This requires you to view the painting of the trees above the couch on four separate occasions. The painting will change seasons based on the loops you complete.
The loops you need to complete are:
Let It Be ("Listen (80G)")
Dinner
Is It Over?
The Truth
Make sure to view the picture after finishing each of these loops. Resetting your progress in the advanced options menu will reset this achievement, as will completing Ending #3 ("Continue (80G)") as that is the True Ending and completes the game.
Below is a full game walkthrough with all achievements and endings!
Achievement Timestamps:
0:00:00 - Listen Achievement
0:06:14 - Seasons Achievement (Step 1/4)
0:06:24 - Ouroboros Achievement (Step 1/3)
0:06:36 - Faun Achievement (Step 1/3)
0:13:45 - Seasons Achievement (Step 2/4)
0:14:08 - Fluidity Achievement
0:37:08 - Coward Achievement
1:12:51 - Groundhog Achievement
1:13:43 - Seasons Achievement (Step 3/4)
1:13:50 - Faun Achievement (Step 2/3)
1:36:08 - Confessed Achievement
1:36:10 - Seasons Achievement (Step 4/4)
1:36:28 - Ouroboros Achievement (Step 2/3)
1:36:50 - Faun Achievement (Step 3/3)
1:43:49 - Alone Achievement
1:44:25 - Gardener Achievement
1:48:26 - Mindfulness Achievement
1:54:03 - Continue Achievement
1:56:42 - Ouroboros Achievement (Step 3/3)
Loop Timestamps:
0:00:00 - Loop 1 (Let It Be) [Listen Achievement]
0:04:47 - Loop 2 (Dinner)
0:13:12 - Loop 3 (Question)
0:20:15 - Loop 4 (Witness)
0:27:27 - Loop 5 (Prove It)
0:33:04 - Loop 6 (Forgiven, Not Forgotten)
0:37:08 - Loop 7 (Betrayal) [Coward Achievement]
0:45:14 - Loop 8 (Don't Betray)
0:56:38 - Loop 9 (More Questions)
1:03:35 - Loop 10 (Is It Over?)
1:12:51 - Loop 11 (Perfect Day) [Groundhog Achievement]
1:22:02 - Loop 12 (Murderer)
1:26:51 - Loop 13 (The Truth)
1:36:08 - Loop 14 (Confession) [Confessed Achievement]
1:43:49 - Loop 15 (Ending #1) [Alone Achievement]
1:48:26 - Loop 16 (Ending #2) [Mindfulness Achievement]
1:54:03 - Loop 17 (Ending #3) [Continue Achievement]