How to Unlock New, Personalized Side Hustle Ideas with AI

What if you could get personalized side hustle ideas that actually fit your life instead of scrolling through another generic listicle?

That’s exactly what we’re tackling in this special crossover episode with Allison Baggerly from the Inspired Budget Podcast.

After 650+ interviews on the Side Hustle Show, I noticed something interesting: almost nobody finds their winning side hustle idea by Googling “ways to make extra money” and picking number 17 from some random blog post.

The ideas that stick are the ones that connect your skills, interests, and available time with real problems people will pay you to solve.

So I created a free ChatGPT prompt generator that asks you the right questions and spits out personalized side hustle ideas tailored specifically to you.

And Allison volunteered to be our test pilot.

Tune in to Episode 712 of the Side Hustle Show to learn:

• how to use AI to brainstorm side hustle ideas that actually match your skills, schedule, and income goals
• the three levels of side hustles and how to choose the right one for your income goals
• how to move beyond generic lists and find ideas people will actually pay for

Get Your Free Prompt Generator

The Three Levels of Side Hustles

Before we jump into the ChatGPT magic, let’s talk about the different ways you can play the side hustle game.

Level 1

Level one is what I call plug and play options like Uber, DoorDash, Rover, or Airbnb. These are largely app-powered gigs that don’t require specialized skills. The platforms do some of the marketing for you, though you should still set up your profile the right way and collect some positive reviews.

The big advantage is speed. If you need to make an extra $250 this weekend, you can probably do it. You don’t have major startup costs, and you get paid relatively quickly.

But the downside is you don’t have much control. What you earn is mostly dictated by what the platform is paying that day and how many hours you can put in.

Level 2

Level two is where you’re essentially starting your own mini business. This might involve some startup costs and a longer timeline to land your first customers.

The big three business models we see repeatedly are:

• product businesses
• service businesses
• audience or content-based businesses

Service businesses can get started pretty quickly. You stick your neck out and say “I’m now a freelancer who does this specific thing” and then you go find customers who need that problem solved.

Product businesses are a bit more complicated, especially if you’re inventing something or importing products. But they can start as simply as decluttering your garage and selling stuff on Facebook Marketplace.

One listener I know even spotted a side hustle opportunity in the “free” section of Facebook Marketplace. They realized people were spending all day collecting free items and flipping them for profit. There’s a niche for everything, including someone who paid their way through college flipping lawnmowers.

Finding Ideas at the Intersection

The most successful side hustles we see on the show happen at the intersection of what you know how to do, what you’re interested in, a network or group of people you might have access to, and a genuine pain point in the marketplace.

That’s exactly what our ChatGPT prompt generator is designed to help you find.

You can grab the free worksheet at sidehustlenation.com/allison and follow along.

The Five Questions That Unlock Your Side Hustle Ideas

The prompt generator walks you through five key questions:

Question 1: What are your skills?

This is about taking inventory of what you’re good at and what you’ve been paid to do in the past.

For Allison, this included public speaking, teaching (breaking down complex concepts in simple ways), video editing, social media, helping people with their money, walking people through budgets, and writing.

She even joked that napping was a skill, which honestly, professional nappers do exist in some mattress testing companies.

Question 2: What do you actually like to do?

The last thing you need is a second job you hate. Bonus points if you can align your side hustle with something fun and interesting.

• How would you spend your time if money were no object?
• What are you curious about?

Alison mentioned hiking, camping, walking her dog, hand embroidery (which she does to avoid scrolling on her phone), diamond art, puzzles, reading, and organizing spaces for that satisfying before-and-after transformation.

She also mentioned she genuinely enjoys looking at other people’s budgets and hearing about their money situations.

Question 3: What did you dream about as a kid?

This question came from an episode with Debbie Gartner, who now runs a successful Etsy shop selling printable card games and trivia games.

In high school, she wanted to be a “game maker” and found a way to live that dream as an adult.

For Allison, the answer was acting. She wanted to be an actress, loved being on stage, doing theater and monologues.

Eventually she pivoted to teaching (which is still performing in front of people every day) and now podcasting.

Question 4: What comes naturally to you that others struggle with?

This taps into the “expert enough” concept. You don’t need to be the world’s leading authority on something. You just need to know more about it than the average person.

• What do people already ask you for help with?
• What comes so easily to you that you’re baffled when others can’t figure it out?

For Allison, this was speaking in front of people without anxiety, helping people with their money while balancing empathy with action, time blocking, setting routines, and establishing boundaries around her time and with other people.

Question 5: What are your time and money constraints?

Be realistic about how many hours you can actually dedicate to a side hustle. This helps ChatGPT avoid suggesting ideas that sound great but would be impossible to execute alongside a full-time job.

Allison said she could work 5 to 10 hours remote, maybe 3 hours on a weekend and the rest scattered throughout her workday.

Nothing that would lock her into a specific schedule because she wanted to own her time.

For income goals, she said within 6 to 12 months, earning an extra $1,000 to $2,000 per month would be amazing. That works out to about $100 per hour if she’s working 5 hours a week.

What ChatGPT Suggested for Allison

Once we fed all this information into ChatGPT, it came back with some surprisingly good ideas.

1. Money Coaching for Real People

This one comes with one-on-one sessions focused on budgeting, debt payoff, and building better money habits without shame or jargon.

ChatGPT even broke down potential pricing:

• $100 to $300 for short-term coaching packages with a couple sessions and email support
• or group programs around $500 per month.

It calculated that 8 to 12 clients at $200 each would hit the income goal with minimal time commitment.

