Nearing 70 i've been self-employed most of 50+ years though never been a great businessman. Have had up to 7 or 8 employees in past years a few decades ago. Among my gigs has been 1600 PA ave, & on outward. Not all small potatoes. So mostly "been there" though with little to show for it.
Agree with kickinchicken.
When starting, people want the work more than the profit, and they hate to offend anyone. So in all good faith (but failing to be honest with themselves) it's easy to overpromise and underdeliver, offending everyone.
Currently i still do small quantity commercial millwork & make construction related specialty tooling, sometimes design/build furniture, occasionally collector (woodworking) planes, and off-n-on, 4 or 6 pt FS simple pool cues (sneakies). You can order furniture from me if the project is interesting enough. Planes and cues i never take orders & there is no waiting list (for the planes). You can't imagine how much that has pissed some people off. But i sleep pretty well and no one can say anything about my business practices, whatever happens.
Millwork & construction custom tooling everything happens on time. There is close communication with the GC, sometimes daily. You don't miss deadlines, you don't deliver substandard if they are paying for the best, and you don't avoid heads-up com the minute you suspect there might be an hour's delay let alone a week or more.
I don't have a stellar record (some would even say it's occasionally been pi$$ poor :sorry
with time & delivery on furniture but at this date the customers i work with expect that, and my comm is almost flawless. Pics and narrative on at least a weekly basis. If it's necessary to stop and do a "real" job, I immediately tell them. They don't have to wonder, and they can decide to hold off on a progress payment if i'm not performing or stop to do a millwork job.
The other items, none of anyone's business but mine.
Sell 'em when they are ready in my own mind, to whoever waves cash at the time. Planes get to my agent in Canada and he finds a buyer and sends me cash.
For collector items unless it is going in a scheduled show, hitting perfect deadlines is seldom critical to the client. Beyond all ability to forecast, ship happens. But steady, reliable, honest communication is essential to most. Wouldn't you want the same?
I can't imagine selling FS sneakies to order. There's no profit in it, so why put yourself through the headache? Build 'em to suit yourself, then put them on the market.
smt