Many former chess-playing friends of mine are reaching retiring stages of their careers. Some have also pondered whether they would be made redundant in time to come as the brutal attrition at the workplace continues at a punishing pace.
I have known at least 2 who have made chess-training their 2nd career option. One is Winston Williams, a former player for ACS and ex Singapore Police Inspector now residing in UK. The other is Marcus Chan, whom I had worked with for 2 years at the CTEP in Malaysia and now a FIDE-rated player. Marcus had switched careers quite early on the contrary but I am sure he has made serious consideration on this matter.
When I decided to become a trainer back in 2003, I had realised that my days in IT were numbered owing to the quick advances in technology which I would have trouble keeping up with. Moreover, my passion in teaching chess started way back in the 80s since my student days in RI which convinced me that I had the knack for this trade.
Since then I had been looking out for strong players who are near 50 or over to consider teaching the game as a career. I would recommend it to them mainly because there is a market for it. Often I received surprising remarks that it is possible to make a living on chess by well-meaning friends and acquaintances.
The fact is chess training itself is mainly a teaching job and one must have the patience, the desire to impart the knowledge without any condition. Hence it is not good for active players to go into it if they worry about grooming their potential competition. Besides, what's often taught in schools are basic knowledge of endgames and simple tactics. Only the private students demand more in-depth knowledge of the game.
Besides having the ability to be understood, the other tools of a chess trainer are a constant lookout for instructional material. There's quite a lot floating on the Internet and if one searches diligently, you can find some good ones which you can adopt as lesson plans. I have great respect for guys like Pete Tamburro and Dan Heisman who willingly share their knowledge and write very good books for club players to improve. Dan also has videos which any budding player should look at if he wants rapid improvement.
Knowledge of chessbase is a pre-requisite I believe. You can prepare your lessons there and use it as a lecture when delivering it in schools. Quite a lot of chessbase files are also available on the Net for use.
For those with children, why not try teach your kids something simple and see if they understand you? A good test would be to explain the Queen and King vs King checkmate. If you can get them to understand it within 1 hour, then you have what it takes to be a trainer. If not, go work on your presentation skills or try to simplify your explanation. It is challenging but attainable.
I welcome any questions of chess training especially those wanting to change careers. Sorry but I cannot share information on incomes online as it is sensitive.