ON MARCH 29, I retired from UMass Memorial Health after 20 years of service.  Some might say I am getting out at the perfect time. 

Massachusetts health care has never been more precarious. Hospitals are overwhelmed with patients and cannot handle the capacity. The day I left, our academic medical center had 84 patients boarding in its emergency department. These are patients who are in need of an inpatient bed, but cannot get there because there is no bed available. As a result, they have to be cared for in the hallway. And this same story is playing out at virtually every other hospital across the state.  

Perhaps even more concerning is the fact that several hospitals are teetering on the brink. Heywood Hospital is in bankruptcy, many of the Steward hospitals may soon be heading there, and a few others are not far behind.  

In short, you could not pick a better time to get out of health care.  

So why am I so sad to be leaving?   

I have spent the last 25 years of my life in the Massachusetts health care ecosystem. I have served in two branches of government, have come to know the cadence of academic medicine, and have learned the inner workings of community hospitals. The truth is that it has never been easy.  

Over a decade ago, a few leaders in my health system engaged in some practices that, let’s just say, did not live up to our high standards. I had to meet with the New Hampshire attorney general to try to provide him some perspective after he said publicly that he wanted to throw someone in jail over the practices. That wasn’t easy.  

When I was general counsel at the Senate Committee on Ways and Means in the late 1990s, I helped to write the new managed care reform law at the time.  I was proud of such brilliant legislative prose. A few years later, when I was general counsel at the Medicaid agency, I was in a meeting with a few lawyers there trying to figure out the meaning of a particular provision of that law.  One said, “Who the hell wrote this ridiculous law?” Guilty as charged, I confessed.

It turns out that easy is not the path to a rewarding career. Perhaps I am a glutton for punishment, but as I now reflect on my own career (incidentally, my wife thinks it may be a tad bit premature to do so early in my retirement), it seems that the tougher the challenge I faced, the more engaged I became. 

Maybe it is because the cause of health care in our state is so noble. Despite its many challenges, Massachusetts health care remains the best in the world. It has the best institutions, the best thinkers, and the best government leaders. We are consistently ranked as the healthiest state in the nation; we were the first state to provide universal health insurance to our residents, setting the standard for the nation; and we are now leading the pack on health equity. We are too good to fail.  

Don’t get me wrong, I am tired. The last few years have been brutal. I need a few months to decompress. But I can’t imagine leaving the field. It is simply too important to society and, after so many years, I finally feel like I have figured a few things out. Surely I can add value somewhere. But where will that be?  

I have known of my retirement date for about nine months. We all have a shelf life in our organizations, and I had determined then that mine was about 20 years. It was time for me to make way for a new generation of leaders here. As a result, over the last several months, I have had the chance to start to think a bit about my next chapter, and I even entertained a few inquiries about roles in other organizations.  

One was for a chief legal officer position at a large health insurance company. I thought it might be interesting to consider contributing to the one part of the health care system I have not yet participated in. I made it to the final two, but lost out to the internal candidate.  

Another was for a CEO position at a large health care system. Again, I made it to the final two, but lost out to an external candidate.  

Interestingly, seven years ago, I threw my hat in to be considered for CEO of the Massachusetts Health and Hospital Association. As you might have guessed, I made it to the final two, but lost out to the other candidate. That candidate, the current CEO, Steve Walsh, has turned out to be a phenomenal leader and was the right person for the job.  

But do you sense a pattern here? I feel a little like Phil Mickelson must have felt in 2003. He was coming off a run of 17 top-ten finishes, and six second or third place finishes, but couldn’t win a major golf tournament. He was routinely described as either a “choker” or, more charitably, the “best player never to win a major.”

Perhaps a better analogy might be to the Buffalo Bills. They went to the Super Bowl four straight years, from 1990-1993, and never won the big game.  

There is one important difference, though. If you are on the PGA tour or in professional football, coming in number two can still win you a lot of money. In my case, as my late Jewish grandmother would have said, coming in number two gets you “bupkis.” 

So why am I torturing myself with such a public airing of my failures? For one, it is a bit cathartic. But I think the larger reason is that, at this point in my journey, I am feeling a compelling need to send an important message to the next generation of health care leaders. Don’t fall for the facade.    

My organization threw me a wonderful going-away party, where close to 100 of my colleagues showed up to wish me well. My team aired a video with interviews from 24 of my closest colleagues from inside and outside my organization. They each reflected on what I have meant to them, and how I showed up as a leader in health care. It was incredibly moving and it will forever serve as a cherished memory for me.   

If you saw that video, you would think my career has been an upward path of rainbows and unicorns (it’s remarkable what people say about you when you tell them you’re leaving!). It hasn’t been. 

I have had as many failures, frustrations, and missteps as I have had successes. And those of us entrusted with the great privilege of leadership have a responsibility to set the record straight. The objects one sees on LinkedIn (or in a retirement video) are less rosy than they might appear. It does a disservice to future leaders to perpetuate the myth that the path to success is always up and always straight. That’s why I am exposing my warts.  

And here’s the other reason. Despite these warts, I have had the most satisfying career imaginable. My take-away is that a great career is less about how many wins you rack up, or how many job offers you get, and more about the struggle. How you showed up. How you got up when you fell. How you put yourself out there, day after day, to further the cause. In the end, life is far more about the process than the outcome. It is the struggle that makes life worth living.   

I will enjoy a few months of travel, exploration, and reflection. And then I will likely emerge to give more of myself to health care. Not because it is easy. But because it is so important. Will I finally break that barrier to the top? Who knows? 

Phil Mikelson went on to become one of the best golfers of all time. The Buffalo Bills still have not won a Super Bowl. Which path will be mine? I’m not worrying too much about it. If all else fails, I will simply set out to write that book about the joys of being number two.

Doug Brown recently retired as a health care executive at UMass Memorial Health in Worcester. Before that, he spent 10 years in public service in Massachusetts state government. He’s also written a number of columns for CommonWealth Beacon. Check them out here.