Many folks dream about having the financial means to retire early and enjoy life not having to work the 9 to 5 job. For those that have the actual good fortune to do just that, it has not always turned out to be the good times that they have expected. I would not say that they entirely regret the decision, but there are certainly some regrets.

• Regret for the road not traveled. For the lucky few who can retire in the fifties or forties, or even thirties, they are likely high achievers who have made it at a young age with enough financial resources to call it quits to the day job. However, one big unknown for them is that with whatever success they have achieved before they retire, they will always wonder how much more they could have done. This is likely not about money, but about regretting the road not taken — and what it could have been.
• There are many moments that you may not feel that you are happier – than before you retire. The expectation is that you will be filled with joy and happiness not having to go through the daily grind of making a living like everyone else when you call it a day. But that is likely not what happens is reality. Yes, you may not have to go to work every day but do not expect some magic change in your level of happiness. In some cases, the opposite is true.
• Finding the right balance between enjoying a leisurely retirement and still finding purpose in life. Most high achievers are driven by just that – the reason to get up in the morning. If you lose that, boredom and lethargy will set it very quickly. Finding the right balance is not as easy as it appears to be. And that is the secret of a happy retirement for many. Yes, you still have to work at it.
• Then there is a fine line between regret and worry — unless you have retired with money to last generations, you will likely have worries whether you have retired with enough money to keep you going. As your post retirement lifestyle and expectations change, you may spend more of that nest egg at a faster rate than you expect. Post retirement life is dynamic – but since you stopped working, your financial means are probably not. And it is not easy to go back rebuilding your nest egg again.

But do not let all the buyer’s remorse stop you from dreaming of an early retirement. If done right, not having to worry about the day to day chore of putting food on the table and paying for your mortgage is a great privilege that is served up to only few lucky folks. Assuming that you are one of them, it’s not a bad idea to learn from those who have living the journey!