Recent studies reveal a startling truth: only 5% of current retirees say they’re actually “living the dream,” while 19% describe retirement as a nightmare.
These sobering statistics highlight why waiting until traditional retirement age to pursue your dreams might be the biggest financial planning mistake you can make.
At Calamita Wealth Management, we believe in living your retirement dream now, not postponing happiness until some distant future that may look very different than you imagine.
As financial advisors, my team and I go well beyond just the numbers when leading and providing oversight and guidance to our clients.
That’s because your life is about more than just money.
It’s a given that we provide top-notch planning and investment management, but if we’re not also helping to improve our clients’ lives, the best-laid plan and money management don’t matter.
We take financial planning further.
Yes, we help you secure your long-term financial future, but we also make sure your right-now life is what you want it to be.
We look at your big-picture goals and find ways for you to start living your retirement dream now.
Let’s talk about how we do that.
The Work-Life Balance Crisis
The traditional retirement model is broken.
Americans think they need $1.46 million on average to retire comfortably, yet less than half of retirees believe they saved enough.
Meanwhile, one in four Americans aged 50 and older don’t believe they’ll ever be able to retire at all.
This retirement crisis has sparked a revolution in how we think about work-life balance and living your retirement dream now.
More people are embracing mini-retirements, sabbaticals, and lifestyle design strategies that allow them to experience retirement joys while still earning income.
The rise of remote work has made living your retirement dream now more achievable than ever before.
Research shows that increased income only correlates with happiness up to about $105,000 annually.
Beyond that threshold, additional wealth brings diminishing returns on life satisfaction.
This finding challenges the endless accumulation mindset and suggests that once you’ve reached financial stability, prioritizing experiences over savings might be the smarter choice when living your retirement dream now.
What Do You Want Your Life To Look Like?
Financial conversations can often be left-brain dominant.
But since money impacts every area of your life, it’s critical that financial discussions also include your hopes and dreams for life.
That means we need to dig into the emotional side of our thinking where decisions are actually made.
One simple example of how we help clients improve their lives is by guiding them to uncover their specific desires for quality of life, which include tangible goals (what would you like to have?), conceptual goals (what would you like your life to be like?), and freedom goals (what would you like to be able to do?).
Studies show that individuals who live a purpose-driven life are happier and healthier on average than those who don’t.
Not only that, they also live longer.
Oftentimes, the busyness of work and family gets in the way of actually fulfilling some of these lifestyle objectives.
We often ask our clients to share their definition of work-life balance and gauge whether or not they have achieved it, and the answers can be eye-opening.
Many people don’t even know where to begin when faced with the above questions and will sometimes provide a surface answer, such as “I’d like to travel” or “I’d like to spend more time with my family.”
These are great starts, but we need to go deeper to get to the core of what will truly enhance your life, looking at the why behind what it is you want to do.
In exploring the questions and exercises that would help us have more meaningful conversations with our clients and get them on the path to living their ideal life, I started by asking these questions and doing these exercises myself.
I brainstormed a list of all of my values and beliefs and eventually narrowed it down to my top five.
Three of the top five were adventure, freedom, and family—all essential components of living your retirement dream now.
Breaking Free from the “Someday” Mentality
Too many people postpone their dreams with the dangerous word “someday.”
But what if someday never comes, or arrives in a form you didn’t expect?
The key to living your retirement dream now is adopting a sub-goals strategy.
Instead of waiting to buy that beach house in retirement, start by vacationing there annually.
Rather than postponing all travel until you stop working, negotiate remote work arrangements that let you explore while earning.
This approach allows you to test-drive your retirement dreams and refine them based on real experience, not fantasy.
According to the Department of Labor’s retirement resources, phased retirement is becoming increasingly popular as workers transition gradually rather than stopping abruptly.
This trend reflects a growing understanding that retirement isn’t a destination but a journey that can begin long before you leave the workforce entirely.
Practicing meditation or mindfulness can have significant impacts on your overall sense of happiness and well-being.
Letting go of rigid expectations about what your life should look like can be a powerful first step in living your retirement dream now.
Principle In Action
As you can imagine, with COVID-19 upending all our lives last spring, it also impinged heavily upon these three values.
My wife and I began looking for ways to creatively and safely travel during those uncertain times, which led us to look into RVs and eventually renting a camper van.
This decision perfectly exemplifies the concept of living your retirement dream now rather than waiting for some distant future.
We spent five days exploring and camping in small mountain towns in western North Carolina and loved the freedom and adventure it provided.
It was also important for us to have our kids spend more time outside in nature—just like we did as kids.
Some of our adventures included zip-lining, rafting, and exploring the many waterfalls in the area.
Our evenings back at the campground included swimming at the campground pool, which both of my kids (ages 13 and 7) looked forward to every night.
After dinner and our swim, we rode bikes, built a campfire, and roasted marshmallows to make smores.
Wanting to continue our adventures of exploring not only NC but other states as well, my wife and I researched the feasibility of purchasing a camper van.
As a frugal person in general, let alone a financial advisor, I wanted to ensure that it wouldn’t impact us negatively from a financial standpoint or hinder our regular monthly savings contributions.
