Personally, I enjoy games that offer you the option to give yourself a penalty to gain some kind of special benefit in some situation. A great example of this would be FATE and the choice to compel an Aspect to gain a fate point.
I've been toying with an option for 5e that would allow one to "push their luck" on an ability check, receiving a temporary penalty in order to gain an additional benefit from the check. The exact nature of the risk and what would be gained from taking it would be decided upon by both the player and the Dungeon Master, however the mechanic for doing so would be the same no matter what.
When pushing one's luck on an ability check, the player receives Disadvantage, but happens to receive an additional benefit or helpful result if the check is successful. For an example, let's imagine we have a player named Jennifer who happens to be playing an elf ranger who's attempting to climb a rather steep cliff.
Jennifer knows that she could probably do this feat relatively easily, but worries that it might take a decent amount of time and she remembers this area is known for wandering monsters. She turns to her Dungeon Master and asks if she can try pushing her luck to climb the cliff faster, which he allows. Jennifer makes the Strength (Athletics) check with Disdvantage, which they decide represents her not being as careful as she should be. Success means she climbs up the cliff at a much quicker pace then she normally would.
Those who feel Disadvantage might be too big of a penalty can go with a simple -4 penalty instead. Either works fine. I elected to use Disadvantage because it's much easier solution. However, use whichever method works best for you and your group.