This song for me is about mortality with a boat race as a metaphor for the journey of life. "You think you have the last laugh, now you know this can't be true"; death has the last laugh. So "you make the best of each new day". At times you think "your dream world's coming true" but then a friend dies ("Was it someone that I knew?"), reminding you of the temporariness of life and if you have plans "do it soon". You are sailing in a race among the ruins (people you've let go of, or who have died). You just continue on with "the best of all that's left, you know this cannot last". This being life. The last six lines may be autobiographical, Lightfoot ended up by his "virtue" (i.e., talent) providing entertainment ("playing jester") to his audiences.
This song for me is about mortality with a boat race as a metaphor for the journey of life. "You think you have the last laugh, now you know this can't be true"; death has the last laugh. So "you make the best of each new day". At times you think "your dream world's coming true" but then a friend dies ("Was it someone that I knew?"), reminding you of the temporariness of life and if you have plans "do it soon". You are sailing in a race among the ruins (people you've let go of, or who have died). You just continue on with "the best of all that's left, you know this cannot last". This being life. The last six lines may be autobiographical, Lightfoot ended up by his "virtue" (i.e., talent) providing entertainment ("playing jester") to his audiences.
[Edit: typo]