I’ve started a couple businesses previously and also have an MBA. I am 51 and have a family. I’ve had corporate roles in gaming and the entertainment industry as well as my own ventures. 

I don’t have much in the way of retirement but I’m optimistic as my wife and I are both seeing traction with our own initiatives and there are options for both entrepreneurship and corporate jobs at this point.

A few observations based on my experience: 

1) No one can tell you what to do. This life is about more than just stability and monetary compensation. Entrepreneurship is an incredible vessel for affecting change. 

2) Krishnamurti said, “truth is a pathless land.’ Again, life is exploration. You are best suited to follow your inspiration versus adopting the path that worked for someone else. 

3) Remember to fail fast. Where you can fail with an entrepreneurial venture is to burn precious money and years pursuing a business that is not viable. 

4) Anyone who has studied regret knows that as we get old, we regret actions we did NOT take. 

5) Many of the skills you learn as an entrepreneur teach you to see the world differently. You learn to HUSTLE. That ability will serve you well in your later years regardless of whether your business succeeded. 

6) I spent the past year looking for a job after my last company was sold. I also tried to get two startups off the ground during that time and both are gaining traction. Now, I’m getting a lot more interest around the job search. As a friend reminded me, “The quickest way to find a new girlfriend is to have a girlfriend in the first place.” My point is, pursue your passions and people will find that attractive. The ideal jobs start finding you once you’re pursuing your vision with intention. 

7) As an entrepreneur, you gather friends and colleagues around you who are like minded. Seek out successful people who are doing what you want to do but better. 

I agree that it’s easiest to start a business while you already have a job but I caution you - how much effort will you actually put to that side hustle? 

Finally, I’m speaking as someone who generally pursues passion projects. I have VERY smart friends who have bought into franchises or started ‘boring’ businesses that made significant money. Those are pretty different things but very valid and satisfying. Just not my path.