How to Create the Ultimate Pre-Retirement Checklist: 15 Questions to Ask Yourself

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Based on a study done in 2019 by the CFP Board of standards,

  • approximately half of adults are not saving for retirement (48%). However, those that are saving are most likely contributing to a 401k (62%) or savings account (53%).
  • 2 in 3 adults do not receive retirement saving advice from a financial professional.
  • Of those who are not utilizing a financial professional, over half, they say they think they would benefit from receiving retirement saving advice (54%).

So it is safe to say that many people retire without a plan and this can have disastrous consequences on their lives.

That can be avoided, by just asking yourself:

“I’m 5-10 years from retirement…what do I need to do?”


The purpose of the ultimate pre-retirement checklist…

It should be obvious, but just in case it’s not, the time might be nearing to think about your retirement.  Seriously.

Like, how confident are you that you will be prepared?

The following set of questions are designed for folks who want a comprehensive view of their pre-retirement situation and need some tips on what they can do to get ready. 

I prepared these questions as “prompts” to get you thinking about your situation and to take action.  That’s the key–taking action.  

These might be things you can do on your own, or with a professional, but do something. 

Ok?  Now let’s go:

Question#1 – Am I financially stable? 
Everyone’s level of stability is different but I like the framework presented on page 91 of The Aspirational Investor (Chhabra) that consists of 3 buckets:  safety, risk, and aspirational.  Allocating your capital across these properly (in the right amounts) allows for financial security and peace of mind–both important, but the latter likely the most important!

Question#2 –Am I debt-free or pretty close?
Having no mortgage or being close to having no mortgage is something to consider.  Even in our current low-interest-rate environment, having 100% equity in your home is just the smart thing to do or be working towards.  If something went wrong, you know you’d at least have a roof over your head.  Depending on your estate goals, you may want to consider monetizing some of your home’s equity with a reverse mortgage (another topic for another day).

Question#3 – Do I have a reasonable Social Security income strategy and savings plan?
Regardless of the myths you’ve heard, the likelihood of individuals retiring in the next 10 years receiving a social security benefit is high.  This means it needs to be planned for as income so you can properly assess your income tax liability among other things.  To haphazardly consider this is a mistake.  Whether you file early, on time, or use a delayed strategy can mean thousands of dollars for you and your surviving spouse. Click here to use the SSI retirement estimator to see what your benefit may be.

Question#4- What is my wage replacement ratio (WRP)? 
If you’re like “wuhh?”  Then you might want to consider the amount of cash it will take each month to allow you to live comfortably compared to what you were living off of as a full-time employee.  Can your investments pay you that consistently?  Even when the market dips and dives?  Be thinking about all income sources:  $ ________________ versus how much you will be spending $ _______________. Oh…I almost forgot to give you the definition of WRP…click here to learn more.

Question#5- Is my family on board with my retirement plans?
This is essential. Your spouse or partner must buy into the plan and play an active role in the execution of it. This will minimize conflict down the road, especially at the reading of your will (believe me I’ve experienced this firsthand and it isn’t pretty).  Putting together an estate plan as well as an aging plan while you are of sound mind is a necessary step.  The latest statistics are that 60% of Americans die intestacy (i.e. without an estate plan).

Question#6- Have I discussed my retirement plans with my family and financial advisor, and we agree on a common course of action? 
I thought to combine this with the above point, but I wanted to keep these questions brief and bit-sized.  That being said, this point includes not only family consensus, but objective outside counsel in the form of a Certified Financial Planner™.  This is someone trained in answering all of the questions in this list.  After 20 years in this industry, I can say definitively, there isn’t another designation that has trained individuals specifically to deal with these topics comprehensively, so make sure you work with one to help you carry out your financial and retirement goals.

Question #7-Have I secured all retiree benefits available to me?
Nowadays employers aren’t nearly as generous with their benefits for retirees (thanks ERISA!), so that might mean you’re leaving money on the table by not knowing all that is available for you!  I usually conduct a benefits review for my working clients, but doing a pre-retirement one is a necessary step to help you make sure you’re getting everything that is available to you (or staying long enough to become eligible).

