Why Can’t I Stop failing – – Discontentment is Feeling you need to measure up

Hey Reader,

Welcome to Living Contentment, your weekly nudge towards a life of Biblical contentment.

We’re currently revisiting some causes of discontentment, so if you’ve been reading this newsletter for several years, some of these may sound familiar.


There’s a good chance every person has had some feeling of God / the gods / the universe / the force is not happy with them. A sense that you’re not trying hard enough, not accomplishing enough, not obeying well enough, not making enough sacrifices – or whatever.

No matter where we are, or what we do to fill our days, there is a strong temptation that when we think about the things we do, the websites we look at, the ways we spend our time, the thoughts we have that no one knows, we are hit by a tsunami of “I’m not good enough.”

Many times this gets referred to as “Catholic-guilt” – but that’s not entirely fair as many other traditions have jumped head-first into this and taken it on as if it were their own. This idea can turn into ‘God expects us to clean up our act’ which is a very strange belief for those who want to follow Jesus. If you read the accounts of who Jesus was, what he did, and what he said, you find the exact opposite. We have somehow made this idea of judgemental-Jesus sitting up in heaven, watching us, keeping track of our mistakes, waiting for the day when we clean up our act enough to be counted among his people. This idea of keeping track of wrong and right sounds more like Santa – it’s certainly not who Jesus showed himself to be.

If we think we have to measure up, we become arrogantly proud when we succeed in managing our outward actions but utterly crushed when we don’t. We create a transactional relationship with God where we think he is happy with us, loves and accepts us when we do (or don’t do) certain things, and he is not and will not ever be when we fail.

In any case, when we take the attitude that we are only acceptable, lovable, or worthy when we do whatever it is we think we should – we’ll live most of our life with discontentment is driven by our disappointment in ourselves.

If a child constantly thinks they need to earn their parent’s approval, to prove their worth, and believes no matter what they’ll never achieve it – imagine the heartache. You would be crushed if you thought your good behavior alone is what made your father love you. This is what we do to ourselves in our relationship with God when we think we have to measure up to some external standard in order to be acceptable to Him.

This sense of not measuring up kills any hope of contentment. If we are stuck in a belief that God is not happy with us either we are crushed by that knowledge, or feel he’s right and are disappointed in ourselves. Either way, we don’t have contentment.


For a moment imagine that you can sit down with God. Face to face. What is the first thing he says to you?

This probably says a lot about how you view God.

If your first thought is God says something like: “I’m disappointed in you” or “You seem to keep screwing up” or anything along those lines, you’ve moved far from a God who constantly says: I love you.


Father of unconditional love,

You have made me the way I am,

You know my faults,

Yet you still love me.

You know my weaknesses more than I do,

Yet you still want to use me.

You see how I’ve failed you, how I’ve abandoned you,

how I’ve ignored and denied you,
Yet you still call me your child.

Thank you.

Talk to you next Thursday!