Desire without the pain

Naval talks about desire as an agreement to be unhappy until we get what we want. That makes me question how I pursue things.

Can I desire something and still enjoy my life while I work towards it? I think I can. I can care about the outcome and pay attention to what I am experiencing along the way.

The same question comes up with winning. We are told we have to win. How much of my experience am I making conditional on that?

I want to keep building, learning and pursuing things. I also want to notice when a desire starts deciding whether I am allowed to be happy.