Retirement isn’t a finish line; it’s a new beginning. Many retirees feel lost at first because they haven’t thought about what comes after leaving their job.
As a part of my series about the “5 Things Retirees Say They Wish They Were Told Before They Began Retirement” I had the pleasure of interviewing Dawn Fleming.
Dawn Fleming is a former attorney turned lifestyle alchemist, dedicated to helping people break free from traditional retirement myths and design a life they never need a vacation from. As the host of the Midlife in Paradise YT, Channel she shares insights on how to Retire Rich, with topics such as financial freedom, purposeful living, and reinventing oneself at any age. Having successfully reimagined her own retirement, Dawn now inspires others to do the same — turn the Golden Years to your boldest years.
Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I started my career in real estate then became an attorney in my mid-30’s, building a life that, on paper, looked like success. But something was missing. In the legal industry, I realized how freedom slips away while chasing the traditional definition of success. I didn’t want to wake up one day, years later, wondering why I hadn’t really lived — worse yet DIE at my desk.
That realization led me to a complete reinvention. I traded legal documents for freedom, moved to Mexico, and built a new life — one where my home literally funds my retirement. Now, I share that journey with others, helping them see that retirement doesn’t have to be about winding down — it can be about waking up to a whole new adventure.
Can you share the most interesting story that happened to you since you started your career?
One of the things I’ve come to embrace is Change, and how adapting is perhaps the most valuable skill we can learn. My husband Tom and I were doing very well financially, living in California. Virtually overnight, we experienced financial devastation in the aftermath of the 2008 crash. We moved and started over from scratch in Florida and regained success. Once again, a loss caught us by surprise in 2018. Our multiple 6 figure income stream vanished overnight, but this time we were prepared.
Fortunately, we diversified our income by investing in an income producing property in Mexico. The house had some design flaws but was located on a double Caribbean Oceanfront lot. We didn’t buy what it was, instead we had a vision of what it could be. We saw an opportunity that so many people had overlooked. We turned the house into a boutique hotel with robust income stream that funds our retirement. Now, I teach others how to make their retirement assets — both tangible and intangible — work for them.
Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or take-away did you learn from that?
I guess it would be about honesty, how being brutally honest can lead to good things. My first job as a lawyer came from an informational interview with a former law profession. I went to see him for career advice. I told him things I’d never have shared in a job interview. That job was an incredible start my legal career and it would never have happened had I held back the truth about what I wanted in my career.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
The one person who’s made a huge impact is my husband, Tom. Before we met, he was a single dad who raised two sons on his own. Back to the honesty, we were friends first. I shared dating horror stories with him, things I’d never have said on a date. He appreciated my candor and direct approach. He took care of me after major surgery, very early on in our relationship. He also treated his mother so well after his father dies (before we met). He’s experienced a business failure several years before we met. He didn’t have a bad attitude, but later confessed that he had no dreams. Life had beat him down.
Seeing his journey firsthand gave me a deep understanding of how challenging it can be to plan for the future when life’s responsibilities and setbacks keep stacking up. Then we experienced setbacks as a couple. Instead of throwing in the towel, we reimagined what retirement could look like. We made strategic choices, found creative ways to fund our lifestyle, and proved that you don’t need millions to retire well — you just need the right strategy.
What advice would you suggest to your colleagues in your industry to thrive and avoid burnout?
Stop chasing the traditional definition of success and start designing a life that works for you. Burnout happens when we stop dreaming and invest too much time climbing up the wrong ladder.
For me, avoiding burnout meant stepping off the hamster wheel of overwork and choosing a life that prioritizes freedom and fulfillment. Whether that means setting boundaries, taking breaks, or shifting your entire career path, remember: success isn’t just about money — it’s about time, energy, and joy.
What advice would you give to other leaders about how to create a fantastic work culture?
Encourage reinvention. Too many workplaces box people into roles and expectations that don’t leave room for growth. If you want a thriving culture, you have to give people space to evolve.
For me, creating a great life after leaving law meant stepping outside the usual playbook. Leaders should foster an environment where people feel safe to pivot, experiment, and redefine success. That’s where true fulfillment happens.
