Five Questions I Wish I Had Asked Before Retiring
What I learned in my first 14 months of retirement—and what I wish I had known sooner
If the word “Retirement” is pounding a rhythm in your mind 24/7, you have landed yourself in exactly the right place.
When I retired 14 months ago, I reveled in the fact that alarm clocks were no longer jolting me from a deep sleep, and morning coffee instantly became a cherished ritual.
What surprised me most, however, was the immediate stripping away of roles, responsibilities, and routines that had defined my life for more than three decades.
And what remains is you, looking at yourself in the mirror and wondering:
What now?
And for many people:
Who am I?
Retirement is far more than a financial decision.
It is a profound life transition that affects your routines, relationships, identity, and sense of purpose.
To help prepare for this monumental shift, here are five important questions worth asking before you retire.
Question #1: How Much Money Is Enough?
Looking Beyond the Numbers
Let’s begin with the question that drives most retirement decisions.
How much money is enough?
If I paid attention to retirement predictions and financial gurus, I would most likely be advised to retire at the ripe age of 95 and not one day sooner.
Thankfully, I listened to the rhythms of my heart, ran the numbers, and stepped away when I realized I had enough of systems that no longer nourished my spirit.
Financial Calculators Are Only Part of the Story
If you type “retirement calculator” into Google, you’ll find no shortage of tools designed to estimate financial readiness.
No matter which one I tried, the message often felt the same:
“Please, please don’t retire. You are clearly not prepared at this time.”
But calculators cannot account for lifestyle choices.
When you travel, do you prefer a tent campsite or a luxury hotel?
Do you shop at thrift stores or designer boutiques?
Do you enjoy eating out regularly, or are you happiest preparing meals at home?
Financial tools can estimate costs and expenses, but only you can determine what truly matters in the daily workings of your heart and soul.
On paper, I never should have retired at age 58.
In real life, I couldn’t be happier with the decision.
Three Changes That Helped Us Thrive
After making the decision to retire, we adjusted a few areas of our lifestyle to reduce financial stress.
1. Set a travel budget and stick to it.
My husband and I now enjoy one overnight getaway each month instead of several longer trips. We still enjoy time away together while saving for larger adventures down the road.
2. Pay close attention to date budgets.
Each weekend, we set aside $50 for dates.
One of our favorites is grabbing a slice of our famous local pizza, ordering a side salad, and watching ferries and ships pass through the inlet.
Total cost: about $30.
That still leaves room for ice cream, gelato, or another small treat.
3. Make sure the money is already in the bank.
This one is simple.
If you don’t have the money for a purchase, wait.
It’s easy for credit card spending to gradually stretch beyond what feels comfortable in retirement.
Anything worth having is worth waiting for until it can be paid for in full.
So, How Much Money Is Enough?
At a minimum, you’ll want to comfortably cover:
• Housing expenses
• Utilities
• Food
• Transportation
• Medical expenses
• Travel and recreation
• Taxes and insurance
Having emergency savings available can also provide peace of mind.
And if you plan to work part-time during retirement, that can significantly change the financial equation.
Ultimately, your retirement portfolio is just that, yours.
Only you can decide when the numbers, your lifestyle, and your heart align.
For me, that moment arrived much sooner than the experts recommended.
It remains one of the most satisfying decisions I’ve ever made.
(The experiences shared here are my own and are not intended as financial advice or a sole guide to retirement decisions.)
Question #2: What Do You Value Most: Time, Energy, Health, or Money?
Before you decide to retire, ask yourself this simple question:
What is more important to me:
• my time
• my energy
• my health
• or my financial security
This question alone can help clarify whether you are ready to step into retirement.
There is no correct answer. I know several people who absolutely love their work and have no desire to retire. My Dad worked until he was 80 years old and passed away at 87. He found deep purpose and meaning in his work throughout his life.
In my own life, age 58 became the point where time with loved ones, exploring new paths, and following shared dreams and passions outweighed all other factors.
Question #3: What Brings You Joy Within Your Daily Rhythms?
This question deserves careful consideration when creating new daily rhythms after work.
Ask yourself:
What are three things I enjoy most in my daily life?
Friendships? Social circles? Exercise? Travel? Hobbies? Quiet moments?
Your answer will help shape your retirement experience.
If you are highly social, have you made plans for maintaining friendships after leaving the workplace? Many people find that work relationships naturally fade over time.
If you enjoy traveling, have you budgeted for it? Will you travel alone, with a partner, or with friends?
How you choose to spend your days will shape your sense of joy, peace, and fulfillment.
Consider creating a list of 20 things that bring you joy.
Keep it close before and after retirement.
It can serve as a daily reminder of what matters most.
Question #4: Have You Made a Bucket List? If So, Is It Realistic?
Do you have things you have dreamed of doing in retirement?
Take a few minutes and write down three things you hope to accomplish in your first year.
Then ask yourself:
Have I budgeted for these activities?
Do I have the health to enjoy them fully?
Dreams can be an essential part of a fulfilling retirement, but timing matters.
Some experiences are best enjoyed when your energy and health are at their strongest.
My husband and I created one-year, three-year, and five-year goals based on one significant factor: health.
As the years pass, energy levels naturally shift.
Planning this way helps ensure that dreams are not only imagined, but actually lived.
Small goals and steady planning can lead to some of the most meaningful experiences of your life.
Question #5: How Open Are You to Change?
I’m here to say it plainly:
Everything will change once you retire.
And yes, I mean everything.
Once you are no longer bound by the rhythms of daily work, life takes on an entirely different shape.
Time stretches. Decisions shift. Identity begins to reorganize.
Sometimes this feels like freedom.
Other times, it can bring uncertainty or discomfort as you adjust to the unknown.
It’s important to give yourself three essential things:
• Time
• Patience
• Presence
Retirement is not learned in a moment.
It takes time to feel at ease in this new way of living.
Like many people, I began working in my teens and continued for more than four decades.
That is a long time to shape your daily rhythms and often define yourself through work.
It takes time to redefine who you are outside of it.
I’ve read that it can take months, even years, to adjust to retirement fully.
Whatever the timeline, the transition deserves patience and care.
To ease the shift:
Begin small daily rituals that nourish you
such as walking, being in nature, or enjoying a hobbySpend time journaling about your experience
What feels good? What feels challenging?Try something new that interests you
Creating something new can refresh your sense of identity
Most importantly, allow yourself to feel everything that comes with change.
You have made a major life transition, and it deserves compassion.
Here is a free Retirement Readiness Assessment to further support your decision-making:
FREE Retirement Readiness Assessment
Final Thoughts
Retirement is not simply the end of a career.
For many people, it is the beginning of something entirely new.
It offers opportunities to redefine what you value most and decide how you wish to spend your time, energy, and attention.
In the words of Joseph Campbell:
“We must be willing to let go of the life we’ve planned, so as to have the life that is waiting for us.”
How you choose to live each stage of your life is your decision and yours alone.
I would love to know which of these five questions resonates most deeply with you.
May your journey unfold with grace and beauty every step of the way.
With much love and gratitude,
Lis 💖
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