Earlier this year I received a call from a very dear friend (and client) that would set in motion a series of events that has impacted my life in ways I would not have imagined. It’s taken me several months to write this, but of all the blogs I’ve written, this might be the most significant to me. Continue reading if you’d like to come along the journey. Trust me; you’ll want to read the entirety.

I met Cleland about 22 years ago when his business manager referred him to me. He was about to have his first child, at the fairly advanced age of 46, and while already married for 10 years to his wife 10 years his junior, he had not yet done any financial, life insurance or estate planning. At the time, Cle was an extremely accomplished cardiovascular surgeon in private practice in Los Angeles, and lived a wonderful lifestyle. Our first meeting consisted of a “get to know you” session where I learned about Cle’s personal and financial circumstances, and his goals and objectives for himself and his family. On our second meeting, where I presented my recommendations, we had dinner together and we learned much more about each other: he enjoyed drinking bourbon and beer, and I loved wine, of which he was self-admittedly a philistine. That was then! After getting to know Cle well and inviting him to attend a few wine and food events, he quickly became an oenophile, then wine collector, and soon his knowledge (and collection) of wine far surpassed my own.

Over the years our friendship grew through our mutual enjoyment of food and wine, joint travel with our spouses, many, many meals together, and continued financial counselling. About six years after we met I received a distressing call from Cle. The retina behind his left eye had become detached, and while doctors were able to reattach it, he was very concerned about his continued ability to practice as a surgeon. However, Cle’s retina re-attachment proved to be successful, and he was able to return to practicing surgery… for about six months, when the retina detached a second time. This time he was not so lucky, and after the second re-attachment, he was left with some blurred vision, which prohibited him from performing any very fine motor actions—like cardiovascular surgery. Cle and his wife now had two young children and were living a wonderful, very busy lifestyle in Los Angeles. His world looked like it was about to spin out of control, but a combination of his resilience and a very special feature of his disability policy took a dire situation and turned it into an opportunity that Cle embraced fully. His maximum benefit disability policy was specific to his “own occupation,” meaning simply that if he was unable to fulfill the specific duties of his medical specialty (regardless of what else he might be able to do) the monthly benefit would be paid per the contract. As Cle could no longer practice his medical specialty, he began receiving substantial monthly disability checks after a 90-day waiting period. Cle, a Harvard-trained doctor, was intellectually brilliant, otherwise physically able, and was not prepared to let his knowledge, years of experience, and intellect go to waste. Shortly after going on disability, Cle was offered the role of Chief Medical Officer for a rapidly growing bio-tech company specializing in heart disease.

While Cle very much missed the direct interaction with patients in a literally life-saving role, he embraced his new life with vigor and enthusiasm. A relocation to San Diego for this new role meant Cle and I saw less of each other, but we still spoke regularly. And any time we were in San Diego, Terri and I (and sometimes our kids) would stay with his family and him. Each time we were together, we enjoyed a meal and always more than one bottle of fabulous wine from his ever-growing broad and deep cellar. Sadly, this joyous period in his life did not last. About five years ago, Cle and his wife separated, and although still deeply connected both through their two boys and their continued affection for each other, they could no longer live together. This naturally put in motion a series of major changes for Cle, including the sale of his home and the transfer of his share of the wine collection to a large walk-in rented wine storage locker in the San Diego area. However, Cle continued to enjoy life through his kids, his friends, his active involvement in a number of charitable organizations, and particularly, the consumption of some amazing wines.

Then came the call earlier this year that shattered me. Cle called me while I was in my car driving between appointments. I remember exactly where I was (on the 101 Freeway), as one often does when confronted with a major event. He seemed relaxed, probably for my benefit, but his words required me to exit the freeway and park my car at the side of the road as we continued the conversation. He informed me he was terminally ill. As his insurance agent—and the trustee for his life insurance trusts—he asked if I would attend an all-hands meeting in San Diego along with his wealth advisor, estate planning attorney, banker and his minister. He wanted to make sure his planning accurately reflected each and every important detail necessary for the care, support and education of his two boys, now 19 and 17. He asked us all to come to San Diego over a two-day period, which (in natural Cle fashion) would include two exceptional wine-paired dinners at his favorite restaurants. Cle asked if I would come down on the first afternoon a little earlier than the others, and meet him at his wine locker, as he wanted me to help pick out the wines for the dinners he had planned. I arrived as requested and began going through his remaining collection of still several hundred phenomenal wines. I was like a kid in a candy store, salivating over some of the labels and vintages. When I began to suggest to him some of my recommendations to pair with the food we were to eat over the next two evenings, he told me his request to assist him was a ruse. The reason he asked to meet me at the cellar was for me to see the collection of wine he was leaving me in his will. As I was the “cause of all of this,” according to Cle, it was only fitting that I ended up with a substantial portion of it. For once in my life I was totally speechless. To say I got emotional is a ridiculous understatement. I needed to sit down, and thank goodness the cellar was big enough that it required a step ladder to reach some of the higher placed wines, as that is where I sat and recovered for the next 10 minutes.

But this piece is not just about Cle’s extreme generosity to me. It is about the love and care he took in preparing for his end of life so that his boys (and his ex-wife, for whom he still cared deeply) would not have a single financial or administrative issue to deal with post his death. While he could not remove the emotional considerations, Cle was able to mitigate those too, by painstakingly preparing love letters, memorabilia, and even a video to his boys. We spent an entire day reviewing and amending the details of his trusts, checking off all of his post-life administrative items and generally engaging in perhaps the most surreal day of my life. Cle taught us all so much that day. How to face the harsh realities of life and death with dignity, care and compassion for the ones we leave behind. And he would not let any of us become maudlin or feel sorry for him. These two days were to be the first of several celebrations of his life. Of course, we don’t all have the “luxury” of such detailed end of life planning, but so many of us are hopelessly under-prepared in the event something was to happen to us prematurely. If nothing else, I implore you to take some time out of your busy schedules to reflect on what you would do if you were Cle… and then do it!

Cle visited with Terri and me two weeks later (accompanied by four bottles of 95+ point wines to pair with a dinner I prepared in his honor). After dinner, while we enjoyed a port and cigar, Cle asked if I would come down to San Diego shortly thereafter and collect the wine he was leaving to me. He wanted me to take possession while he was still alive. The following weekend I rented a van and drove down to San Diego. It was the most bittersweet experience of my life. Cle joyfully helping me pull the wines off the racks and case them, all the while chattily reminding me about when we’d drank some of them together, or how he’d come to acquire them. When they were all packed in the van and we hugged and said goodbye, I knew in my heart it would be the last time I would see him. How do you say thank you and goodbye under those circumstances?

Cle passed two weeks later.

I toast to his memory on a regular basis.