Welcome to the Say No Challenge! In our previous posts, you have learned the strategies of being assertive and set your boundaries. No we are trying to put that into real practice. In this following game, you’ll step into the shoes of our protagonist, Anna, and face off against her demanding coworker, pushy boss, a needy friend and her guilt-tripping partner. As you read through the following dialogues, try to put yourself in Anna’s position and come up with assertive responses that honor your boundaries. Then, compare your responses with the suggested ones at the end to see how you did. Can you find the most effective way to say no and win the Say No Challenge? Let’s find out!
Meet Anna, a young professional who works at a marketing firm. Anna is a hardworking employee who wants to leave a good impression with her boss and coworker. She takes on more work than she can handle and often finds herself working long hours to complete tasks that are not even in her job description. Anna always says yes to other’s request, even when it becomes too much.
Challenge #1
One day, Anna’s coworker, John, comes to her with a request to help him with a project that is due by the end of the day.
John: “Hey Anna, can you help me with this project? I know it’s last minute, but I’m really swamped and I can’t do it alone.”
Anna: “___________” (How would Anna respond? Please help her come up with an assertive response to set a boundary.)
John: “Oh, come on, it won’t take long! Can’t you spare a minute for me?”
Anna: “___________”
John: “I guess I’ll just have to do it all by myself then. You’re always too busy for me.”
Anna: “___________”
Challenge #2
Another day, Anna’s boss, Sarah, asks her to take on a project that would require her to work overtime for the next few weeks.
Sarah: “Anna, I know this is a lot to ask, but we really need someone to take on this project. Would you be willing to work overtime for the next few weeks to get it done?”
Anna: ” ___________”
Sarah: “But this is really important and needs to be done. Can’t you just push your other obligations aside for a while?”
Anna: “___________”
It’s hard for Anna to say no to her coworkers and boss because she wants to be seen as a team player and a hardworking employee. However, saying yes to every request can quickly lead to burnout and resentment. It’s important for Anna to learn how to say no in a firm but polite way that sets boundaries and preserves her well-being.
How did you do? Did you find it easy or difficult to say no if you were Anna? Feel free to go back to our previous posts about assertiveness and boundary setting skills to fresh up your memory and sharpen your tools. When you are ready, you can scroll down this page to see some suggested response.

Possible responses for Anna:
To John: “Hey John, I appreciate you coming to me for help, but I’m currently swamped with my own work. I won’t be able to assist you with this project.”
or: “I’m sorry, but I need to finish this task first. Maybe we can schedule a time to go over your project together later.”
or: “I understand that you’re frustrated, but I need to prioritize my own work to meet my deadlines. I hope you understand.”
To Sarah: “Hey Sarah, I understand that this project is important, but I already have a lot on my plate right now. I’m not able to work overtime for the next few weeks. I hope you understand.”
Or: “I understand this is very important. Is there anyone else who can take on this project?”
Challenge #3
Now let’s take a look at Anna’s personal life. Turns out that she needs you help in that area as well.
Anna values her relationships with her loved ones, but she often finds herself saying “yes” to their requests, even when it means sacrificing her own needs and wants.
One day, Anna’s friend, Rachel, calls her on the phone.
“Hey, Anna! How’s it going? I miss you so much,” Rachel says. “Listen, I know it’s been a while since we’ve caught up, but I need your help with something. Can you come over and help me move this weekend?”
Anna hesitates. She’s been looking forward to some much-needed downtime after a busy workweek, but she also doesn’t want to disappoint Rachel.
“_________,” Anna says.
“Oh, come on, Anna! I really need your help,” Rachel responds. “You know I’d do the same for you.”
Anna feels torn. She wants to help Rachel, but she also knows that she needs to take care of herself.
Anna: “______________________”
Challenge #4
Later that week, Anna’s partner, Alex, approaches her with a request.
“Hey, Anna, I was wondering if you could pick up my dry cleaning on your way home from work,” Alex says.
Anna feels a sense of frustration rising within her. She knows that Alex could have easily picked up the dry cleaning themselves, but they always seem to rely on her to do these kinds of tasks.
“___________” Anna responds.
“Come on, just help me out this one time. I have to stay late at work today,” Alex says. “Please, Anna, it’ll only take a few minutes.”
Anna: “_____________”
_
It’s hard for Anna to say no to the people she cares about. She wants to be there for them, but she also wants to take care of herself. It’s a difficult balance to strike, but it’s essential for her emotional health and well-being.
Here are a few possible responses for Anna to consider:
- “I’m sorry, Rachel, but I can’t help you move this weekend. I’ve had a busy week at work, and I really need some downtime to recharge. I hope you can understand.”
- “I love you, Alex, but I can’t keep doing all of these errands for you. I need to prioritize my own needs and responsibilities. Can we come up with a different solution together?”

Hooray! You did it!
Congratulations on completing this challenge! You have just practiced a valuable life skill that will help you set healthy boundaries and take control of your personal and professional life. Remember, saying no is not a sign of weakness, but a demonstration of self-respect and self-care. Assertiveness requires practice and can be challenging, but with time and effort, you will become more comfortable in saying no and communicating your needs. Keep practicing, and don’t be afraid to seek support from friends, family, or a therapist. Good luck on your journey to assertiveness!
*Disclaimer: The characters mentioned in this post are fictional and created solely for educational purposes. While their experiences may be relatable to some readers, they are not meant to represent any specific individuals or situations.
If you find yourself struggling with low confidence or difficult in boundary settings, and they have a negative impact on your life, it may be time to seek professional help in a supportive and safe environment. Please feel free to contact Dr. Fei Yi at drfeiyi@silkroadpsychology.com for more information about individual therapy.