Two Decades, Still Drawing Deep: The Columnist’s Enduring Well

Celebrating Two Decades of Real Estate Humor: A Look Back at 20 Years of Industry Insights with REM

It’s a milestone that almost slipped past unnoticed, perhaps a casualty of the bewildering, ongoing global distractions, or simply a testament to the capricious nature of memory as the years accumulate. As I sat down to craft this month’s column, the realization dawned: October marked the extraordinary 20th anniversary of this very space. Two decades of consistent writing within a single platform is a remarkable achievement in any writing career, and for me, it represents an unprecedented journey.

My path through the world of words has been varied and extensive. I’ve penned numerous pieces for newspapers, including a long-running weekly humor column that delighted readers in British Columbia, and an even lengthier stint as an entertainment reviewer for the Calgary Herald, a chapter that concluded with my recent return to Winnipeg. Beyond traditional print, I ventured into the digital realm with both personal blogs and those affiliated with newspapers, using these platforms to champion the incredible talent of singers and songwriters, particularly those hailing from across Canada. The sheer depth of artistic skill within our nation continues to inspire and impress.

Yet, this particular column, the monthly REM contribution, holds a uniquely surprising position in my literary endeavors. It has, against all odds, significantly outlasted my own active career in real estate, which spanned a dedicated 11 years. Despite this temporal disconnect, I continue to discover fresh topics and perspectives that I sincerely hope resonate with the dynamic, currently active Realtors navigating today’s complex market. My enduring aspiration is that these words not only provide relatable insights but also, crucially, elicit a much-needed chuckle.

Some might playfully contest the latter point regarding the chuckle-factor, but my commitment remains unwavering. As long as the wellspring of creativity doesn’t run dry, I intend to keep metaphorically “shooting blindly in the dark.” Imagine me in a bucking pickup truck, hurtling over Winnipeg’s notoriously challenging potholes, aiming over my shoulder to hit the bullseye – to unearth that shared observation, that collective absurdity, that universal truth we can all laugh about. In our present era, perhaps more than ever before, the gift of shared laughter is a precious commodity we collectively need and appreciate.

Indeed, the transformation within the real estate industry over these past two decades has been nothing short of astonishing. From communication methods to marketing strategies, and from client expectations to agent branding, the landscape has continually reshaped itself. Join me now on a nostalgic, humorous journey as we revisit some memorable snapshots and timeless observations extracted from the archives of this column:

December 2000 – The Era of Pagers and Client Expectations

Cast your mind back to the turn of the millennium, a time when the digital revolution was still finding its footing, and cellular phones were not yet the ubiquitous mini-computers they are today. For many real estate professionals, the pager was a primary, often insistent, lifeline to clients. This posed unique challenges, particularly in managing client expectations regarding agent availability and communication frequency. It highlighted the ever-present tension between an agent’s need for focus and a client’s desire for immediate updates.

The humor in this Q&A from December 2000 underscores a fundamental aspect of client-agent relationships: the balance of communication. While technology has evolved dramatically, the core issue of managing client expectations around contact and information flow remains a central part of a Realtor’s day. Today, pagers are relics, replaced by smartphones, instant messaging, and email, yet the question of “how often is too often?” persists, merely manifested through different channels. This entry serves as a wonderful reminder of how far we’ve come in connecting, and how some human behaviors, when it comes to service, are timeless.

Q & A: When is the most appropriate time for any one of your clients to use your pager to touch base on your marketing of their home?

a) once a week.

b) once a year.

c) 16 times a day, 30 on weekends.

September 2001 – Navigating Agent Motivation and Office Dynamics

The early 2000s were also a period when real estate offices grappled with innovative—or sometimes, bizarre—methods to ignite their sales teams. Motivating agents to meet targets has always been a cornerstone of brokerage management, but the approaches could vary wildly, often reflecting the era’s corporate culture and a dash of creative desperation. This particular snippet from September 2001 playfully pokes fun at the often-over-the-top incentive programs designed to push agents beyond their perceived limits.

This Q&A highlights the enduring quest for effective motivation in a commission-based industry. While dressing as a pirate might be a charming, albeit impractical, approach, it underscores a deeper truth: agents thrive on recognition, clear goals, and often, a touch of fun. Today, management strategies are far more sophisticated, leveraging data analytics, personalized coaching, and advanced CRM tools to track performance and identify areas for growth. Yet, the underlying challenge of inspiring a team to consistently hit — and exceed — sales targets remains a key focus for any brokerage manager. This reflection reminds us that while the methods change, the human element of motivation is constant.

Q & A: The office has an easily attained sales target, yet once again they are miles away from hitting the bulls-eye. You need a great contest to get them going. Do you:

a) dress as a pirate and offer free parrots to each person making a sale that week,

b) set a goal and provide a free tour of Canada’s Wonderland to anyone that makes it,

c) put everyone on electronic monitoring until they break past the target.

March 2002 – Phrases That Send Chills Down an Agent’s Spine

The market dynamics of the early 2000s, much like today, could sometimes create incredibly fast-paced environments where properties sold almost instantaneously. While a quick sale is generally a positive outcome, an *instantaneous* sale, especially with multiple offers flooding in, can sometimes signal an agent’s worst fear: the property was significantly undervalued. This scenario places the agent in a precarious position, managing the seller’s elation against their own potential professional oversight.

