On Winning

These past few weeks, everything has felt on the up and up. I’ll call that feeling, ‘winning,’ to be used as its own emotion, i.e. “I’m happy, I’m sad, I’m angry, I’m winning,” with noun form “winningness.”

Winningness feels great: I am generally more optimistic, upbeat, energetic. It also changes my behavior: I am more likely to take good actions, more likely to be generous and loving towards the world, and less likely to make decisions out of fear. Being winning also changes my experience of the world, because others around me can feel and react to all of the above, making me more likely to have wonderful social interactions, creating a positive feedback loop. And as a blanket statement, everything feels more meaningful, more fulfilling.

This also applies directly to my spiritual health: when I’m winning, I want to act with integrity, read my Bible, be charitable and generous towards my neighbor, and I feel closer to God throughout.

The issue is that winningness, for me, is dependent on several things, which feed into each other. First, I’m winning if the startup is clearly moving forward. I’m also more winning if I’m meeting and impressing eligible women, or going on dates with them. Of course, this is more likely to happen once I’m already winning. (This is a side note, but I think women are incredibly attracted to men who are feeling winning. I think this is actually what they want when they say they want wealthy men, or find themselves attracted to married men.) Finally, I’m even more winning if I reach a spiritual high, akin to Tanzania, although this again feels easier once I’m already winning.

There are two ends of the spectrum for how I frame winning:

Winningness could be the response of my subconscious, even my spirit, when it is in the right place (successful search). This would parallel other subconscious parts of me, like my curiosity, which I cannot control or direct but have learned to try and follow. I could substitute winning with the word fulfilled, and then orient my life around chasing fulfillment, which does’t seem like such a bad thing to do.

Or, winningness could be the result of me making my wellbeing contingent on external circumstances (your heart is where your treasure is). This would mean winningness is a pleasurable but morally neutral emotion (like happiness), while the cause of it is good or bad.

Each framing changes how I approach the feeling of winningness. If it’s search, then I want to optimize for feeling winning more of the time. For now that would mean really pressing towards startup success, and from there meeting more women, and seeking peak spiritual experiences. But if it’s a bad heart-treasure link, then I really want to let go, surrender, and allow God to move in me and my life, apart from my effort.

That second framing lends itself to an interpretation of winningness by inversion: it is merely a lack of anxiety, what baseline could look like without being anxious. (I would otherwise characterize the opposite of anxiety as peace, but I’ll try this on for size.) So perhaps, in setting certain desires for myself, I make a contract with myself to be anxious until that desire is fulfilled. In that vein, I am anxious when the startup doesn’t seem to be going well yet, or when I’m unsure about my romantic future. And that anxiety prevents me from attaining spiritual highs, which are characterized by a divine peace (it makes sense that I would be blocking that peace by choosing anxiety).

I’m still torn. I want to feel fulfilled, and I don’t want to be anxious. I also want to be able to be a good man, even when I’m not great at my job, or things are in a learning instead of a winning phase.

And I would like to say that I want to divorce my sense of wellbeing from my performance at work, but then I think, ‘Man was made to work’. I don’t want to feel good if I’m slacking, if I didn’t sow my field, or forgot to harvest the crop. But it’s circular, because how I put in the work depends on whether I’m winning or not. For example, when I feel winningness, I work harder, think more clearly, and do the things I’m still afraid to do - and so I can be proud of my effort. And when I’m not winning, it’s the opposite on every front.

So life seems to be either a virtuous or a vicious cycle - with no in between. Winning begets good things that beget more winning. And there is no stasis, so the alternative is that losing begets bad things that beget more losing.

But then I think I’m actually still in that contract of my own making. Yes, work is a form of worship. But my worth is not tied to how worshipful I am - it was settled and confirmed on the cross, by nothing of my own doing. I am a beloved son. The father loved the prodigal even before he returned.

Perhaps this is the great question behind a lot of Christian philanthropy. What I call winningness, or even fulfillment, could be termed ‘human flourishing.’ And it seems like such a good thing to pursue that flourishing, to enable it for others. And truly, truly, so much of flourishing seems good to me. But then the question I’m dancing around with this whole essay: what if the fruit looks great, but is not from Christ’s vine? If I am flourishing, but it is tied to a paradigm of self-worth based in achievement and anxiety-until-fulfilled-desire contracts, then the Christian in me says it cannot be the abundant life that Jesus promised.

But if I jump fully into the ‘I am a beloved son,’ what if I stop tending to the fields, and forget to harvest? What if I am lazy, incompetent, but at peace? Perhaps that is the tension of this whole issue. A large part of me wants to make my peace contingent on my competence (won’t that just be better, for everyone involved?). But another part of me says that is not the good news I was taken in by, the words of Jesus I found so compelling.

Unless the Lord builds the house, they labor in vain who build it;

Unless the Lord guards the city, the watchman keeps awake in vain.

It is vain for you to rise up early, to retire late,

To eat the bread of painful labors;

For He gives to His beloved even in his sleep.

How blessed if everyone who fears the Lord, who walks in His ways. When you shall eat of the fruit of your hands, you will be happy and it will be well with you.

(Psalms 127:1-2, 128:1-2)