With that in mind, I began to explore the option of renting out the van while we weren’t using it.
It turns out there are various websites, like rvshare.com and outdoorsy.com, that make it easy to rent out your camper van and cover the monthly costs.
This creative financing solution allowed us to enjoy a retirement-style lifestyle of adventure and travel without waiting decades or sacrificing our financial security.
Although we chose the camper van route to realize some of our lifestyle objectives, another creative option could include renting a house or condo for a month, or even the summer, at your favorite travel destination.
I also have a client who is currently exploring a locum tenens in another country, something he and his wife originally thought was only reserved for their retirement years.
With the rise of remote working over the past year, it’s become more acceptable and doable to work from anywhere, so why not live part of your retirement dream now?
Practical Strategies for Living Your Dreams Today
Successfully living your retirement dream now requires both financial strategy and mindset shifts.
Here’s a framework we use with clients to make it happen:
Financial Framework: Start by determining your “enough” number—the amount you need for security without endless accumulation.
Once you’ve secured your baseline, redirect excess funds toward experiences rather than just savings.
Consider creative income streams that align with your passions, like consulting, teaching, or monetizing hobbies.
These can fund your dreams while keeping you engaged and purposeful as you’re living your retirement dream now.
Time Management: Negotiate for flexibility in your current role.
Many employers now offer sabbatical programs, compressed work weeks, or remote work arrangements.
Even a four-day work week can dramatically improve your ability to pursue retirement-style activities.
Consider phased retirement where you gradually reduce hours over several years rather than stopping abruptly.
Health and Wellness Integration: Don’t wait until retirement to prioritize your health.
Build sustainable habits now—regular exercise, stress management, preventive care—that will enhance both your current life and future retirement.
A healthy 50-year-old has more retirement options than an unhealthy 65-year-old.
Common Obstacles and How to Overcome Them
Several barriers often prevent people from living their retirement dreams now.
Here’s how to address the most common ones:
Fear of Not Having Enough: This paralyzing fear keeps many people in perpetual saving mode.
Work with a financial advisor to calculate your actual needs versus wants.
Often, you need less than you think, especially when you factor in reduced expenses in retirement.
Workplace Culture: Some organizations discourage work-life balance.
Start small by using all your vacation days, then gradually negotiate for more flexibility.
Document how your productivity remains high or even improves with better balance.
Analysis Paralysis: Waiting for the “perfect” time means never starting.
Remember, living your retirement dream now doesn’t mean abandoning all responsibility.
It means thoughtfully integrating dream elements into your current life.
Social Expectations: Society often judges those who prioritize lifestyle over traditional career advancement.
Surround yourself with like-minded people who understand that success isn’t just about money and titles when you’re living your retirement dream now.
What Are Your Dreams?
All this to say…what are some of your dreams that you can start pursuing now?
What action steps do you need to take to make them a reality?
What are the reasons and values behind what you want your life to look like?
You may be surprised to realize that some of your goals can be accomplished sooner rather than later.
Living your retirement dream now often comes in the form of just slowing down for a moment.
It means realizing that the laundry list of stuff to buy, deadlines to meet, and things to do is important, but so is connecting with and learning from those around you.
The great news is, you don’t have to wait until retirement to do that.
Here are some achievable “now” goals to consider: Take a month-long working vacation to test a potential retirement location.
Start that passion project as a side business while you still have steady income.
Volunteer one day a month for a cause you care about.
Learn a new skill or hobby you’ve always wanted to pursue.
Schedule regular mini-retirements or sabbaticals every few years.
The beauty of living your retirement dream now is that it doesn’t require waiting for permission or the perfect moment.
If you would like help diving into the questions that will help you lead a fulfilling life or help you think outside the box, schedule an introductory phone call using our online calendar or reach out to us at (704) 276-7325 or todd@calamitawealth.com.
If you’re an existing client and would like to dig deeper into this conversation about living your retirement dream now, let us know.
About Todd
Todd Calamita is the founder and managing principal of Calamita Wealth Management, an independent, fee-only wealth management company located in Charlotte, NC, serving people locally and across the country, that focuses on providing wealth management solutions to affluent individuals over age 50 and their families.
Todd has more than 20 years of experience in the financial services industry and is passionate about helping people have a better life by designing and implementing customized financial plans that bring clarity and confidence.
Todd is a CERTIFIED FINANCIAL PLANNER™(CFP®) and CERTIFIED DIVORCE FINANCIAL ANALYST® (CDFA®) and holds a Bachelor of Business Administration from Ohio University and a Master of Business Administration from the Weatherhead School of Management at Case Western Reserve University.
He has authored a book, Plan Smart: Conquering 10 Common Money Traps, as well as numerous articles on wide-ranging personal finance topics, from taxes to retirement accounts.
He has also been featured in a Financial Boot Camp TV series as a volunteer showing people how to make smart decisions with their money.
When he’s not working, you can find Todd spending time with his wife, Teresa, and their two sons, Colin and Cameron.
He enjoys rock climbing, swimming, and traveling, and he has a black belt in Tang Soo Do, a Korean martial art.
To learn more about Todd, connect with him on LinkedIn.
