Summer break isn’t just for relaxing—it’s also the perfect time for students to experiment with entrepreneurship. Whether launching a tutoring business, selling digital products, or offering freelance services, today's teens have more tools than ever to start small, low-cost businesses. Thanks to AI platforms like ChatGPT, they can accelerate their progress with a bit of help from smart prompts.

Research shows that working during adolescence can have a lasting impact on future success. According to EducationNext, teens with summer jobs are 7% more likely to graduate on time. And for each year they work during their teen years, they earn 14% to 16% higher wages in their twenties, reports the Foundation for Government Accountability. With over 6 million teens competing for traditional summer jobs, creating your own opportunity offers a distinct advantage.

Create Your Job With ChatGPT

Recent research from Google Workspace and The Harris Poll (November 2024) reveals 82% of young leaders (ages 22-39) already leverage AI tools, with 98% anticipating AI will impact their industry within the next five years. This widespread adoption shows that AI fluency is quickly becoming a career essential. But why limit yourself to using AI for existing jobs when you could use it to create your own?

Starting a side hustle doesn’t just provide income; it builds the exact skills employers value. According to the same Google/Harris Poll research, 50% of young professionals recognize AI's potential to automate routine tasks, freeing time for more strategic work. Using these tools to launch your venture, you develop entrepreneurial abilities and the AI proficiency that increasingly drives workplace success. With 88% of respondents saying they would use AI to start tasks that feel overwhelming, these prompts can help overcome the initial barriers to launching a business.

1. Brainstorming The Right Side Hustle

Use this when you're unsure what kind of side hustle you should start, or want ideas tailored to your skills, interests, and situation.

Prompt:

"I'm a [high school/college]

student interested in starting a side hustle this summer. I have [list your skills, hobbies, or interests], access to [list your resources: internet, Canva, transportation, etc.], and about [number of hours] per week to work. I want ideas that I can launch with under [$100/$50]. Please generate 10 side hustle ideas that fit these criteria and explain for each: 1) Why it's a good fit for me, 2) What I'd need to get started, 3) An example of a first step I could take."

Why this prompt works: Instead of generic ideas, it helps ChatGPT deliver personalized, feasible business ideas based on what the student already knows, removing confusion and focusing attention.

One student, Maya, used a similar approach to identify a personalized study guide service for AP courses. Focusing on five subjects she knew well, she generated over $6,200 in three months while working just 20 hours weekly.

2. Writing A Product Or Service Description

After choosing your side hustle, use this to describe what you're offering on your website, flyer, or social media.

Prompt:

"I need specific feedback on this work in progress. Here's my draft product/service description: [paste your description]

. My goal is to attract [describe your target customer] and clearly explain what I'm offering in a persuasive but simple way. Please review this with the following in mind: 1) Does it accomplish my goal of attracting my target customer? 2) Is the wording clear and engaging? 3) Would a customer know exactly what I'm offering and why it's valuable? Give me actionable suggestions for improvement, with examples of implementing each change. Explain your reasoning for each suggestion."

Why this prompt works: This prompt teaches students to seek constructive, objective feedback and improve their copywriting without outsourcing it entirely to AI, building real communication skills.

According to a 2022 Network For Teaching Entrepreneurship (NFTE) report, successful young entrepreneurs typically start by solving problems they've experienced or observed in their communities. A clear description of how your service solves these problems is essential.

3. Writing A Cold Outreach Message

Use this when contacting potential customers by email, Instagram DM, or LinkedIn message.

Prompt:

"I need help improving this message I'm writing to a potential customer. Here's what I've drafted: [paste your message]. My goal is to [get them to book a service, buy a product, respond to a question]. Please review this with the following in mind: 1) Does it sound friendly and professional? 2) Is my ask clear and reasonable? 3) Does it explain what's in it for them? Give me actionable suggestions for improvement, with examples of how to rewrite any unclear parts. Explain your reasoning for each suggestion."

Why this prompt works: It empowers students to refine their outreach skills rather than rely on AI to write them from scratch while ensuring they hit tone, clarity, and persuasion goals.

Sydney Day Weikart, a teen entrepreneur who started a greeting card business at age 13, grew her business to over $10,000 in sales by age 16 through consistent outreach and marketing efforts.

4. Creating A Basic Marketing Plan

Use this to map out an actionable, simplified marketing strategy.

Prompt:

"I'm a student starting a [describe your side hustle] this summer. I want a simple marketing plan to help me get my first 5-10 customers. Please create a plan I can follow that includes: 1) three low-cost or free ways to promote this business, 2) how often I should do each action, 3) one example message or caption I could use for each promotion method. Keep it realistic for a beginner with no marketing experience."

Why this prompt works: Students leave with concrete steps, not theory, and can start acting on a clear plan immediately.

A focused marketing plan helps teens maximize their digital presence. Harish Kolli, a high school junior who created Guardial, a personal safety app, found that having a structured marketing approach helped his team secure over 350 positive survey responses and $6,400 in equity-free funding when starting their venture.

5. Writing A Reflection Or Testimonial Post

Use this after completing a project or getting first customers—great for website, social media, or even brainstorming for college applications.

Prompt:

"I want to write a short reflection about my experience running [name of side hustle] this summer. I'd like it to cover: 1) what I learned, 2) what I'm proud of, 3) what I'd do differently next time, 4) a thank-you to people who supported me. Please help me organize my thoughts and write a draft I could use for a website or social media post, keeping it authentic and inspiring."

Why this prompt works: Encourages reflection and personal storytelling while doubling as marketing content or résumé material.

These reflections often become powerful material for college applications. According to Harvard Graduate School of Education research highlighted in a 2024 Forbes report on college admissions, admissions officers increasingly value entrepreneurial experience because business ventures demonstrate initiative, real-world skills, and time management—all qualities that help applicants stand out.

The Bigger Picture: Beyond Summer Earnings

These prompts aren't just shortcuts—they're conversation starters with AI, helping students think critically about their side hustle while building communication, marketing, and leadership skills. With the right guidance, a summer side hustle can be much more than extra cash—it can be the beginning of an entrepreneurial mindset that lasts a lifetime.

The key step is to begin with current resources and refine the business model through experience. By solving real problems, maintaining quality service, and building genuine customer relationships, students can transform a summer side hustle into a profitable venture and powerful learning experience that will serve them long after summer ends.