I apologize in advance for the length of this post. I have trimmed as many of the non-neccessary details as I thought I could.
I'm needing a bit of advice, perhaps a reality check. I'd love to hear from some fellow entrepreneurs who've been in this situation, or even who didn't but managed anyway. I tend to overthink things to the point of anxiety, so I'm reaching out to y'all for help. What has precipitated this mini-crisis of mine was speaking to my sister on my way home today. I have told her before that I thought the time was coming that I would need to choose between my jobs, likely sooner than we were ready for. I was stuck in traffic so I was complaining about it, wishing I could WFH fully, and she told me that Dad wants me to quit my day job so he can make me full partner. He hasn't said anything to me about it. I don't know if I trust that, she tends to miss important details and context in convo. But .... hope is kindled and refuses to die!
My day job is project manager for a specialty construction company. I make good money, and I'm very good at what I do, but the negatives are that I am around the most bottom of the barrel scrotes all day every day. I'm talking the guys that didn't even graduate high-school, felons, dudes who want to do the absolute bare minimum so they can drink and eat themselves to an early death kind. I deal with an insane amout of downright dumb BS babysitting these morons, grown-ass men who should know better. I usually spend at least 8 hours a day at that job, not including commute time (my jobsites are generally in the largest nearby metro city, a good hour drive when traffic isn't too bad, but has been known to triple at peak traffic times). I'm also starting to get a bit bored of the work. The 'cool' projects we work on usually have the absolute worst BS paperwork and bureaucracy attached to them because of the nature of our specialty trade. The upside of this job is the benefits. The people at my company are generally pretty great, and I don't want to leave my boss in the lurch so I will have to give them time to find a replacement and get him up to speed with our current commitments before I leave. I also will be completely abandoning all my current skill sets for that job, unless I start freelancing which I doubt I'll have much motivation for.
Now for the side hustle, my family runs a huge steel & machining/manufacturing shop, my dad is an inventor. The family business has always been a decent source of income for all of us, and because I have experience I do all the bookkeeping. My sister handles sales and customer service for the shop, she helps out when I get overwhelmed but she doesn't have the organized mind or the drive to do what I do. In October 2020 I started listing some of my dad's patented products on Amazon as an experiment, because I wanted a challenge. I figured I might see if it was a viable option, maybe make a couple hundred extra and learn the system. I now make 150% what I make at my day job, in less hours, no commute, minimal BS, and I LOVE the challenge. It's gotten to the point that I spend two hours working on it every morning before work, and another 3-4 hours every evening, and most of my Saturdays and Sundays preparing for the week in order to keep up with our current sales. On 3 products, with a laundry list of at least 9 more that I can start on if I had the time .... I've farmed out the manufacturing of the actual products, and streamlined packing & shipping, and I still barely have the time to get everything shipped on time. I've currently got 3 distinct patented products up that are as of right now netting us an additional 60% of our monthly revenue. But, I am tired. I can tell it's starting to affect my motivation and mental state.
The problem is that if I leave my day job, I lose my health, vision, dental benefits (since I live in the USA that's a pretty big ouch, however it's one of the things I can change at the family business eventually), the stability of a W-2 job, and that portion of my income. I also will have to find a way to work more closely with my dad, who thrives in chaos, where I am just on the sane side of OCD. We usually get along just fine. But when we do argue boy is it EPIC. He gets mad while I get very logical, and we're both equally as determined and stubborn. Usually Mom has to intervene on my behalf (he likes to think of the world as how it SHOULD work, not how it actually works which causes problems). He also has no compunctions calling randomly and expecting people to drop what they're doing, which is why when I moved back here I got a job outside the family business in order to set some boundaries. Which I will have to figure out how to keep.
However, I will gain a completely WFH job, with amazing growth potential, on my own terms and schedule, away from the BS of construction. I will be able to use my spare time to make extra money at some of my other side jobs which are seasonal/sporadic but very lucrative. I will also have the time to catch up on projects that I haven't been able to work on, as well as working on my house which I have made little progress on over the last year because, well, I have to sleep and do laundry at some point. My stress level will drop dramatically and I won't have to deal with random men unless I want to (which will likely help eradicate my extreme bitterness towards men in general). I will be able to concentrate on my diet, health, and happiness again because I will have spare time and energy to work out and cook for myself. I can paint and read and go to bed on schedule again .....
Typing all that out geez I really am overthinking this. But the niggling doubt remains about whether I am leaping without checking the water first.
That brings me to the title question. How do you know when it's time? Am I jumping the gun or am I making more stress for myself by trying to do it all?