10 Years in Real Estate... 10 Lessons Learned...

Real Estate Agent with RE/MAX Revolution

Wow, a decade ago I walked out of that testing center with a passing grade on my very first try... a Realtor ready to make it big. Did I think I'd be reflecting back on that test ten years later?

The timing of this anniversary comes at a perfect moment, when I've been wrestling with the idea in my life of how we "manifest our own destiny" verses acknowledging "God being in total control." I've had amazing discussions with some trusted friends over the past week about that topic because it keeps coming up in conversation! I have to believe it was preparing my mind and soul to grapple with that concept concerning my big-picture career... did my "vision" get me here or am I just enjoying the "path" that God has set before me? 

Speaking of The Path, there have been quite a few lessons along it (concerning both life and real estate, but both boil down to PEOPLE and RELATIONSHIPS) so I'll hit my top 10 list here... I've been pondering these all day long... in no particular order:


1. People will surprise you, if you give them the chance. 

One of my best memories is one of my Sellers who received the inspection reports a day late from their Buyers. The contract says they have to do nothing on that document because the window to turn it in was missed. I explained that to my client and he responded: "Jay, if it were me, I would want these things taken care of and we want to deliver a good and safe home to these new owners. We will do what's on this list." Yes sir. They are probably still enjoying that dose of karma they gave out that day.


2. The agent you work with on the other side of the deal MATTERS.

Pros want to work with pros because that's how deals get closed. It's in the best interest of MY client if THEIR client is represented well. I love to play with the best. 


3. Value your time.

I find it easier to assess a buyer who needs to save more money before rushing out to buy a home or maybe refer that client to an agent further south of me if I don't want to make that drive over and over. Years ago that may not have been the case. I have worked with so many A+ clients over the years I know what to look for and those are the experiences I want to keep adding.


4. Communicate. Even when there's nothing to talk about.

Clients like to hear from us. (And I'll go so far as to say our People in our lives do too...) So talk to them often. And if you have to make up a reason to call or text, that's fine. It will get the ball rolling and they will know you care and are thinking of them. Relationship.


5. The fun happens AFTER closing!

An agent friend told me a story of once a deal was done they never wanted to see their clients again. Next! Like a machine. "Why would you want to have lunch with them?" .... Um, that's the point, right? I love the after-party... client events, pop-bys, seeing client-friends in public with kids. It's great! 

Best story: an out-of-town couple moves here and after closing I get invited to their wedding! Turns out, I'm the ONLY non-family member there at the intimate ceremony! So honored!


6. Agents don't appreciate how EMOTIONAL this experience is.

Really. We do this every day. We push papers and make calls and "do the deal" but this is their LIVES and their MONEY and their FAMILY. We are agents and stay ABOVE the emotion but I feel it's good to swim in that sometimes and remember what our People go through. So when they are having a moment, we have to show a little grace and understanding. Empathy and love go a long way in this business. 


7. Veterans can spot a rookie, no matter how much you try to fake it (and that's ok)

I appreciate a hard-working hungry new agent. They often have been through the classes and read the books and are ready to "win that offer!" but the street-smarts just isn't there when they are on the phone or we go through their paperwork. I can spot them off the bat. They try so hard, and I won't call them out, rather I will encourage them along and help them through when needed, but I wonder if I was so obvious ten years ago when I submitted paperwork to those listing agents and called them to ask questions. (yep)


8. Know your numbers.

Tracking. Spreadsheets. Leads. Referral sources. Days on market. Then study it and make decisions based on it. How do you advertise based on where your referrals come from? How many leads to get to a closing? Metrics are the engine that we can tinker with to improve our performance.


9. Take time away.

Go to the kid's sporting event. Take the long weekend with the family. Run in the morning and start work a little later. Whatever works for my formula. My family is my Why and real estate has given me the flexibility to be present at more of my kids' events than I ever thought possible. I would never trade those for "one more deal done" and often that's been a factor, but when my Why is clear, those choices are easy.


10. Enjoy the game.

Love what you do (whatever it is). My FAVORITE part of any deal is the moment the offer is accepted. I get chills and butterflies in my stomach every time like a little boy... I can't wait to call the client! I'll get them on the phone and have them get their Person on the line too (not to give away my news yet with a monotone voice) then when they are both on the line BOOM! and I sit back and drink it in as they scream and freak out over the offer being accepted!! PURE JOY! I'm telling you, if you're having a bad day, just make a call like that and you're on a Joy-High the rest of the day!



These last ten years have had so many experiences. I started in the down market of 2010 and now the booming market of 2020. I've been blessed to help over 200 families into new homes in Kansas City, all with the same RE/MAX office, filled with agents that I would call my family.

Often I have used this career to facilitate my Big Why, which is to allow time to raise my five kids and invest the time with them that they deserve, which means I have chosen not to sell 100 homes a year nor work 60 hours per week.

But now these kids see a world where you don't have to sit at a cubicle or punch into a time clock or call in to some manager and ask if you can stay home today from work... there is a better way. I LOVE they my kids are understanding that.


