Thinking About Retirement? Here’s What You Should Do.


I’ve heard countless clients tell me how they ‘failed’ at retirement.  They enjoyed it for the first three weeks or even three months, then yearned to return to work.  They were not ready for it.  In some instances, I take blame for this as I did not adequately prepare them for this new freedom.  The freedom to do what they wanted, when they wanted.  The successful ones were ready for this new way of life, as they had already practiced via a trial run what they were going to do.  The unsuccessful ones didn’t.  They did not plan.

To increase your odds of a successful retirement, here are a few things to keep in mind as you contemplate this new way of life:

Are you emotionally ready?

Feelings, nothing more than feelings….as the old song goes.  Search your feelings….as the Star Wars script commands.  Hah, you may think this is stupid, but it’s not.  Your day-to-day life will change dramatically when you retire and it’s best to anticipate this reality. Your job often provided a sense of purpose, structure, and a comforting routine that may be hard to replace. Many have struggled to find purpose in retirement, which is tightly tied to happiness.  You need to find a new purpose for this life stage or you are always going to struggle with finding happiness.  If you derive most of your purpose from working, it might make sense to cut back your hours and/or responsibilities in advance so you can ease into the change.  You could also develop a hobby pre-retirement that will help engage a passion in the future.

Business owners have another issue they often encounter, and that is tying their identity to their business.  They see it as one and the same.  If you are to fully sell the business, this will be something you will have to overcome.

Retire to something, not from something:

Many studies show that the earlier one retires, the higher the chance for an early death.  As I like to say, there is only so much golf you can play in one day.  Write down what an ideal schedule looks like for you and your spouse.  Write it down for each morning, afternoon, and evening for each day of the week.  This will help determine if you are ready or not.  See a lot of holes?  That is not necessarily a good thing.

Write down your hobbies.  Speak to your family and significant other about your thoughts.  Are they okay with you being around the house more?  Around the grandchildren more?  You might be surprised by their answers.

Do you have enough money?

To answer this question, you first need to know how much you plan to spend each year.  A number of studies show that spending drops in retirement.  In my experience, the opposite holds true (at least in the first ten years).  You will want to travel more or do more extracurriculars as you have more time on your hands and are in good health.  An easy gauge to determine if you have enough money to live comfortably is called the 4% withdrawal rule.  This states that you should feel safe pulling 4.0% of your portfolio out every year.  A word of caution when tapping tax-deferred 401(k)s or IRA accounts, or assets with significant capital gains, paying taxes will need to be included in this 4% rule.  Speak with an advisor to help you determine if you are financially ready to retire.

To help with this analysis, track your budget every month.  Be sure to factor in annual expenses like insurance, real estate taxes, auto maintenance, etc.  If you plan to live in another state or city in retirement, I encourage you to go live in that city for two to three months.  It might be hard to take off that kind of work before retiring, but it will be in your best interest to try.


There are many other items you should think about including when to take social security, how to efficiently pull money out of your portfolio (and out of which account – taxable savings, IRA/401(k), or Roth), and whether you need to purchase health insurance if you are not yet eligible for Medicare (the short answer is yes).


Let me know if you want any recommendations on books that will help you explore this next stage and determine whether or not you’re ready for it.  One of my favorites is Mitch Anthony’s The New Retirementality.


If you’d like to discuss whether this stage is right for you at this point in life, please contact me.  We might just need to reframe the question!


Thank you for reading and best of luck!

About the Author: Alex Perkins

Alex is a Wealth Advisor for WealthPoint Advisors, LLC. After a successful career in management consulting where he helped business executives solve their corporate challenges, he decided to pursue a passion in helping families and individuals on the personal side. Alex now enjoys helping his clients answer their most pressing financial and life questions, through a comprehensive, evidence-based wealth management approach.