An expression for someone who makes difficulties for himself

Question

Is there a word or expression for someone who is often a cause of difficulties that he later has to overcome?

For example, a man who always has to work extra hours to finish his job at time just because when he has time he slacks instead working.

Or maybe a good chess player that makes silly mistakes because he always underestimates his opponent (and later has to try hard to compensate for these mistakes).

So basically I want a word or expression for someone who makes avoidable and totally unnecessary difficulties for himself.

Answer 1

This is a bit of a neologism, but I suppose "self-saboteur" captures the person you are describing adequately.

If you don't necessarily need a single word you could go with the more traditional:

He has a habit of shooting himself in the foot

Answer 2

You could say

He is his own worst enemy.

or

He can't get out of his own way.

Answer 3

If I were an employer describing this person to a third party, I would call him/her:

A Liability

If I were describing this person generally, I would use:

Self-destructive

More generally:

A trainwreck

Or, even moreso, and in the strictest sense of the word:

A fool

Answer 4

If an adjective will suffice, "improvident" or "shortsighted" or any of their synonyms should work.

Your question's phrasing suggests that maybe you want a noun. A "micawber" is a person who assumes that things will be better in the future and thus avoids working hard in the present moment.

Answer 5

You could say that he

shoots himself in the foot.