We keep getting to this point as well. Trying to run a legit business where you bring more to the table than a paycheck for employees and a tree cutter to clients is a chore, let alone all of the regulation, paperwork, brown nosing, etc. It sucks at times. I was there this week. Lol.
I am coming to realize that most of the issues I feel in my company come from minor decisions I made a while back. It doesn't mean they were right or wrong, but I have to deal with those (i.e. bad hires, buying new instead of used, (or visa vis and shit breaking) learning a whole new biome while building a business, etc). And much of my mal content come from my own goals and striving. I could have stayed smaller and had a decent paycheck myself, with less equipment, people, reputation, marketing, etc. But it was hard then too. That's why we grew.
We hit these inflection points about every other season where we feel like we've lost our minds in doing this. I could go sell for someone else, make way more money and have more time. But would I have more time? I'd be under someone else's thumb. I'd have more consistency, but less leverage, equity, autonomy, and control of my life (as dissolutioned my control is).
These pain points help us know where to put effort. I recently read a post on LinkedIn about a guy who is a coo for a couple of 50+ mil a year companies. He's built companies from the ground up. He said the pain points every single business owner feels are rarely unique. Employees, government regulation and red tape, bitchy customers, competition being hacks, seasonal and economic swings, isolation, are all things that business owners feel. These are the things that never go away. No matter how big you get, in fact these issues grow as your tolerance and ability to handle it grows.
Which leads to the question. Why TF do we keep doing it? Well, on Tuesday when I woke up sick and it was raining and shitty, I stayed home. My employee is buying a house and needed some numbers changed on paper to appease the bank, I can help with that. I get to give to events in my community that have an impact, and I can make more of an impact with people who support what our ideas are, i.e growth.
I've had to reshift my priorities. It's helping some. It really depends on what you are hoping to gain by leaving. If in selling out you move to an island and retire, climbing palm trees and drinking mimosas watching the sunset, then hell yeah (or whatever plan you can envision/enact after selling).
Build yourself out as a consultant/specialist to do tasks for clients that you want without the overhead, sub out the rest to folks you trust.
Talking to lawyers and accountants is a way to get a better understanding of what closing can look like. There's also (iirc) some investment networks that work through TCIA helping folks with solid companies when they hit the "end of what a single man can realistically accomplish by himself" stage.
The weight of loss still weighs heavy. Thank you for sharing. Ownership isn't for the weak, and still showing up as a friend, partner, parent, boss, mentor, punching bag, what have you, is tough enough without the rest of life. You're killing it, and whatever direction you pick just whole ass it. Haha.