Carefulness is an interesting thing to consider. It's possible that we can be too careful at times.

I recently saw an interview with Donald Miller in which he described how carefulness can be a negative by-product of success. When he writes a book he becomes aware of the critics, as well as the pressure to live up to all the 5 star reviews from previous work.

As a result he feels compelled towards carefulness because it suddenly seems like there is a lot to lose. So he would remove the fun and playful voice that was a part of what ironically created the original success, choosing instead to become careful and attempting to people please.

Are you being too careful in certain areas of life?

Procrastination may often come from success. What takes you there is an element of carelessness and freedom, but once you feel the pressure of expectation and a fear of disappointing people, procrastination can halt action.

Of course carefulness has its place in life. It protects us from many dangers, it keeps us away from the cliff edge in many respects. But it can also keep us from acting on the things we believe in and want our lives to reflect. It can lead to procrastination that stops us from doing and being what we feel pulsing away in our deepest beings.

So how can we tell if we’re caught in the trap of carefulness? It can take many forms and look like a whole range of different things:

Procrastinate When it Comes to Meaningful Action

Feel Very Aware of The People Who are Watching, and Wonder How they Will React

Think About Criticism and Are Willing to Change What You’re Doing

Are On The Lookout for Ways to Fit In, Rather Than Ways to Be More Yourself

Want to Replicate Something From Your Past Rather than Exploring New Territory

Don’t be cruel.

In many respects people love real carelessness, but only if it comes from a big heart. They don’t want to feel manipulated, and they don’t want to feel judged. Anything else is kind of open for experimentation.

Donald Trump is an example of someone who became popular through his carelessness. Even those who don’t like him, do enjoy the fact he’s not careful. There is something compelling about him, something that people cannot take their eyes off. Don Miller says that the key to carelessness is to be kind rather than cruel. It's to have grace and positive intent. To mean well even if you don't always make great decisions. This is where Trump has found himself floudering.

I imagine you know someone for whom you question, “how does he get away with that when someone else would get fired?" It comes down to integrity to oneself. If you pretend to be perfect and gaff then it costs. It you admit your non-perfection then it’s a hell of a lot easier. No one believes we’re that great, so if we’re ourselves, non-judgemental, kind, and authentic, then no one is looking for you to mess up.

The best way to ensure grace for your own slip ups is to be gracious to others when they make their own slip ups along the way.