Regrets - How to Avoid Regrets in Retirement

Matthew Gray |


We all have them. 

Looking back, there are many things we would have done earlier, sooner, or differently. In fact, you likely have already remembered at least one just in the time it took you to read the past few sentences. 

Some regrets are unavoidable. We didn’t know any better or were put in a bad situation. 

Unfortunately, many are not of that variety. Often regrets are caused by decisions we saw coming. They didn’t blindside us. We simply did not prepare for them. 

In my life, it can happen like a slow motion train wreck. 

There is an action I know I need to take. Maybe it’s studying for a test. I know the exam day is coming, but it’s 90 days away. That’s plenty of time!

I start reading the materials once every few days. Then life gets busy with a project at work. Add in a family vacation, a new book which catches my attention, and a few more distractions. 

Before I know it, the deadline is only 15 days from now and I still have three more modules to complete!

Most of the time I can cram the last few days and make it to the end. I may pass the course, but it tends to be stressful and takes away from other important areas of my life. 

The next course begins, and guess what happens? All too often, we find ourselves pushing off studying again. The cycle continues.

You may not be taking any classes or are no longer in school but does this pattern seem familiar to you?

We find it difficult to learn from our mistakes. Unless a task is both important and urgent, we kick the can down the road. We are constantly fighting fires, always between emergencies.

The truth is, we don’t have to live this way. 

My perspective was shifted when I discovered this matrix in college. 


We all tend to spend our time in box #1. The demands of daily living scream for our attention and act as if the world will crumble if they aren’t addressed RIGHT NOW!

However, there doesn’t seem to be enough time to take care of the #1 items because we often can’t distinguish them from box #3 which are urgent but really of no importance.

The fatigue of fighting these never ending battles push into square #4 where we try to ease the pain and stress via distraction. 

What gets ignored in this rat race? Box #2. Of course, this happens to be the most essential area. 

The “Focus” square represents the important but not urgent. In this sector sit the foundational pieces which are most crucial but will compete for our attention. At least not until they reach a point where disaster is imminent. 

Going back to my studying example, the course began in box #2. I knew it was crucial to pass the class, but there was no urgency. After all, I had three months to complete it!

However, as I spent my time in the other three spaces, the class crept quietly away from box #2 until it suddenly confronted me as a box #1 catastrophe!

Financial planning can often be treated in the same fashion. We know we need a plan for our money, but right now, things appear to be going ok. Besides, school is about to start, work has been crazy the past few weeks, and now is really not a good time. 

The dilemma is, “a good time,” rarely presents itself. Because we frantically fight box #1, can’t properly identify box #3, and succumb to the temptation of box #4, we never get around to actually planning. 

Before you realize it, you are behind on your retirement savings, the debt pile continues to grow, and the kids are another year closer to college with nothing set aside for them. 

There is another way.

Amazing things can happen when we tackle the essential before it becomes urgent. Having a proper plan in place allows you to better manage the pressing, avoid the interruptions, all while limiting and enjoying the trivial. 

If you want to get started, here are three keys to maximizing the essential:

  1. Identify an area in your financial life you know is important but have not addressed.
  2. Pick an action you will take by a deadline you set for yourself. 
  3. Share the action and deadline with someone you trust. 

When we live with intention, create a strategy, and invite accountability, it’s amazing how much more fulfilling life can be. 

If financial planning is a box #2 item you want a plan and accountability for, you can schedule a time to meet with us by clicking here. Also, take advantage of our FREE DOWNLOADABLE GUIDES such as Five Tax Strategies Retirees Often Overlook and Six Mistakes Grandparents Often Make.

And remember, education is worthless without the willingness to act, so be proactive and plan your financial future with confidence!