Ask Bear: On Making Decisions -The Toast

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Previous Ask Bear columns for The Butter can be found hereIf you have a question for Bear, The Butter’s advice columnist, send it along to

Dear Bear,

I really like your column, and it makes me want to ask you a million questions. What should I do about my shitty landlord – move or sue? Should I quit my job and go back to school to study art history and look at paintings all day? Is this boyfriend I have The One or am I settling? I want to confront my mother about her terrible behavior toward me and my sisters. Is this a good idea or should I keep stuffing it down and hope for some magical resolution? Boxer briefs or jockbriefs? Vodka or gin?

Because in one version of my life I am a single gay condo-owning curator who wears a jock every day and doesn’t speak to his mother anymore. That version of me seems like he would be very happy. But isn’t everything we don’t have just a dream we can never compare to what we do have? That version probably also has problems. How do I compare without knowing what they are? And if I can’t compare how do I decide? And if I can’t decide do I just wait until things happen to me?

Maybe my real question is this: “How the hell does anyone ever decide anything and then act on it without second (third, fourth, fifth) guessing themselves about it until they just stay stuck?”

Dear Brave Correspondent,

First, start easy: gin on a warm summer night, vodka in the winter. Underwear that makes you feel cute and doesn’t chafe, regardless of fashion.

From there, we move to the bigger questions. Some of these are answered in a similar way – some choices are better for one season (actual or metaphorical) than they are for another. Sometimes what makes us happy (in our pants or in any other way) is not the most au courant situation, but the one that suits our own personal topography the best. Of course, it’s easier to experiment with booze and underpants than lovers, careers, or parents. So let’s look at some things here, shall we? Because these are all very good questions.

Here’s the first thing I need to tell you: doing nothing is never neutral, even when it feels like it. When I was an academic advisor, I used to explain this to my students as follows: if you have a paper due, and you have no idea what to write and just don’t turn anything in, what mark do you earn? A zero. If you write a paper, any paper at all even if it’s a total goat rodeo, what mark do you earn? An F, typically, which is a 50. It does not take a genius of mathematics to grasp quickly that your total average is vastly less damaged with the 50 than the zero. So too in our lives. Even a terrible decision is valuable to the average of your life – you learn from the process, you learn from the outcome, you generate some motion of your own.

Here, a caveat – that doesn’t mean it’s nice when you make a terrible decision. Repercussions are real and can be awful. But even still, even still it’s better than just staying frozen and indecisive and waiting for something to happen to you. It’s better for two reasons. One, deciding and acting is how we learn to decide and act. Bad decisions lead to better ones as surely as gentrification leads to $4 coffee. But two, and maybe even more importantly – you took the wheel at all. You’re steering your own ship. This is how a heart grows stout. This is why they have the saying “A smooth sea never made a skilled mariner.”

Another thing about deciding is that we never decide in a vacuum, no matter how much we might imagine that our deliberations are private or that we’re not seeking input. The culture in which we live, our families and friends and work environments all dump their input all over us every day. There are some decisions that we know, instinctively, will earn us the approval of our circumstances and other things that would have to be unimaginably shiny in their specifics to make it even remotely possible to consider actualizing them. So an additional part of my advice is to peer very carefully into your decision-making process and discern whose voices you’re hearing in there. How much of what you’re being advised to do by the people you ask is steeped — whether they mean it to be or not — cultural values? Is it really better for you to grind away at your job? Is it time to break it off with your boyfriend? Maybe. Who in your head is telling you it is or it isn’t? Is staying with your boyfriend somewhat about the narrative that it’s better to be the one who stays than the one who leaves? Will you be able to find some other job if you need to? Are you worried about how you will explain an “irrational” choice to your parents or your friends? Are you half-convinced that if you leave no one will ever love you again? Are you the-other-half-convinced that no one really, actually, loves you now?

Let me tell you, Brave Correspondent: that’s not just you, with those thoughts. Many of us carry them around. Almost all of us are lovable, even if sometimes we are the last to know it. Queers, especially, we are sometimes the last to know it.

When I made a great leap of faith in love, I was 32 years old. I moved to another country to live there with my brand new lover who was supposed to be a one night stand; a hot conference fling. We utterly failed to remain a fling. After a) knowing him for eight weeks and b) having spent perhaps 60 hours total in his actual physical presence, I was in my car on the way to Canada, to him. It was TREMENDOUSLY unlike me. I am cautious and methodical and resistant to change and my planning horizon extends into forever. But I was so shaken loose by this love, so completely unable to resist the yearning gravity of it, that I sublet my apartment for the summer before the last of anyone’s hickies had completely faded away.

(At this moment in my life, I flipped a coin a lot when it was time to decide things. I didn’t flip to do what the coin said, I flipped to be able to notice in the instant of reading what “fate” had decided for me how I felt about it, deep in my gut, where I was otherwise not tuning in the signals well amidst all the upheaval and emotion and distraction. You might try this, too – flip a coin and see how you feel about the random decision you’re handed.)

For sure, people had reactions to my choice, and I listened to what they said. But I began to discern a certain subset of people who said “Maybe you should look before you leap,” but actually meant “Don’t leap. Stay here, so I can find you when I want you.” I imagine they felt that they had good intentions. There’s value in being constant. Sometimes, though… sometimes we just need the people who embolden us.

Change is hard. New things are scary. Even if you have something or someone standing by, waiting in the wings in case or until you need them, making decisions and acting on them is a challenging and uncertain business. So, be gentle with yourself. You get all the points for doing the hard work. Because you’re right – there’s no way to know what will happen, or what the faults of the new situation might be. Maybe that single gay curator loses his job or gets a rash from the elastic of his new $35 underpants; maybe his condo floods with raw sewage or his new hot date turns out to have warrants in three states. That guy, though – that guy gets to move forward. That guy gets to find a job or discover what else he can do without one maybe; maybe he gets to send the underpants home with a hookup that turns out to become the kind of intimate friend we cherish for decades (sewage is horrible no matter what and you should just pray that doesn’t ever happen to you, and also get really good homeowners insurance). That guy, he will try and fail and discover where he is flexible and where brittle, where he’s resilient and where defeated. He can work toward his best self. He can strive. He can fly, even if his wings are yet a little damp. The best news of all here, Brave Correspondent, is that you — your very own precious self — are the guy in question. You, too, can fly.

Love and courage,


PS – the guy for whom I moved to Canada on hardly any acquaintance? He’s now my husband of six years and the other dad of our three children. I leapt, and was caught. Caught and held, and still so loved.

S. Bear Bergman is an author, editor, storyteller, publisher and loudmouth.

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