The next decade will be filled with new challenges, some of which I'm certain will be a portfolio of investment properties, ramping up sales as the kids get older, and maybe bringing older ones into the mix in the next couple years or so.... Real estate has been good to me, and I'm thankful that God has provided his direction and guidance on this amazing journey. More to come!

Posted by

  Jay O'Brien, Kansas City : Social Media Guy (RE/MAX Revolution)Jay O'Brien
RE/MAX Revolution, Kansas City, Missouri



Comments (15)

Laura Cerrano
Feng Shui Manhattan Long Island - Locust Valley, NY
Certified Feng Shui Expert, Speaker & Researcher

This is your soul; this is part of your soul and part of who you are and people don’t get that.

Sep 23, 2020 09:38 PM
Jeff Masich-Scottsdale AZ Associate Broker,MBA,GRI
HomeSmart Real Estate - Scottsdale, AZ
Arizona Homes and Land Group/ Buy or Sell

All great decade observations Jay O'Brien and having some fun along the way is ROCK SOLID! Congratulations. Jeff 

Sep 23, 2020 10:03 PM
Carol Culkin
Diamond Partners Inc - Overland Park, KS
Overland Park Residential Real Estate

I would say that this is an excellent summary. Every day is a learning experience, every transaction is different even at the 10 year mark but you covered some of the good stuff to point out. Congrats on TEN. 

Sep 23, 2020 10:08 PM
Richard Weeks
Dallas, TX
REALTOR®, Broker

Great information, thanks for sharing.  I hope you have a great day.

Sep 24, 2020 02:08 AM
Nina Hollander, Broker
Coldwell Banker Realty - Charlotte, NC
Your Greater Charlotte Realtor

You nailed it, Jay. I learned all those lessons many years ago, having been in the business some 27 years now, and I continue to learn all those lessons each and every day. Congratulations on your 10th anniversary in the crazy profession!

Sep 24, 2020 04:13 AM
Nick Vandekar, 610-203-4543
Long & Foster Real Estate Inc 610-225-7400 - Devon, PA
Selling the Main Line & Chester County

Adore your post, it is all so true, I cannot pick anything out to say this was my favourite as I agree totally with everything you say. Well done, here is to your next ten.

Sep 24, 2020 04:23 AM
Michael Jacobs
Pasadena, CA
Los Angeles Pasadena 818.516.4393

Hello Jay - congratulations on reaching/passing that ten-year mark in real estate.  There are many lessons to be learned.  What happens in preparation for passing that state exam is only the beginning.  

Sep 24, 2020 07:50 AM
Joan Cox
House to Home, Inc. - Denver Real Estate - 720-231-6373 - Denver, CO
Denver Real Estate - Selling One Home at a Time

Jay, it is fun to look back and see what lessons you have learned over the years.  You are spot on, and thanks for sharing.

Sep 24, 2020 07:54 AM
Kathy Streib
Cypress, TX
Home Stager/Redesign

Hi Jay- You truly did nail this!  I love #8 because agents are told all of the time about keeping in touch etc, but you have to know your numbers too. 

Sep 24, 2020 04:49 PM
Anna Banana Kruchten Phoenix Broker
HomeSmart Real Estate - Phoenix, AZ

WOW Jay O'Brien love, love love your ten points!  This is a MUST READ for all agents. I bet that so many of us will relate to it.  I certainly do! Bravooooooo! And here's to your next 10 years. 

Sep 25, 2020 01:51 PM
Kris Collis, Associate Broker
Smart Way America Realty - East Stroudsburg, PA
Professional Results you Expect 570-801-5525

Jay, very wise for 10 years in the business, congrats on a well-deserved post. 

I agree with Anna, this content is very important for all agents regardless of years in the biz.

Sep 25, 2020 03:16 PM
Brenda J. Andrew
Professional Realtor in Conroe/Willis, TX

You have a lot of wisdom from your first 10 years Jay.  Congratulations!  There are some lessons I wish I could have learned during that time for myself.  This is great information for new agents just starting out.  I love the part where you managed your time with your family, and are setting that example for them.  This is one of the biggest lessons to learn because this business can consume you if you let it!  Have a great day and congrats on the well deserved feature!

Sep 26, 2020 04:31 AM
Kat Palmiotti
406-270-3667, kat@thehousekat.com, Broker/REALTOR® - Kalispell, MT
Helping your Montana dreams take root

What a fantastic look back over the last 10 years. I started at the end of 2010 as well, although not really full-time dedicated for a few more years. BUT.. I can say I learned all the same things. Re: #5 - I have made some great friends and think #5 is one my favorite parts!

Sep 26, 2020 04:50 AM
Chris Ivy
Ivy Vine Investments - Memphis, TN
Sell Your House Fast For Cash In Memphis Tennessee

Jay I always like getting advice from the Vets who have been doing the job longer than me.  I enjoyed this post man!

Sep 26, 2020 09:18 AM
Lyn Sims
Schaumburg, IL
Real Estate Broker Retired

I'm not going to agree with #6 - we have to keep a lid on their emotions but maybe slow down a little with the lingo.

Sep 27, 2020 12:09 PM