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7 Retirement Decisions You'll Never Regret

They'll impact your happiness, fulfillment and options in retirement

By Joe Hearn

(This article previously appeared on

One of the benefits of my job as a financial planner is that I get to see a large group of people all making decisions about the same thing: Retirement. Over the years, that has given me a large data set of decisions and their consequences.

Some of those decisions are minor, while others have consequences that ripple out for decades. Some of those decisions pay off big, while others tend to blow up — often in spectacular, catastrophic, almost comical fashion.

Below are seven decisions —big and small —that will impact your happiness, fulfillment and options during retirement. They are decisions that you won’t regret:

1. The Decision to Decide

A palliative nurse recorded the regrets of her dying patients and compiled them in a book called The Top Five Regrets of the Dying. The No. 1 regret was “Not living the life I wanted.”

To avoid this regret, you need to (surprise!) decide what kind of life you want to live. But don’t stop there. Once you decide what you really want out of life, you need to start taking those plans very seriously.

Imagine the satisfaction you could have if you arrived at the end of your days knowing that you did everything you possibly could to live the life that you wanted. For some practical ideas on how to do this, read Part 3 of my free Intentional Retirement Manifesto: A Brief Guide to Retirement Bliss.

2. The Decision to “Cut the Branch”

A few summers ago, I brought in an expert to help me trim and prune the trees in our yard. Most of the work went pretty quickly until we got to a large tree in our backyard. He informed me it had a branch that shouldn’t be there, but it had been allowed to grow for so long that cutting it now would make the tree look a bit silly for a few years.

As I pondered what to do, I asked him: “When that little branch started growing ten years ago, should I have cut it then?” He said "yes." Then I asked him: “Ten years from now, will I look back on today and wish I had cut the branch?” He said "yes" again. So I fired up the chain saw (it was a big branch) and started cutting.

No doubt each of us can listen to that story and use the branch as a metaphor for something in our own life. What is it for you? A job? A relationship? An unhealthy habit? Whatever it is, maybe now is the time to cut the branch.

3. The Decision to Do Less

If you’re like most people, your default setting is for more. More commitments, more work, more stuff, more relationships, more money, more sporting events for your kids, more television, more house, more projects. More, more, more. The funny thing about “more” is that it can be incredibly diluting.

If you have 30 projects at work, for example, you’ll probably have less impact than if you were allowed to focus on three. This is the paradox of more.

The more you try to do, the less you end up doing. If you want to do more, figure out a way to do less. Cut the unimportant (especially in retirement) so you can free up space, time and money to focus on the things that really matter to you. Less > More.

4. The Decision to Improve Your Marriage

Middle age is a risky time for your marriage. Hardly a year goes by that at least one of my clients doesn’t call it quits in that phase.

Divorce is never fun, but it’s even less so when you’re on the doorstep to retirement. Your assets get divided in half. Your kids will likely take sides. Your friends will certainly take sides. The dreams you had for “Someday” are off the table.

How much better would it be to enter retirement in a happy, fulfilling marriage — plans, family and finances intact — ready to enjoy the next phase? Yes, that takes work. Especially if the problems have been allowed to fester over the years. But take a long, hard look at the consequences before deciding that divorce is a better option.


5. The Decision to Bury the Hatchet

A client called me last year and told me that her ex-husband had just stopped by. They had been through a messy divorce due to infidelity about 20 years previously and hadn’t spoken since. Needless to say she was a bit surprised to find him on her doorstep with tears in his eyes.

He wasn’t there to try to fix things. They had both moved on and married other people. He simply wanted to apologize and ask for forgiveness.

My client later found out that when her ex left her house, he went to her parent’s house and several other people in the family and did the same thing.

It’s tough to go through life without hurting someone or being hurt by someone — usually our kids, friends, spouse or extended family. Carrying that baggage around can cause bitterness, resentment, and regret.

Why live with that pain year after year until one of you eventually takes it to the grave? If it was your fault, acknowledge as much, apologize and ask for their forgiveness. If it was their fault, have grace and move on.

6. The Decision to Bet Some Chips

Have you ever seen the movie Rounders? It’s about a poker player, starring Matt Damon. I was watching it on Netflix and a quote stuck with me. Talking about poker, Damon said: “You can’t lose what you don’t put in the middle. But you can’t win much either.”

It’s easy to play life too conservatively. God knows I’m guilty of this more often than I’d like to admit. Too often we go through life unwilling to take a chance and bet some chips. This can feel safe in the short run, but like Damon said, it never results in much of a payoff.

Is there something that you’ve always wanted to do, but been afraid to take the risk? The clock is ticking. Maybe it’s time to bet some chips. Win or lose, you’ll at least have the satisfaction of having tried.

7. The decision to get healthy.

Most of my clients are in the 50 to 75 age range. They seem healthier than most, but here’s an abbreviated list of health problems that they have dealt with: prostate cancer, breast cancer, diabetes, hernia, heart attack (survived), kidney stones, dementia, severe back pain, glaucoma, TIA stroke, broken wrist (due to osteoporosis), arthritis, lung cancer and depression.

Obviously we can’t prevent all illness, but doing everything you can to be healthy can improve your odds of a long, active retirement.

Joe Hearn is a blogger at, where he writes about how to live an intentional, meaningful life. He has also written several books and has been a financial planner for nearly 20 years. Read More
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