This humorous Q&A perfectly captures the anxieties that can accompany a red-hot market. It emphasizes the delicate art of pricing in real estate – aiming for maximum value without leaving money on the table, or worse, inadvertently triggering buyer suspicion or seller regret. The phrases offered are comedic in their extremity but touch upon real agent fears: questioning commission, hidden seller secrets, or unrealistic advertising demands. In today’s data-driven world, agents have access to far more sophisticated comparative market analyses, but the human element of client interaction and managing expectations in a volatile market remains paramount. This snapshot serves as a funny, yet poignant, reminder of the pressures agents face when a deal goes from good to almost too good to be true.

Q & A: Your new listing has had 16 offers since you put the sign up 15 minutes ago. There is a slight possibility you undervalued it. What DON’T you want the sellers to say?

a) “So the commission is based on time on market?”

b) “Quick, let’s sign one of these bad boys before somebody notices we’re tenants!”

c) “You’re still going to advertise in every major state and province, aren’t you?”

October 2004 – The Enduring Power of “Location, Location, Location”

The timeless adage “location, location, location” has long been the undisputed mantra of the real estate world. It speaks to the fundamental truth that a property’s geographical placement profoundly influences its present value, future appreciation potential, and overall resale appeal. In 2004, as now, understanding and articulating the nuances of a property’s location was, and still is, a critical skill for any successful Realtor. Beyond the basic address, it encompasses proximity to amenities, quality of schools, accessibility to transport, and the overall character of the neighborhood.

This column entry playfully veers into the whimsical with its “gingerbread house in a German forest” analogy. While hilariously outlandish, this comparison cleverly reinforces the core message: in the real estate market, conventional attributes and practical considerations almost always triumph over fantasy. It underscores the importance of agents guiding clients toward sound investments based on tangible market factors, rather than romanticized, albeit charming, idealizations. In the modern era, “location” has expanded to include digital connectivity, community vibe, and even environmental factors, but the principle of assessing a home’s surroundings as a primary value driver remains absolutely sacrosanct. This piece, therefore, serves as a delightful reminder to always ground advice in reality, even when dreaming.

When buying a home, one must consider the many varied attributes that might ultimately enable ongoing appreciation of value and foster strong resale appeal. Location is often the leading barometer of these attributes.

Being a home built of gingerbread, out in the middle of a German forest, featuring jolly folks in lederhosen playing accordions might also be a barometer of sorts, but we’ll stick to conventional examples for this particular piece…

July 2005 – The Quirky World of Realtor Mascots and Branding

The mid-2000s saw a growing trend of real estate agents attempting to differentiate themselves in a competitive market through personal branding, sometimes leading to rather unconventional choices. The desire to stand out, to be memorable, and to forge a relatable connection with potential clients is a powerful drive in commission-based sales. This often manifested in posing with pets or embracing unique personas. This column entry from July 2005 delves into the humorous, and sometimes baffling, world of Realtor mascots, questioning the fine line between creative branding and simply overextending one’s marketing efforts.

The thought of a chimpanzee as a mascot, as humorously suggested by the Barenaked Ladies song “If I Had $1000000,” perfectly encapsulates the imaginative extremes agents might consider. While the idea of a trained chimp drafting contracts is pure fantasy, the underlying sentiment speaks to the desire for an edge, a way to delegate mundane tasks, and free up time for more lucrative activities like golf. Today, personal branding has exploded with the advent of social media, offering Realtors unprecedented avenues to showcase their personality and expertise. The challenge remains: how to create authentic, professional, and memorable branding without veering into the territory of the absurd. This section playfully reminds us that while creativity is key, sometimes the simplest, most human connections are the most effective in an industry built on trust and relationships.

I can understand the philosophy of posing with the family dog, and even the odd cat or Toucan if the intent is to try and establish common ground in the often unforgiving, competitive world of commission sales. But is there a point where, as a sales agent, you just plain over-extend the market potential of your mascot?

Like The Barenaked Ladies sang: “Haven’t you always wanted a monkey?” Man, a chimpanzee would be the cat’s pajamas as a mascot! You could train a smarter one to do your more menial work, like measuring homes and drafting contracts, leaving you way more time to be on the golf course!

And so, our retrospective journey through two decades of real estate humor and observation comes to a close. Reflecting on these past columns, it’s clear that while the tools, technologies, and market conditions have undergone monumental shifts, the fundamental human elements of the real estate profession remain remarkably constant. The drive to connect with clients, the pursuit of successful transactions, the challenges of market valuation, and the need for a good laugh amidst the pressures – these are the threads that weave through the fabric of every Realtor’s experience, from 2000 to the present day.

It’s been an immense privilege to share these thoughts, sometimes insightful, sometimes just plain silly, with the dedicated professionals of the real estate community. My hope is that these snippets, both old and new, continue to provide a refreshing dose of perspective and a much-needed moment of levity. The creative well, though occasionally a bit dry in the Winnipeggian winter, always seems to find new springs. And rest assured, as long as there’s a story to tell or an absurdity to highlight, this column will keep rolling, aiming to hit that humorous bullseye.

Thank you for being part of this incredible 20-year journey. Here’s to many more years of navigating the exciting, challenging, and endlessly fascinating world of real estate, one chuckle at a time.