15 Years and 15 Lessons in Real Estate: Reflections from Helping 1,500 Winnipeg Families

Logan reminded me last week that I was celebrating my 15-year anniversary in real estate.

Honestly, it feels like just yesterday that I walked around the corner of what was then the largest real estate office in Winnipeg after signing a contract that locked me in for a minimum of two years and thought:

"Oh crap. What have I just done?"

At the time, I had no idea where this career would take me.

I didn't know that I would spend the next fifteen years helping more than 1,500 families buy and sell homes across Winnipeg and the surrounding communities.

I didn't know I would witness some of the strongest real estate markets, some of the most challenging markets, and one absolutely bizarre period we now refer to simply as "the COVID market."

I didn't know I would build friendships with clients, celebrate new babies, attend housewarming parties, help families through divorces, estate sales, relocations, downsizing decisions, and countless life transitions. And I certainly didn't know how many evenings in May and June I would spend answering texts from driveways while waiting for offers to come in.

Fifteen years later, I'm incredibly grateful I found the courage to take that leap. So, in honour of fifteen years as a Winnipeg REALTOR®, here are fifteen lessons I've learned along the way.

1. Always Check to Make Sure the Water Is On

If you know, you know. There are certain lessons in real estate that only need to be learned once.

This is one of them.

2. Keep Your Ego Out of It

Your clients are always better served when the transaction is about them and not about you. Real estate can be competitive. Awards, rankings, production numbers, social media followers. There is no shortage of opportunities to make the business about yourself.

But the best decisions almost always happen when you set your ego aside and focus entirely on what is best for the people trusting you with one of the biggest financial decisions of their lives.

3. Be Kind, Even When It's Really Hard

Kindness costs nothing.

And some of my biggest regrets over the years stem from moments where I was shorter with someone than I should have been. The reality is that we rarely know what someone else is carrying. The stressed-out client. The difficult Realtor on the other side of the deal. The lender, lawyer, or contractor who seems frustrated.

Everyone is fighting battles we can't always see.

Kindness has a way of making difficult situations a little easier for everyone involved.

4. Go Out of Your Way to Help People Entering the Business

I've seen so many potentially great Realtors struggle simply because they didn't have the right opportunities, mentorship, or support.

Real estate can be an incredibly lonely business in the beginning.

Many people enter the profession with talent, drive, and good intentions but never receive the guidance they need to succeed. Whenever possible, help people. Share what you've learned. Open doors.

You never know how much of a difference a small act of generosity can make.

5. Time Block. Then Time Block Some More

One of the biggest lessons I've learned about productivity isn't about working harder. It's about creating space to think.

For me, that means dedicated desk time: usually at least three uninterrupted hours.

No showings. No meetings. No phone calls unless absolutely necessary. Just focused time to think, plan, write, review files, and move important projects forward.

The older I get, the more I realize that clarity rarely happens by accident. You have to create room for it.

6. Follow Up

For the love of God, follow up.

Do what you say you're going to do.

This sounds incredibly simple. Yet it's one of the easiest ways to stand out in both real estate and life. People remember reliability. They remember when you called back. They remember when you followed through. Trust is built one small promise at a time.

7. Build Systems Around Your Weaknesses

I'm almost embarrassed to admit how many reminders exist inside our CRM. But the system works. And that's what matters.

Successful people don't necessarily have fewer weaknesses. They simply build systems that prevent those weaknesses from becoming problems.

My memory isn't perfect. My calendar certainly isn't perfect. But our systems help make sure important things don't fall through the cracks.

8. The Way You Follow Up Matters

Nobody wants to feel like a lead. Nobody wants to feel like they're being sold to. People want value. They want guidance. They want information.

Whether someone is buying a home in Winnipeg, selling a home in Winnipeg, relocating, downsizing, or simply thinking about their options, the goal should always be to help first.

The business follows naturally when you do that consistently.

9. Protect Time for What Matters Most

Not just work time. Family time. Personal time. Reading time. Vacation time. Rest.

Schedule it.

Protect it.

Honour it.

Because success isn't much of a success if you don't have time to enjoy the people you're working so hard for.

10. Real Estate Is Surprisingly Simple at Its Core

People often assume success in real estate comes from:

• The newest CRM

• The fanciest videos

• The latest marketing trend

• The perfect social media strategy

Those things can help. But at its core? Real estate is conversations. Thoughtful conversations. Curious conversations. Conversations where you're genuinely interested in another human being.

If you need more business, figure out how to have more meaningful conversations.

11. Collaboration Beats Domination Every Single Time

Don't be the Realtor who walks into every room trying to prove they're the smartest person there. Nobody enjoys that person. And honestly, they usually aren't helping anyone. The best outcomes happen when:

• Clients feel heard

• Professionals work together

• Solutions are created collaboratively

I've never once regretted choosing collaboration over conflict.

