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I hear you.
I think I can and want to retire from insurance in 5 years. I have perpetuation in place. I'm too young not to do anything and don't want to sit around. Just ready for a change.
Passion is reason I looked into wine. I knew PA recently changed regulations, but was unaware they were still the only wholesaler if you want to retail.
I would love a gourmet food shop, but don't think the area demographics will support it.
I was considering buying/selling gold/silver. Need to learn more. Not sure that's a risk or exposure I want to take on.
I'm also considering looking into SAT/ACT prep and/or franchised tutoring. Seems to be a need and on the rise.
I'm also worried about getting a bad tenant for the sake of $12,000/yr.
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Those don't seem bad, i'd run the numbers and see if your area can support it.
I took bigger risks when I was younger and lost my life savings in my early 20s with a failed business. Now, i'm on a set path for retirement at a young age. I work a job and invest in a business with my family. I could invest in some businesses that have huge upside in the industry I work in. Hit a home run so to speak, but i'd rather hit a bunch of singles. The end goal is already set if I aim for singles. If I try to hit a home run I may end up bankrupt in my early or late 30s and have to try again.
It's hell of a lot easier to eat a grand a month than support a failing business. The company I just left had a bar/restaurant at one point. On good months we broke even, on bad months we lost 10 to 15k.
I'm not saying don't do it, but 5 years from retirement is possibly time to just hammer debt. I'm 9 years from retirement and I set my threshold for borrowing/expanding at 4 years from retirement. At that point i'm going to wind down and focus on whatever I truly want to do, if any. And prepare to have a blast on my hobbies.
Just my 2 cents.
Personally the wine idea sounds good, I think that would be fun but you I can see why you don't want to or think it may not work.