[boznz]

I guess retirement is a form of suicide. I run a successful one-man programming business but it too will need to shut-down as I would like to retire in 4-5 years.

It is especially hard as the company is totally viable, in a great location in the world and has great customers who are really happy to keep giving me work, this means I cannot really shut-down until they are taken care of by either selling off the company to another programmer who will support them or transitioning them (very expensively I guess) to another system

I wonder how many people in the same position are thinking this far ahead

[existencebox]

Selfish response: Why not sell it?

I've worked for larger corps for most of my career but have certainly cultivated the desire to be the maker of my own success. That being said, I've had remarkably little luck in finding any side effort enough traction to get off the ground, and hit my stride the most when I can improve a system with a proven value prop. (Without sugarcoating it, I'm a terrible "idea guy")

Later in my life if I get a degree of financial stability, I'd like to buy or work for a proven small company (working for would be hard but not impossible given the aforementioned desire to be the driver and recipient of the fruits of my labor) and taking over from someone in your situation sounds almost ideal.

[pandapower2]

Migrating customers away from a one-man band is a pretty thorny issue. Unless you happen to know another one person operation who can take over no other vendor will offer the same level of personalized, hands on service or the same level of trust that comes from always dealing with the same person.

The experience of dealing with "Jane the programmer" Vs dealing with "Outsourced software agency incorporated" is dramatically different.