After retirement from a 30-year career working for the worst/best largest company in the country (Bell System) I went into business for myself. I started two, one-man companies. One installing phone, data, and alarm wiring as a subcontractor and the other selling a few specialized after-market enhancements for one type of military vehicle. I was happy, and successful, because like you, I was enthusiastic and knowledgeable about my subjects and was confident in my skills. After 15 years and through no fault of my own, both businesses faded away, and I went back to "work" at the local government. I now make, in round numbers, only about the same money that I was making 20 years ago, when I retired from a union job. But it beats climbing poles and sitting in manholes.
During the time that I ran those businesses, I had a small office at home. No big overhead to speak of. I had fax machines, credit card machines and linked bank accounts. I did all the paperwork myself, including accounts payable and receivable. To this day, an "800" number seems to be desirable, even though long distance calls are free, and most transactions are done over the 'web. Some older folks (in our hobby) still see the world the way it was a decade or so ago.
I created my own websites and printed my own advertising, made print-ready art work for magazines, and answered the phone 24/7/365. I realize that my experience in a small office just a decade ago is now a lot different from the present technology, but the theory is the same. There is whole bunch of tedious "back office" stuff that needs to be tended to. It's almost as bad, I would imagine, as owning a farm with animals that need daily attention. Fixing the trains will probably still be enjoyable, but you will feel like you need an extra set of hands and brains to do the parts buying, inventory, mailings, shipping, taxes, taxes, taxes, insurance, phone calls and other business stuff.
The good experiences were meeting and speaking to customers (in the case of the military truck business) from all over the world, and exchanging stories. The not-so-good experiences were the ones that involved trying to get paid, (occasional attempts to defraud me) explaining the facts of life to customers who didn't quite understand what they were really buying, dealing with USPS, UPS and FedEx -- er, shall we say -- "experiences," trying to get paid, dealing with cheatin' lyin' schemin' suppliers, trying to get paid, and trying to get paid. I would advise you to speak to some of your friends who run their own businesses, and pick their brains. Ask the guy who runs his own repair garage how many hours after "work" he spends "working." I'm not cynical, just trying to be realistic and practical.
Trying to be practical here: Think about, as an example, a day when you fixed a train and it took an hour, because you knew exactly what to do to get it fixed. You need to bill the customer, get paid, post the payment, wrap carefully, prepare the shipping labels, get the package sent off via a shipper, and pray. Those tasks just took about an hour. So, if you are getting $60 an hour for your actual work, and it took another hour for the miscellaneous stuff, you just made $30 before taxes. After taxes, you made $15. Paying for light & power, insurance, shipping materials, and all the little expenses, figure you made $12.
If you're a fan of freedom, nothing beats BEING your own boss.
When the household bills are due, nothing beats HAVING your own boss.
Whatever you decide, I sincerely wish you the best of luck and happy experiences!!!
