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Free Character Writing Prompts #53:
Work Obsessed

Check out these 10 character writing prompts about those who work hardest for the money: the work obsessed. Whether they were born with the ability to endure 80+ hour work weeks or they developed it along the way, I commend workaholics for putting in the hours that most people aren't willing to. These employment addicts throw themselves into their jobs with such fervor that they may have less time than the rest of us to spend on health, family and recreation. While these characters are often vilified, many of them are working this hard to provide for their families. Then again, some may just be looking to buy a new Ferrari. 

Free Character Writing Prompts #53: Work Obsessed

1. When his first son was born, he and his wife were not what you'd call financially prepared. After all, she had decided to take an entire year off of work but only had a few months of maternity pay. This mean that he would have to work harder and put in more hours to keep food on the table. Shortly after his first child was born, his wife became pregnant again and this caused him to work even harder. He started to really enjoy his time at work because he knew that he was providing his family with the life it deserved. When his wife went back to work, he decided to keep up his 80 hour a week habit, because he got so much satisfaction out of it. Does he have any reservations about spending so much time away from his family?

2. When his parents asked him if he ever planned on settling down he laughed uproariously in their faces. After all, he already had a lady in his life, his company, and if stopped for a second to try to get married, he feared that everything would collapse on him. His business was strong but he knew it would have to expand to become something to sustain him and as a result he put in even more time and energy. He downed coffee and energy drinks by the bucket and he went as long as he could without sleep as a sort of challenge to himself. When his company did finally break through to the big time and was sold for hundreds of millions of dollars, he wondered what the next step would be. Will he ever add anything other than his business to his day-to-day life and if so what would that be?

3. She knew during her college days that work was going to be the thing for her, no matter what activities she participated in. She had made a few close friends during school, but knew it would be nearly impossible to keep them after she immersed herself in her first job. She felt bad as she lost touch with them, but knew no other way, because she felt the need to make her career into her life. She frequently worked over 60 hours a week and became well-liked around the office. One day, nearly three years after she'd left college, her three best college friends surprised her at work and have decided to stay in the city she moved to. How will this workaholic balance her social life with her career?

4. When she first started her law practice, she was one of the first female-run practices in existence and she worked hard to get as many clients as possible. She could be found in the office over 90 hours a week, because she rarely delegated any responsibility out and assumed she was the only one who would be able to produce the results she wanted. Now over 40 years later, she was especially contemplative about the opportunities she missed throughout the years. She wondered what life would have been like if she'd structured her priorities differently. As she heads into retirement age, will her life be one of regret or one of gratitude and why or why not?

5. Throughout high school and college, you loved him like a brother. He was the kind of party animal that you kept with you as many nights as possible because you never knew what trouble he'd get you into. By the end of college and the beginning of graduate school, he started to mellow out and became as focused on his career as he used to be as getting girls' phone numbers. Despite your best efforts, you hardly ever saw him anymore and you started to get the feeling he'd rather be working than hanging out with you guys. Eventually, he even moved out to the suburbs and getting a drink with him was a major inconvenience. How did he make the transition to being such a workaholic?

6. When he was younger, the best way to describe him was "a hopeless romantic." He wrote poetry, bought gifts and went out of his way to be larger than life with these women he loved. He always came on a bit too strong and for the most part, he scared these ladies away. He became depressed after a few years of heartbreak and he through himself into his work so that he wouldn't even think about how badly he felt. After getting a position that caused him to work nearly twice the average of other people, he found the love of his life working the completely opposite schedule. How will he be able to balance his romanticism with his new love: working around his feelings?

7. Though she'd been brought up in a world in which women went to college to get married, she found her true calling as a workaholic without a spouse. She found that she was in love with television and she made her living as one of the hardest working women directors in the business. She had an amazing sense of comedic timing and she made all of her actors feel at ease, even though she rarely felt at ease herself. After all, she'd go from one project to another and she rarely turned down work, which caused her to more frequently turn down the opportunity to sleep. Her parents were proud of her, though they wish that at some point she would settle down and think about her own needs, rather than trying to direct as many episodes and films as possible. What are some of her best qualities as a director and what do some famous actors say about working with her?

8. Her meticulous mindset had made her an A+ student when it came to copyediting anything from websites to student publications. She now spent a great deal of her time editing one of the most profitable online businesses in history. An error on a site like that could cost the company millions of dollars in sales and she was the primary workhorse to keep things in order. The only potential mistake in her life was that she was unable to put down her error hunting when she left her long days at work. She would chastise her friends and family for "errors" in the way they lived their lives or ways in which they were out of the ordinary. Will she ever be able to make her work and home life separate?

9. He had been one of the most loving parents and husbands known to man, but when his wife died and his kids went away to start their own families he felt like he had nothing. So, in order to add more purpose to his life, he became completely obsessed with work. At first, this gave him a great deal of satisfaction, after all, he received three promotions in five years with his new concentration. Eventually, he got to a level of responsibility and income that he could have only dreamed of when his wife was still alive. But it was extremely stressful and he barely had any time to move on with his life. Will he be able to once again feel fulfilled with a balanced and happy life?

10. Though the ownership of the baseball team came to her through her inheritance, she promised her father that she would always take care of the team as if it were her own. She was more involved in the fate of her organization than most players and managers were and it was because of her never say die attitude that they won five world championships during her tenure there. Her family loved how hard she worked to keep her late father's business afloat, but they wondered if she wasn't putting too much time into the team. When they tried to tell her they wanted her to live her life, she said, "This team is my life." What is her day-to-day schedule like in her running of the team? 

Did you enjoy these character writing prompts? Check out an entire collection of them on Amazon 

Done with Character Writing Prompts about the Work Obsessed? Go back to Creative Writing Prompts. 

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Written by Bryan Cohen

Bryan Cohen is the author of more than 30 books, many of which focus on creative writing and blasting through that pesky writer's block. His books have sold more than 20,000 copies. You can find him on and Facebook.

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