What Should I Be Thinking About as I Approach Retirement?

Question: After years of working and saving, I’m looking at retirement. What should I be thinking about, and what should I watch out for as I approach retirement?

The Superstore of Retirement

My son has a wide variety of ever-changing interests. He often finds something he likes, dives deep into learning about it, and spends the next few weeks or months engrossed in it. The cycle of interests shifts from various sports he plays to video games. Most recently, he’s enjoying regular recaps of a popular TV show with his friends at school. I can remember bits and pieces of being nine years old and what was important in that stage of life. Although my list of essential things might look a little different than his today, I find it fascinating how similar the basic process we use to make decisions in the various stages of life.

Michael and I had to make a trip to the store a few weeks ago to pick up some things. In exchange for chores around the house, I agreed he could pick something out for himself while we were shopping. So we set out into the store, starting in the toy section without any idea of what he would choose. Each aisle was stacked with an overwhelming amount of options – building blocks, toy guns, action figures, fidget spinners… We combed through the options, studying some and overlooking others. It was challenging to decide without any clarity of what “IT” was.

After an unsuccessful search for the perfect item, we had a deeper conversation about what he hoped to take away from the store that day. Upon further thought, he decided he wanted something that would be both fun today and won’t run out. That helped us narrow all the choices to just a few, making the decision-making process much more straightforward. We came up with the pros and cons of each, and he ended up deciding on some “V-Bucks” for a video game he loves to play.

Walking through the store with Michael in the hunt for the perfect choice reminded me of many crossroads we face daily. Sometimes decisions are easy to make and sometimes so complicated they cause undue stress and anxiety. I’m fortunate to help many people with the transition away from a career of earning and saving into a life of relaxation and financial independence. Moving into this phase of life can be very complicated with all the changes. It requires decisions to be made which carry a life-lasting impact. I often hear similar questions: How do I transfer from my health insurance at work to Medicare? What if I retire before I’m eligible for Medicare? When should I take my Social Security or pension benefits? These questions can have informed, educated, even mathematical answers, but other questions are more philosophical. How can you end your career well? What will you do with your time when you no longer have to wake up and go to work? Have you ever explored what you’re genuinely passionate about? Navigating these questions in a world of virtually unlimited information can be daunting, and it is often difficult to even know where to start.

It doesn’t have to be complicated, and you don’t have to do it alone. It does require some work, but most importantly, it requires consideration of what’s most important and what you’re trying to accomplish. We get to have these conversations daily, which often provide confidence, clarity, and focus. So if you find yourself in the superstore of life trying to find the perfect item to help you retire, let us do the work for you. Collectively we can make prudent decisions and let you return to enjoying the fruits of your labor.