A great conversation is often ignited by a simple question and always fueled by curiosity. Really, it doesn’t have to be profound. It can be something like:

“Do you miss selling real estate?”

Evan asked me that. Big freakin’ deal. It wasn’t the first time (nor merely the 56th time)  I had been asked because after 20 years of a successful career — any career — it’s not common (or smart?) to pack up and leave the business of your own volition. For some reason, however, the way Evan asked, with her inquisitively narrowed eyelids squished around focused eyeballs, made me know that she was really interested in the answer. Or maybe it was because she was paying me for my advice.

“Yes,” I admitted. Then I exercised my breathing-through-my-nose technique to STFU and make sure her question wasn’t just a courtesy.

“Why?” Evan asked, again with the squishy eyelids.

No one would ever accuse me of being a Pollyanna Sunshine (although it does sound like a delicious cocktail). I prefer snark to sap. When I try to provide insight, my mind often jumps to incite. However, as I tried thinking about my life in real estate with the constant interruptions, dizzying market fluctuations, frustratingly inaccurate market prognosticators, smelly carcasses of panacea technology attempts, and know-it-all everyones, I still couldn’t turn those into negatives in my mind. I loved the challenge and grit of it all…even when I sort of hated it.

I do miss my career as a real estate professional, but I do not regret leaving. That was always my plan — 20 years in and then out onto the thin ice for the next exciting chapter.

I admitted all this to Evan.

“Huh?” she wisely asked.

Evan is one of those smart people who doesn’t have to constantly show it. She also knows the difference between simple and simplistic and the power in what lies between. I admire that in her.

What I miss most about life after real estate

5. The money  
I miss the money. I’m not referring to the amount of money, but rather to the transactional way I could easily measure what I thought was my worth — by my commission checks. This is different than how a salaried executive measures her compensation. It’s even different for a salaried executive with a juicy bonus because those bonuses are not necessarily earned (see banker bonuses circa 2008). It’s more like a stripper or a pole dancer or an exotic dancer (only less exotic). What is they say? Gyrate-or-perish is the price-to-sell of the stripper world?

It’s also not the same as selling books and writing, speaking events, television/film/radio shows, advice and time. If you buy my book, for example (Great idea! Buy the book, for example), I get paid whether you read it or not or whether it helps you or not (although it will help you if you do read it).

If you were my client and I facilitated your schlep around town, educated you on your potentially new city, and you loved my service but decided to move to Cleveland, no amount of gyrating would have earned me a commission. Call me a masochist, but I liked that because it made me clearer on how I could help future clients come to that conclusion more succinctly. It even made me analyze new high-tech gizmos to decide whether they would help or harm the process. In every way it helped make me more efficient and a better real estate professional. That, in turn, would earn me more referrals and I would have more time to help clients close great transactions that they were happy about.

I’m sure if I was more clever I could have come up with better ways than commission to measure my effectiveness, efficiency and benefit to clients, but that was an easy way for me and I was too complacent to look for another. I miss that easy cheat.

4. The technology Screen Shot 2014-06-05 at 7.29.48 PM
Technology is not unique to real estate so why would I miss it?

Here’s a secret that many real estate technologists should know: Although the real estate profession seems easy with its low barrier-to-entry and high stakes, it is not as easy at it looks. Investors, who often know a lot about real estate because they bought or sold a home or two, love the real estate sector. Technologists, who often know a lot about real estate because they bought or sold a home or two, target the real estate industry with disproportionate excitement. It just doesn’t seem that complicated so there are constant attempts to build applications, websites or tools that will cause The Big One–the big disruption in the industry that will earn billions and render the industry professionals obsolete. Someday one (or several) might.

Investors are 68% more likely to invest in technology targeted at the real estate industry than any other industry. Courtesy of Sortafacts.

Perhaps the big disruptor has been born already or maybe the stem cell lives on from the hopeful company that came before. Internet graveyards are littered with the rotting carcasses of real estate technology attempts. Much like my classes in Paleontology, I love the lessons they have taught us. I miss testing (and chuckling at) many of these attempts.

Technology has committed justifiable homicide to many industries and professions. However, the real estate profession has had more than it’s share of technology attempts on its life. To survive has taken adaptation that many dead industries failed to consider. Admittedly, the real estate industry should probably consider more adaptation. While watching from a consultative position is interesting, I loved adapting while in the trenches. It was exhilarating and I miss that.

3. The pretty houses and interesting properties Screen Shot 2014-06-05 at 7.33.55 PM
Although pretty houses and lovely environs are nice, they were never the big draw for me in my real estate career. I do miss how houses told me things about people that stoked my curiosity and helped me connect with my clients in profound and lasting ways. They whispered clues to uncommon commonalities that made it easier to know how to relate, help and sell.

Real estate professionals often squandered opportunities to go into clients’ homes. They didn’t always jump at the chance to go with their client into the home of someone with whom they may later negotiate. I miss the amazing ways those voyeuristic adventures helped me help my clients. What other profession gets you so up close and personal? What other profession places you in someone’s kitchen one minute, and across the negotiating table from them another? Turning this voyeuristic opportunity over to technology and online experience often seemed counter-intuitive. This was especially true when reviewing results of scientific studies on sales and negotiation.

I miss the interesting properties for similar reasons and also because they were interesting. Duh.

2. The Drama drama
For most people, real estate is their most personal, high stakes transaction. I loved the resulting drama. I know this is not something most real estate professionals enjoy because they tell me all the time. I’m not talking about loving all bad drama — I loved the good and the bad because I have a secret and sneaking suspicion that one of my stand-out skills was helping turn bad drama into tolerable and tolerable into good. Spouses, partners, children, finance, pets, illness, grooming habits, celebrations, frustrations, sadness, happiness, smugness, suspicion, skepticism (one of my favorites), hate, love — nothing really phased me that much. I generally thought I could help.

I also miss the drama of working with other real estate professionals. Most of the professionals with whom I worked were good. Some were not. Very few were awful. The best ones knew that they could always get better. They knew that good ideas don’t care who they happen to. Even when they were successful they remained curious about what might make them better. They knew that real estate is obviously a competitive industry but less obviously and most effectively a collaborative one.

 1. The Cross-Pollinating   Screen Shot 2014-06-05 at 7.43.32 PM
When you work in a law firm you mostly work with people in the law profession. When you work for a national basketball team, you mostly work with people in the sports industry. I loved variety and mixing and matching lessons from everyone and everywhere — the cross-pollination. Nothing facilitated it more than being in the car or walking down the street every day with different clients from different industries, cultures, sub/counter-cultures. When I followed my curiosity they took me with them into their lives. I miss that.

The lessons you learn are astonishing when you cross-pollinate. The lessons you provide others can provide astonishment for your clients and customers, too. Sharing insights from my special ed teacher client with my software engineer client and cross-pollinating with lessons from my professional athlete and entomologist clients fertilized great ideas. Cross-pollinating was what I loved the most about being a real estate professional.

“If this cross-pollinating is what you loved and miss the most about your real estate career, why don’t you make it a priority?” Evan asked after what I’m sure was my insomnia-curing answer to her simple question of “huh?”

Evan sparked the best idea I never had. Since then, with every project on this new and excellent adventure, cross-pollinating has been (and will continue to be) a priority.

I do miss my real estate love but I do not regret leaving her. Like all great relationships, I’ll try to take what I loved most with me.