After the battle of the five armies and the fall of Smaug the dragon, when the dwarves first began reclaiming the Lonely Mountain, Okili travelled with them.  Already getting on a bit in years, he had less interest in the treasure the other dwarves dreamed about and more interest in reclaiming the lost caverns for their kind.  He was ready to do the hard work the others might forget in their quest for riches.  Nevertheless, he ended up joining a band that sorted treasure from Smaug's vast hoard.  As he sorted however, he came across things the others discounted that he felt were important;  strange stones inlaid with runes.  The others were so interested in their gold and silver and gems they didn't notice when they picked up these strange stones, the power that radiated from within them.  So Okili collected and saved them, sending word back to Thorin's hall of his discovery.

Time passed, and Okili settled in to a life of work and evening play.  He gained a reputation for holding his drink better than most.  He tinkered around with fashioning some simple jewelry for his own, and even a few more complicated pieces, though the more complicated ones didn't come out so well.  But what he most loved out of his days under the mountain were the stories, the stories of dwarves through the ages.  Some of the dwarves who actually retook the mountain were still there and he especially loved their stories, for he could see the locations for himself and imagine what it must have been like.  And there was that grand time when the wizard Gandalf visited and spun a few stories of his own.  Among these stories was the one about the little one, the hobbit who travelled with them and got them out of so many scrapes.  He almost found it hard to believe that one so small and reluctant could manage to do so much.  He wondered what it would be like to meet this...  "hobbit," Bilbo Baggins.

Then one day there came two visitors to the Lonely Mountain, specifically to see him.  One was an old grizzled dwarf.  The other was an elf ancient in days but magnificent in appearence.  They had heard about the stones and wanted to see them.  It turned out they were ancient runestones from ages past.  The dwarf was an old keeper of runes and, also being a jeweller, knew how to fashion them.  The elf was steeped in ancient lore.  Together they learned that there was an immense treasure trove of runestones that likely would have been lost or forgotten had not Okili found and saved them.  The dwarf realized Okili, having felt the power of the stones, already had an affinity for their use.  The Elf gathered a few of the more powerful stones and returned with them to Rivendell.  The dwarf remained behind and began training Okili in the manufacture of jewellry and the use of runestones in commanding the elements.  Okili was just getting a good grasp on their use when he heard of a band of dwarves planning a special trip to the west.  It was Bilbo Baggins 111th birthday.  There was going to be a huge party (Gandalf had sent word), and some of the dwarves wanted to surprise him.

It was quite a band of dwarves Okili joined.  There were only a few going to the party, but there were several travelling to Thorin's Hall and other dwarf holds and keeps.  Okili's trainer travelled with them, figuring it as good a time as any to return to Thorin's Hall.  The journey went well most of the way though a few scattered encounters provided them a some excitement they could have done without.  Orcs and goblins were settling into Mirkwood and it took an additional escort of elves to see them through safely.  When they reached the passes in the Misty Mountains they found them rife with goblins. The Goblins' scouts spotted them first, and were quick to send word.  The main goblin tribes came onto the mountain in numbers and surrounded them.  The dwarves fell back into a cave and fought hard.  Over and over the goblins came in waves as they replenished their numbers.  The elves and dwarves were being bled down until the goblins could finish them once and for all.  But then one of them discovered an exit on the far side.   After one more hard fight they pushed the goblins back, and while the goblins waited for more to arrive, they passed out onto the western side and escaped into Rivendell.  Elven scouts were sent up and when they reported in it became clear that the passes were cut off.  There would be no return to the Lonely Mountain.

The dwarves travelled with a fresh elven escort from Rivendell across the Trollshaws and the Lone Lands into Breeland.  There the elves turned back.  The dwarves continued across the Brandywine Bridge into the Shire, those looking forward to attending the party now a bit downtrodden.  The delays brought on by the Goblins had made them late.  Not only had they missed the party, they'd missed Bilbo altogether.  He had vanished right in front of everyone's eyes at the party, never to be heard from again.  Some of them, including Okili, stopped at the Green Dragon and listened to tales of the party.  But with nothing else to do, they finally moved on to Thorin's Hall.  There, Okili was shocked to learn that his old grizzled mentor had fallen to Dourhands in Ered Luin.  There was yet more.  Spiders, Goblins, and worse had begun stalking the once quiet wilderness.  Evil was afoot.  Emissaries had returned from important meetings with men and dwarves and it was clear that hiding in their halls was no longer good enough.  Dwarves would have to set foot outside their forts and halls and join the fight.  There was talk of the ancient evils of the Second Age rising yet again.  As one of the rare few trained by a master in the craft of runes, Okili was summoned early by Dwalin and enlisted into the cause.  He now finds himself on a road that seems to grow ever more dangerous and hopeless.  Yet he hangs on to that one rumor he heard first from Lord Elrond, and also from Dwalin.  "I can tell you no details.  I can only tell you there is hope."