When can I expect to start making decent money?

As mentioned you’ll usually see the highest salaries in markets where it’s hard to find good designers and corporate environments.

If your boss doesn’t value you now, he probably won’t start - that’s just your boss, not the industry in general.

Your goal should always be to learn as much as possible from any job, continuously refresh your portfolio as much as possible, grow your network of other designer contacts through IDSA Conferences or similar events, and try to figure out your next move.

If you’re in a big expensive city, you may have to decide if you like being in a big city and living at the poverty level (like many in NYC do) because of all the other fun stuff that city life affords socially, or if you would rather make more money but be stuck in a suburb with no night life, no social culture, etc.

There are a lot of designer friendly cities that have enough big industry to get a job, reasonable costs of living and social life. Charlotte, Austin, Chicago, etc. $35k would go a much longer way in any of those places compared to NYC or SF.