Retirement is a dramatic ‘life course transition’ that can impact nearly every aspect of one’s life. Obviously everyone’s experience is different. But In your experience, what are the 5 most common things that people wish someone told them before they retired?
- Retirement isn’t a finish line; it’s a new beginning. Many retirees feel lost at first because they haven’t thought about what comes after leaving their job.
- You don’t need as much money as you think — but you do need a plan. Smart lifestyle choices can stretch your savings further than you realize.
- Your social circle will change. Work friends fade fast, so building new communities is crucial.
- Health matters more than wealth. No amount of money can make up for neglected health.
- You might outlive your plan. Retirement can last 30+ years. A flexible strategy is key
Let’s zoom in on this a bit. If you had to advise your loved ones about the 3 most important financial issues to keep in mind before they retire, what would you say? Can you give an example or share a story?
- Passive income is the real security blanket. Whether it’s rental properties, dividends, or a side hustle, ongoing income trumps a big savings account.
- Geography is a financial decision. Where you retire determines how far your money goes. Mexico, for example, offers a high quality of life at a fraction of US living costs.
- Flexibility is wealth. Being adaptable — whether with spending, location, or investments — keeps you financially secure.
Example: Our property in Mexico not only provided us with an incredibly beautiful place to live, but also funds our retirement through rental income. That’s a strategy more retirees should explore.
If you had to advise your loved ones about the 3 most important health issues to keep in mind before they retire, what would you say? Can you give an example or share a story?
- Live proactively, not reactively. Get checkups, monitor health markers, and invest in wellness before small issues become big ones. Sit less, Move MORE — every day!
- Healthcare quality and access matters. Research how and where you’ll go for care. In Florida, it could take 4 to 6 months to get a medical appointment. Mexico, for instance, offers extremely accessible, and excellent quality private healthcare at a fraction of US costs.
- Mindset affects longevity. Retirement is a mental game as much as a physical one — staying engaged, connected and positive keeps you healthier.
Example: I know many retirees in Mexico who feel younger because they’re more active, social, and engaged than they ever were while living in the US.
If you had to advise your loved ones about the 3 most important things to consider before choosing a place to live after they retire, what would you say? Can you give an example or share a story?
- Cost of living: Your chosen location should align with your financial reality. Many retirees find they can live better abroad than in the US.
- Lifestyle fit: Do you love city energy or small-town charm? Beachfront relaxation or mountain adventure? Paradise is internal, where ever you go there you are! Focus on what brings you joy.
- Community: Moving is easier when there’s a built-in support network. Look for places with like-minded retirees or strong expat communities.
Example: I chose Mexico because it checked all three boxes — affordable, vibrant, and filled with a welcoming community. It turned my retirement from “settling down” into a full-blown adventure.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
I believe that we are all more wise and powerful then we can imagine. One thing I love about Mexico is how much they respect and honor their elders. Conversely, the US values youth and often dismisses older people. I would love to start a movement to tap into, share the wisdom of retirees. It is such a waste to see people with so much to share die without passing on what they’ve learned. Once these elders are gone, it like entire libraries have burned to the ground.
Is there a particular book that made a significant impact on you? Can you share a story?
The book that made the biggest impact in my life is Rich Dad, Poor Dad by Robert Kiyosaki. Once I understood his Cashflow Quadrant the entire trajectory of my career changed. I grew up in a blue collar family that only knew trading time for money to earn income. I thought I’d “arrived” after becoming a highly compensated professional (attorney). Everything changed for me after that book, as I sought out, pursued and eventually succeeded in generating passive and leveraged income. All children should be taught that information.
Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?
Whatever you vividly imagine, ardently desire, sincerely believe, and enthusiastically act upon… must inevitably come to pass! — Paul J Meyer This is a quote that hangs in my office — always.
I had the privilege of hearing Mr. Meyer speak many years ago. His is truly an incredible, profoundly moving Horatio Alger story. In some circles, he’s known as the Grandfather of Personal Development.
What is the best way our readers can follow you on social media?
The best way to connect is my YouTube Channel: https://youtube.com/@midlifeinparadise
Thank you for these fantastic insights. We wish you only continued success in your great work!
Dawn Fleming: 5 Things Retirees Say They Wish They Were Told Before They Began Retirement was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.