160: Chat GPT-5 Prompts, to Save Hours and Grow Your Side Hustle

If you’re running a side hustle, you already know the reality: there are never enough hours in the day. You’re wearing all the hats, juggling customer service, marketing, product creation, bookkeeping ... and that’s on top of your actual paid work.

So when a tool comes along that can help you get more done in less time and compete with bigger players, it’s worth paying attention.

Recently, Sam Altman, CEO of OpenAI, said something that really stuck with me:

“GPT-3 felt like a high-school student. GPT-4 felt like you’re kind of talking to a college student. GPT-5 is the first time that it really feels like talking to an expert in any topic, like a PhD-level expert.”

That caught my attention, because couldn’t we all use a PhD-level expert to brainstorm with? So this episode — and now this post — digs past the hype and into what’s really in it for you and your side hustle. What improvements can actually help you make more money, save hours of your time, and even outsmart the big players in your space?

Below, you’ll find five tested ChatGPT-5 prompts you can copy, paste, and customize. These aren’t fluffy “ask me anything” prompts. They’re designed to give you specific, actionable answers tailored to your business, so you can move faster, grow smarter, and get back to the parts of your side hustle you actually enjoy.

Prompt 1 – "Opportunity Radar" - Quick Win Profit Booster

I run a [type of side hustle] in [your city/town/state]. My average sale is [$XX] and I've done [XX] jobs in the past three months.

Here are six actual customer reviews: [insert reviews].

Here's a summary of what my top competitor [name them] offers: [summarize their main services, prices, unique features].

Based on this, suggest three realistic ways that I can add at least [$XXX] a month in profit without increasing my hours worked.

Include one idea that my competitor isn’t doing, and tell me exactly how I could test it within two weeks.

Why it works: ChatGPT-5 can now connect multiple layers of context — your pricing, customer feedback, and competitor details, all in one go. That means the suggestions are far more targeted and usable than what you’d get if you fed GPT-4 the same data in separate chunks.

Prompt 2 – "Rapid Repackage" - Multi-Platform Content Repurposing

This is my 1,200-word blog post about [insert topic]. Repurpose it into:

• Three Instagram captions, under 200 characters each, with strong hooks and calls to action.
• Two Twitter/X threads, each with 5–7 tweets that create curiosity.
• A 60-second YouTube Short script with the hook in the first three seconds.
• A LinkedIn article in a professional thought-leadership tone, written in my voice.

Why it works: With GPT-5’s improved context window, you can drop in a long article and get platform-specific rewrites that can actually sound like you. 

Prompt 3 – "Time Trade Analyzer" - Your Outsourcing Plan

I earn about [$XX] an hour when I’m doing paid client work for my [type of side hustle].

Here’s my weekly task list with estimated time for each: [insert list].

Which tasks should I outsource first to free up the most billable hours? For each suggested task, tell me what type of person to hire, the skills they need, and a fair hourly rate in [your country].

Then write me a job post I could use on [platform] to attract reliable candidates.

Also, based on the type of work I’m hiring out, suggest the best platform to use and why.

Why it works: GPT-5 seems to be better at operational thinking, so it’s not just giving you a list of “outsource your admin” — it can weigh time spent against your billable rate and suggest the highest-leverage hires first, plus hand you a plug-and-play job ad.

Prompt 4 – "Test Market In A Box" - Feedback from Multiple Perspectives

I’m launching a [product/service] targeted at [target audience] in [your city/town/state].

Here’s my draft product description: [paste description].

My main competitor is [competitor name/details], who offers [key competitor features].

Pretend you are three different people in my target audience:

• An excited enthusiast
• A busy professional unsure if it’s worth the cost
• A skeptic who prefers my competitor

For each persona, tell me what they like most about my offer, what would stop them from buying, and one change that would make them sign up right away.

Then summarize the top five changes I should make before launch.

Why it works: GPT-5 is reportedly better at roleplay and audience segmentation.  With it's ability to hold multiple personas in mind at once, it should provide you more rounded, realistic feedback.

Prompt 5 – "On-Demand Micro-Mentor" - Your 90-Day Growth Plan

Pretend you are a veteran [type of business owner] who built a six-figure business in under three years, mainly through [key strategies].

Here’s my situation: I’ve been doing this part-time for [X years], averaging [$X] per [unit of work], and have [X] booked for this year.

My budget for growth is [$X] and I have [X] hours per week to dedicate to it. My goal is to [specific goal].

Create a 90-day plan that includes:

1. The three highest-impact moves to start with
2. At least two low-cost marketing tactics I can use immediately
3. One unconventional client-getting strategy most overlook
4. A weekly checklist to track progress

Why it works: GPT-5’s strategic thinking seems to have leveled up. It’s better at balancing short-term wins with long-term positioning, so it has the capacity to get you a plan that takes into account what is both immediately actionable and sustainable.

Final Thoughts

The jump from GPT-4 to GPT-5 isn’t just about speed or bigger data, it’s about depth of thinking. With these prompts, you’re not getting generic answers; you’re getting the kind of nuanced, tailored advice you’d expect from a skilled consultant who already knows your business inside and out.

If you’ve been feeling like you’re constantly playing catch-up with bigger, better-resourced competitors, GPT-5 might just be the ally you need to start outsmarting them. Let me know how it goes!