Odds of Hanging On
Once a shark, always a shark. When you break in, you probably won't be making any decisions for yourself. Later on, you might earn some independence and gain enough trust to make some plays of your own. If they go belly up and it turns out you've just been coasting at work, you might be in trouble; but if you've been paying attention and have learned to spot a good opportunity, you should be fine.
Really, what it comes down to is an ability to read the market. As more people move back to cities from their sprawling suburban outposts, new kinds of developments will begin to trend more heavily. If you can spot these trends, preferably before they start, you'll have a leg up not only on your competition but on the market itself.
You may even become so adept at reading markets that you'll start trends, thus changing the face of the real estate development world. But before we get ahead of ourselves here, the most important thing involved in holding onto this career is the standard answer: money. If you don't have the money you need on your own, you need to be great at finding and keeping investors.