9 Timely Conversations to Make Your Retirement Shine

May 30, 2018


Let’s face it — transitions are hard for everybody. Retirement is no exception. For many people retirement is really stressful.

Your self-identify suffers. You don’t know how to fill your day anymore, you no longer have any good excuses why you can’t go to the gym today, you just feel a sense of loss.

One of the most effective ways to counteract this sense of loss is to prepare ahead of time.

Prepare every detail like Michael Phelps, prepare like you’re giving a TED lecture on your “retirement vision” on front of thousands of viewers, prepare as if your life depended on it! Ah, wait a nanosecond — your life does depend on it. At least if you care enough to enjoy the next 30 years of your life!

Do I have your attention, baby boomers?

Wake up before it is too late or do you want to wait until after you have gone through three bouts of depression before even collecting your first Social Security check?

You know the old saying by Ben Franklin,

By failing to prepare, you’re preparing to fail


Do you have a vision of your ideal day in retirement?

No sweat you say. I would wake up when I wanted, read the paper from front to back (yes, some baby boomers still do this), catch up on ESPN and the latest news from the “swamp”, play some golf, have lunch, relax with friends, go to bed whenever.

Substitute your own version of events and you are all set with your first day in retirement!

What about the second day? Do the same routine? Ok, not too bad so far. Still beats that 2 hour commute and reading through another TPS report (read beat-down) from corporate, right?

What about day 3, 4 and 5? Now, you sense something is wrong. The law of diminishing returns has set in — you are losing interest in playing golf every day and you start wondering what the old gang at work is up to.


You experience some loss. The loss of purpose, the loss of connections, the loss of your daily rhythm.

Who wants to feel like that? Not you, baby boomers. You are doers, right?

Bad news, boys and girls. Before you can be a doer you need to decide what you are going to be doing.

Ouch — that means thinking and planning ahead, right? Is there a pill for that? Unfortunately not, but it all starts with something you are already familiar with — a conversation.

This is not the time to keep your thoughts to yourself.

Interested in getting going?

Don’t you want everybody to be jealous when you retire to a life full of possibilities?

Time to start chatting. Let’s get the conversations going.

Here is the list of who you need to talk to:

  1. Somebody that is already retired or even better a whole bunch of them — do you mind if I ask you a personal question?

It could be a family member that you trust or a long-time neighbor that has been retired for a while. These are people that have gone before you and understand the terrain.

Look for a variety of perspectives. Are they enjoying their retirement? What unforeseen hurdles did they have to overcome?

If they could do it over again, what would they have done differently? Did they prepare ahead of time?

Retirees are a resource that you should tap into. You can learn a lot from their wisdom.

2. Somebody at the Social Security Administration — I really don’t want to have this conversation but please don’t put me on hold again!

Find out what your likely monthly benefit will be under the various program terms offered. Will you take early retirement at age 62? How much will you be leaving on the table if you elect to wait as long as possible?

How is the cost of living adjustment calculated? What happens if your spouse has already filed for benefits? Will you have to pay taxes in your home state?

The more you know about Social Security the better choices you can make.

That Social Security check replaces in part that steady work-related income that you have become used to over the last 3 or 4 decades. You will come to love it!


3. Your Financial Advisor — I am here to talk about spending all my money and buying that yacht (just half-joking of course)

A lot of people dread the part of opening up their kimono and exposing their financial parts to a stranger.

Just like we often dread going to the dentist or discussing our taxes with a CPA people need to deal with their fears. It is better to know where we stand than to just obsess over the unknowns.

You might feel inadequate, you might feel judged. You’ll be asked to talk about money matters — Yuk. You really don’t want to be reminded again of that disastrous investment you made in your cousin’s startup or asked about how much money you are spending on going out to dinner and club memberships.

But nothing changes the fact that knowing the state of your financial health is a key part of a successful retirement. Deal with your fears now when you have time to make course corrections.

