I joke that I have retired 5 times so far. I've never really decided to 'start' a business since retiring but somehow I have 'fallen into' several things along the way.
After I officially retired at age 43, I discovered that people seem to think that you must know something if you managed to retire early. They then move on to thinking about how they might be able to use what you know to their own advantage somehow. So they offer you jobs etc.
Most don't interest you but sometimes something does. I was living on a Greek island one winter and some local acquaintances kept asking me, 'what are you going to do when the season(tourist season) begins?' I say I was hoping to continue doing more or less nothing. 'Oh, you can't do that' they said, 'You'll spend your time in bars drinking, trying to pick up tourist women, etc. and end up like so many have. Old before your time, dissipated and broke. No, no, you'll have to get a job just to give your life some structure and keep you from overindulging.' I wasn't sure what they saw that was wrong with overindulging but I got tired of them working of me and said, ok, I'll do something.
So I thought about how could I get paid to sit in bar, pick up tourist women and generally overindulge myself. If I was getting paid to do it I figured they'd leave me alone. So I opened a bar with a local partner. The first year was fun, the second year was OK, the third year was getting to be just work and truthfully I was getting tired of the 'overindulging'. So I sold out to my partner at a profit.
I was renting a pretty luxurious(by island standards) apartment and told my landlord that I would need to move out and 'downsize' to save some money as I wouldn't have the supplemental income the bar gave me. He asked me if I knew how to build a garage. I said I probably could but why would I want to? He said, 'I'll let you stay rent free if you spend 3-4 hours a day building one for me.'
From that we moved on to my doing all the drawings for a new 6 unit apartment building he wanted to add to the property. I'm not an architect, but I could wing it. All in all, I ended up rent free for 4 years doing one thing or another for him a few hours a day on weekdays.
At the same time, a friend who owned a bar with a pool table in it asked me if I wanted to earn a little money socializing with his primarily Brit tourists every night. Hmmm, free drinks, pocket money, socialize with people and play pool every night. The only stipulation, I had to let the tourists win on the pool table. It isn't easy to lose without it looking like you lost on purpose you know. It takes real skill.
So I had free rent, free pocket money. All I needed was to buy groceries. Enter the live-in girlfriend. She was an English teacher and she bought the groceries. Financial independence, who needs it?
Living on a Greek island you can probably understand that finding Birthday cards, Christmas Cards, etc. that are in English is not easy to do. One winter, an Australian friend who owned a hotel on the island was having a Birthday Party. So I got a bootleg Desktop Publishing program for my computer and printed a Birthday card for her. She liked it a lot and asked, 'could you print menus for my hotel?'
I reluctantly said, I supposed I could but I figured I'd discourage her and quoted what I thought was a ridiculous number. She ordered 25. Then she showed the finished menus to a guy who owned a restaurant and I got a phone call from him. Before you knew it, I was up to my ears in orders for menus, all through word of mouth.
The only redeeming thing about it is that there is only around a 6 week window just before the tourist season starts when anyone is interested in buying new menus. That and the limitions of just how many you can print out on a printer limit the whole business. I could earn enough in those 6 weeks though (I did it for 3 years) to say buy groceries for a year or something. Instead, I just banked the money and then used it to buy a 1980 Triumph TR7 I found for sale online, in England.
When I went to England to buy the car and drive it back to Greece, I met a woman. Long story short, a year later I was married and living in Scotland.
Decks in backyards were just becoming popular in the UK at that time even though they don't really get the weather to enjoy them that much but hey, they like to fool themselves that they do. I noticed that they used pressure treated boards with grooves on them.
http://walestimber.co.uk/images/arbordeck_products_deckboards_02.jpg
I was curious as to why and phoned a decking company to ask them. I had an interesting conversation with the company owner about it and at the end of that discussion, he asked if I was interested in designing and selling decks for his company. I said I might be but only if it was cash, I wasn't interested in having to get into the whole payroll and taxes bureaucracy. He didn't have a problem with that.
Working about 10-15 hours a week making 5 or 6 sales calls on qualified potential customers I was able to earn enough cash to pay for 2 or 3 vacations of a week or two in other parts of Europe like France and Switzerland. I did that for around 6 years while waiting for my wife to retire. She had too much to lose pension wise to retire when we first got married.
When she retired, we decided to move from the UK to Canada. I have dual citizenship and now so does she.
So my advice dd564, is don't worry about deciding to 'start your own business' when you retire. In my experience, early retirement is like quitting smoking. You have to keep saying, 'No I will not work, no I will not work, no I will not work'. Eve then it doesn't always work out that way.
It's like Alcoholics Anonymous. 'My name is Jack, I'm a workoholic. It's been seven years and 26 days since the last day I worked'.