The key to a successful second act, or Life 2.5, as we call it on our retirement planning site GangsAway!, is to spend the time researching, experiencing and then actually test-driving your new career long before you leave or are downsized from the job you have. USA Today's Rodney Brooks just wrote a great article (8/26/13), titled "Help! I'm ready to retire but I still need a job", which gives a great overview of the challenges for both figuring out what you want to do and the steps you will need to take to get there.
There are loads of cautionary tales about people who thought retirement was going to be one thing and it didn't turn out that way. I know of someone who spent his entire career in banking and decided after he retired to do something else, something more altruistic. He wanted to give back, but also needed to make some money. He thought it would be great to teach in tough schools and make a difference. Schools can always use smart dedicated teachers with passion, right? He left the bank and went back to school to get his teaching credentials. After a lot of time and expense, he started student teaching. By the end of the first week, he realized that he hated teaching.
Then there was Celia, who was fortunate enough to save money in the early part of her career, had a bit of luck in the stock market and was able to retire from her corporate job in her late 40's. At first Celia was thrilled to be able to fix up her apartment, go to the gym more often and try out all of those recipes she'd been saving. She took a couple of trips, caught up with friends, but pretty soon the leisure life started to wear thin. In a relatively short period of time, Celia was bored out of her skull. Not so surprising for a person who had been working 50+ hours a week for 27 years.
She volunteered as a court advocate to help foster kids. She liked it (for a while) but it was very difficult and emotionally draining. Next, Celia decided to become an EMT. She enrolled in an Emergency Medical Training school (that cost a fair amount of money) and went through the extensive training. She graduated and went into the field. After several weeks on the job, she was exhausted and frazzled and cried every night. She realized the stress of that kind of work was too overwhelming for her.
You might think the story of Celia is just a Goldilocks tale: too hot, too cold. But actually, it's not uncommon. As someone who has worked in the executive recruiting field, and as the founder of a site about retirement, I can tell you it's essential to put time and effort into figuring out how to "test drive" your retirement. Think about all the time and energy you put into your first career, or planning your wedding or even researching your kid's college choices. You need to put in at least that amount of time or more when planning the next 20-40 years. Volunteer in the field you are considering, or work part-time to make sure you like it. If you do like it and need education to actually do it, then take the courses in the years leading up to retirement.
The bottom line is, you are likely going to be around for a good, long time. Do your homework, figure out how much money you will need, find something whether it's paying job, school, volunteering or a combination of all those things, and give it a test drive before you jump off the cliff. It's your life and you only get one ride on the merry-go-round. Make it count!