4. Your Attorney —I promise, I won’t make any jokes this time, they are costing me an arm and a leg given your fees

Do you have the four essential documents — a will, a living trust, a power of attorney, and an advance medical proxy? Do they reflect your current circumstances and wishes?

Again not the most pleasant conversation. You will have to face up to our own mortality. You need to think of this step as partly for you but mostly for your surviving spouse and family.

5. Your Primary Care Physician — ok, I have heard this before (eat better, lose weight, drink a bit less, exercise), now I just have to do it

Get a solid health assessment and plan to maximize the quality of your health. Take some lessons from the Blue Zones where people routinely live into their 90’s. Your health is your wealth as they say.

It’s not really about longevity — what you want is to live in the best possible shape for as long as possible.

Take care of both your engine and chassis. Plan for your overall health — physical and mental.

6. At least three real estate brokers — these people seem so friendly and they always send me the Red Sox schedule for the year

Figure out what your house is really worth should you need to tap into its equity (don’t just rely on Zillow).

You might decide to move to another city or even downsize. Knowing what your likely “net” receipts would be if you sold your home is important as a planning tool.

Also, if you need cash flow in the future and you wish to stay in your home you will likely consider a reverse mortgage. How much cash flow you will be able to generate depends to a large extent on the underlying value of your home.

For most people the value of their home represents their largest source of financial wealth. Having an accurate assessment of the value of your home will give you a much better view of your overall financial health.

7. A retirement or life coach— I have never considered this, but isn’t it great how many new professions the New Economy is spewing out?

A life or a retirement coach can help you stitch your “retirement vision” together. You’ll identify lots of areas where things don’t feel right. Fix them now because these things unlike wine don’t tend to get better with age!

With the help of your coach you can bring harmony to the plan. Addressing your fears is a big part of this exercise. Your retirement coach can make sure that everything is said and explored, not swept under the rug.

You need to feel that this is the right decision and that you and your spouse are ready.


8. Your spouse or life partner — the dreaded, honey, we need to talk

Sounds a bit scary, right? This is probably the most important conversation of all. Most likely this won’t be a one and done, but will involve a series of conversations.

Your partner could have wildly different expectations of your golden years. Some of the questions that you both should answer are:

  • Where do you want to live?
  • Who do you want to spend time with and how much?
  • What is on your bucket list? Things you must absolutely do before you die.
  • What is your comfort level with the finance or money side of retirement?
  • What are your biggest fears?

It takes two to tango — retirement as a couple is a huge transition. In fact according to the Holmes-Rahe scale, retirement is the 10th most stressful event that people experience during their lifetime.

Making sure that your individual visions and expectations are aligned is very important. Discussing your fears is a critical part of this conversation.

9. Yourself — it’s back to Me, Myself (Minus Irene)

Like in the Jim Carey movie, you will find yourself talking to yourself. Just don’t do it in public. Maybe best to journal this one.

Are you mentally ready? Are you transitioning to a desirable lifestyle or are you simply making decisions based on your chronological age?

Have you sat down and thought deeply about what type of life you want?

What will your obituary say after spending 30+ years in retirement?

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Has your view of retirement changed based on your conversations?

I hope so or at least that these conversations have clarified what matters to you and your spouse/partner. After all retirement is a team effort.

Do you have that sense in your gut that the time is now? Do you feel prepared for this transition? Or maybe you need things to settle a bit and come back to them.

Maybe your vision and that of your partner are at odds? A retirement coach might be able to really help out.

Are your finances in order? Open up to your financial advisor and have them design a retirement strategy where your financial assets are aligned to your “retirement vision”.

Your retirement could last almost as long as your work life. Make it work for you and your loved ones. Plan ahead and retire with possibilities!

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About the author

Eric Weigel

My goal is sharing my experience as an investment manager, certified retirement coach, and fellow Baby Boomer to enable people to design the life they want and that matters to them in their next phase in life. We all want to live longer, but we also want to lead a life of meaning, joy, and fulfillment.


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