After the Meteor affair, Cloud is genuinely enthusiastic about his New Life (which is certainly worthy of a capital 'N' and a capital 'L'). For the first time, he's given a chance to live his own life; he has the opportunity to make his own decisions and to find himself. Even when Tifa's feeling overwhelmed and depressed when the events of the last few months finally catch up with her, it is Cloud in a surprising reversal of roles who is there to support her. He knows she's stronger than that; he knows she'll overcome all that's before her, and when she forgets, he assures her that he'll be there to remind her.
One of his first steps in starting over is to find a job. When Tifa re-opens her bar in the new city of Edge, Cloud volunteers to make supply runs. It becomes his job to bargain for ingredients, something the old Cloud would have more than likely scoffed at, but the new Cloud -- the real Cloud -- works at it in ernest. He wants to move on and start his New Life. If that means he has to memorize the names of vegetables and travel to get the supplies Tifa needs, then that's what he'll do.
With Shinra in shambles, the rebuilding process after Meteor is slow, and the Planet is dangerous to traverse. Monsters still roam, and many roads are unstable due to the damage caused by the Lifestream. It's not long before Cloud begins running extra errands for others while picking up supplies for Tifa, delivering important packages and keeping people connected. At first he does this solely as a side job; he makes a little extra pay to buy and tune a bike, but he doesn't even consider organizing it into anything professional. He doesn't even tell Tifa of his extra trips until she answers a call for him; he guiltily details his secret errand runs, apologizing profusely for keeping them from her. Tifa of course holds nothing against him and encourages him to make a business out of it. They live at a bar, after all -- it's the perfect place to meet people and take orders -- and any calls can be managed by Marlene or herself.
Cloud is reluctant at first, no doubt still feeling guilty about hiding the whole affair from his family, but by the next day he's resolved to start his business. Strife's Delivery Service, they call it, his room upstairs serving as its office. Just as they had planned, Tifa and Marlene take and file the orders while Cloud spends his days on the road.
Although he is encouraged and supported by Tifa and Marlene, Strife's Delivery Service is a huge step towards independence in Cloud's self-decided New Life. He's not repeating some distant memory nor is he walking in a dead man's shoes; he's making the decisions and calling the shots. He's doing this job because he's good at it and he likes it--he's helping people, traveling the Planet, and doing some desperately needed soul searching. He discovered through the whole ordeal with Sephiroth what he is -- he knows what made him the way he is -- but he still has yet to find who he is. Being on the road gives him that freedom to think, to explore his avenues and figure out the man behind it all.
Of course this freedom comes with a price. Naturally, traversing the Planet and making deliveries consumes much of his time, and his absence from the bar puts a notable strain on family life at the 7th Heaven. Even if Tifa closes shop once a week to spend time with Marlene, Cloud keeps going. When he does return home, he's distant, drinking by himself and starring off into space whenever Marlene tries to talk to him. In running his jobs and inadvertently searching for himself, he is forced to revisit his past. Every locale is home to some memory from their fight, and it all comes to a head in Elmyra's request to deliver flowers for her fallen daughter to the Forgotten Capital.
Although it is important for him to come to terms with his past in order to move on in the present -- a fact that is drilled into the audience's heads upon each installment in the franchise -- the necessity of facing such memories does not lessen the pain they inflict. Cloud is barely in his 20's, but he has seen much more tragedy than anyone should. It's only natural that, now that he has the time to think about it, he's having trouble sorting it all out. The fight for the Planet involved quick decision making at breakneck speeds and gave little time for mourning or reflection. Now he, like many of the characters, has arrived at a time of peace -- he's living with Tifa, Marlene, and later Denzel; he has a regular job -- and he doesn't know what to do with himself. He doesn't know how to approach the memories he didn't have time to face during the initial conflict.
When he learns of his Geostigma affliction and leaves home, Cloud maintains his job. Whether he realizes it or not, he has not settled his past. His mind and heart still roam in search of penance and belonging. Strife's Delivery Service is the only thing that keeps him moving until he can properly collect his thoughts.
After the film, when Cloud has finally made peace with himself, we see that he continues his business. He spends the film credits racing around a deserted highway on Fenrir, and phone messages overheard in Reminiscence of FFVII (a bonus included with all editions of the DVD) also suggest an active life on the road. However, the final call of Reminiscence is one between Cloud and Tifa in he requests of her to shut the store down for the day and to get the kids ready. Yes, Strife's Delivery Service is still in business, but it is no longer a way to run from responsibilities or forcibly face past pain. He's found his place; he knows who he is and what makes him happy, and he's able to balance his time between what has become his two greatest loves: the freedom of the open road and the people he calls family.
