Published July 3, 2026
The Cost of Success: What 25 Years in Real Estate Has Taught Me
After more than 25 years in real estate, I’ve had the privilege of helping over a thousand buyers and sellers navigate one of the most important financial and personal decisions of their lives. Along the way, I’ve watched families purchase their first beach cottage, move into their dream waterfront home, and create memories that will last for generations.
Looking back, I wouldn’t trade the relationships, experiences, or lessons this career has given me.
But I would be dishonest if I said success didn’t come with a price.
The truth is that real estate demands sacrifices that most people never see.
When someone notices a “Sold” sign in front of a home, they see the outcome. What they don’t see are the weekends spent away from family, the dinners interrupted by phone calls, the vacations shortened by urgent situations, and the countless hours spent behind the scenes keeping a transaction on track.
Over the years, I’ve missed birthday celebrations, school events, family dinners, and quiet evenings at home because a client needed guidance, a lender required information, an inspection issue surfaced, or a deal was hanging by a thread.
There were seasons when I started my mornings with a laptop and ended my evenings the same way.
I’ve searched for new listings before sunrise to help buyers gain an edge. I’ve stayed up late reviewing contracts, negotiating repairs, analyzing market trends, and responding to emails because timing can make all the difference in this business.
While many people are enjoying a Saturday afternoon, Realtors are often showing homes.
While families gather around the dinner table, Realtors are writing contracts.
While others disconnect during vacations, Realtors are answering calls from clients who need immediate answers.
For many years, I told myself those interruptions were insignificant.
“It’s only one phone call.”
“It’s only one email.”
“It’s only one weekend.”
But over time, those moments accumulate.
The public often sees the commission check but rarely understands everything that goes into earning it.
They don’t see the months spent helping buyers who ultimately decide not to purchase.
They don’t see listings that never sell.
They don’t see transactions that collapse days before settlement after hundreds of hours of work.
They don’t see the constant balancing act of inspections, appraisals, financing, title work, insurance concerns, contractor schedules, settlement timelines, and the emotions of multiple families all moving through major life transitions at once.
Real estate is one of the few professions where you can invest hundreds of hours into a transaction and still earn nothing if it doesn’t close.
That isn’t a complaint. It’s simply the reality of the business.
And yet, despite all of it, I still genuinely love what I do.
I love helping a young family purchase their first home.
I love handing keys to buyers who have dreamed of owning a place at the beach.
I love helping sellers transition into the next chapter of their lives.
And I love introducing people to the coastal lifestyle that my family and I have been fortunate enough to enjoy for decades.
What experience has taught me, however, is that success should never be measured solely by sales volume, transactions, awards, or recognition.
Success should also be measured by the moments you protect.
The time you spend with your spouse.
The conversations you have with your children.
The family vacations where you are fully present.
The memories that cannot be recreated.
If I could offer one piece of advice to younger agents entering this profession today, it would be this:
Build a successful business, but don’t lose yourself in the process.
Serve your clients with excellence, but remember that your family deserves the best version of you as well.
Because one day, when you look back on your career, you may realize that while the homes, transactions, and commissions were important, the moments that mattered most happened away from the closing table.
After 25 years in real estate, I remain grateful for every client who placed their trust in me, every family I’ve had the privilege to serve, and every lesson this profession has taught me.
Perhaps the greatest lesson of all is this:
A successful career can help build a life, but it should never replace living it.
As I continue helping clients invest in the beach lifestyle throughout Maryland and Delaware’s coastal communities, I’m reminded that the most valuable investment any of us can make isn’t in real estate.
It’s in the people we love and the time we get to spend with them.
Erik Windrow is a real estate professional with more than 25 years of experience helping buyers and sellers throughout Maryland and Delaware’s coastal communities. When he’s not assisting clients, you’ll likely find him on the water, in the woods, or spending time with his wife, Colleen, and their family while enjoying the beach lifestyle he proudly shares with his clients.
