The Retirement Transition Plan: Day One.

By Richard Rosso | February 9, 2023

The Retirement Transition Plan: Day One is a blueprint for moving forward in your new retirement adventure.

First, keeping a foothold on the habits of a working past is a vital psychological comfort factor for new retirees. Those who passionately redefine the worth of their human capital and find ways to share years of wisdom ease gracefully into the next phase.

However, it all begins with an attitude inspired by gratitude from day one.

As a recent retiree so beautifully shared: “What’s the experience of life but what you do at the dawn of difference between last night and today?”

Second, retirement is a chance to begin again. It’s like hitting the reset, not a snooze button. Imagine going to bed as an employee or a business owner and awakening with a fresh, new mission ahead.

If one chooses to take on the challenge.

Interviewing retirees about their first hours has been a passion of mine. Understanding how a written retirement strategy takes on dimensions is an ongoing curiosity for this financial planner. Seeing a financial plan live and breathe is exhilarating for me.

Ultimately, there’s nothing eventful about the rituals of new post-work life. And there lies the beauty. Retirees crave simplicity, peace, and enrichment. Their rewards stem from taking successful actions and consistently refining them to fit a current retirement lifestyle.

Seeds planted in the past forge current behavior in several cases back to childhood. Consequently, a robust harvest springs eternal. Retirees return to the field, the familiar, for years after that first day (I document that, too).

Third, Retirement Transition Plan: Day One doesn’t require math. No formal retirement strategy review. Retirement rolls in quietly and with minimal fanfare. After all, the heavy lifting of working on a traditional retirement plan began years earlier.

Looking back, a comprehensive financial plan was the best flight plan for a well-timed emotional leap from an accumulation to a distribution mindset. Yes, the plan is reviewed regularly. But not today. Not on the Retirement Transition Plan: Day One.

Over the decade, I documented hundreds of first days. Scribbled lines and faded sentences were kept close by.

Last, several themes consistently rise to the top, and as a result, my goal is to share experiences with future retirees and get them started on the right foot from the get-go.

The alarm clock remains essential.

“I’m keeping the buzz alive,” said a retiree.

The alarm clock is no longer a drag but an awakening in a greater than literal sense. A clarion call to days filled with activities that grow in richness and variety. Unlike the previous weekday, when the alarm meant the same old grind. From now on, the alarm is an ally, not the enemy. It now represents a schedule under a retiree’s control.

An employer or a business no longer takes up precious hours. Time takes on renewed significance, especially in the morning. Research on cooking or painting classes, plans for upcoming trips, family visits, and friends.

All accomplished in the calm, in the early. Along with fresh, hot coffee.

“When the alarm goes off, it reminds me I still count.”

Ad for RIA Advisors. Need a plan to protect your hard earned savings from the next bear market? Click to schedule your consultation today.

Retirement Transition Plan: Day One Lesson: I’m cash-flow sensitive.

Right out of the gate, spending awareness is significant, primarily through the first year. Getting real with the numbers is raw and elemental. Retirees feel secure in their past planning if they prep for monthly or quarterly spending without the assistance of electronics.

“I used to keep a simple budget like this when I worked my first job.”

A heightened sensitivity to spending is a powerful technique used to reduce the emotional vulnerability of shifting from an accumulation mindset to a distribution way of thinking. Boundaries are formed and monitored using pen and paper.

Specifically, I recommend recent retirees use the budget books available at for six months before their official retirement date. The company has been marketing the same simple budgeting product since 1940 for under 10 dollars.

“I go through my budget weekly. On a Sunday. It only takes 10 minutes. It keeps me on track. I feel better doing it.”

Retirement Transition Plan: Day One Lesson: Goal setting is just as important today.

“My goals aren’t driven by a job or career anymore. They’re for my family and me.”

Frankly, you would think goal setting is happily left behind along with the company break room’s rancid coffee, but it isn’t. A surprising number of people new to the retirement game continue establishing benchmarks. The difference is how goals center around self-improvement (maintaining mental acuity), family gatherings (grandchildren-focused), and creative efforts (cooking, painting).

In addition, several want to establish businesses and invest in new ventures. Goal setting is still relevant.

Following a theme of returning to pen and paper for planning, I suggest retirees go big and splurge on a diary designed by Best Self Co. to tackle the day-to-day actions required to meet life goals. As a self-journal, it warrants personal reflection in the lined morning and evening gratitude sections.

It’s a bit pricey, but I’ve found it worth the investment, especially with daily flexible space available to sketch ideas, an area to document daily targets, and lessons learned.

The journal is designed for 13 weeks. However, I’ve seen retirees use it for more extended periods.

