Retirement is a hard-earned destination, but often folks lose the “golden” sense of this season because they just aren’t properly prepared for life IN this stage. After saving for years, their retirement path can seem stuck in a rut, or even painfully off course. They all long for this season to be the capstone of their lives rather than just a bookend. As they consider how to flourish financially and personally in this time, here are a couple of important strategies to guide the way:  

Strategy #1: Have a financial plan AND a life plan.

Many retirees have had good financial investments, but what got them TO retirement might not be the best strategy to get them THROUGH retirement. A financial plan in retirement is required. Reducing investment risk and increasing income are just two of the major shifts their portfolio needs to undergo. Plans include having money structured specifically to meet the retiree’s income needs, neutralize the risk of catastrophic life events, and making sure they have proper documents in place for any assets to get to the right folks, with minimal delay and effort (and minimal taxes being due). Planning for retirement should include more than having “enough” money.

When most folks prepare for retirement, they primarily focus on finances—their Money Track. However, their Life Track can be even more important. Retirement is the “great lifestyle reset” where responsibilities and requirements are replaced with wide-open options. The Identity retirees once had in their careers is set aside. When they say they are a “retired ___ (teacher, banker, electrician, etc.),” it says more about who they once were than who they are now. It’s vital that they create a new identity for who they want to be that provides enjoyment as well as fulfillment. Just “enjoying retirement” will leave retirees feeling empty and their longing for meaning. It’s important for a retiree to reflect on what their Life Purpose is now that they no longer work. 

Strategy #2: Get the advice needed 

The professionals spend their time and energy so that retirees don’t have to. Whether it’s advice from a life coach on how to re-invent themselves, or advice from a financial planner to align their investments with their needs now, getting expert guidance is helpful. For example, many retirees who handled investments themselves before retirement may benefit from considering engaging a retiree advisor who specializes in handling concerns that are specific for folks in this stage in life. These concerns include how to get the income they need and make sure it lasts for their entire lives, reduce taxes,  and how to protect what they have from bad life events like long-term care—things retirees might not have given any thought to when they were working. Using professionals well can empower retirees to flourish in their Life and Money Tracks.  

Strategy #3: Get connected 

Community becomes more important the less competitive people become. This is part of the great lifestyle reset called “retirement.” For some that means seeing people more as collaborators than competitors and being more flexible. This may mean trying new things or reconnecting with parts of their lives that were once important but got crowded out by other priorities. With retirement comes a potentially new circle of friends with different interests and points of contact. Doing it alone is a drag. There is so much to do, but what is critical is not just being busy having fun, but creating connections that lead to enduring relationships. Retirement is most enjoyable when doing the things we enjoy most with those we love the most.  

Strategy #4: Be decisive 

Decisions should be viewed as empowering opportunities to direct the retiree’s life. Being decisive will free them to move in a direction they want instead of subjecting themselves to continuing lingering doubts, confusion, and perhaps worry that come with uncertainty. It’s important for retirees to make purposeful decisions about what they want their life to look like to put them on a path they are confident and energized about. 

For retirees, it’s important to take time to invest in their well-being by considering the long-term impact of current, ongoing choices. Especially in retirement, it’s important to be intentional and realign their resources (time, energy, and money) with what’s most important to them.  


Len is a Retiree Advisor, with over 30 years’ experience. As a fiduciary, Certified Financial Planner™ and Certified Life Coach, he has advised many individuals and families regarding both Financial and Retirement Planning. Len’s Amazon International Best Seller, MaxAMAZING™ Your Retirement, combines both his financial and life coaching expertise into free resources to help guide retirees into a more enjoyable and fulfilling season of life. Catch Len, Sundays at noon on ABC 47 for “MaxAMAZING™ Your Retirement.” 

For more free, helpful resources, Len offers both his websites for public access: |

Len is the founder of The Delaware Retiree Connection, and the CEO and owner of Dedicated Financial Services. Investment Advisory services offered through SGL Financial, LLC