How to Retire, Part 1
“Often when you think you’re at the end of something, you’re at the beginning of something else.”
(Quick note: This will be Part 1 in a two-part newsletter series on this topic. Be sure you're on the list so that you automatically receive Part 2 next Friday!)
I've been rolling a "Retirement Planning" newsletter around in my mind for a while now. Because after working with clients in every phase of preparing for, adjusting to, and successfully moving through retirement, I knew I had things to share...things that could potentially help someone move forward in their own lives toward the kind of retirement they wanted.
Writing the body of this newsletter was pretty easy. Stopping myself from saying allllll the things was not as easy, however...hence the two-parter 🤣. The title, however, may have been the most challenging part.
Here's a few of the drafted-but-eventually-discarded titles:
“How to Retire With Confidence”
“How to Save for Retirement”
“How to Ensure You Are Ready for Retirement”
As I backspaced and rewrote the title in a multitude of ways, it eventually hit me: One of the reasons “Retirement” planning is hard is because it doesn’t look the same from one person to the next.
Some people wake up one day, fed up with all the chaos and politics around their work environment and simply decide to be done because they feel confident in their financial capacity to walk away.
What they do next is a blue ocean of possibilities, and while their decision may have been abrupt, their happiness and freedom catapults them into discovery mode. As a financial planner, this is usually exciting to witness, and one reason why I love what I do.
Some people save and plan meticulously, well aware that retirement is only possible for them if they approach it with intentionality and discernment.
Transitioning into retirement for these folks often reminds me of elite marathoners crossing the finish line and falling to the ground: while their bodies are certainly capable of continuing forward, they have completed the work required and they are ready to rest. The celebration and the joy that ensues, once they are assured of their finish, is something that moves me (usually to tears) and fills me with gratitude for the important role I get to play in their lives.
Then others may approach retirement with trepidation - not always because of the financial uncertainty, but sometimes because of the identity uncertainty: WHO will they BE when they no longer have a job title? WHAT will they do with all of their newfound free time? And WHY?
The fact of the matter is that traditional retirement planning (i.e., planning for retirement, based on the assumption that having enough money is all that is important) doesn’t even touch the conversations needed by someone who is dealing with identity uncertainty. I love stepping in and coaching people through this aspect of retirement planning as well, as they shift away from fear and toward peace and clarity.
And of course there are a million possibilities in between and all around the scenarios above.
In fact, in all my years working with clients, I’ve never seen two people retire with the exact same circumstances.
While money will inevitably be a vital tool in the execution of your retirement plan (just as it was in executing your pre-retirement goals), you’ll need more than money to find fulfillment in retirement.
Finding fulfillment in retirement is a quest that goes beyond identifying a target dollar amount in your bank account and encompasses identifying what that money will do for you and why that matters.
To help you get started on making this mental shift toward a life of fulfillment in retirement, I’ve created a list of five exercises (two and a half here, with the remaining two and a half to be continued in next week’s newsletter):
1. Write Your Retirement Chapter
Consider your life in retirement as a brand new chapter in the story of your life. Where do you live and go? What are you passionate about? What more do you want to learn/see/do that you haven’t been able to yet? Are you a part of new social groups? What do those social groups do and look like? How do you make time for loved ones, friends, and community in this new chapter? If career was important, would you like to continue working on a more flexible basis? Does this mean starting a business?
Reminder: You only get this one life!
And since the first few years in retirement are likely going to be the ones where you can “Go-Go," you’re going to want to start retirement with a plan to maximize the quality of that time.
Two important things to keep in mind while you’re writing your chapter:
Dreaming/Storymapping can feel scary, because you’re allowing yourself to explore ideas that you haven’t yet mapped out a plan for. As you move through the dreaming process, avoid becoming the antagonist of your own story (trust me, there will be plenty of people who volunteer for that role as you move forward). Remember that you aren’t acting on any plans yet, so nothing is ACTUALLY at risk during the dreaming phase. Fully commit to seeing where your ideas take you, and save the editing (read: catastrophizing) for later.
Who else plays a main character role in your retirement chapter? If you have a spouse, a partner, or other family members that will be mapping out their own dreams during this time, consider setting aside some time to share your dreams with each other. For dreams that everyone agrees are worth pursuing, you get to now double the excitement and anticipation of sharing in those future realities together! For areas that may seemingly conflict, you’ll have extra time to consider how to prepare for those things and also avoid the frustration of finding these things out while also trying to transition into a new phase of life.
2. Pick a Date
Once you have a bigger and better vision for your retirement, it’s time to pinpoint WHEN you want to start living that dream!
I encourage my clients to start this process by picking a date based on their dreams and goals in retirement, rather than picking a date based on their financial situation. In other words, start by identifying what retirement age would allow you to accomplish the dreams and goals that are most important to you, instead of picking a date that corresponds to having *x* amount of dollars in savings.
While it’s very tempting to chase numbers (this method feels so concrete and controllable!), I've seen this fail for two reasons:
On one hand, if your number is chosen abstractly ("I want to have $1 million in savings) and not tied to the goals and dreams you have, you *could* end up not having enough to find true fulfillment during your retirement years.
On the other hand, chasing a number could lead you to hanging onto work for longer than necessary, due to the allure of having more for the sake of having more.
Think about it this way:
When was the last time that you felt like you were strong “enough” to stop getting stronger?
Or had reached a perfect physique and no longer needed to pay attention to your health habits?
Never, right?
No matter how good the numbers are, there’s usually always a tug to strive a little more when something more CAN be attained (even if we don't need to). This same "tug" tends to occur when we approach retirement date planning. When you’ve been using numbers as the benchmark for success, instead of determining exactly what those numbers allow you to accomplish, it can be extremely difficult to detach from the idea of sticking around to bank a little “more.” And the price you’ll end up paying will be years of time you could have used to pursue those dreams you had envisioned.
3. Get Organized
The numbers do definitely matter when you start putting plans to pavement, and it's important to note that sometimes the initially chosen date isn't achievable when you begin considering: how much time you have until retirement (to save) and how much time you will then potentially have in retirement (to spend).
So why pick a date first?
Because motivation matters.
Identifying the gap between where you are and where you want to be can help you identify (maybe for the first time!) what it will take to execute your dream retirement plan as soon as possible.
To determine your numbers, you'll first need to get organized.
Next week, I'll be back to offer tips on how to organize your financial information and two things to consider doing if you realize -- after organizing everything -- that you might not be on track for your retirement goals and/or date.
Thanks for reading! Hope to see you back here next week for Part 2!
~ Jess
P.S. Have a more specific question about "How to Retire" or another question you'd like me to answer in a future newsletter? Send me a message and let me know!
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