A Homily upon Paradoxical Optimism

Donald Guy
4 min readJun 6, 2014

“You can do anything you set your mind to!”

That’s what I was told as far back as I can remember. It is in some sense an encapsulation of the American Dream; Horatio Alger soaked through the self-esteem movement and the dreams of a post-scarcity economy.

Just believe in yourself, that’s the key. That’s what they said.

Maybe that was the advice for everyone, but I interpreted it as a personal message, as a vote of confidence in me: me personally. Narcissistic though that reception is, it was also often the intention. I believed: I really did. I was special. We were all special, but I was special. I was destined for great things.


“We’ve all been raised on television to believe that one day we’d all be millionaires, and movie gods, and rock stars. But we won’t. And we’re slowly learning that fact. And we’re very, very pissed off” — Tyler Durden / Chuck Palahniuk

A recent survey going around found that 56% percent of U.S.-based software developers expected to become millionaires in their lifetime. Now, granted when you extrapolate out a 2% inflation rate year over year, a million dollars in 2084 is just over $250k today, and n=1000 ain't some high certainty, but the intended message seems nevertheless clear: impending disillusionment abounds.

Today was MIT commencement (and sincere congratulations to those folks). I don’t know what Ellen Kullman or President Reif said, but I imagine it was pretty optimistic and cheerful. Many of those graduating, perhaps most of them, will lead very successful and remarkable lives. Some without (further) hardship. And to them, optimistic words will ring prophetic.

But some may, probably some will, look back in two years time with a bit of a bitter taste in their proverbial mouth.

Lowered Expectations

Thinking of commencement addresses, I can’t help but think of controversial/antagonistic comedian Daniel Tosh’s take (for “average” high schoolers):

I refuse to give that generic speech: “as I look out here, I see future lawyers and doctors.” I gave the real speech: “There’s felons here” (laugh break) “Some of you will die in a D.U.I accident. Tonight.” Oh. I’m sorry; explain to me why a dose of reality before community college is a bad thing.

And that’s antagonistic and played-for-laughs, but its also not necessarily wrong.

I’ve spent a decent chunk of time over the last couple weeks listening to (history of) philosophy podcasts. And I’ve noticed that divergent threads of Classical philosophy have an interesting commonality: they don’t advise expecting control over your life or fate.

  • Stoicism says expect the worst (but be intentional in reaction)
  • Cynicism says, essentially, “hahaha! Welcome to nature! Shit happens”.
  • Epicurean metaphysics says “dude its just atoms. Whatever”
  • And indeed much of (early) Christian philosophy is pretty certain it’s in God’s hands and out of yours.

Each of these essentially remarks that expectation is the enemy of contentment

But Optimism?

So what of confidence? Confidence is optimism and optimism is good for you. The TED talk I posted 2 days ago says essentially that. If you interpret a stress response as your body revving up to come to your aid, so it is. There’s a chapter too (Chapter 17) in Full Catastrophe Living that alludes to studies on optimism and the related concepts of self-effacy and hardiness. The cited researchers are Dr. Albert Bandura of Stanford and Dr. Suzanne Kobasa of CUNY. There is depth I won’t delve into but the point essentially reduces to “If you expect to be able to handle life, if you think you are essentially good at handling things, you have a better time”.

So… wat?

denying the antecedent — a logical fallacy

These premises read to me intuitively as opposing. And I imagine they might to you. But that is largely cause I am reading the latter as presented at left.

And there I am denying the antecedent, and there for all the intuitive validity, I am committing a logical fallacy. But also I jumped too far…

The middle way

Talk to people who luad the Meditations of Marcus Aurelius or its modern day rewrites (like this recent best-seller), read further research Full Catastrophe Living cites, perhaps contemplate Taoist conceptions of Wu wei or the Buddha’s middle way, and a weird pattern emerges.

It’s one I still haven’t entirely wrapped my head around. But I think it goes something like this:

  • Abandoning consistent positive expectation (or abandoning expectation entirely) gives rise to openness to possibility and patience.
  • This may lead to mixed fortune and perseverance.
  • This may lead to some success, some failure, and development of resilience.
  • Understanding thus gained breeds a new optimism and deeper appreciation of success. (These qualities often leads to more success.)

The gap between can and will

I think the important difference between (my) positive expectation, my traditional notion of optimism and self-confidence, and this optimism I now hope to find is basically notions of entitlement and probability.

I was told
“you can do anything you set your mind to”
and I fear I (and perhaps other Americans or millennials like me) heard
“you will be successful in whatever you set your mind to”

Now I look to reassess and find what I could have heard in the first place
“you might be successful at something you set your mind to” and
“if you try things consistently, you will likely find success”.