6 Crucial Steps to Planning Your Life After Retirement
October 22, 2019

All through school and my career, I was a planner. I planned every day, week, month, quarter, year, and sometimes several years out. This planning helped me achieve goals, both personal and professional, and gave me a road map to follow. For me, this has been more than 50 years of planning, almost every day.

Part of my planning was to make sure that when I retired, I would be financially secure and able to afford the lifestyle I imagined for myself. And I am happy to say that Jody and I have been able to do that. But now that I am in retirement, I’m finding planning is just as important as it has been for the past 50 years, actually more important!

I envision myself living for another 30-40 years, so why would I stop planning now.

For many people entering this phase of their life, they want to slow down, plan less, take each day as it comes, and coast a bit. Everyone has their vision of retirement, and that’s important. But even if you plan is to slow down, do less, and take it easy, you still need to plan that out. If you just let each day unfold as it comes, and you don’t do activities that bring you joy, happiness, and fulfillment, you can end up on a path of disaster.

I have met so many executives and entrepreneurs who have had illustrious careers, leading companies, influencing teammates, and making huge strides personally and professionally. This type of active job cannot be followed up by a lazy lifestyle filled with meaningless tasks and activities. It did not work for me, and I’m confident if you are honest with yourself, it won’t work for you either.

During my career and my wife Jody’s career, we somehow were able to show up every day for our companies, support all our teammates, and at the same time, be involved with the busy lives of six children. Once we left our careers and found that we had 40+ new hours of free time, it seemed logical that things would get more relaxed, and we could go from day to day. This idea was not a good plan as we both ran into trouble and soon realized we need a better, more actionable plan.

We developed a full 11 weeklong course that’s available on our website, Your Retirement Game Plan. This course will take you through the entire process Jody, and I went through, but today, I’m just going to focus on how Jody and I planned our first few years of retirement.

Step 1 – 18 Month Calendar

The first thing we did was to go out and buy an 18-month calendar. We felt having a paper calendar would be better. We both have become big proponents of journaling, so we prefer writing over electronic. We sat down, and over a few hour-long meetings, we planned the next 18 months. We now look at this every month and update it more regularly for any significant events coming into our lives. For instance, one of our children just got engaged, so we need to keep our calendar open for that. Here is what we made sure was in the calendar:

  • All birthdays and anniversaries of family and close friends. Recurring events like this all go into our electronic calendars as well with alarms, so we always remember.
  • We still have two children in college, so we needed to make sure, and key dates for that were written down.
  • All major holidays. We are a blended family, so we are sensitive to where our children will be on any given holiday. We always want to be able to spend as much quality time with them as we can.
  • We have a family retreat home, so we made sure any long weekends or holidays we invite our kids or friends and keep track of that.
  • We have work commitments like conferences and masterminds that require travel and time away from home.
  • Any vacations that Jody and I want with the kids and alone.

I think you get the idea. What we have found is that once we commit to a date and write it down, it happens. This monthly calendar is supplemented by our daily morning routine, which includes planning our day, which I will write about in an upcoming article. This daily planning is where we make sure during the day and week, Jody and I plan time together like date night or just something fun during the day. We have our own lives and activities every day and make sure we do things together too.

Step 2 – Children and Family

Our core culture at home is family first, always. So, it’s critical we get this right.

The second step in our annual planning process includes our children. As I said, we have six, and all of them have significant others. They are spread out all over the northeast and California, so if we want to make sure we see all of them, we need to plan that proactively. Some of that is just meeting them for dinner, but other times it includes combining a business trip with a visit. We look at this regularly to make sure we are connecting as much as we can with all our children.

We have our children’s essential dates on our calendar, so we don’t miss anything. These will always come first before anything else, so it’s critical to get them written down.

We also extend this to the rest of our family and close friends.

Step 3 – Relationships in General

The third step is all about relationships. In our course Your Retirement Game Plan, we spend a lot of time on this subject. When Jody and I left work, we immediately realized that we lost hundreds of relationships that we had nurtured for decades. We have kept in contact with some of them, but most of the relationships were situational. What I mean is they were friends because of our careers and business connections. Such as teammates, clients, and strategic partners.

