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4 Year Quit Anniversary and 4 Lessons Learned

It was 4 years ago today as I write this that I didn’t go to work at my at my “9-5” day job for the first time. 

Every year I like to reflect on the decision to make the jump and any learnings. 

Before leaving I had worked for 8years at Imperial Oil in a variety of jobs and although I for the most part enjoyed my job and appreciated the skills I was developing leaving has been incredible for both myself and more importantly my family. 

Here are the new learnings from this year…

4 New Learnings this Year

Illusion of Job Security 

When I left the day job I felt like I was increasing my family’s financial risk level significantly. Despite having planned it out with runway I and many others thought that my decision to leave was increasing my family’s financial risk. 

However, given the current economic outlook and specifically the outlook for the Oil and Gas industry I am certain my family’s financial security is far greater than if I had stayed at my day job. Layoffs are likely and job prospects within the industry are weak.  

Talking with many of my old co-workers the outlook is not great. Although many of my businesses have done well over the last 4 years others have not but on balance it has been a good 4 years financially. However, even if it was not the options and skills I have developed I believe will make me more employable/able to generate income then if I had continued on the career trajectory I was on. 

Many large employers are great at creating the illusions of job security but once you get outside of their intentionally created bubble the realization is that it was just an illusions and the perceived security is not as solid as you think

Kids Grow Up FAST! 

It is such a cliche to say they grow up fast but so often it is true. 

This Image was a large part of the reason why I wanted to pursue online entrepreneurship.

Having the ability to get to spend time with both my family and some of the active activities I like (skiing & mountain biking) is something that simply would not have been possible

At the time of me leaving my day Job this was the timeline to retirement vs my age and my oldest Childs age. 

Basically by the time I was 65 my oldest child would be 36 (my age) and the number of hours I would have spent with them would have been minimal. 

Being able to work around the weather and get to go on an adventure (mountain bike ride, hike or trip to the cottage) during the summer is something I am extremely grateful for. 

Embrace New Opportunities and Optionality 

One “tip” or “suggestion” suggested to me multiple times is to focus on a single business. Although I believe this is likely good advice most of the time. 

This year has been another reminder that launching new projects can increase my capabilities, allow me to tap new markets/diversify and learn new things. 

Launching MotionInvest has been both fun and gone very well.

My thinking over the last year has evolved to have me focus not on reducing the number of new projects but focus on making sure any new project is tested as efficiently as possible. Testing new projects is great if it can be done efficiently and that is the new focus. Quick inexpensive tests of business opportunities with an unfair advantage to its first customers and ideally have some overlapping benefit to existing projects is the focus.

Focusing on a single project is likely good advice but I have both had fun and some success working to launch other projects since leaving. 

My learning this year is to not fight this but work on getting better at building organizational capacity to launch these tests.

Invest in Compounding Improvements

Another evolution of my thought over the last year is to try and really focus my personal time on compounding improvements. 

As the window of time since leaving my day job grows my timeline really stretches out.

If my focus can be on any of these improvements that have a compounding benefit over time I know I am adding value…

  1. Improved systems (like morning meetings, Trello kaizen board as a to-do list, OkR goal tracking all integrated into the Traction system etc.
  2. Auditing systems to make sure they are working as intended and improving the SOPs are things that all have a long term payoff.
  3. Most importantly investing in getting the best people on the team possible whether formally employed or strategic partnerships

Hustling for the next deal was something I had done for years and still do but making sure I am more focused on implementing improvements that will pay back over years and years as I extend out my time horizon is key.


Tracking my monthly income numbers was something that gave me a lot of focus while I was working to leave my day job.

Reflecting now on why I started down this journey is a very rewarding experience while also helping to shape some of my new learnings.

My hope with this post and serious is it provides a framework for others looking to make the job for them to know it is possible and ideally shortcut the long process I took.

Other Posts in this Series:

I Quit My Day Job –

1 Year –

About the Author Jon

I am a 36 year old husband, father of 3, engineer and a huge fan of developing systems to build useful and profitable websites. The reason I build online businesses is to provide financial independence for my family and yours AND so I can spend time outside skiing and biking with my family.
Jon Gillham, Online Entrepreneur

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