At some point, the question sneaks up on all of us: What’s next?
For some, it comes the morning after retirement papers are signed. For others, it shows up when the kids move out, when a job ends abruptly, or simply when the familiar rhythms of life no longer feel fulfilling. You may not be finished working, but you may be done doing the same thing.
Here’s the problem: planning your “next chapter” can feel overwhelming. Do you start a business? Pick up consulting? Volunteer? Travel? Write that book you’ve been talking about for years? The choices multiply until your brain feels like a browser with forty tabs open — and half of them are playing music you can’t find.
That’s where AI comes in.
No, it’s not going to live your life for you. But it can help you brainstorm, organize, and test ideas in ways that make the blank page a little less intimidating. Think of it as a conversation partner that never gets tired, doesn’t roll its eyes when you repeat yourself, and has an endless supply of “what if?” scenarios.
I know because I wrote a whole book about it. With my digital sidekick, Max Bandwidth (who likes to think he’s the star of the show), I’ve been exploring how AI can become a partner in everyday life — not just for tech insiders, but for the rest of us who want something practical, human, and maybe even a little funny.
So let’s get specific. Here are five ways you can use AI while you plan your next chapter.
1. Give Your Résumé CPR
If your résumé hasn’t been touched since the Clinton administration, you’re not alone. Many of us paused résumé updates once we settled into a long-term role — until one day, we needed it again. Suddenly, you’re staring at a document that lists jobs from three decades ago and describes you as “enthusiastic and detail-oriented,” with no clear focus on what you actually did.
Here’s the reality: the modern résumé isn’t a full career biography. It’s a snapshot — designed to be age-neutral, skills-focused, and streamlined. That means trimming work history to the last 10–15 years, minimizing date-heavy formatting, and highlighting recent accomplishments, not just job titles.
AI can help you do this fast and pain-free. Try pasting your résumé into ChatGPT and asking something like:
“Modernize my résumé. Keep it age-neutral, highlight transferable skills, and focus on results from the last 10–15 years.”
Within seconds, you’ll get a clean, professional draft that sounds like you — but tailored for today’s expectations. It won’t hide your experience, but it will reframe it in a way that keeps the focus on what you bring to the table now, not how long you’ve been at it.
Max (my AI co-pilot): Trim the years, keep the wisdom. No one needs to know you once faxed a résumé.
2. Test Your Side Hustle Ideas
We all have them: the daydream side hustles. Writing a memoir. Selling crafts. Starting a consulting practice. Launching a dog-sweater empire on Etsy. Some of these ideas are brilliant. Some are… less so. The trick is finding out which is which before you invest too much time or money.
AI can act as your instant focus group. Feed it an idea and ask:
“What’s the demand for this?”
It won’t sugarcoat things. And that’s good. AI might gently point out that the market for artisanal dog sweaters is small — unless you live in Minnesota. But it might also highlight unexpected opportunities, like packaging your skills into workshops or online courses you hadn’t considered.
3. Practice Interviews Without Breaking a Sweat
If you’ve been out of the interview loop for a while, reentering can feel brutal. Questions like “Tell me about yourself” or “What’s your biggest weakness?” have derailed even the most seasoned professionals.
Here’s where AI shines: it’s the world’s most patient mock interviewer.
Try:
“Pretend you’re interviewing me for a communications role. Ask me common interview questions one at a time and provide feedback on my answers.”
You can rehearse without fear of judgment, refine your answers, and even test different tones. Nervous? Do three practice runs. Want to experiment with a lighter, storytelling approach? AI will let you.
Max: I’ll never ask about your weaknesses, but I’ll know if it’s potato chips.
4. Seek Clarity
Sometimes the hardest part of a transition isn’t the résumé or the interview. It’s figuring out what you actually want. Do you want part-time work? Consulting? Volunteering? A new venture altogether? Or just a clearer balance between family, hobbies, and occasional paid projects?
AI won’t give you your life’s purpose on a platter. But it can help you explore it.
Try prompts like:
“Ask me ten questions to help clarify whether I should pursue consulting or volunteering.”
Think of it as journaling with feedback. AI reflects your words back at you, highlights themes, and nudges you toward clarity.
5. Simplify Everyday Decisions
Here’s the truth: not every part of planning your next chapter is grand. Sometimes it’s the small stuff that eats your energy — meals, errands, travel logistics, emails. AI can clear those hurdles so you can focus on the bigger picture.
It can:
- Suggest meal plans that fit your dietary needs
- Draft that awkward email you’ve been putting off
- Organize a packing list for your next trip
- It can even remind you of the difference between goals and wishes when your plan starts to blur
Sometimes, freeing up mental space for the little things is exactly what allows you to take the next big step.
The Bottom Line
AI isn’t here to live your life — it’s here to make planning your life easier.
Planning your next chapter isn’t about having every answer lined up. It’s about asking better questions, testing ideas safely, and building confidence as you move forward.
That’s what led me to start exploring how AI could support real-life reinvention — not for tech pros, but for people like us who are navigating change with decades of experience, not startup buzzwords. Out of that curiosity (and a few misfires), a book emerged.
It’s called The AI Gossip Grid — and unlike most guides that treat AI like a technical tool, this one treats it like a partner in conversation. A co-pilot who can brainstorm, refine, and maybe crack a joke while you figure out what’s next.
Max: You bring the life experience. I’ll bring the prompts. Together, we’ll figure it out.
Want more like this?
Explore The AI Gossip Grid: Everyday Life with AI, Tips on Communicating Like a Human, Not a Template — your humorous, beginner-friendly guide to working with AI, written for those of us who weren’t raised on screens.
This article was originally published in Navigating Encore eXperiences & Transitions (NEXT) on Medium. Jim Newcomb is a contributing author and the creator of The AI Gossip Grid: Everyday Life with AI, Tips on Communicating Like a Human, Not a Template.