
Entrepreneurship isn’t new. We hear and read about it a lot. And it isn’t just a younger demographic. Older entrepreneurs are hitting the headlines, too.

What comes to mind when you think of your retirement? Excitement? Uncertainty? Dread? All three? The best retirements are planned.

The two extremes with retirement planning are: to go into retirement with no plan; or to over-plan. No plan means you’re beginning a substantial part of your life (perhaps 20 to 30 more years) with no direction. Over-planning leaves no space for spontaneity—which is one of the major delights of retirement. The key is to focus on what’s important with your planning.

What are your dreams for retirement? A more important question is: What is your life dream? That’s about what you want to do but linked to how you want to live. In other words, who do you want to be in retirement?

Know yourself’ (‘know thyself’, if you prefer) is an ancient Greek saying that rings true for those approaching retirement. Knowing yourself is important as you plan your retirement because it’s your retirement.

Afraid of retirement? Really? What’s there to be afraid of? The answer to that depends mostly on how you tackle life. But, however you tackle life, retirement is a dramatic change. Even with the best preparation, it’s a step into the unknown.

We can learn a lot from other people’s mistakes. At the very least, it can make us wary about making the same mistakes. In no particular order, here’s a list of seven regrets current retirees have had.

Are You Ready for Retirement? That’s a question investor advisor Ken Heise asks. ‘Retirement is a huge transition,’ he says, ‘much like getting married or having kids. And just like those other life events, it takes preparation.’

I retired more than four years ago. I was well-prepared (having completed the first draft of my book, Retirement Ready? helped). But there were still surprises and issues to address.