Shakespeare Blog: View from the Lake

Group 512

Teaching Clients How to Retire

Written By: Kevin Reardon, CFP®


Many people work for decades towards the goal of retiring someday. They dream of what it would be like to be free of the bonds of work, living a life of relaxation and contentment. Then suddenly that ‘someday’ arrives, and many people are unprepared for the non-financial aspects of retirement. Based on the wisdom and examples of our clients, we’ve assembled top ideas that make up a successful retirement.

Identify Values

Much like our pre-retirement life, our values determine how we spend our time, energy and resources. The same is true in retirement. Whether your most important values include family, friends, community, faith, etc., retirement is an opportunity to spend more time living your values. Review your core values, and the structure of your retirement years will begin to take shape.


Emanating from our core values comes our purpose; the reason for getting up every day with a drive towards accomplishing something important (to you). If family is one of your core values, your purpose may involve taking care of your grandchildren a few days a week, helping your adult children manage a business or assisting them with a home remodel project. If your faith is a core value, your purpose may involve volunteering at church, serving as a leader in a youth group, or starting a Bible study. The clients who are living their best life in retirement have a purpose that provides the weekly activities to energize them and pull them forward.


Our health is frequently neglected during our working years and retirement is an opportunity to reclaim your wellbeing. Without good health, you won’t be able to fulfill your retirement expectations. Set clear goals on being active and working out. Consider joining a local gym to get active, and don’t hesitate to hire a personal trainer to provide guidance if your sneakers have a little dust on them. A strong recommendation is to join group exercise classes at the gym or various sport leagues (golf, pickle ball, racquet ball, bowling, etc.) as these will provide added motivation and an opportunity to build your social network.

Social Network

One of the strongest determinants of a happy and successful retirement involves a healthy dose of social interaction and inclusion in a community of like-minded people. People build these social networks in various ways, including interactions through their neighborhood, church, family connections, and hobbies (car or motorcycle club, knitting club, photography club, etc.).

Hobbies, Travel & Adventure

Having a hobby (or two) to occupy your remaining free time each week is imperative. For some, this may include gardening, wood working, painting, scrapbooking, tinkering in the garage or countless other hobbies.

Travel is near the top of everyone’s retirement to-do list. Write down your top 10-15 destinations you want to visit and map out the trips you’ll take the first five years of retirement. Once these trips are (tentatively) on the calendar, you’ll fill in other activities around them.

If traditional travel destinations aren’t enough to satiate your newly liberated retirement spirit, you can add a few adventures to your list that can be quite fulfilling. This might include a cross country bicycle trip, an extended hiking trip, a pilgrimage, living in a different city for an extended period of time, climbing Mt. Kilimanjaro, scuba diving the Great Barrier Reef, sailing through the Caribbean or whatever else your heart desires. If your adventurous spirit has been tempered during your working years, now is the time to release it!


If you really want to have direction on what you should be doing to have a successful retirement, start with the end in mind. Sit down and write your obituary. This will help clarify what you want to accomplish before you die and how you want to be remembered. Every day is precious and there is no guarantee we’ll have thirty healthy years in retirement, so begin accomplishing your retirement goals NOW!


Viewing retirement to be a continuation of your already fulfilling life, rather than a starting line (or a finish line), is a big determinant of whether you’ll be happy and fulfilled. Of course, there is nothing stopping you from learning a new skill or pursuing a new hobby in retirement, but this is the exception and not the norm. Please share your retirement goals with your Shakespeare Advisor, so we can build them into your financial plan and provide feedback to help make your golden years a success.