Scary Exit Planning Stories to Tell in The Dark

Scary Exit Planning Stories to Tell in The Dark


A man holds his head in his hands as he reviews a stack of documents on his executive mahogany desk. A brass name plate adorns the front of the desk. “Jack Miller, Founder and CEO” glints under the light cast from a lamp in the corner of the room. An exhausted exhale escapes his mouth as he begrudgingly lifts himself out of his worn leather chair. He paces around his desk as a cool night breeze blows through his open window. The wind carries the pile of shuffled papers on his desk to the ground. Seeing the calamity surrounding his once-organized office, the man walks towards the window to shut out the crisp night air. 

The sky is a blend of navy and black, mirroring the ink stains on his hands from his day reviewing reports. Jack checks his watch. It’s 10:15 in the evening. He had missed dinner with his wife again. Making a mental note to ask his assistant to have flowers delivered to her, he peers out the window and sees a figure slowly moving in the shadows. It can’t be, he thinks. He’s just tired and imagining things. Surely the figure in the shadows is just his mind playing tricks on him. Jack rubs his eyes and looks back out the window, gazing at the spot where the man who bore an eerie resemblance to him was standing mere seconds before.

But no man was there. 

He shook his head in disbelief and chuckled to himself. He had been working for so long today that he was hallucinating. As he bent down to collect the papers strewn across the floor, a faint creak sounded from the direction of his office door. Jack paused as he held onto the “Cash Flow Statement” and “Daily Sales Report” paperwork in his hands. Slowly, he scanned the floor in front of him and saw a shadow of a man stretch across his office. He looked up and saw a familiar pair of brown wingtips, followed by a crisp navy suit. The figure from the shadows was standing in the doorway. The dim fluorescent bulbs in the hallway cast an eerie glow around his face, masking it from his view. 

“Who… Who are you?” Jack asked. Although he was fairly certain he knew the answer. He recognized the shoes – they were identical to the pair he bought himself as a reward for securing a large account two weeks ago. But the soles were worn, the leather was separating at the seams, and the laces fraying at the ends. Jack stood and braced himself on the edge of his desk as he awaited the answer he knew was coming.

“I’m you,” the figure said as he stepped into the office and was illuminated by the light of the moon. “If you continue on your current path, you will become a ghost of who you once were. You will wander aimlessly, with no direction, no purpose, and no business to show for it.”

Jack gripped his desk even tighter, pondering what his future self just shared. He couldn’t believe what he was hearing. He did not understand how his future was this bleak. 

“I don’t believe you.” He stammered out. “My business is thriving. I just landed our largest client who is going to bring in hundreds of thousands of dollars in annual revenue. We are on track to make more this year than ever before.”    

The figure moved ever closer to Jack. “That’s just one client. A client who will take your entire staff’s time and energy away from the rest of your customers. Soon your other customers will grow weary of your company’s inability to effectively handle their needs. They will leave and you will be entirely reliant on this one new client.” 

A cold sweat begins to form at the base of Jack’s neck. He loosens his tie as questions race through his mind. His business will collapse if he loses his other clients. Was this figure telling the truth or simply trying to scare him? Was he really headed down a dangerous path? 

He sunk into the cracked leather of his chair and turned to face the night sky. With his back to the figure of his future self, Jack asked, “How long do I have to fix my business before it’s too late?” 

He impatiently waited for the figure to answer him, but only the sound of the wind hitting the window pane and the soft rustling of the trees echoed throughout the office. 

He spun his chair towards the figure and asked again, more frantically, “How long do I have to fix my business?” 

“It’s not just your business you should be worrying about.” the figure responded. “Think of your life outside of this office. What do you see?” 

Before Jack knew what was happening he felt his body leave his chair. He floated up for a few seconds and immediately felt a rush of cold air hit his face. He closed his eyes to block the blast of air. When he opened his eyes once more his house flooded into view. He saw his wife sitting on the floor with his 4-year-old son. They were laughing and playing with a colorful train puzzle. Jack glanced around the living room and noticed photos lining the wall from their most recent vacation. A vacation that took place before their son was even born. 

Amidst the sound of laughter and puzzle pieces clicking into place, was the sound of Jack’s voice in a nearby room. Jack followed the sound of his own voice to his home office. Behind the closed door, Jack was busy at work. He looked at the computer screen and saw the date and time stamp in the corner. It was a Saturday morning. But not just any morning, it was his son’s birthday. On his only child’s birthday, Jack was where he always was. Behind the closed door of his office, celebrations and life took place without him. 

Jack wanted nothing more than to scream at this vision of himself. But before the words could leave his mouth, he was pulled back to his dark office. 

A single tear left his eye as he sank back into his chair. He thought back to every game, every family dinner, every date night, and birthday he had missed over the past few years. Jack looked up at the figure. “How much of my son’s life do I miss because I am working?”

The figure’s eyes glance at the floor. Jack recognized this averted gaze. He was trying to hide the fact that he was about to cry. “More than enough,” the figure responded while wiping his eyes. 

There is something quite unsettling watching yourself cry. Jack was ashamed he had led a life that caused this much pain and disappointment to his future self. The figure before him had lost his business, missed out on quality time with his family, and was stuck in the past. If he didn’t change his life now, that figure in front of him would not only serve as a warning but would be his future. 

“I want to fix this. How do I make sure my business is successful without compromising my personal life?” Jack pleaded. 

The figure brought his gaze back to Jack, who was impatiently waiting at his desk. The office was buzzing with anticipation. What this figure was about to say would impact the rest of Jack’s life.  

The figure took a deep breath. “You need to learn that you are not your business. You are Jack. For you to be successful in your business and your life, you must find a balance between work and personal goals.” 

“That is easier said than done. How do I find that balance?” Jack responded, eager to learn more. 

“Trust your team. Right now you are managing all new customers, running the day-to-day operations, and generating all new initiatives. You have people in place who can take some of those responsibilities off your hands. The less your business depends on you, the more valuable it will be for your team, your customers, and even future buyers.” The figure explained. “By relinquishing some control to your team, you will have more time to spend with your family and begin achieving your personal goals.” 

Jack thought about what the figure said. He glanced down at this desk and saw the large pile of documents he was reviewing before he noticed the figure in the shadows and realized he was right. It was almost 11:00 pm and he was still at the office because he believed no one could do what he could for his business. He was spending all his time working on one client’s needs and neglecting his other customers. He had missed so much of his young son’s life and had not had dinner with his wife in weeks. Jack looked up at the figure of his future self and vowed to change how he ran his business to not only improve his life now but change the outcome for his future self. 

The second the thought crossed Jack’s mind, the figure began to slowly fade from his office. Before the figure vanished completely, Jack heard a faint, “Thank you, Jack.” escape its mouth. With that, he was gone.   

Jack looked at the spot where his figure just stood. “No. Thank you.” 


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