“The oppressed are allowed once every few years to decide which particular representatives of the oppressing class are to represent and repress them.” –Karl Marx

“A leader is a dealer in hope.” –Napoleon Bonaparte

Hello friend,

Here is a small sampling of the kinds of thoughts dominating my mind in recent weeks: Do we really see eye-to-eye? Does she share my passions? Do I want someone more experienced, or less? Is she in this for me or for herself? Will she go all the way? Sounds exciting, right? Sadly (or not), no, I am NOT back in the dating game or perusing Match.com for options. Instead, I am in a different kind of market, one that, at this critical juncture in American history, may be even more consequential than my love life. I am searching for a President.

I remember the primary season four years ago, watching the earliest Republican debates. Like the current crop of Democratic candidates, it felt like an enormous cast of characters to pare down. I figured that in our back-and-forth country, it was probably the Republicans’ turn to win the Presidency, so it was especially intriguing. Not that I was going to vote for one of them–I don’t belong to a party but am very liberal and thus typically end up choosing among the Democrats in our antiquated, two-party system–but my keen interest in politics and the future of America keeps me fascinated by the happenings and characters in both parties.

In that Republican debate, I remember taking notice of John Kasich for the first time, thinking he might make the best nominee in the end, one that would try to be a President for everyone in our fractured country, even as the leader of one party. He was personable enough and seemed somewhat open-minded, seemingly a decent guy in spite of his politics. I figured he may even try to work with both parties, something I fancied given both that I was expecting a Republican President and that things in Washington had become stubbornly divided and petty. I also remember noting Marco Rubio in that debate, figuring him to be someone to look out for in the future, maybe the next Vice-President and/or a future President. Jeb Bush seemed like the kind of guy that would be nominated. Others seemed out of their depth. Ted Cruz repulsed me in every way. Donald Trump seemed to be every bit the nightmare that he still seems to me now. Well, we know what the Republican voters decided.

The Democratic primary at the time, though technically open, seemed like a done deal with an eventual Hillary Clinton nomination. Though in a much smaller field, it was clear in the first debate that Martin O’Malley, Jim Webb, and Lincoln Chafee were going nowhere. The then-new-to-me message of Bernie Sanders, though appealing to these ears, just seemed like it wasn’t going to get a fair or full hearing (and maybe I was too quick to pick a candidate because of that). Clinton had policies that I like, she was exceptionally smart and well-qualified, and electing the first female President appealed to me greatly. I thought she would do a good job despite an obviously hostile opposition stemming from the decades-long, Fox News-led assassination of her character. I voted for her in the primary and again in the general election. And again, we all know how that went.

So, here we are again, four years and several debates later, and, for the moment and for the Democrats, at least, there is still a wide variety of characters to choose from. The policy choices range from the center to the far left, and the range of personality styles and types of experience is even broader.

Looming over all of them, too, is the elusive quality called “electability.” Disgust of Trump is so strong that poll after poll shows that voters in the Democratic primaries prefer someone who will beat Trump over someone who shares their values. I have seen interviews with voters who actually preferred a woman or person of color (when there were some) but put that preference aside and chose a white man for fear that sexism and/or racism would cause their preferred candidate to lose in the general election. The problem I see is that I don’t think anyone really knows what electable is. Look at Trump. Like him or not right now, you would have to agree that four years ago, he did not seem electable. Establishment Republicans were in a state of shock and gripped by the fear that someone with such an arrogant and petty personality, prior support of Democrats, and history of racist and misogynistic actions not only wouldn’t win but that he would cause so many others down-ballot to lose as well. The experts agreed. And they were all wrong.

Right now the same hand-wringing is happening in the Democratic Party over the recent emergence of Bernie Sanders as the frontrunner for the nomination. They fear someone with such liberal (“democratic socialist”) views will alienate not only the party’s moderate voters but also the “swing voters,” independents and disaffected Republicans that the Democrats were planning to win over in this election. But who is to say if these fears are well-founded? Doesn’t winning the contests make you electable? In any case, because I don’t think people know what electable looks like until after the votes are tallied, I wish folks in these primary contests would vote for who they think would actually be the best President rather than looking at it like a horse race, trying to predict the winner rather than select one.

