I haven't lived my life with many regrets so far. As a young man, this is fairly manageable. There's simply not that much life behind you to regret.
But as a young man, you tend to think of regret as wishing you had done something differently in the past, or perhaps not at all. Regret is something you feel when looking back over the choices or mistakes you may have made in the past.
But as I get older, I'm becoming familiar with a different kind regret. It's not the bitter kind you feel in relation to a past you cannot change, in the sense that there's a moment you back on where you could have gone right and instead went left.
But as more life accumulates behind you, the question of what could have been simply gets larger too. And it's not so much a situation of looking back and imagining what things might be like now if you had done differently then. It's more like looking at the totality of your life you have right now and wondering what things would be like if they had simply been differently.
It's not the kind of regret that hangs on a particular moment or choice or wrong turn that you would go back and change if only you would. It's more like not even knowing how things could have turned out differently, but wondering what life might have been if they did.
But as you get older, this kind of regret can eclipse a lifetime. And it gets to a point where the sheer gravity of it all actually makes it easier to dismiss; where so much has happened by now that questions of "what if" can be almost thoughtfully entertained without seriously weighing upon one's heart. Almost like cracking a joke about a distant tragedy in one's past.
In more certain terms, The Everyway is sort of about the relationships we have with people over the course of our lives. And how as we get older we have less time with each other left. Do we want to spend that time lamenting what could have been? Or carry on in spite of it? It's an open question that these lyrics explore.
— David Kennedy
