You’ll always feel nostalgic whenever leaving behind anything that provoked strong emotions in you.
Nostalgia combines the pleasant memory of the past with the cold realisation that a desirable aspect of that past is irredeemably lost.
And sometimes you’ll feel regretful about a road not taken.
The thing about regret is that we tend to imbue those roads with idealised connotations that aren’t real, fantasising about a “what-if”, perceived life that essentially exists only in your imagination.
And it is your imagination that paints this inexistent experience with a wide array of colours and hues.
“There are people in your life who inspire art. And you blow them up into mythical characters and you give them all these magical qualities. Maybe they’re just stepping stones to something bigger and better.” – Californication.
But you’ll never know if you’re actually better or worse off for not having taken that road.
Maybe the decision itself was there in the first place for the sole purpose of carrying you to where you are now (that is, if you believe in destiny).
Either way – it was a stepping stone.
I think you can’t avoid regret though.
It’s a natural by-product of living an analysed life. I’d try keeping your life moving in one direction though: forwards.
Christopher Hitchens once said you have to choose your future regrets.
You’ll often have enough information at the time to know what you’d rather end up regretting in the future; but in any case you can’t know where either path will end up.
“Even with all the advantages of retrospect (…) you can’t make your life look as if you intended it or you were consistent. All you can show is how you dealt with various hands.” – Christopher Hitchens
It’s great to reflect and to analyse in retrospect but you always have full information in terms of you ended up living your life and the benefit of hindsight after the fact.
Only after you’re in that position, can you connect the dots:
“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.” – Steve Jobs
And as you look back, you can poke holes in how certain decisions made lead to some dead-ends and things didn’t pan out how you’d initially hoped they would.
But if it felt right in the moment, then you can’t be hard on yourself or regret making the decision (unless it was a snap decision that wasn’t thought through).
So all you can do when making a decision is try to make the best decision at the time, given all available information at the time.
Even if it blows up in your face, you know that you’d do the same thing given all available information.
Live life to the fullest, look back on your experiences and heed the lessons from them, and move on.
After all – “life must be lived forward and reviewed backwards.”