Empathetic systems, even better than flowers.

When I was running my real estate business in my late 20’s, early 30’s, my process for getting projects completed largely consisted of remembering what needed to get done and jotting down ‘to-do’ lists on pieces of paper I had lying around. It is still a toss-up as to which is more incredible: how much I managed to accomplish this way or how much I could have accomplished with better systems.

My then business partner- 30 years my senior- had built a successful career by writing down daily, quarterly and yearly goals. Whatever he didn’t get completed today was added to the top on tomorrow's list. As you can imagine, my ‘process’ provided him little comfort. When we’d sit down for meetings, he’d constantly ask me, “Are you going to write this down?“. My typical response was, “No, don’t worry, I’ll remember.” And, for the most part, I did. Eventually, my business partner not-so-subtly started bringing an extra pad of paper and a pen to every meeting ‘just in case’ I thought I may need to jot something down.

The biggest blind spot in my life was thinking in a vacuum only about whether something was working for me. I failed to see the impact my lack of organization and systems had on other people. My process created stress for my business partner, who not only needed to BE organized but also to FEEL at ease. He could only relax when he knew those on his team were not going to drop the ball. If he couldn’t feel that way, he’d do it himself to know it was getting done. This meant my systems were impacting his health.

My system also kept people I loved in continuous crisis mode when inevitably the limits of my own capacity broke under the weight of the company’s growth. Then, there would be the inevitable frantic call home to my wife, who’d be nursing one of the kids, and I’d say, “Hey, I left a piece of blue paper laying around somewhere! I think it is on the back of an envelope and it has a guy’s name and phone number on it. Would you mind finding that for me?”

My problem was that I had sympathy, but not empathy. When I tried to imagine myself in other people’s shoes, I thought, “It wouldn’t matter to me at all if someone acted and worked as I do.” But, I was asking the wrong question. What I needed to ask was “What impact would my processes have on people who weren’t wired like me?” It took me over two decades and a lot of hard knocks to learn my limits and to see how and why I needed systems in my life. Systems not only maximized my potential and output by supporting my weaknesses but served as a practical way to show applied love through creating empathetic systems for those who support me. As penance, and to make sure these lessons stick, I am redoing our house from top to bottom including this most recent project, a closet organizer for my wife.


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Will your life cast a nuclear shadow? Answering the final question of Hamilton.