A Personal Note from Diamond Real Estate Group
This is hard to say, and even harder to type, but here it is: I failed.
Let’s start from the beginning.
2025: A Year of Change, Loss, and Growth
2025 was a rollercoaster, full of surprises, challenges, wins, losses, pivots, heartbreak, and joy. I began the year in California, laying my first cousin to rest after a tragic car accident that took his life on my birthday. The loss was devastating, but we celebrated his life and legacy, and being surrounded by family during that time meant more than I can put into words. We lovingly called him J3, and his memory will forever stay with us.
January also marked a period of significant changes emanating from Washington that directly impacted the stock market and the real estate market. As a leader at Diamond Real Estate Group in Orlando, navigating the constant shifts in market conditions required focus, adaptability, and strategic thinking. Like many of you, we faced uncertainty, but we made it through.
Family, Travel, and Life Beyond Real Estate
In February, we leaned into joy where we could. My husband’s work with the Milwaukee Brewers took us on an incredible journey during an exciting season that ended in Los Angeles against the eventual World Series Champions, the Dodgers. Travel, family time, and baseball became our reset.
Spring brought one of the greatest gifts of my life: my mom moved to Orlando. Having her less than ten minutes away has been truly life-changing, and in May, we started a new tradition with a Mother’s Day mommy-and-me trip to France. Bread, cheese, wine, laughter, and memories I’ll cherish forever.
The Hustle Behind the Scenes
Summer was fun, but exhausting. My son thrived on the baseball field, earning trophies left and right, while my daughter crushed her first competitive season as a level 2 gymnast. Between practices, tournaments, and competitions, I became a full-time chauffeur. (If there’s a trophy for parents who give up every free weekend, please let me know, I’ll drive anywhere to pick it up.)
Like many working parents and entrepreneurs in Central Florida, I was balancing business, family, and ambition, all while trying to show up as my best self.
The Real Failure I Didn’t See Coming
Fall is when things shifted.
As the kids started a new school year and I adjusted to having a 3rd and 4th grader, I went into overdrive professionally. With an ever-changing Orlando real estate market and a deep commitment to my clients, I planned, replanned, strategized, and re-strategized, determined to guide every client toward success.
And we did have wins.
We also learned hard lessons.
But we never gave up.
Here’s the failure: I lost time I can never get back.
I was present in body, but not always in mind. When I look back at photos and videos, I see myself on my phone, with an iPad in my lap, or mentally somewhere else. I missed moments with my kids during the years that matter deeply.
I failed them.
Accountability, Not Sympathy
I’m not sharing this for pity or praise, but for accountability.
So many of you are clients of Diamond Real Estate Group, colleagues, friends, fellow entrepreneurs, and parents. My ask is simple: help keep me accountable.
Real estate is my passion. My clients are the reason I love what I do. But if I lose sight of the most important people in my life, my not-so-little monsters, then none of the success matters.
And many of you already know the answer to that question:
There isn’t a point.
Looking Ahead to 2026 with Intention
Thank you for always giving me the space to be transparent and authentically me. Thank you for trusting me, supporting me, and being part of the Diamond Real Estate Group family.
As we step into 2026, my hope for you is the same as my hope for myself:
more presence, more laughter, deeper connections, strong family bonds, meaningful friendships, and unlimited success.
Cheers to a new year and everything still to come. 💎
📲 Call or text 407-797-2931
📧 Email tiphany@dregorlando.com
🌐 Visit www.dregorlando.com to start your home-selling journey.
Meet Tiphany
Orlando Real Estate Pro
Buying a home is one of the most important purchases one can make, but it doesn’t need to be complicated. I’m Tiphany Weeks, the founder and broker of record for Diamond Real Estate Group. While traveling the world as a baseball wife we moved around a lot; and it wasn’t always easy. I realized the search to find a realtor that knows exactly what you need can be a very daunting task, so I decided it was time to create a new solution for helping people find their way home.
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