The Question I Dreaded (That Nobody Asked) When I Became a Real Estate Agent at 56

When I became a real estate agent at 56, there was one question I was sure would expose me as a complete beginner. I spent far too much time worrying about how I’d answer it, only to discover something surprising about starting a new career later in life.

When I got my real estate license at 56, there was one question I was absolutely dreading.

“How long have you been in real estate?”

I was sure someone was going to ask it. A prospective buyer, a seller sitting across the kitchen table from me, or, heaven forbid, another agent standing nearby while I was trying very hard to look like I knew exactly what I was doing. 

Remember sitting in sixth grade social studies when you hadn’t read the assigned chapter, avoiding eye contact with the teacher and silently repeating, Don’t call on me. Don’t call on me. Please don’t call on me?

It was a little like that.

Except I was 56 years old, there was no Chapter 7 to hurriedly skim under my desk, and the person doing the asking might be deciding whether to trust me with a several-hundred-thousand-dollar transaction.

So, yes. I had answers prepared. I had rehearsed them in the car. I wasn't going to lie about being new, obviously, but I also wasn't exactly looking forward to announcing that I had been a real estate agent for approximately twelve minutes.

And then something unexpected happened.

Almost nobody asked.

The Advantage I Never Saw Coming

Over the next eight years, I can remember being asked how long I'd been in real estate only a couple of times. It wasn't until I'd been doing this for a while that I realized why.

People assumed I'd been doing it for years.

There it was: another unexpected advantage of starting real estate later in life. My age apparently gave me the appearance of experience before I'd actually earned it.

Is that fair? Probably not. We make assumptions about people based on age all the time. A 25-year-old agent may have years of experience and dozens of successful transactions behind her, but someone may still assume she's new. Put a woman in her late 50s in the same room with a folder and a confident expression, and apparently people assume she's been selling houses since granite countertops were considered an upgrade.

Who knew gray hair came with complimentary credibility?

Looking Experienced Isn't the Same as Being Experienced

There was, of course, one small problem with my newfound appearance of authority.

I really was new.

My age couldn't teach me a contract. It couldn't tell me what to do when an inspection went sideways, how to handle a difficult negotiation, or what to say when a client asked a question I'd never encountered before.

I still had to learn how to do the job, and I took that responsibility very seriously. I studied. I prepared. I asked questions. I leaned on my broker and more experienced agents when I needed help. I learned as much as I could about the property before an appointment and tried to anticipate the questions someone might ask me.

And when somebody did ask me something I didn't know, I eventually became perfectly comfortable saying, “You know, I'm not sure, and I don't want to misspeak. Let me double-check and get back to you.”

Nobody fainted. Nobody snatched the keys out of my hand. Nobody pointed dramatically across the room and yelled, “I KNEW SHE WAS NEW!”

They simply expected me to get the answer and follow up.

So I did.

You Don't Have to Introduce Yourself as the New Agent

I think this is something many new agents get wrong, particularly those of us who start later in life. We're so conscious of everything we don't know yet that we assume everyone else is thinking about it, too.

They probably aren't.

That doesn't mean you should ever misrepresent your experience. If someone asks how long you've been licensed or how many homes you've sold, answer honestly. Trust is far too important to begin a relationship by pretending to be something you're not.

But honesty doesn't require an apology.

You don't need to walk into every interaction wearing an imaginary sandwich board that says, HELLO. I AM NEW HERE. PLEASE LOWER YOUR EXPECTATIONS ACCORDINGLY.

Instead, be prepared. Know the property. Learn the market. Understand the documents you're using. Ask thoughtful questions. Listen carefully. Do what you say you're going to do. And when you don't know something (and trust me, that will happen), know whom to ask or where to find the answer.

That's professionalism.

And here's the part I didn't fully appreciate when I was 56: professionalism doesn't begin the day you get your real estate license.

You Aren't New at Everything

When you start a new career later in life, it's very easy to focus on everything you haven't done yet. You haven't written a contract. You haven't held an open house. You haven't negotiated an inspection. You haven't sat across from sellers and explained why their beloved house probably isn't worth what Zillow says it is.

All true.

But by your 50s or 60s, you've probably spent decades doing other things that matter enormously in this business. You've walked into rooms where you didn't know anyone. You've handled uncomfortable conversations. You've dealt with difficult personalities. You've learned how to listen. You've solved problems that didn't come with an instruction manual. You've made mistakes, recovered from them, and gone back to work the next morning.

Chances are, you've learned how to talk to people, read a room, and show up when you've promised to be somewhere. And you've probably learned that sometimes the smartest person in the conversation is the one willing to say, “I don't know, but I'll find out.”

Those things don't make you an experienced real estate agent on your first day.

But they do mean your first day isn't really Day One.

You're bringing decades of experience with you. It simply came from somewhere other than real estate.

Maybe They're Not Thinking What You Think They're Thinking

Looking back, I find it funny that I spent so much time worrying about that question.

I was concerned that people would see my age and wonder why I was starting a new career so late. I worried they would discover I was new and immediately question whether I could handle something as important as buying or selling their home.

Instead, quite often, my age seemed to communicate something entirely different. Experience. Competence. Maturity. The assumption that I'd been around long enough to know what I was doing.

In the beginning, some of that credibility was borrowed. The outside packaging had gotten a little ahead of the contents. But I kept learning. I kept showing up. Transaction by transaction, the experience people sometimes assumed I had became experience I'd actually earned.

So if you're considering real estate after 50 and worrying about walking into a room as “the new agent,” here's something I wish I'd known when I was 56:

You may feel brand new. That doesn't mean everyone else sees you that way.

Sometimes getting older comes with advantages nobody bothered to put in the brochure. Apparently, this is one of them. And if a few gray hairs come with complimentary credibility, I say we've earned it.

Believing in what's possible,

Gwen Holloway
Founder, The Sage Agent™

p.s. If you're wondering if real estate could be your next chapter, join the waitlist for The Sage Agent™ Signature Course, created specifically for women 50+ who want to build a relationship-based business that feels authentic, sustainable, and true to who they are.