The Challenge

An: I do not own Arrow.

Summary: Robert Queen challenges his son to live for one year without any of the benefits of the Queen name and fortune. Can Oliver survive? AU, no island. Olicity.

Prologue – The Challenge

It was a month before Oliver Queen's 27th birthday; it was a day that would change the course of his entire life. He had an appointment to see his father at 10:00am. His father was Robert Queen, the CEO of Queen Consolidated, one of the multi-billion dollar companies based in Starling City. Oliver chose to wear ripped jeans, a grey Henley T-shirt and a baseball cap on backwards to the meeting. He had already agreed with his father that at 28 he would start working at the family company and eventually take the reins from his father. Robert had forced him to get his business degree and despite having dropped out of six colleges, the seventh one managed to be the lucky charm. He had one last year of freedom before he became a corporate slave and he was going to enjoy it.

He arrived half an hour late to the meeting. There was nothing unusual about that. Oliver was always late. His father's Executive Assistant, a lady in her mid forties, Grace, shook her head in disappointment at his outfit but she still sent him straight in to see his father. Robert frowned at his appearance but said nothing. He pointed to the seat opposite him and he told Grace to hold all his calls. A few pleasantries were exchanged before his father got right down to business.

"Oliver before you take over this company I want you to learn the value of hard work and money," Robert said sternly.

"Wasn't that what college was for," Oliver quipped.

Robert sighed, he had realised too late in life that he had over indulged his son. As his father it was his responsibility to try to correct this error. It was a million times harder now that Oliver was older and had grown accustomed to a certain way of life but Robert found that removing certain privileges from his son forced Oliver to make the behavioural changes that Robert wanted to see. It had worked before to get Oliver to actually complete his degree.

"Oliver these are important lessons to learn," his father stated.

"I finished the business degree you wanted," Oliver stated defensively. After his father threatened to cut off access to his trust fund, he managed to pass enough classes to get enough credit to graduate. Granted he didn't graduate with honours or anything close to it but at least he graduated.

"I know," his father started but Oliver cut him off.

"That wasn't the deal" Oliver replied angrily. He thought his father's main goal in life was to annoy him.

"I'm modifying the deal, live for one year under an assumed identity without connections to the Queen name and I'll give you two more years of freedom. You won't have to here until you're 30," his father offered him.

"What are the strings?" He knew his father well. There were always strings attached to deals.

His father smiled. Business school was paying off. Oliver had in fact learned something. If he had offered Oliver this deal four years ago, his son would have taken it blindly. "If you use the Queen name or funds for anything the deal is off. You're back in the company at 28."

"What if someone recognises me?" Oliver asked. His face was regularly splashed across the tabloid magazines. In the last year or two the frequency had died down a bit but every time he got himself a new model girlfriend, he'd be right back on top.

"Make sure that they don't. You might find that if you cut your hair and grow a little beard that you would look far more mature."

"Why do I get the feeling that you came up with this entire scheme just to get me to cut my hair," Oliver grumbled.

Robert laughed. He had wanted his son to get rid of that ridiculous hair style for years. A short crop cut would look much better on his son.

"Do I get to choose my identity?" Oliver asked hopefully.

Robert presented him with a file. "Your new name will be Oliver Arrow. Your age and birth date remains the same."

Oliver looked through the file. He had a criminal background. All of the charges that he had ever faced were listed as if he had been convicted of those charges. He had served over 500 hours of community service for an accumulation of DUI's and 6 months jail time for assaulting an officer. There was no college degree listed either. His high school record was dismal at best.

"You can choose any city but Starling City,"

"Any city?" Oliver repeated thinking maybe his father hadn't thought this whole new deal through properly.

"Any city," his father reiterated.

Oliver smirked, "I choose Las Vegas,"

Robert sighed again, at least he didn't choose to go to the opposite coast, "Ok then. I'll give you enough money to survive for one month. Get a job,"

"No problem, I'll start packing my bags." Oliver smirked. This was going to be a piece of cake.

Robert watched his son leave his office and prayed he was making the right decision. It was going to be an eye opening experience for Oliver but he hoped that his son learnt the lessons that he was trying to teach him. He was trying to undo the mistakes he had made, mistakes he was determined not to repeat with Thea. His daughter was going into her last year of high school. She needed to pick a college and a degree to study. He wanted her to have an older brother that she could look up to. He didn't want her to have the lost years that Oliver had.

Later that day Robert Queen met with another man, a tall dark well built man who had served his country in the Army Special Forces Unit.

"Mr. Diggle, welcome, your brother has highly recommended you for this job," Robert said firmly shaking Diggle's hand.

"Mr. Queen," Diggle replied shaking the other man's hand firmly.

Robert motioned to the chair in front of his desk and Diggle sat down.

"As your brother would have briefed you, I've challenged my son to live for a year on his own, without the Queen family name. I know that I have failed him as a father but I'm trying to fix my mistakes. My lawyer has drawn up this contract. Your responsibilities are clearly outlined in Schedule A," Robert said handing him the contract.

"I understand. You essentially want a babysitter for him that he doesn't know is there. If anything goes wrong, I swoop in and get him out of it."

"That is correct," Robert agreed giving Mr. Diggle time to review the contract.

After fifteen minutes, Mr. Diggle signed on the dotted line. Robert was paying this man well to keep a close eye on his son.

"This will be his identity," Robert said handing Diggle a copy of the file he had given Oliver earlier, "He's chosen to make Las Vegas his place of residence for the next year."

"Seems appropriate given his reputation," Diggle commented.

"A driver will drop him on off on the Strip and from there he will make his own way. I will inform you where we leave him."

"I'll keep you updated regularly," Diggle informed him.

"Good,"

With another firm handshake the deal was settled and Diggle rose to leave. As the tall man reached the doorway Robert called out to him,

"Mr. Diggle, I hope I don't see you for a year,"

"I hope so too Mr. Queen,"

An: This story started as a challenge to myself to write a 10,000 word one-shot. It quickly spiraled out of control. It was too large to post as a one-shot so it's been cut up into a month by month breakdown of Oliver's life during the challenge. This story is mostly complete so hopefully I will be updating it every day. There are 15 chapters. For anyone wondering about the 10,000 word one-shot, that's become another story that hopefully won't spiral.