Here’s the scenario: Over 20 years in the business. Passion still intact. But the pipeline has gone quiet. If that sounds familiar, you’re not alone — and more importantly, you’re not broken.
What you may be missing isn’t a new lead source or a shinier CRM with all the latest bells, whistles and sparkles. What you may be missing is the mindset that separates the agents and brokers who endure from those who simply survive the good years and disappear in the hard ones.
I’ve been thinking about this a lot lately, and a recent conversation with Pamela O’Connor — the founding president and CEO of Leading Real Estate Companies of the World, who built the world’s largest residential network over a 21-year tenure — crystallized something I’ve been teaching for years: longevity in this business is less about tactics and more about how you think.
The trap of perfection
Here’s the first mindset shift every agent and broker must make, and the sooner the better: you don’t have to have all the answers.
Pam put it plainly when she reflected on being named CEO at 35, with zero experience running a major organization. A board member told her, “If we have faith in you, you need to have faith in yourself.” Her instinct, like so many of ours, was to disqualify herself before anyone else could.
Sound familiar?
A lot of people — women in particular (and Pam was the first woman to head a major real estate network) — often wait until they feel ready. But here’s the truth: readiness is a myth. The agents who last aren’t the ones who knew everything on day one. They’re the ones who get comfortable not knowing, ask questions without shame, and hire or partner around their weaknesses.
As Pam said: “It’s important to know what you don’t know.” That’s not a consolation prize. It’s not about what you know, but the discovery of what you still need to learn. Understanding the gaps in your knowledge. That’s the whole game.
Confidence isn’t what you think it is
There’s a mistake that many agents and leaders often make. We’ve too often confused confidence with certainty. The agent who walks into a listing presentation with all the answers isn’t necessarily the most confident one in the room — they might just be the most anxious!
Real confidence, the kind that sustains a 20+ year career, is about knowing your strengths and owning your gaps without letting either define you. Here’s the line I keep coming back to: acknowledging your weaknesses doesn’t make your strengths any less strong.
Pam told a story about a CEO of a large credit union who always kept a professional distance from his employees. At a company event, he shared that as a child, his family was so poor that when his school collected donations for struggling families at Thanksgiving, the basket went to his house. The whole mood of the room changed completely. His team’s relationship with him changed — not because he’d suddenly become more competent, but because he’d become more human. They could relate to him in a way they had never been able to before.
That’s the paradox of vulnerability in leadership. The more you let people see you, the more authority you actually carry.
Real estate is a “Chicken Little” business — play the long game anyway
Every few years, something comes along that everyone is convinced is going to “kill” real estate. The internet. Zillow. The 2008 crash. The NAR settlement. Huge companies buying up just about everyone.
Pam laughed a little when she said: “I did always love to call it a ‘Chicken Little’ business, because, you know, every time some new thing came along, it was going to put us all out of business. But no matter the highs and the lows that you have in the business, over time, real estate is always going to be a great investment.”
The agents and brokers who thrive through disruption aren’t the ones with the best market timing. They’re the ones who understand that you can’t always control the environment — but you can control how you respond to it. When everyone else is panicking, the professional who stays steady, keeps prospecting and maintains an optimistic (not delusional, optimistic) posture becomes indispensable.
This matters in very practical ways right now. With consolidation reshaping the landscape — Compass acquiring major franchise networks, tech companies continuing to push into the transaction more and more — there will be agents and teams looking for a new home. There will be clients who feel uncertain. There will absolutely be opportunities waiting in every disruption for the person paying attention.
Pam shared something Barbara Corcoran once told her: “The opportunity is only there if you recognize it’s there.” She went on to add, “When there’s any big breakup or problem in the business, there’s always an opportunity embedded in there somewhere that.”
Finding those opportunities? That’s where you can shine.
Stop calling yourself a salesperson
Here’s something I’ve been pushing with my coaching students that Pam validated: the language we use about ourselves as real estate agents matters.
A car salesperson doesn’t need a license to sell cars. There’s no continuing education or Errors & Omissions insurance. No car salesman has any sort of fiduciary responsibility. Their job, quite literally, is to sell you whatever’s on the lot. They sure as heck aren’t going to put anyone in their car and drive them to another dealership to shop for cars!
That’s not what real estate agents do.
Real estate professionals carry fiduciary responsibility. We’re licensed, insured and required to keep learning. We’re closer in obligation and expertise to doctors, lawyers and financial planners than we are to any traditional sales role. When we accept the “salesperson” label, we’re volunteering to be measured by a standard that doesn’t fit us — and then wondering why the public undervalues what we do.
Pam framed it this way: “You’re not selling a product. You’re solving a problem.” You’re matching people to outcomes — and that’s a consultative, professional service, not a transaction.
Start there. Change the language. It changes the perception of your value — yours first, then theirs.
What the Long Game Actually Looks Like
Here’s what I want both agents and brokers to walk away with:
Build like you’re going to franchise it. Michael Gerber wrote about this in E-Myth Revisited — when you build a business as if someone else will eventually run it, you systemize, you document, you train. That discipline creates something transferable. Something that holds value that goes beyond you.
Think about succession before you have to. Pam was deliberate about this. She started transitioning LeadingRE well before her 2018 retirement, because she understood that a leader’s last act of service is making sure the next person doesn’t start from scratch. Agents need this mindset too — your database, your relationships, your reputation. Those are assets. Treat them that way from year one so that one day, when you want to retire, you can hand your book of business off in the best way possible.
Your checkbook is not your scorecard. When you’re in a slump, the most dangerous thing you can do is let the dry spell become a story about your worth. It isn’t. Slumps happen to the best in the business. What gets you out is gratitude, self-assessment without self-punishment, and staying visible — not desperate, but visible — in your market.
The agents who will still be thriving in ten years aren’t necessarily the ones closing the most deals right now. They’re the ones who know who they are, stay curious, lead with service, and understand that this business rewards the long game above all else.
As Pam put it: “You can’t always control the environment, but you can control the way you respond to it.” That’s the mindset where careers are truly built.
See the full conversation with Pam O’Conner here!
Darryl Davis, CSP, has spoken to, trained, and coached more than 600,000 real estate professionals around the globe. He is a bestselling author for McGraw-Hill Publishing, and his book, How to Become a Power Agent in Real Estate, tops Amazon’s charts for most sold book to real estate agents.
This column does not necessarily reflect the opinion of HousingWire’s editorial department and its owners.
To contact the editor responsible for this piece: tracey@hwmedia.com
