by Bob Ronan

4 keys to a happy and successful retirement

Sep 29, 2016

For many workers, imagining life after their careers end can be difficult and more than a bit scary. This post shares advice on how to embrace the retirement lifestyle and provides suggestions to make it a success.

beach relaxed vacation
Credit: Thinkstock

Most workers think about what it might be like to retire, and I was no exception.  I knew a number of people who had retired but, unfortunately, they seemed to disappear rather quickly after leaving the workforce, and my understanding of the retirement lifestyle was very limited. Because of this, I have tried to make myself available to the people I worked with and thought I might summarize what I have shared with them in two to three blog posts.

My former colleagues rarely ask me how I might handle a complex business situation.  Instead, our conversations often center around their curiosity about retirement. What is the secret to being happy in retirement? What do you do all day? How did you know you could do it financially?

This post will deal with a simple concept that has worked for me and seems to be resonating with others: treat retirement like a job. At work, there is a great deal of structure already in place. It should be no surprise that it can be a struggle to move from an environment like that to an unstructured lifestyle. So while it is great to get away from some of the work structure, I believe it is important to retain some techniques. The following sections describe a few ways I have found structure to be helpful in guiding me through retirement.

1. Keep a to-do list

Just like at work, you need to keep a list of the things you want to do, or you are going to forget them. I can’t tell you how many times I have felt like I had nothing important to do until I looked at my list.

When I first retired, I developed a to-do list with three sections: longterm projects (writing a cookbook), short-term projects that might take a few days (moving to a new laptop), and quick hit items (balancing the checkbooks).

I also created a “go-to” list. These are activities I like to do any time I have 20 or 30 minutes of free time. They are activities I could spend hours doing but I limit myself so they are always a treat when I do them. For me, reading is my No. 1 go-to. I always have a book going that I can pick up and read.  

2. Write yourself an annual review

I write myself an annual review every year. I know that sounds strange, but I find it to be a reflective exercise. It reinforces for me that I have accomplished a great deal, and it reminds me of the areas where I want to maintain focus.

I have found it is important to make the annual review a “living” document. I keep it current as the year progresses by making updates one to two times per week, so the “annual” part is little more than adding commentary.

In my review, I list my accomplishments as follows:

  • Athletics: races, major hikes and fitness DVD programs completed.
  • Reading: books I read, sorted by the ones I liked and the ones I thought were overrated.
  • Travel: places I visited with my family.
  • Financial: any work I did financially, such as completing our tax returns or establishing trusts.
  • Nonprofit: work done for a university board I sit on.
  • Firewood: This one is atypical. I enjoy cutting and splitting the trees that fall on our property so I keep track of my major projects.
  • Writing: the blog posts I publish.
  • Other: anything that doesn’t fit elsewhere.

I then document any areas that have not gone as well as I would have liked and include ideas for making the next year better.

Finally, I create my list of goals for the following year, which I’ll discuss in the next section.

3. Create goals for yourself

Just like the performance goals you document for yourself at work, it is important to have a list of goals you want to accomplish in retirement. I draft this when I do my annual review and then modify it frequently throughout the year as things change.

These goals are the starting points for the next annual review. I keep them at the bottom of the annual review document and move them into the review once they are completed. For example, I have a list of the books I want to read and, as I finish a book, I give myself credit for it by moving it from the goals section to the accomplishments section.

4. Understand the true importance of your goals

Whatever goals I set for myself, I treat them like I would if a company was paying me to do them. At work, I wouldn’t move a meeting unless I had a very good reason, so now I use the same criteria before moving an activity I want to do. My morning workout is just as important to me today as a key meeting was when I was working.

I do find I am less efficient in retirement, because almost everything can be done “tomorrow,” and perhaps that’s inevitable. But the best days I have are when I put some pressure on myself to get things done. When I am asked what I did on any given day, it often doesn’t sound like a lot, but I feel good because I accomplished many items that were important to me.

When you are working, your non-work tasks — planning a vacation or working out — are often secondary priorities. I believe I turned the corner on retirement when I began to think of these tasks as critical.

If I told you going on vacation was a goal that I accomplished, you might think of that as odd, but that’s the secret! It is really important to think about “accomplishing” a vacation in the same way you would think of hitting a milestone at work. If you don’t do this, you may get discouraged in retirement because you won’t feel like you are doing anything important. If you believe travel is an important part of retirement, why wouldn’t you consider traveling somewhere exciting an accomplishment?


Many people see retirement as something completely different from working, and they struggle to figure it out. However, the difference is only that your non-work life has emerged from the background to become the priority.

When I wrote my annual review after my first year of retirement, I was amazed at how much I had accomplished. But I shouldnt have been. In retirement, you are the CEO of your own life, and your activities are focused on moving your life forward rather than moving forward the goals of a corporation. So, with all that time to focus on things that are important to you, it should be no surprise that you get a great deal accomplished. 

If I knew retirement was going to be this great, I would have done it years ago.

I hope you have enjoyed this deviation from the IT topics I usually write about. I do have plans for at least one more retirement article, and that will be to answer the question I receive most frequently: What do you do all day? But first, I have a big oak that needs some attention.