I'm not going to tell you NOT to start a side business, but think long and hard before you do.This has crossed my mind as well. I like the idea if growing a business while your income is secure, until you don't need the old income anymore. Would also probably help me mentally to be working towards change.
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I've been suffering from some career dissatisfaction for several years. I have a pretty good job with a good company, decent money, pretty good benefits, good schedule, paid holidays off, 401k, they pretty well leave me alone, etc, but my job is fairly boring and unfulfilling. I've wanted to get out of it for a while but overall I feel like I just have it too good to quit just because.
My wife is a self employed entrepreneur. She started her own business about 5 years ago and is doing really well with it. She was able to quit her corporate gig and go full time. After her success, she had been on me for years to start my own business. I resisted this for several years as I just wasn't really interested in it and then eventually convinced myself that a side business would fix all of my problems and make me a decent amount of extra cash.
So, last winter I got to work on it. Spent about $15k getting the business up and running. Equipment, website, business phone, insurance, some marketing. The whole deal. I got about two months into it and realized what I had done. Now, not only am I worried about and stressed about my 9-5. Now, I'm also worried about and stressed about my side business. I quickly realized how much time and effort was going to be involved in doing things the right way and making it successful. No time for myself. No hunting, no fishing, no camping, no hiking. Less time with the wifey. Less time with the family, etc. It was a real wake up call.
So, this past summer, I should have been out on evenings and especially weekends marketing, drumming up business, and completing the work that resulted from it. But there were constant conflicts between personal time (fun stuff: weekend trips with the wife, vacation, out of state wedding, family cookouts, etc.) and doing side business stuff and pretty much every time, the personal time won out. The problem is the whole time I'm doing personal stuff, I'm not getting work for the side business and the expenses keep rolling, which causes even more stress, which makes the personal stuff less enjoyable. I haven't done a job in two months and the phone has stopped ringing and this thing is now nickle and diming me to death.
Hunting season is here now and winter is right around the corner so I wouldn't be doing any side work during colder months anyways. I now have to really evaluate whether I want to keep it going or not. If I do, I've got a ton of work to do. If not, I close shop, sell off what I can, and probably lose several thousand dollars in the process. Maybe an expensive lesson learned. Not sure yet.
Like others have said, at the end of the line, nobody wishes they had worked more. I think a lot about all the experiences and memories I've missed and continue to miss by working so much. Maybe I already have my answer and just not willing to admit it yet.
Either way, sorry for the long post. Hopefully this helps.