But how does each person select one? What factors weigh heaviest when deciding amongst a cast of characters who all belong on the same half of the political spectrum as you do? Because let’s be clear, this is a totally different challenge than just voting in the general election, when you are probably going to be voting for the nominee from your preferred party whether you like that person or not. [Let’s face it: Donald Trump may have a very high approval rate among Republicans now, but when many of those same folks filled in that little oval by his name in November of 2016, they were biting down hard and hoping for the best rather than gleefully squealing, “This is sure to go great!!!”] But when it is basically a choice amongst characters from your own tribe, you get to (have to?) drill down on the different qualities that each one brings to the table and parse out what really matters most to you.

And that can change from one election to the next and one group of candidates to the next. Some eras call for an emphasis on personal character. Other eras–in your mind, at least–call for revolutionary policy ideas. Another calls for a status quo candidate, like an outgoing Vice President, to keep riding the wave you are on. Some years I am looking more for someone who inspires me. Other times intelligence and steadiness seem more important. Maybe it means something more to you to be a part of electing a woman or someone from another historically underrepresented group, but maybe this time you prioritize whoever feels like the safest bet. Experience in government can be looked at either positively or negatively, depending upon how fed-up you are with the system. The entire question and answer is a most volatile and thorny puzzle.

So, what am I looking for in this moment from these candidates? What will sway me most when I step into that voting booth in a few days?

Before the contest began, I would surely have told you I wanted the most humble, pleasant, intelligent, unflappable, inclusive, positive-messaged, male, and white candidate in the field. Essentially, other than the “safety” of the whiteness and the maleness, I wanted everything that Donald Trump is not. I wanted that contrast to be so glaringly obvious to any open-minded voter. That seemed to be the wisest choice to ensure a Trump defeat.

But then, as is often the case in this complex journey called Life, the real, live humans entered into the equation and mucked up my whole plan. Suddenly my natural inclinations to be inspired and to make bigger change in the world took over my better judgment. I saw safe, and it just didn’t feel like enough for me. I moved past just winning the White House and focused on the more sweeping changes that could make life better and more just for more people in the long run. I slipped away from the cold, calculated path to victory and moved toward the candidates that appealed most to me.

I am big on candidates who are serious about the environment and eliminating our dependence on fossil fuels. That one is pretty common to all of the current Democratic candidates–though some seem more passionate than others–as are things like gun law reform, women’s rights, drug law reform, a reduction of the prison-industrial complex, and putting more federal money into our schools, among many other issues. It is why I could imagine voting for any one of them if they were to win the nomination.

But there are a couple of points of separation that help me to narrow my preferences.

I believe health care should be guaranteed to all people–I have written to you before about this–and that personal finances should not keep any American from getting the care they need. I also think our current health care system is predatory, immoral, and way too expensive for what we get out of the deal. Because of these–but mainly because of the first one–I am a huge proponent of a single-payer health care system, now referred to as “Medicare For All” on the campaign trail. This may be my biggest pet issue, and it narrows my candidate choices down to just a few. Thankfully, those candidates happen to also be genuine champions of the working class, minority communities, and others who have not fared as well as people born into advantage. These candidates have plans to raise the minimum wage, to build more affordable housing, to make it easier for black and brown people to get loans for homes and small businesses, to build infrastructure in these communities, and to ensure that the schools in these areas get the funding for teachers and mental health professionals that they need to achieve some measure of equity. This genuine care for people who need and deserve a boost is very important to me in a candidate. I feel that with a couple of them.

When I am left with two whose policies I can really get behind, it is then that I dig into the personality, intelligence, and “electability” aspects of the candidates. I have watched a couple of town halls with one candidate in particular who definitely impresses me with her depth, both of caring and intelligence. The tone just feels right to me; I get that she has listened, been moved, thought it all through, and come up with very specific plans to help. That stuff ticks the boxes for me. I could see her on a debate stage with Donald Trump and coming across as the only adult in the room. But not just as the only adult–that is easy to pull off when Trump is your comparison–but the only one who has done the work to understand the situations of the people in this country and the complexities of the world we live in, and then who actually cares enough to steward both the ship and all of its passengers toward better. And though her policies are bold and to some far-fetched, she both makes them seem more do-able and also seems willing to compromise to at least move in that direction. And I don’t see her as so easily falling prey to being cartooned by Trump and his Fox News propaganda machine, though no doubt that effort will be forcefully made.

