Well, If I must boast,

In the two letters we have that Paul wrote to the Corinthians, he repeats something he borrowed from the prophet Jeremiah,
"But he who boasts, let him boast in the Lord".

What was it exactly that Jeremiah said?

"Let not a wise man boast of his wisdom, and let not the mighty man boast of his might, let not a rich man boast of his riches; but let him who boasts boast of this, that he understands and knows Me, that I am the Lord who exercises lovingkindness, justice and righteousness on earth; for I delight in these things," declares the Lord." Jeremiah. 9:23-24

Of himself, Paul says, "If I have to boast, 
I will boast of what pertains to my weakness". 
2 Corinthians 11:30

What was this weakness Paul was talking about?
Whatever it was, he prayed for God to take it away repeatedly, without the result he wanted.

Been there, done that.
I've been in that place many times, asking God, pleading with Him, to relieve me of what makes me feel weak, especially before anyone else notices it.

But for Paul, God did not take it away and people noticed. He was often criticized for not being up to snuff with other visiting preachers. Did that criticism prompt him to beg God to change his weaknesses? Was there some point where he thought all these critics were right and he needed to be fixed?

That's what I would be thinking.
"Fix me God, make me better, or more accurately, make me as good as others."
(Did you see that? Did you see what I was doing, again? I was playing the comparison card. Who keeps slipping them into my hand?)

In the end, Paul realized that his weakness was meant to keep him humble. He discovered, through experience, that his greatest strength came through his weakness.

So it would be logical to conclude...
if strength and power (and I mean the really authentic stuff) were what we wanted, weakness would be better. If we were willing to embrace weakness, we could have super power at our disposal.

But we aren't, are we?
We aren't willing to appear weak to the rest of the world.
Why is that?
Because our goal isn't really true strength, but rather the appearance of strength.
And that my friends is our pride taking charge, our flesh exerting dominance.

If I were walking in the Spirit, I would say like Paul,
"if I have to brag, then I'm gonna brag about everything that makes me look weak".
Sound ridiculous?
Seem backwards?
Yep,
but we should be used to this by now.
Everything about walking in the Spirit doesn't "make sense" to our natural selves.

In the flesh, I'm too proud to be weak, but in the Spirit, I will talk about my weaknesses as if I were proud of them, not to bring glory to myself, but to bring glory to God.

Obviously, it would be annoying and unedifying if I constantly bragged about my weaknesses, so please do not think that is what I am recommending. Besides, most of the time when we broadcast our weaknesses, it's just because we are fishing for positive comments to boost us up.
True boasting is in the Lord! Therefore, our speech should bring glory to Him, not to ourselves.

However, Paul's 180 approach to weaknesses must dramatically change the way I see them and react to them. To boast in my weaknesses means they are no longer a source of shame, it means that they should not frustrate, nor anger, nor cause me to despair, it means that I no longer hate what makes me feel weak. To boast in my weaknesses is to stop taking pride in my strengths, and to the contrary, take pride in my weaknesses.

Think about the things you want others to see you do, those things you secretly hope to hear others credit you with brilliance, those things that make you feel just a little bit more superior, those great things you've accomplished.
If you could, you would brag about them,
a little.
Maybe you already do.

Now think about your weaknesses in the same way.
Rather than inferior, think of your weaknesses as what commends you to greatness in the Lord.
Rather than shameful, think of them as glorifying God.
Rather than hate them, rejoice in them.

If I had fuses in my brain, they'd be blowing right now.

Boasting in my weaknesses saps power from my flesh, causing it to die just a little bit more, and taking me one step closer to cross-walking.