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The Art of Letting Go: What Diana Finegan Needs to Do to Maximize her Leadership

One of the worst strategies you can use to connect with someone is to tell them you know how they feel, yet sometimes situations are so similar that there is little other way around it.


I know, at least in part, how Diana Finegan feels right now. It’s raw, it’s borderline vengeful and, in honesty, both of those feelings may even be justified. But I hope they are temporary.

Let’s back up a moment to explain how my past feelings are similar to the Republican nominee for district 2's current mindset. I started working on and off for Mike Prendergast in 2010, managing both his successful races for Sheriff and I consider him a dear friend who even appears as a witness on my marriage license. My wife and I first met at one of his 2016 campaign events and coincidentally celebrate 4 years of marriage on our anniversary today.


More than any other client I’ve worked with, attacks against Sheriff Prendergast are affronts I take personally. This made 2020 a difficult year.


The Chronicle’s news coverage was inconsistently reported to match its editorial stances, the Chamber was housing signs for our opponent with the organization’s president a frequent sign waver during business hours and our only friends felt like the members of the Republican Executive Committee as well as the clubs.


Bitter doesn’t begin to describe it. I was furious.


A 21-point landslide victory in the primary and a general election victory of almost 75% didn’t mitigate a thing. It wasn’t enough to win big. How dare they think they can control what people think? Someone had to pay.


However, in hindsight, I wish I hadn’t wasted two years holding a grudge. This is not going to be a plea for unity. Community conformity is not only overrated but is a poison that has led to some disastrous decision making from the commission itself.


It is possible to reach a threshold of tolerance, and as time goes on, even understanding. Let me be clear: this does not have to happen through a compromise on principles nor does it mean holding back criticism.


In fact, I am far more outspokenly critical of the Chronicle now than I have ever been through the second topic of a weekly podcast serving as a direct reaction to the publication’s Sunday commentary and yet I would categorize my relationship with their staff as at its all-time best.


This is because communication is more important than agreement, yet it is categorization that allowed me to get over the mental wall I had built against my perceived enemies.


This categorization did not happen overnight. I had written (my best form of thought collection) over 100,000 words before arriving at these conclusions. But once I did, just attaching a name to what was happening helped dampen how personally I took their perspectives.


The Chronicle believes in a philosophy of community journalism rather than objective journalism. Past publishers and reporters alike have unabashedly admitted to this. The difference is community journalism allows for advocacy in news coverage so long as this editorial slant can be justified as what is best for the community, even if it violates professional standards of objectivity.


Is it right for the Chronicle to do this? Of course not, and I vehemently argue against this philosophy. Is it going to ever change? Maybe.


There were some trouble spots through the 2022 election cycle but I do think the new leadership team is top-notch talented and already starting to professionalize paper to new heights. After all, you don’t turn a tanker on a dime - it takes time and a wide swing - and so too would it be impossible for the new leadership to fix the ingrained culture of the county’s oldest business in their first year on the job.


Chamber leadership, on the other hand, moral licenses. They think that the good they bring to the community, and the Chamber through festivals, networking opportunities and business advocacy does do well for us, that this gives them leeway to cut professional corners like a balancing act. You can stretch the ethical limits on one end if you offset it with the good you’ll do on the other.


This is no way to lead and people will soon stop taking you seriously if stretched too far.


Just naming these concepts, though, can help define exactly where the disagreements lie. If Ms. Finegan recognizes that, she can disagree with their processes and philosophies rather than with them as people, and the grudge might begin to melt away.


While it may be easy to dismiss the need for any interaction with them bolstered by an electoral victory, it does benefit the community as a whole to do so. Future commissioners have a responsibility to everyone, not just those who elected them.


The freedom of naming it and letting go benefits both the individual's personal relationships and the people she will represent. It sure did for me.


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