You’ve Met Your Retirement Goals – Now What?

We’ve all heard the famous Shakespeare quote, “All the world’s a stage, and all the men and women are merely players….”. This is a line from one of his plays, As You Like It. In the play, Shakespeare takes the audience on a journey of the complete lifecycle of a human being, made particularly vivid by its visual images of the different stages of an Elizabethan’s life. Each phase of life is an act in the drama. Generally, plays can be as short as one act or can have five or more acts, although Shakespeare’s plays always have five distinct acts.

When I think of this quote, I too like to think about the different phases our lives as acts in a play in the grand scheme of life. However, in real life I think the individual dictates how many “acts” their life contains. Most people move through a few distinct phases of life, from birth to death, but one phase that almost all of us have is our own retirement – transitioning from a lifetime of hard work and perseverance to the time to relax and enjoy the fruits of our labor.

In fact, it’s helping people prepare for this tremendous life change that I find so exciting. Each day, I get to meet folks to help them prepare for the day they can begin to live the retirement they’ve planned for so long. Gone are the commutes to the office, the zoom meetings, the paperwork, the office politics, and more. Now it’s time to start living life truly on their own terms. And surprisingly enough, I find that many folks think this new phase somewhat frightening. After planning years for this time, folks often find that the transition from working to retirement requires a real adjustment.

After all, for years they’ve read all about traditional financial planning topics – tips for saving money, investing wisely, implementing tax strategies and more. The focus has been on the steps necessary to achieve their retirement goals. So, they often wonder, “now what?” 

Folks, there is no one answer to this question. Everyone’s retirement will look a bit different, so I’d like to spend our time together this week to consider what happens when all of your planning has worked and the time to retire is here.

I believe one of best things to do first is to truly celebrate this time. You have worked long and hard to arrive at this day, so you should be proud of your accomplishment. And I believe that we should remember to be grateful, too, because we’ve reached a life phase that so many dream about – and yet some might never reach. It takes hard work and overcoming challenges to attain retirement success, so being thankful is a great place to start.

But what then? You will now be waking up on a “Saturday” for the rest of your life, and this requires a real shift from your working mindset. 

I often suggest to my clients that they consider doing a thorough self-assessment. Now’s a great time to regroup and determine if your life is where you want it. And if it isn’t, you now have more energy, time, and money to focus on making some of these things your next goal. You may find that there is another goal you want to achieve – perhaps you want to learn how to ski, to play the piano, or even turn a hobby into a side hustle. The idea here is not to become stagnant. Humans are meant to continuously learn and grow, and you now have extra time on your hands to pursue this with less financial stress. 

There is no absolute direction to take when considering what to do next, as long as it’s something that brings you joy and satisfaction. For example, I have one client, I’ll call her “Beth”, who recently retired and decided to turn her love for children into a regular volunteer opportunity at her local library, reading books to preschoolers three days a week. And then there’s my client, “Jack”, who turned his garage into a woodworking shop and builds beautiful custom pieces of furniture. The revenue from this “hobby” isn’t needed, but it fuels his passion – and he certainly doesn’t mind the extra money!

Most people use this phase to spend more time with the people they care about. They often make their health a priority to ensure they can continue to enjoy life to the fullest. Some take more time to practice their faith to incorporate greater meaning in their lives. 

And folks, if you have not made the adjustment within your investment system from an accumulation to a distribution system . . . what are you waiting for?  You see, for the first time in your life your investments must now produce income. So, if you have an outdated investment strategy that is strictly buy and hold, well, what happened to that system in 2008, how about 2020?  And the argument that “…it always comes back” is not relevant anymore since your system must produce income and if you are losing 40-50% every 6-8 years, there goes your income. 

No, as the Cutter Family Finance faithful know, a sound distribution strategy must incorporate quantatitive data to help manage the downside risk.  As you know, if you manage the downside (limit losses), the gains can take care of themselves.

So, whatever retirement looks like to you, make sure to take the time to fully appreciate the hard work that brought you here. This is the beginning of the exciting next act and you deserve to play your part to make the most of it!

This week I would like to take a moment to celebrate and to thank our Veterans this Veteran’s Day because they are always vigilant and they stay alert, and they deserve more!

Have a great week folks.

Jeff Cutter, CPA/PFS is President of Cutter Financial Group, LLC, an SEC Registered Investment Advisor with offices in Falmouth, Duxbury, and Mansfield, MA. Insurance offered through its affiliate, CutterInsure, Inc. We do not offer tax or legal advice. Jeff can be reached  at

This information is intended to provide general information. It is not intended to offer or deliver investment advice in any way. Information regarding investment services is provided solely to gain a better understanding of the subject of the article. Different types of investments involve varying degrees of risk, including the potential for loss. Therefore, it should not be assumed that future performance of any specific investment or investment strategy will be profitable. Insurance product guarantees are backed by the financial strength and claims-paying ability of the issuing company. Market data and other cited or linked-to content is based on generally-available information and is believed to be reliable. Cutter Financial does not guarantee the performance of any investment or the accuracy of the information contained in this article. Cutter Financial will provide all prospective clients with a copy of Cutter Financial’s Form ADV 2A, Appendix 1, applicable Form ADV 2Bs and Form CRS as well as the firm privacy policy. Please contact us to request a free copy via .pdf or hardcopy