2. Public Speaking and Presentation Coaching

Since most people fear public speaking more than death, there’s clearly demand. The suggestion was to offer group workshops or one-on-one coaching for job interview prep, presentations, or conference talks at around $150 per client.

Allison’s immediate reaction was classic imposter syndrome: “I never took a public speaking course. It just comes naturally to me. How can I teach someone else?”

But that’s exactly the point. The things that come naturally to you are often the things other people desperately want to learn.

3. Time Blocking and Productivity Coaching

For this one, it’s helping overwhelmed people create personalized systems. ChatGPT suggested a four-week program for $200 to $300 with a cohort-based group format, and even proposed a 30-minute time audit as a lead magnet.

The fourth idea was a podcast or YouTube channel called “Money Made Simple” (which Allison already does with her book called Money Made Easy).

5. Decluttering and Productivity Coaching Hybrid

This one is about recognizing that people don’t just want a clean space but also a mindset shift and sustainable system.

ChatGPT even suggested niching it down to busy moms, neurodivergent adults, or empty nesters downsizing to help her stand out.

6. Accountability Buddy Subscription

This reminded me of a business called Boss as a Service. It’s essentially accountability-as-a-service for solopreneurs and freelancers who suddenly don’t have someone looking over their shoulder anymore.

Our friend Pete McPherson ran something similar called Most Productive Month Ever, and people loved having that external accountability to hit their goals.

When Coaching Isn’t the Answer

At this point, Allison said something interesting: “What if I don’t want to do any coaching? I already do so much talking and teaching in my day job. For a side hustle, I’d almost want a break from that.”

This is a totally valid point. Sometimes your ideal side hustle is the opposite of your day job. For example, my wife, an engineer, might take photos at weddings on the weekends.

So I asked ChatGPT to pivot away from one-on-one coaching and suggest more creative options.

The Creative Side Hustle Ideas

ChatGPT came back with some different angles.

YouTube or Podcast Ideas

ChatGPT doubled down on the YouTube or podcast idea, which Allison already has covered.

Digital Tools and Templates

ChatGPT suggested creating and selling digital tools and templates. This scratches the creative itch while giving you the advantage of creating something once and selling it over and over again.

Ideas included “Declutter in a Weekend” guides, seven-day challenges with checklists and photo trackers, budget templates, time-blocking planners, and speaking prep worksheets.

ChatGPT even calculated how many sales at different price points would be needed to hit the income goal.

Low-Cost Digital Courses or Workshops

Another option was a low-cost digital course or workshop, though that’s still adjacent to the coaching Allison wanted to avoid.

A “Money and Life” Newsletter With a Twist

One idea was a “Money and Life” newsletter with a twist. The twist suggestions included “budget autopsies” where you anonymously break down real budgets, or “time audit Fridays” where you show how someone could reclaim 10 hours a week.

Allison already does “real people budgets” but loved the term “autopsy” for the branding.

Challenge-Based Businesses

Another direction was a challenge business: the 30-Day Decluttering Challenge, 30 Days to Better Speaking Confidence, or the 21-Day Budget Reset. These could be free lead magnets that introduce people to a paid product, or they could be the paid product themselves.

Physical or Digital Products on Etsy

ChatGPT also suggested creating a physical or digital product on Etsy. One suggestion was “hand-embroidered budget affirmations,” which Allison wasn’t into.

But she did mention that she hand-embroidered a picture of her grandmother’s 100-year-old house for her mom and siblings, and could see herself doing custom architectural embroidery for people’s first homes.

That reminded me of Jesse Spencer Smith from my book 1000 100 Ways. He specializes in pen-and-ink architectural drawings on commission, and his business has grown quite a bit since then based on his Instagram following.

How to Take It Further

Once ChatGPT gives you ideas, you can keep the conversation going with follow-up prompts.

You can ask for more details on any specific idea: “Tell me more about number three. How would you monetize this?”

You can ask it to choose: “If you were me, which one would you pick and why?”

You can ask about speed: “Which of these is likely to be the fastest to hit my income goal?”

You can ask for an action plan: “Given my time constraints, write me a realistic 30-day action plan to launch idea number five.”

ChatGPT will remember what you told it earlier and keep those constraints in mind as it gives you more specific guidance.

Why This Approach Works Better Than Generic Lists

The beauty of this ChatGPT method is that it helps you see options you might not have considered before.

Sometimes when you’re talking with a friend, they can see your gifts and talents in a different light than you can. ChatGPT can function like that friend, connecting dots between your skills, interests, and market opportunities.

It’s not perfect, and it won’t do the work for you. But it’s a much better starting point than scrolling through “101 Ways to Make Money Online” and hoping something randomly clicks.

The AI-assisted brainstorming is just step one. What’s really cool is that you can start clarifying what you’re looking for and hone in on certain ideas based on your reactions.

Notice Allison’s immediate responses gave us valuable information. She lit up about certain ideas and immediately found objections to others. That emotional reaction is data you can use to narrow down your options.

Try it Yourself: Get Your Free AI-Assisted Brainstorming Tool

Episode Links and Resources

• Allison Baggerly
• Inspired Budget Podcast
• sidehustlenation.com/allison (Free ChatGPT Prompt Generator)
• Uber
• DoorDash
• Rover
• Airbnb
• Money Made Easy
• Boss as a Service
• Pete McPherson – AI Assisted Project Ideas
• 1000 100 Ways
• Debbie Gardner – Mini Digital Products

Looking for More Side Hustle Help?

• Start Your Free $500 Challenge. My free 5-day email course shows you how to add $500 to your bottom line.
• Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
• Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.