Personal Risk for Business Potential

I'm not really sure if I can answer your question but I know where you're coming from. I always knew I wanted to be my own boss and make my own rules. I started a business not too long after I graduated from college. It was challenging and a good experience, but I knew it was going to take too long to scale so I sold it.

At that point, I decided the best thing to do was own my own business and work for someone else. A W2 job got me access to a good amount of credit which helped my get into real estate. It's been able to get to scale quickly and you can grow it exponentially. I'm not going to get into too many details, but what has been great is my RE income is now enough for me to live off of and I should be fully retired by the time I'm 45 if I so choose. The reason I say this is it's nice when you can do both as they help take the pressure off each other.

For me, starting a business has always been the goal. Having autonomy is one of the biggest drivers for me. I cannot be happy in life by having others dictate how/why/when I do things. I have the mindset that even if my current company we’re to go away for some reason, I can either start another one or go get a high paying job to support my family. For me, there’s more risk to not starting a business. My partner and I started a construction based business 4 yrs ago and things are going well. We started with minimal investment ($10k each) and 2 people and have grown to employ 30+ people. We have 3 companies now that are all related. We’ve been successful thus far due to our relationships and the time we put in earlier in our careers developing those relationships. We individually put in the time for 10-15 yrs and now we’re where we’re supposed to be. The biggest risk in life to me is playing it safe and I believe this is something that motivates a lot of business owners.

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If I worked what you call a “regular job” I wouldn’t have the time or ability to take as much time with my family- be it a vacation, coming home early, or making extracurricular activities work. What matters most to me in the flexible lifestyle and if I didn’t have my own gig, I wouldn’t be as flexible.

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I struggled (and still do but to a lesser extent) with the same thoughts of the OP. One thing that helped me was knowing my wife had a fair amount of income from her job and that she supported my decision to go on my own. Working as an employee, you can be let go in a heartbeat. I've been there and hated it. There are risks in anything you do that's worthwhile so my thinking is to do what you think is right and where you will have the greatest impact.