Getting Your Foot in a Closing Door
Try to imagine a career in which experience is actually a liability, where the better you are at something, the less hireable you become.
Personally, I don't have to imagine it. I spent 15 years in it.
I moved to New York in 2003 to be a copywriter, and soon landed a job at a big legacy brand agency. I thought I'd made it—my foot was in the door, and I was all set. That is until I looked around, and noticed that most every copywriter in their 40s and 50s was being shown the door (or worse, assigned to meaningless accounts where they'd quietly fade into obsolescence). It was ageist and it was unfair, but I came to accept early that it was also inevitable.
You had to be either exceptionally talented or exceptionally savvy at navigating corporate politics to keep working through middle age. I was neither, and I knew it.
One day, I would have to find something else to do.
That day came in 2019. I was on a layover in Dallas, coming home from my honeymoon, when my boss called. “It’s nothing you did wrong, cuts had to be made, if anything changes,” etc. etc. etc. I'd been laid off from what would turn out to be my last full-time advertising job.
I got my salesperson's license knowing almost nothing about the business except that the barrier to entry was low and the earning potential was real. A few people suggested I'd be good at it. That was enough. It's not an easy business to break into—something like 85% of people who try it leave within the first year. But I had burned my ships; there was no going back. I was a real estate agent now, so I'd better make it work.
What I didn't expect was how much of what I'd spent fifteen years learning would turn out to matter here.
The core of an advertising brief is simple: a client has something they want to sell, and your job is to find the insight that makes someone want to buy it. Every product is different. Every buyer is different. You can't use the same approach twice. Real estate works exactly the same way. You meet a client, you learn what they have, you run the numbers and the strategy—and then all of that falls away and it comes down to one thing: finding the soul of the problem and figuring out how to solve it.
The marketing piece transferred too. In advertising you're doing it for someone else's brand. In real estate you are the brand. Every listing, every email, every conversation is a reflection of how you think and what you stand for. All those years of learning how to make things worth paying attention to turned out to be useful after all.
And then there's the client dynamic, which anyone who's ever worked in advertising will recognize. Some clients listen. They hired you because they trust your judgment, and they let you do the job. But others are certain they know better—the apartment is worth more than the comps, the timing doesn't matter, the marketing is fine. You don't get to choose. You make it work either way, and you do the best job you can with what you're given, because that's your job. I'd been navigating that tension my entire career. I just hadn't realized it was a transferable skill.
In advertising, I was competent at the work and genuinely bad at the politics. I never quite figured out how to manage up, how to make the right people feel seen, how to perform the kind of enthusiasm that keeps you in the room. It cost me. But in real estate, none of that matters. What matters is whether people trust you—whether they believe you're telling them the truth, whether they feel like you're actually on their side. People come to you in the middle of some of the biggest decisions of their lives, and what they need is someone who will be straight with them. And in that regard, I might actually be one of the talented ones.
Still, it’s tough to open LinkedIn and see people I started with in the business—genuinely talented people, some of whom were better at the work than I was—posting that they haven't worked in six months, a year, longer. Publicly wondering if they’ll ever work again. They've become the 40 and 50 year old copywriters I watched disappear when I first arrived. It's not a failure of talent—it's an unsavory but inevitable destiny in an industry that eats its young and spits out its veterans.
I’m now seven years into my second act, and I’ve found it infinitely more enjoyable, rewarding, and lucrative than my first—due in large part not just to the similarities, but to the differences as well. No internal politics. No endless conference calls in which you can’t conceal your boredom. No one to impress except the person sitting across from you. Most importantly, the more work you’ve done, the more marketable you become.
Experience isn't a liability in real estate. It's the whole point.