There's something quietly radical about Frost's approach here. Most of us have learned to temper our hopes—to protect ourselves from disappointment by keeping expectations modest. We call it being realistic. But Frost suggests something different: that maintaining great hopes isn't naive; it's actually a discipline, almost a daily practice. "I always entertain" implies this isn't something that happens to him once. It's a choice he keeps making.
What makes this interesting is that Frost wasn't a cheerful optimist blindly believing everything would work out. He was a farmer, a teacher, someone who watched things fail and break. His poems often sit in darkness. Yet he refused to let those experiences shrink his capacity to hope. He entertained great hopes despite knowing better, not because he didn't.
This matters now because we're surrounded by reasons to dial down our ambitions—economic uncertainty, news cycles designed to scare us, the constant comparison trap. But Frost reminds us that hope isn't about predicting the future accurately. It's about choosing to stay open to possibility, to keep imagining that things could go well. That choice itself, renewed again and again, changes how we move through the world.