Real Life Decisions
Money and Work
Relationships and Boundaries
Staying on Track
Wild Card
100

You realize you're going to be late for an important appointment. What should you do instead of just not showing up?

Contact the appropriate person as soon as possible, explain the situation, and communicate when you expect to arrive.

100

Name something employers value that doesn't require a college degree.

Reliability, punctuality, honesty, communication, willingness to learn, teamwork, or work ethic.


100

True or false: Setting a boundary means you're trying to control another person.

False. A boundary identifies what you will or will not accept or participate in.

100

Name one person you could contact when you're having a difficult day.

Counselor, sponsor, mentor, trusted friend/family member, peer support specialist, case manager, faith leader, etc.

100

Would you rather have a job you love for $17/hour or a job you hate for $25/hour? Why?

NA

200

An old friend invites you somewhere, but you know being there could put your progress at risk. Name one healthy response.

Decline, suggest meeting somewhere safer, leave the situation, or contact a healthy support.

200

What's the difference between a need and a want?

A need is necessary for basic living or responsibilities; a want is something desirable but not essential.

200

Someone repeatedly borrows money from you and never pays you back. Give an example of a healthy boundary.

“I'm not going to lend money anymore.”

200

Name one personal warning sign that stress may be getting too high.

Irritability, poor sleep, cravings, impulsivity, withdrawing, arguing, racing thoughts, missing responsibilities, etc.

200

Finish the sentence: “One thing I handle differently today than I did in the past is _____.”

NA

300

Someone disrespects you in public and you immediately feel angry. What is one thing you can do before responding?

Pause, breathe, walk away, consider the consequences, or give yourself time before responding.

300

Your supervisor corrects you in a way you don't like. What's a professional way to handle it?

Remain calm, listen, ask questions, and address concerns respectfully—preferably privately.

300

Name one warning sign that a friendship or relationship may be interfering with your progress.

Pressure to break rules, return to substance use/criminal behavior, neglect responsibilities, spend irresponsibly, or violate personal boundaries.

300

You wake up having a terrible day. Name three things you still have control over.

Your next decision, who you contact, where you go, how you respond, whether you attend obligations, whether you ask for help, etc.

300

BAD ADVICE ONLY: Your boss makes you furious at work. Give the absolute WORST advice possible for handling it. 😂 Then tell us what you should actually do.

Let them have fun with the first part. Healthy responses could include pausing, regulating emotions, communicating professionally, requesting a private conversation, or walking away temporarily.

400

You make a bad decision and nobody else knows about it. What does accountability look like?

Taking responsibility without excuses, addressing the consequences, and deciding what needs to change.

400

You get paid Friday. Before spending money on entertainment or something you want, name three things you should consider first.

Housing, utilities, food, transportation, debt, required payments, savings, or other necessities.

400

Someone you care about asks you to do something that could jeopardize your freedom, employment, sobriety, or other major goal. What's a healthy response?

Say no and protect your long-term stability, even if the other person becomes upset.

400

What's the difference between a setback and giving up?

A setback is a problem or mistake that can be addressed; giving up means stopping your efforts toward the goal.

400

You legally receive $100,000 tomorrow. What are the first three things you do with it?

No single correct answer. Afterward, discuss saving, housing, transportation, debt, investing, helping family, impulsive spending, etc.

500

You're faced with a decision that feels good right now but could negatively affect your life six months from now. What question should you ask yourself?

Something like: “Is this worth the possible consequences?” or “How will this decision affect my future goals?”

500

You unexpectedly receive $10,000. Name three financially responsible things you could consider doing before making a major purchase.

Build emergency savings, pay debt, address transportation/housing needs, create a budget, save/invest appropriately, or establish longer-term financial goals.

500

What's the difference between supporting someone and enabling someone?

Support helps someone make healthier choices; enabling protects someone from consequences or makes unhealthy behavior easier to continue.

500

Name three things that can make someone's reentry support system stronger.

Healthy relationships, employment, treatment, peer support, recovery meetings, faith/community involvement, structured activities, mentorship, transportation/resources, etc.

500

You get one billboard that everyone leaving incarceration will see on their first day out. You can put ONE sentence on it. What does your billboard say?

Personal answer — then have them explain why they chose it.

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