This year, I’ve embedded myself back into the day-to-day happenings in the business—both on the staff side and on the agent side. 

I’m not actually selling homes and actively working with clients, but I’m out shadowing appointments with agents three times or so each week, sitting at open houses, participating in buyer consults, and going to listing appointments

A few weekends ago, I was humbled—deeply. 

Our inside sales team booked a listing appointment at a home located in a prestigious suburb of Boston. The notes provided by the inside sales team stated that the seller said he thought his home was worth $1.6 to $1.7 million. The home had seven bedrooms, was situated at the end of a cul de sac, and was being freshly painted top to bottom, both inside and out. The seller was super motivated and wanted the home on the market and sold ASAP so he could move out of state

I was reading these notes with Jason Posnick, and we both thought, “Easy! We’ve got this!” We have agents that work at that price point, and we knew no one in our local market had a better marketing plan. We kept reading to discuss which agent would be the best fit for this appointment. 


The thing that was most important to the seller was hiring an agent who had a deep understanding of the local market and a serious track record of sales in that community. In the past three years, we have only sold five homes in this community. And we represented the buyer in each of those transactions. 

But as we all know, there are ways to navigate this. And I wasn’t worried at all. 

We selected an agent to cover the appointment and got to work. The marketing package was ready to go, the CMA was completed masterfully, with four comps, all within a half mile and sold within the past four months—and they showed the $1.6 to $1.7 million range the seller was expecting—all with five or more bedrooms and around the same square footage. One was even on the same street. 

The research was completed for schools, local highlights, country club details, market data. 

You name it, we had it. 

The appointment

On the day of the appointment, we got to the house, and I suddenly had a lump in my throat. The exterior of the home was rough! The painters didn’t scrape before painting, nor did they replace any rot. The windows were original to 1962. The landscaping hadn’t been attended to in a very long time. 

When we walked in, it got worse. Someone told the seller to paint everything white—and I mean everything. There wasn’t a drop of color left anywhere in the house. The bathrooms—all five of them—were either original or from 1985. The hardware floors were in rough condition; all clearly needed to be sanded and refinished. We even learned that the seller’s last dog had an affinity for claiming various spots in the living room. Those various spots were permanently stained. 

Normally, this wouldn’t be an issue. But the comps in our CMA were all beautifully renovated and maintained. 

Now, there were some offsets. This property was over three acres with the most bucolic private pond and a red barn for horses. It sat at the very end of a cul de sac. And it had a first-floor bedroom suite for someone who needs multigenerational living. But would these things offset the home’s general condition? 

Honestly, I didn’t know. We didn’t know the market well enough. We left that day without a signed contract and scheduled a return visit for a few days later. Hours of time spent poring over MLS and market data, and I still had no real clarity on how to price this home or whether the seller’s number was realistic. 

I knew how we’d market it and knew the strategy, and I was passionate about all of that. But as we sat in that appointment, and I knew there was a smidge of doubt and hesitation in my voice. The seller said he still had one other agent to meet with and would then decide. I didn’t even present the contract at that appointment. This was not at all how I do things. 

I walked out and said to the agent with me that we weren’t going to get this one—that the seller definitely picked up on the lack of confidence in my voice. Sure as shit, Sunday afternoon, we got the call. He loved us, it was a hard decision, he loved our marketing plan and saw our passion for the industry, blah, blah, blah… but he went with an agent who lives in town and who sells 20 homes a year in that town. We didn’t deserve that listing. And truth be told, I was kind of relieved as I wasn’t confident in pricing. 

But we still lost. We finished in second. And that stung. I hate to lose.

The silver lining to second place

You might be wondering why I chose to share this. It’s not because I think my sales skills are phenomenal or because I never lose. Because I don’t think my skills are phenomenal, and I do lose. But trust me, there’s a silver lining to coming in second. And I’d like to share that perspective with you today. 

When you finish in second place, you’re presented with a unique vantage point. You’re close enough to taste success yet far enough to still feel the hunger. 

It’s a delicate balance that can push you to analyze, learn, and adapt. 

Consider the example of famous Olympic sprinter Usain Bolt. In the early stages of his career, Bolt faced numerous defeats. But did he let those second-place finishes define him? Absolutely not. Instead, he used them as stepping stones. 

He meticulously studied his races, recognized areas of improvement, and trained even harder. The result? He became the fastest man in the world, shattering world records and leaving his competitors in the dust. 

You see, when you come in second, you gain insights that the winner might overlook. You become acutely aware of the gaps in your strategy, the areas of improvement in your execution, and most importantly, the mindset shifts that are required to get to that coveted first place. 

But here’s the catch: How you rebound from finishing in second is entirely up to you. You have the choice to view it as a step back or as a step up. You can either let it define your future or use it as a defining moment that propels you to greater heights. 

Our industry is no different. The real estate landscape is, as you know, ever-evolving, especially right now. And the path to success is paved with challenges. 

Finishing second in a deal, missing out on a prime listing, or not hitting your quarterly targets can be disheartening. But remember each of these moments offers a lesson, an opportunity to refine your approach, and a chance to come back stronger. 

Your resilience, determination, and willingness to learn from your second-place finishes are what will set you apart. These experiences will mold you, shape you, and prepare you for the many wins that lie ahead. 

Embrace the power of second place. Let it fuel your passion, drive your ambition, and be the catalyst for your success. 

Remember, it’s not the one lost that defines your future but how you choose to respond to it.