Have you ever questioned the status quo? Went against the grain despite personal fears or warnings from others? Have you ever broken established rules, or stepped outside the box?  How did it feel? Were your efforts successful? Was it worthwhile?Did you learn something valuable or acquire something useful in the process?

No matter what you have or haven’t done in the past that went against the grain, the opportunity has arrived to turn retirement planning upside down and engage clients and prospects on a new level. I’m referring to a contrarian style that can bring new life to old, traditional (and boring) retirement planning concepts, and an educational approach that meets clients and prospects where they are at. 

One of my favorite contrarian ways of marketing to new and existing retirees is to take the glass is half empty approach. In other words, take the flip-side of what most people think and say. For example, most advisors spend time helping clients dream big, beautiful things about retirement -- taking long walks on the beach, embarking on worldwide travel, watching grandkids graduate from Ivy League colleges and so on. 

Fundamentally, that’s all great stuff. However, talking the same as everyone else makes it’s hard for you to stand out in the crowd. Unless, that is, you take the same concepts and turn them upside down. By revealing the reverse side of things, you can breathe new life into old topics.  As an example, I recently wrote an article to include in my Retirement Wellness Report about "things that only aeem like a good idea before you retire." They may sound great at first, but ...

Play Golf Every Day 

Hitting the links every morning and becoming a scratch golfer resonates with many pre-retirees.  At least until they feel the shoulder and back pain from swinging a golf club over 70 times each day.  Throw in the snail’s pace foursome ahead of you, or your group’s talkative fill-in who takes five practice swings only to duff the shot, and you begin to realize golf isn’t all that relaxing, or something you want to do every day.

Watch Grandkids

There can be immense joy in spending time and spoiling future generations, but doing it on a full-time basis can quickly turn pleasure to anguish. Whether it’s those constant requests for junk food, miniscule attention spans, incessant video gaming, constant texting or good old-fashioned drama queen acting out, retiring to the role of nanny, cook, chauffeur and more can make those old days of boring work meetings, frustrating bosses and annoying co-workers seem like a weekend BBQ with friends.

Travel The World

Thoughts of visiting quaint villages, marveling at architectural masterpieces and experiencing natural wonders can evoke strong emotions. That is until you have to pass a kidney stone on a European river cruise, need a prescription filled in a foreign country, get a credit card bill showing international charges, or gasp at roaming fees for cell phone use abroad. Add in the complications of a flooded basement while you’re on the road, a missed connecting flight or a mom/dad injury at home, and you may be happy being relaxed -- but accessible -- at the local bed and breakfast. 

The upside-down approach hits home with a variety of people because most have experienced one or more of those real life aspects of retirement. Whether you get a laugh out of them, or a “hmmmm,” it provides a fresh perspective, which is exactly what many people are looking for.  Additionally, it touches upon my second technique to turn retirement planning upside down:  meeting people where they are at.

Like other financial planners, I often find myself talking way above the heads of clients and prospects. I do love the finer details of investing and portfolio management, but many people don’t care about modern portfolio theory or security selection as much as I do. So I’ve found it extremely valuable to infuse retirement planning concept into their current situations as a means of broaching issues that most people would prefer to postpone or avoid altogether. 

In another piece entitled, "What If Portfolios Could Talk," I made light of the way many people manage their portfolios … and the need to get professional help with them. Instead of hitting people over the head with the need for asset allocation or diversification (concepts that have been discussed to death), I posed a more personal question: “What would your investment holdings say about life in your portfolio, the conditions and care you provide for them? What secrets would they reveal about you? If portfolios could talk, which of the following categories would your investments put you in?” 

Military Family

If you’ve ever known or talked with a “military brat,” you know life for them can be one of frequent moves, costly transitions and feeling as if they never fit in. A similar profile can be applied to investors who constantly changes their portfolio holdings and never settle into a disciplined strategy. Whether they’re chasing performance, trying to avoid a market meltdown or jumping on the latest-and-greatest bandwagon, their individual holdings never have time to come together, establish an identity or role within the portfolio. Consequently, they often suffer because constant trading costs and fees reduce overall return. While many investors do it in an effort to secure their own financial freedom, it may be time to change your portfolios trajectory and acknowledge that a stable, disciplined approach offers a less stressful path to the same goal.

Fashion Emergency

Leg warmers, pagers and Member’s Only jackets aren’t cool anymore, and friends are laughing at those who still have them. Likewise, the investment options inside your 401(k) or 403(b) may have changed when your company switched providers, or if you switched employers, but that risk tolerance questionnaire you took five or 10 years ago is now completely out of date. You’re not only older and have more money inside the account, but your personal situation has probably changed. No doubt you once looked cool in the headband, and felt like a VIP when your pager went off, but now you’re approaching retirement and it may be time to shift some equity assets to fixed income and adjust your growth holding to include some dividend-paying value options. Yes, some fashions do eventually come back into style, but that’s not the case with investments. You may have liked the old stuff, and find it’s still easier to wear those comfy clothes, but admit it’s time for a makeover, starting with re-alignment of your asset allocation based on your age, risk tolerance, and retirement horizon.

Once again, by emphasizing familiar situations, such as those typically found in a military family or lagging behind the fashion curve, advisors can help clients and prospects uncover retirement planning concerns they may have and need to address. 

Another way I like to turn retirement planning upside down, and even inside out, is to address taboo subjects. This notion is supported with a number of previous FA columns that include topics such as religion, sex, suicide, addiction, divorce and other “dark side of retirement” issues.  These occurrences are likely to increase as more baby boomers reach retirement. 

In fact, in response to the recent passing of actor/comedian Robin Williams, I wrote a new guide titled, The Dark Side of Retirement: Mental Health Challenges Facing Baby Boomers.  It’s not fun or flip in any way; it’s real, genuine and a topic retirees need to be aware of … and one that has to make it into more retirement planning conversations.  (You can download a free copy of it here).

My business partner cringes at stuff like this because it can be uncomfortable.  But for me, having spent years as a social worker before getting into retirement planning, I know its real life and what people are seeing and dealing with everyday… which is why it is important to bring these issues out of the shadows and into the conversation.

Fact is, our lives get turned upside down on a regular basis: It could be the result of divorce, addiction, job loss or a call about a family member or friend in the hospital. It’s all very real and very much a part of retirement. This fact has and will continue to help me break old molds, and keep turning retirement planning upside down.

Robert Laura is the creator of the Retirement Wellness Report, co-founder of RetirementProject.org, and author of Naked Retirement. He can be reached at [email protected].  Please connect with him on LinkedIn and follow him on Twitter @robertlaura.