Career turning points are a two step process.
First, you have to recognize that you have, in fact, reached a turning point. You’ve hit that level where your next step is going to determine how the next ten years are likely to play out. So how do you do this?
By being reflective.
Build it into your schedule. Open up your calendar app and on the first day of each season write in “Quarterly Review”. When the day comes sit with a pen and paper for 20-30 minutes. List the quarter’s wins and losses. Then predict where you’ll be in three months.
This should be enough to get you in the reflective mood and open to the possibiltiy of a turning point.
Second, you have to decide to act. A turning point implies direction, so you have to decide which way you are going to move.
Do you want to turn towards a new challenge, or back towards predictability? Neither choice is objectively right or wrong. But only one choice is the right decision for you.
Sometimes the simplest tools are the best ones. Make a good ol’ fashioned pro/con list and see where you end up. More often than not the right decision will be obvious once you have looked at it objectively.