“It’s rewarding to wrap up the day with positive notes I create.”

advertisement for our bull/bear report newsletter. click to subscribe today

Retirement Transition Plan: Day One Lesson: I cringe at my grandparents’ stories and experiences.

“He sat in that chair in front of the TV all day.”

Personally, I recall my grandfather’s retirement years and grimace. After he left his job as a janitor for a public junior high school, he lost his purpose even though he was cleaning floors and bathrooms for a living.

The first day of retirement is replete with promises and maintaining the passion for keeping them.

As a result, the essential personal vow is never to allow the days to roll into each other. A weekend will ‘feel’ like a weekend. The rest of the week, a schedule shall exist. Retirees create boundaries to ensure they’re not cascading into a dark hole where time gets lost.

Candidly, the thought of days bleeding together and becoming indistinguishable scares every new retiree I engage.

“Now that I’m retired, I’ll never say that I don’t know what day it is or that Saturday & Sunday feel like any other day.”

The Retirement Transition Plan: Day One Lesson: The wish list is a reality. Light and heavy.

“My wish list is simple. I don’t want to stress over it.”

On average, wishes are light and revolve around strengthening connections. Moreover, simple efforts outweigh complicated projects by at least 3 to 1. The first wishes are intimate and bring together friends or family for food, conversation, and memories.

The big wishes, which tend to be expensive or require formal planning, are sketched out for future deliberation. Just one or two broad sentences to describe each heavy item on the wish list. That’s it. However, nothing is big on this day.

The first day.

I prefer to sit on the big items on my bucket list until I get a better handle on my real expenses in retirement.”

The Retirement Transition Plan: Day One Lesson: It’s clean up and clean out time.

“See that garage? I’m going in! If I don’t come out by noon, call 911!”

There’s a passion for reducing clutter, organizing, and purging unnecessary items. This first-day delight fascinates me the most. There is a semblance of calm and control with every outdated document shredded and old article thrown out or put aside for charity.

Four out of ten retirees I interviewed continued these organization exercises for a couple of years and then took it to the next level by downsizing their primary residences. There was no regret, only relief.

“First, I realized I didn’t need all this stuff. Then I realized I didn’t need a big roof to keep the stuff under.”

The Retirement Transition Plan: Day One Lesson: The first communication out of bed is with…

“I hear this voice inside. I think it’s mine. Maybe younger. I’m reviewing like a movie in my head, my entire career and how quickly the time goes.”

Flashes of self-reflection and rhetorical questions bounce around in a retiree’s head all the first day and throughout the first six months. Thoughts of the past are tucked in-between current minutes. They pop up out of nowhere. I can’t pin down the triggers for these intermittent thoughts.

Some describe the brief, memorable periods as “being in a daze,” but in a good, settled way (with a slight melancholy.) A playback of the actions, the mentors that got them to this spot on the first day of retirement life.

I encourage new retirees to explore these feelings by writing about them in a journal. The exercise has turned out to be impactful.

Several retirees have turned journals into an ongoing project, a family legacy. They chronicle handwritten thoughts and memories created in retirement and before.

“I have lessons to share that my grandkids or their kids will find interesting. Who knows? I may influence someone generations from now.”

banner ad for SimpleVisor, our do it yourself investing tool. sign up for your free trial now

The Retirement Transition Plan: Day One Lesson: Don’t push me!

“I keep a schedule, but I’m not in a hurry.”

The day-one retiree is extremely sensitive to feeling rushed—pressure to act blossoms anger and frustration.

Sure, the passion for a schedule still exists. However, strict deadlines are avoided early in retirement. Occasionally, those still working, including family members, will comment to me how retired parents are “on their own time clock,” and it’s challenging to deal with their attitudes. Some of the stories are entertaining, but there are times when real conflict arises.

Remember, these reactions warrant patience and understanding as, eventually, these intense feelings dissipate. Seasoned retirees admit to stubbornness and overreaction to even informal deadlines dictated by others, as they recall unpleasant or similar episodes with former bosses or management.

“As the years passed, I didn’t mind having deadlines again. Mostly because they were mostly my choice or for causes I believed in.”

Undoubtedly, the first day of retirement is unlike any other but similar to the work days past.

As one cycle ends and another begins, the bridge that connects a life remains relevant through habits and rituals forged long ago.

And it all leads to that first day.

Talk with an Advisor & Planner Today!


Richard Rosso, MS, CFP, CIMA is the Head of Financial Planning for RIA Advisors. He is also a contributing editor to the “Real Investment Advice” website and published author of “Random Thoughts Of A Money Muse.”  Follow Richard on Twitter
Customer Relationship Summary (Form CRS)

> Back to All Posts