When do I sell?

I'm not a very risky investor, but about 7 months ago I invested ~$10k instead of putting it into an IRA. The original goal was to invest and hold until it hit $250k because that would be life changing money for me.

However, now that we're closing in on $1k ETH I'm getting nervous.

Do I stick with my original plan and hold?

Do I sell enough to cover my initial investment?

How do you guys make these decisions?