So, we now try to manage our relationships regularly. We have lists of our closest friends, together and individually. It’s nice to look through it to see a name and decide to call them that day — the kind of person who when you speak to them, it’s always a positive experience.

A copy of the worksheet we use to help create a useful list of relationships. This has been helpful to us to help identify new and old friends and make sure we stay connected

We now look for what we call “Growth” friends. People who are on the same journey as us, looking to live this time of their life with purpose, passion, and clarity. So, get out a piece of paper and start writing down all your relationships. Add their email and phone to make it easy to contact them. As you plan out your day, week, and month, you can refer to this to make sure you set up calls, meetings, and meals to keep engaged with your circle of friends.

Step 4 – Fulfillment Bucket

The fourth step is checking our fulfillment bucket. It’s critical always to keep this bucket full.

This could be as easy as planning a great dinner with some of our kids, good friends, or date night. During these events, we are purposeful in making sure we connect with family or friends in a meaningful way. Having a great conversation is critical.

Being grandparents is new to us, and like most people, we love it and adore our grandson. He is a long way away in California, we live on the east coast, but luckily, Jody and I have many business reasons to get to California, so we do the best we can always to see him.

Jody and I have always been big volunteers, and that has continued for us. Our most profound connection with giving back is our weeklong volunteer trips to developing countries under the auspice of Bridges to Community. For the past twenty years, we have been a combined 25 times, leading groups of 20 people there to build homes for families living on the edge of survival. It is these relationships with the local families that have impacted Jody and me so much. We stay in touch with some of these families as they are on Facebook and messenger. These families are friends and always in our thoughts and prayers as they struggle to live as normal a life as they can.

Since these trips are either annual or semiannual, we need other ways to stay fulfilled on a daily, weekly, and monthly basis. We both enjoy serving on nonprofit boards and helping those less fortunate in our hometowns. There is no shortage of need wherever you live.

So, we are always making sure we have the right balance of leisure time, family and friend time, and fulfillment time.

Step 5 – Our New Careers – Sharing Our Wisdom

Jody and I both decided before we retired that we would continue with some work. It took several years of writing, self-reflection, and learning to come up with our current plan.

First, we started a consulting company in which Jody, and I run together. Our first venture is, where we help entrepreneurs and executives rewrite their story of retirement. Just like we did for ourselves. This initiative takes a lot of time and planning, so we must make sure that this all first around our core life of family, leisure time, and volunteering.

Right now, our focus is building more online courses, working with one on one coaching clients, and speaking about Retirement Transformed. It is our goal to help as many people as we can make this transition into a fulfilled retirement just like we have.

Jody is back as school working on her masters in the area of positive psychology, so this needs to fit into our calendar as well.

Sharing our wisdom has become core to what we are doing with the rest of our lives. We spend a lot of time looking back on our careers and lives to see what we know and love to do so that any “work” we are involved with brings us fulfillment.

We just finished up a week-long vacation in French Polynesia, where a portion of that time was spent working on our next 18 months of retirement planning. We will do this every year as part of our plan to not only work a bit but also relax, recharge, and reconnect with each other.

Step 6 – Weekly and Daily Updates

The last step in our planning process is checking in with each other weekly and daily. We try and keep weekends like when we were working, so we rest and do fun things together.

Sunday nights, we always allocate some time individually and together to reflect on the past week. We have an informal checklist on how we did in those areas that are important to us. We always take time to celebrate any big wins.

Then we look out at the week coming up to make sure we know what each of us is doing and any commitments we have together. Our calendars are always open, and we make sure we are filling it with some meaningful experiences and events.

This whole process has become crucial to keeping us aligned, organized, and engaged with each other, our family and friends.

Please leave any comments below and let me know what kind of planning you are doing in your retirement. Get our latest tools, teachings and join our community of like-minded post-retirement professionals at, and start your journey toward living a retirement transformed.

Markham Rollins is dedicated to developing meaningful, transformational journeys for career-oriented professionals when they’re facing—or anticipating—retirement. He serves as a guide for successful individuals who, up until now, have built their identity around their business and professional successes. Markham helps entrepreneurs and executives rewrite their story of retirement so that it is filled with purpose, passion, and clarity.