Question #8- Have I reduced my monthly living expenses and optimized as much as possible?
What does this mean exactly? Well…for starters you should be committed to reduce monthly living expenses and optimize before retiring. What does optimizing look like?  Spending less money on your monthly expenses will by default increase your retirement income. If you don’t optimize, the chances are good that you may outlive your income and not be able to support yourself in the future.  No one wants to have more month than money, right?

Question #9 – Do I have a solid tax strategy in place?
Making money is great, but keeping what you make is even better! Are you taking advantage of all available tax-deductible retirement planning options (i.e., long-term care insurance premiums, health insurance premiums, mortgage payments, high deductible health plan, charitable contributions, spousal IRAs, etc.)? There are so many things that get missed when tax preparation is separated from a decent tax strategy. You might continue to pay more than your fair share without one.  Click here to access a quick quiz I created.

Question#10- Do I have a well-diversified portfolio so that when the stock market takes a downturn, my portfolio doesn’t take as big of a hit?
I call this investment positioning. How much volatility does your current portfolio contain? Will you be able to handle the roller coaster ride when you’re no longer employed or would you prefer less “thrills”?  Remember, it’s not just about your ability to handle risk but also your willingness, and to be honest, your willingness may change despite the strength of your balance sheet. Willingness is about emotions, ability is about logic…you need a portfolio that considers both factors.

Question#11- Do I have an emergency fund to help me through life’s crises so that I don’t have to go into retirement savings?
Along those same lines and taking a page from the Aspirational Investor (notice the second reference in eleven questions means you probably need to read the book 😀), having an adequate amount of liquid cash is very necessary. You’d never want to be in a situation where you have to sell an investment while it is performing poorly just because you need the cash flow. Having a dedicated emergency fund that you can fall back on of at least 3-6 months of living expenses is ideal.

Question#12- Do I have a sufficient amount of life insurance to take care of my family and pay off any remaining debt (if there is any)?
This includes insuring against death–no matter when it happens. There are different ways to approach this but mainly includes considering what would be needed by those who are economically dependent on you. You may also want to consider donating to causes or charities in your life insurance planning.

Question#13- Have I looked into whether or not a long-term policy makes sense for me?
Long-Term Care (LTC) Insurance – LTC insurance provides protection against huge out-of-pocket costs that are incurred when you have to live in a nursing facility or at home.  Granted, long-term care insurance is usually a subject that makes people cringe because of the premiums (cost to insure), but wait until you see the bills from the assisted living facility or in-home care!  Not pretty. Not to mention the cost (usually intangible) incurred by the caregiver. Believe me, this is a necessary element inside your aging plan that you’ll need to consider.

Question#14- Have I created a list outlining my short-term and long-term plans as well as goals?
If you can’t articulate them or they are not written down, then they’re nothing more than dreams.   Sometimes we overcomplicate the process by trying to be perfect.  This past January, I challenged all of my wealth management clients to create a 30 Goals list composed of hard, medium and easy goals that related to their happiness and well-being. I challenge you to do the same.  If you’d like a copy of the exercise, just email here.

Question#15- Do I regularly review my progress towards each of these goals so that I can determine if there are any potential holes in my strategies that may need attention?
How is this different from the previous point made in question #14? Because tracking your progress is essential to staying focused and achieving your goals–the previous point is about creating a list of goals that you can track. Look, I know you probably hate this part, but it’s the most important!

Some final thoughts…

I compiled this list of questions based on hundreds of client cases over many years. It is conclusive and is by no means meant to be recommendations for you specifically–that’s why you want a professional to help you evaluate the context for your situation.

I want this to be more of a starting point for your planning experience and I hope it contains some valuable perspective for you to consider. 

Most of all, I hope it helps you in your journey to find success in transitioning into the next phase of your life.

If you’d like to understand how DJH Capital Management can help you in answering these questions, CHECK OUT OUR PROCESS.


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Jessie Holloway

Thanks so much for the list of questions to ask yourself when you planning retirement. My dad is reaching retirement and they want to make sure they’ll be okay when he does. My parents have been looking into hiring a professional to help them plan for retirement. https://cashflowinretirement.ca/services-and-fees

Mia Evans

It really helped when you said that having an emergency fund that can be used for about three to six months would be ideal. I will keep that in mind and be prepared with that when I get older so that I will be able to fend for myself. Also, I am thinking about going to a retirement village when I am a senior, so I have to save up for the expenses for that as well so that I will not be a burden to my kids.

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