All the typical roadblocks were apparent. I had no job and no place to live. Would I have enough money to survive? If I couldn’t find work then what would I do. Would I be able to afford rent? Would I run out of money for food?

I decided to say screw it. I’m going to just go ahead with it.

You have to jump off the cliff first before you see the net below

One of the things that holds humans back the most is the fear of the unknown. When we can’t see the end of the tunnel before we enter it, we’d rather not go in to it. We live our lives in fear of the unknown. It’s this fear that stops people from pursuing what they want to. This fear is crippling and leads to us living lives that we’d otherwise not want.

When I first moved out to British Columbia, I didn’t see any net. I had just jumped off the cliff and was still flying through the air. I ended up at a friend’s place in Courtenay, BC. For a few weeks, I had no idea what I was going to do. I didn’t want a job, since I had just gotten out of one. My friend’s I was staying with mentioned that I should look in to doing a house sit.

A house sit is when the owners of a house want someone to look after their house and pets when they go on vacation. It usually isn’t paid (but can be) and the agreement is that you look after the house and not have to pay rent or utilities.

I thought this would be an awesome idea and since I had no other options present at the time so I started applying to house sits in the area via a site called I ended up finding one with in a few days and had a quick interview with the owners. Everything really started to flow very quickly for me.

So I went from having no place to live, to having a place to live rent-free for 5 months in just a few days.

I still didn’t have a source of income though. The very last thing I wanted to do was to get a job somewhere.

Steal ideas from others

Tarah from

My friend Tarah in Courtenay, BC  was a full time fundraiser. She collected bottles, sold watermelon by donation and had bake sales. She was fundraising money for an activist trip to Taiji, Japan to expose the brutal dolphin slaughter that happens every year. She said to me, “Derek, it’s easy to do what I do, you just have to find a cause you’re passionate about and people will support you.” She was right. I was impressed with her passion and drive. She received monetary donations from friends and even strangers.

I kept thinking to myself, this girl is on to something but I didn’t have a cause that I was overly passionate about at the time.

My unemployment insurance that I was collecting had run out and I kept the fundraising idea from Tarah in the back of my mind. I had the plan of going Thailand in May for the world famous durian festival. I also wanted to visit my friend in Hong Kong. So the plan was to stop in Hong Kong and jump on a flight in to Thailand. It would work but I didn’t want to have to go through the trouble of packaging my bike and trailer back up to take a 4-5 hour flight.

The bike tour project is born

I thought to myself… could I not just ride my bike from Hong Kong to Thailand? I didn’t see why I couldn’t.

Then I thought, where could I end up? Hmmm, looking at google maps, I thought India was a great place to end up since I’ve always wanted to be there.

Then I thought, why would I bike all that way? Well… I want to see more people eat a healthier diet and it’s the 2nd most sustainable way of traveling.

The bike tour project was born.

What am I doing now?

I have 10 weeks of fundraising time left till my house sit is finished here in Campbell River. My days are spent knocking door to door telling people about my trip and getting bottle donations. Going to businesses and local media to get my name out. Learning lots of cool new stuff.

My expenses are food, online phone ($10/month) and fun things I want to do.

I have successfully gone from living the 9 to 5 lifestyle to doing something that I am so passionate about doing.

This is just one way of making the transition but I think this is a great way of doing it. The keys here are :

  • to reduce your expenses to absolutely nothing
  • find something you are passionate doing and could do day in day out.

If you have any questions, leave them in the comments and I’ll be sure to answer them :)

All the best in 2012,



  1. Windlord

    January 7, 2012

    You’ve gone from existing to living, Derek.
    All the best on your Journey!

    • Derek Howlett

      January 7, 2012

      Thank you for the continued support Windlord :)

      It’s been an amazing shift!

  2. Stephen James

    January 7, 2012

    Your Awesome Derek! and so is Tarah and you Windy!!!
    I love reading these inspiring stories about how you can achieve living your life! I’m in what I believe to be a transitional period to this outcome of living this life my way!
    Great blog post Derek, I heartfully wish you all the best on your journey bro! :0)

    • Derek Howlett

      January 7, 2012

      The transitional period can be a little scary but you just have to trust that the universe will deliver what you need. You just need to follow your heart :)

      Thanks for the continued support Stephen! We’ll for sure have to meet up!

  3. Freelance Audio Engineer Bart

    January 7, 2012

    Great article :) I’d love to read about your experiences with house sitting (maybe in a future post :) ) Also, did you have any fears about leaping before the net appears, or did it come naturally to you?

    • Derek Howlett

      January 7, 2012

      Sure Bart! That would be a great topic. It’s a great way to reduce your expenses for an extended period of time.

      I had feared it for so long that I had just gotten to the point where it came naturally out of frustration.

      Thanks for the comment! Subscribe to my newsletter on the left sidebar to make sure you get future posts :)

    • Derek Howlett

      January 8, 2012

      Thanks David! Good luck with your site :)

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Howler is a world cycle tourist, high carb high raw vegan, frugal minimalist and a grateful manifestor of his passions and dreams. Not to mention a fruit addict too!
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