The Art of Balancing Opportunity and Principle: “Is the Juice Worth the Squeeze?”

Starting my career as a commercial real estate broker, I quickly realized that every deal that came my way had the potential to be a lifeline—keeping the lights on and the bills paid. But, as any newcomer to the field knows, not all deals are created equal. I had my fair share of challenging deals that made me question the effort I was putting in. This is where a valuable lesson, imparted to me by Aaron Sklar, came into play and has stuck with me throughout my career.

I was in a vulnerable position when I first ventured into the world of commercial real estate. I was just beginning to build my pipeline and establish my career, and I needed money to keep things moving forward. The deal I was working on had been listed for around 10 months after a buyer fell out of contract, and it was far from a straightforward fix.

It was during this trying time that Aaron approached me with a question that would become a guiding principle in my career: “Is the juice worth the squeeze?” This seemingly simple question resonated with me, prompting me to take a step back and reassess my approach.

In this industry, especially when you’re just starting out, it’s easy to become emotionally invested in a deal. I found myself pouring an extraordinary amount of time and energy into trying to salvage a deal that might not be worth it in the long run. This is where the importance of staying true to your principles becomes evident.

I realized that I had been dedicating too much time and energy to a deal that was becoming a black hole, siphoning away valuable resources I could have been using to generate new business and build my future. It’s a common pitfall for new brokers: letting emotions and pride cloud your judgment. My experience taught me that in this competitive industry, it’s crucial to be honest with yourself and make the hard decisions.

Closing the deal was not the end of the story. While I did eventually manage to close it, I realized that I had sacrificed valuable time, energy, and even my sanity (albeit in jest) in the process. In the world of commercial real estate, time is your most valuable asset. If you’re not using it to benefit your future business, you risk getting stuck in the cycle of chasing diminishing returns.

So, what’s the key takeaway from my experience? It’s the importance of asking yourself the hard question: “Is the juice worth the squeeze?” It’s a question that every broker, new or experienced, should keep in mind. It’s a reminder to stay true to your principles and not let ego and pride drive your decisions. It’s a lesson in balancing opportunity with practicality, ensuring that you’re investing your time and energy where it truly matters for your long-term success.

In the fast-paced world of commercial real estate, where every deal can feel make or break, remember this valuable lesson. Keep your eye on the bigger picture, and make sure that the “juice” is worth the “squeeze.”


Jack Lambert