The funds are probably the easiest to solve! In our case, John had the idea of a relatively early retirement in mind when he set up pension savings in 1981. Mo has always had a discipline of saving and these were invaluable. We were also lucky in investing in a house before the recent boom that we were able to improve and capitalise on, and which became an enabler for our other funding projects.
The sea does not take prisoners, and the skills required do have to be acquired over a period of time and in different circumstances. A classroom certificate is useful, but cannot substitute for experience. It is easy enough to do the courses, and do the miles necessary, but you will never encounter the range of conditions that you might encounter in different geographical locations and climates. You will inevitably encounter the unexpected, and conditions that you have not had to deal with before.
Systems on boats are increasingly complex. A good understanding of everything from the workings of your diesel engine, your water pumps, refrigeration, electrical installations, and how your electronic instruments interact, is necessary if you are to deal with problems as they arise. Engaging local experts is a risky and expensive business: rarely will they have the knowledge of your particular equipment and installation, and you will be paying for their learninng. With a good appreciation of all these aspects, you will be able to undertake a range of projects, and where you do have to involve other trades you may be able to limit and control your costs.
While you can make your opportunity, you have to be comfortable that you also have the space. Factors such as families, elderly parents and siblings, have to be taken into account. Will you need to return to work, and will this be possible? We are fortunate in taking early retirement, and do not have too many ties, but they are still a consideration. Some people are fortunate to have skills that they can take with them aboard their boat, and with the reliability of internet communications, work remotely.
The crew, if any, has to be a ready and willing participant! Leaving aside for a moment the problems of living together in a small space, you must share (or be able to negotiate) the same objectives! It is no good wanting to set out to go around the world, if the crew wants to find a marina in Majorca, and fly home regularly.
Finally, it goes without saying that you need to be sufficiently fit and healthy. The majority of cruising people are doing so in their later years where health issues can play a part, and ultimately may force you to give up the lifestyle (fondly known as 'swallowing the anchor'). In our case, two seasons have been seriously impacted by health issues, with unforseen consequences in terms of finances. In 2005, John had a heart attack followed by surgery in the UK, and in 2007 an infection of the leg (cellulitis) required hospitalisation and a lengthy convalescence. In each case, there were implications for boat storage, travel, and accomodation expenses, as well as living expenses, that we had not planned for.
In many ways it is harder to reverse the process in order to return to living on dry land. Firstly, unless you are particularly fortunate, you will need to sell the boat. You may also have surrendered your status with the banks, and will find it almost impossible to finance the transition.