12. Prepare for Tomorrow Before Today Ends

I'm still working on this one. Particularly during the chaos that is late June in Winnipeg real estate. But life gets significantly easier when tomorrow's priorities are already identified before your head hits the pillow.

Even ten minutes of planning can save hours of stress. Plus, in real estate things change by the hour. So preparing for what you CAN in advance makes all the difference when you have to adjust on the fly!

13. Reputation Is Built in the Small Moments

It's not the big wins people remember. It's not the record sales. It's not the social media posts.

It's whether you called when you said you would.

Whether you stayed calm when things got messy.

Whether you treated people fairly when nobody was watching.

Those moments don't feel significant at the time. But over the course of a career, they become your reputation.

14. Never Lose Sight of Why People Are Moving

This business is emotional. How could it not be? We're helping people buy and sell some of the most personal spaces in their lives. Behind every transaction is a story.

A new baby.

A divorce.

A promotion.

A retirement.

An estate.

A fresh start.

Always understand what's driving the decision. Always remember the story belongs to the client, not the Realtor.

15. Build the Tallest Tower

One of my favourite quotes has always been:

"There are two ways to build the tallest tower in town. One is to tear all the others down. The other is to simply build the tallest tower."

Choose the second option. Every time.

There will always be competitors. There will always be criticism. There will always be people doing things differently.

Focus on building something worthwhile instead. Focus on serving people well. Focus on improving your craft. Focus on building your tower.

Bonus Tip

I had a very difficult time narrowing this down to 15. But I also feel that this needs to be said: don’t forget to set money aside for your taxes. And adjust, monthly. Avoid having that scary conversation with your accountant by doing so!

Looking Back and Looking Forward

Fifteen years later, I'm still grateful for that nervous decision made in a Winnipeg real estate office. I'm grateful for every client who trusted me. Every colleague who taught me something. Every teammate who helped carry the load. Every family who allowed me to play a small role in a major life decision.

To my family, friends, clients, colleagues, and teammates:

Thank you.

Helping more than 1,500 families navigate the Winnipeg real estate market has been one of the greatest privileges of my life. And if the last fifteen years have taught me anything, it's that there is still plenty left to learn.

Here's to the next chapter.

Key Takeaways

• Relationships matter more than transactions.

• Reputation is built through consistency and follow-through.

• Systems help overcome weaknesses.

• Collaboration creates better outcomes than competition.

• Real estate is ultimately about people and life transitions.

• Protecting family time is just as important as building a business.

• The best careers are built through continuous learning and service.

Frequently Asked Questions About a Career in Real Estate

What is the most important lesson you've learned in real estate?

That real estate is fundamentally a people business. Relationships, trust, and communication matter more than any marketing tactic or technology.

What makes a successful Realtor?

Consistency, follow-through, curiosity, and a genuine desire to help people tend to matter more than flashy marketing or production numbers. Today, my business is built almost entirely on repeat and referral. Our outbound marketing is almost spent entirely on marketing our listings, not on attracting new business because of this. Doing a quick check of the aforementioned CRM I can see that over 80% of our business has been from repeat or referral clients. If you are a year into your career, and nobody has sent you a referral, then it is time to take a deep dive into ways you could improve and love on your clients even more.

How has the Winnipeg real estate market changed over the last 15 years?

Technology, consumer expectations, and market conditions have evolved significantly, but the importance of trust and relationships has remained constant. It will continue to remain the same. And in today’s market, referrals and repeat clients are still what keep most realtors in business. So work on building those relationships!

What advice would you give someone entering real estate today?

Find good mentors, focus on learning, build systems early, and remember that helping people should always come before chasing transactions. Sometimes that means joining a team. I would say that is likely the quickest way to expedite your success. However, if you are starting with a brokerage that offers really good mentorship and you are a go-getter and okay with rejection (and a lot of it), then branching out on your own might be the better fit. I was the latter.

What lesson took the longest to learn?

That protecting personal and family time is every bit as important as growing a business. There are times that I have missed family events in an attempt to keep a client happy. But in retrospect, those clients did not appreciate me or my time and I think for my own growth, would have been better to let go.

Thanks for reading. I love Winnipeg, I love my people. I hope that has come through!

Your Friend in Real EstaTe,

Jennifer Queen

Phone: (204) 797-7945
Email: Jennifer@QueenTeam.ca

About the Author

Jennifer Queen is the team lead of The Queen Team and has spent the last 15 years helping Winnipeg families navigate some of life's biggest transitions through real estate. Over the course of her career, she has assisted more than 1,500 families with buying, selling, downsizing, relocating, estate sales, and investment properties. Her approach combines market expertise with a deep belief that real estate is ultimately about people, relationships, and helping clients make confident decisions during important moments in their lives.