This points up the contrast between her and the other candidate whose policies I like: I just think he will too easily fall prey to the cartooning by the other side, both with his ornery, shouting personality and with the bold positions that will no doubt have the other side screaming “COMMUNIST!!!” at every turn. It’s a problem of approachability, to say nothing of the likability factor once you get that close. There is an unbending quality to him as well, which may be great if he is your personal champion but is difficult if you are anyone else. I wish more people wanted to join his movement, but I understand that its popularity at the moment, as with his personal appeal, is limited. I hate the idea of equating him with Trump, but the one similarity I sense and worry about is having a very loyal but somewhat limited following, with little possibility for growth. I would prefer to not end up with two old, stubborn, shouting, white men on the final debate stage, even if one is shouting things I like to hear. It just feels tougher on the country, leaving less room for middle ground.

That is why I prefer my other candidate. She has the policy positions that are my minimum qualification, but she also has the other things–the intelligence, the empathy, the specifics, the experience–to fill in the rest of the picture and appear as a reasonable option to a broader range of people. And frankly, to be a better President, which, if I remember correctly, is what this whole process is all about. So, even though I abandoned my initial, cold, calculated plan to pick the “safest” bet, in the form of a white, male, middle-aged moderate, and instead went where my principles led me–to an older, more liberal female–I am pleased with where I have landed and what the journey taught me. I am ready to fill in the oval!

How about you? What qualities do you value most in choosing your President? Open up your journal and explore the appeal of the candidates that you have voted for in the past and others that you have passed on. Whether it was in the last primary if you lean toward Republicans or this primary if you tend to prefer the Democrats, which aspects of their candidacies tend to hold the most sway with you? In a setting like a large debate stage, do you tend to feel for personalities and energy first and then, after you have found some that you are drawn to, listen more closely for the policy specifics? Or, do you tend to ignore the personality part and go straight to policy positions? Somewhere in between? How much does gender factor into your equation? Race? Religion? Sexuality? How much does a candidate’s intelligence impress you? How much do you weigh a person’s political experience? Is it better if they have been in Washington for a long time? Is it more appealing to you if they have succeeded in other fields, like the current billionaire candidates? How much does the person’s past matter to you, whether it is a voting record in Congress or something they have said (Trump’s “Grab ‘em by the pussy” comes to mind) or written or been charged with? How do you weigh that against what they say they stand for now? Can you put all of these other personality, history, and demographic questions aside as long as the person shares your policy positions? What is the most important issue that you want your candidate to share your vision on? How much more important is that issue than the others? What are the rest of your pet topics, in order of importance? Have you ever been fully satisfied with a politician’s positions? How much do you tend to factor in “electability” when narrowing your candidates? Do you feel like you have a good sense of what electable is? How would you draw up the “safest” candidate in your party? Is there someone you have in mind as a model? Do you pay close attention to the candidates and issues central to the party that you don’t generally vote for? Considering that one of them might become your next President, what kinds of qualities do you look for in those opposition candidates that make you think, “Well, I suppose I could live with that one for four years,” or “That one does not make me totally sick to my stomach, anyway,” or the like? Is it all about whoever is the most moderate of the bunch, or is it more about which one has a decent personality? How do the qualities you look at for the opponents differ from the ones you prioritize for your own party? Have you ever watched a debate or town hall performance by someone from the opposition party and thought to yourself, “I would actually vote for this person?” On the whole, would you say the qualities you value in a candidate change from election to election depending upon the group and the circumstances, or do you prioritize the same thing every time? What is the best predictor of your vote? Leave me a reply and let me know: What qualities matter most to you in choosing a Presidential candidate?

Think big,

William

P.S. If this letter resonated with you, please pass it on. Let’s all engage this special process!

P.P.S. If this way of questioning yourself to uncover your values and idiosyncrasies is appealing to you, consider buying my book Journal of YOU: Uncovering The Beauty That Is Your Truth at your favorite online retailers. Namaste.