6 AI Assistants, 1 Busy Human: The Scheduling Battle You Didn’t Know You Needed

TL;DR — I put six different AI assistants to the test, asking them to help me schedule my chaotic life after a job rejection. Here's what happened.

The Setup

I'm no slouch. At any given moment, I've got at least a half-dozen plates spinning in the air. Just this weekend, I learned hand lettering basics, made my first ratatouille, and tackled some pretty gnarly crosswords, all while binging The Final Table on Netflix. My family will tell you—I don't do idle.

But lately, the juggling act has gotten a bit more intense. After a long, somewhat grueling interview process for what felt like a dream job, I learned yesterday that I didn’t make the cut. I gave myself a minute to feel it, but now? It’s go time. I’m revamping my weekly schedule to fit in some new priorities that’ll support my search for the right role. That means, on top of consulting, earning a degree, and everything else I’m managing, I need to squeeze the most out of my week. While I love a good checklist (watching those tick marks accumulate is so satisfying), I realized this needs something much more complex, and I'll need a little extra help. Enter AI.

I typically turn to ChatGPT for everything from synthesizing complex academic papers to analyzing market trends. But this time I wanted to see how many different AI engines would handle a complex scheduling challenge. So I put six to the test: ChatGPT, Perplexity, Claude, MetaAI, Gemini, and NinjaTech AI.

The Challenge

I asked each AI to create an optimized schedule incorporating my fixed commitments (like my self-care routine and weekly calls with mom) with new priorities like creating an interview video and rejoining social media after an 8-year hiatus. The full prompt was pretty intense—exactly the kind of complex challenge that makes AI assistance so valuable.

The Method

I judged each response on five key criteria:

1. Accuracy (Does it get the facts right?)

2. Clarity (Is it easy to understand?)

3. Relevance (Does it address my needs?)

4. Tone and Engagement (Does it recognize the human element?)

5. Completeness (Does it cover everything?)

The Results

5th Place: NinjaTech AI (D)

Cold and clinical, NinjaTech AI missed the emotional context completely. While it nailed the formatting, it dropped the ball on project work and crammed all networking into one day. Not exactly the smooth schedule I was looking for.

4th Place: Gemini (D+)

Points for positivity and strategic advice, but the schedule? A hot mess. Apparently, I only need to eat once a week, and what's with all the mysterious "personal" time blocks? Back to the drawing board.

3rd Place: Perplexity (C-)

Finally, some emotional intelligence! Perplexity acknowledged the sting of rejection and offered a solid schedule. The double daily networking sessions seemed overkill, but overall, not bad. Just short about 5 consulting hours per week, but I was expecting to tweak, so not a deal-breaker.

2nd Place: Meta AI (C)

A stronger showing, though math isn't its strong suit (2 hours of schoolwork in a 1-hour slot? Nice try!). Loved the thoughtful recommendations and energy management, even if it did assume I needed a formal dinner time (hello, apple slices with peanut butter dinner club!).

1st Place (Tie): ChatGPT (B+)

ChatGPT brought its A-game (well, B+ game technically). The schedule was realistic, detailed, and actually acknowledged my human needs. It balanced work blocks with breaks, and even remembered my guilty-pleasure soap opera time is weekdays only!

Key Strengths:

• Perfect balance of empathy and practicality

• Realistic time blocks

• Smart project integration

• Detailed strategic recommendations

1st Place (Tie): Claude (B+)

Claude matched ChatGPT's practical excellence while adding some unique touches. The strategic recommendations were gold, especially the gradual social media re-entry plan.

Standout Features:

• Excellent strategic planning

• Energy-conscious scheduling

• Built-in buffer times

• Protected family time

• Smart social media approach

• CSV file for uploading into a spreadsheet

Next Steps

My next step is to take the two calendars and pull the best from each, build my calendar in my planner of choice and get my tasks sorted in my favorite project management tool, Monday.com. Should take a couple of hours, but I can squeeze it in while we watch the Buffalo Bills and Baltimore Ravens battle it out for the division.

Need Help Getting Organized?

Whether you're bouncing back from a setback or just trying to juggle life's many demands, I'd love to help you create a schedule that actually works for you, your projects, or your large strategic initiatives. With or without AI assistance, we can build a plan that honors commitments while making space for what matters most.

Drop me a line on LinkedIn, and let's turn your chaos into clarity. After all, sometimes the best way to keep all the balls in the air is to have someone help you refine your juggling act.

✨ Pro tip: Keep the human touch in your scheduling. AI is amazing at optimization, but you know yourself best. The perfect schedule balances efficiency with reality—and maybe leaves room for a soap opera or two. ✨

Here are the actual responses, in case you're curious...

NinjaTech AI

I'd be happy to help you create a schedule that balances your commitments and priorities. Here's a suggested weekly schedule in a table format:

One-off projects:

• Create a LinkedIn video interview:

  • Write script: Monday, 8:00 am - 9:00 am

  • Film and edit: Tuesday, 8:00 am - 10:00 am

  • Goal: Showcase personality and communication style to skip recruiter interviews and connect directly with hiring managers.

  • Recommended length: 3-5 minutes

  • Recommended content: Introduction, career summary, skills, and achievements

  • Recommended structure: Introduction, body, and conclusion

• Rejoin social media for professional visibility:

  • Create profiles: Wednesday, 8:00 am - 9:00 am

  • Strategic advice: Use a professional profile picture, header image, and bio. Post updates regularly, engage with others' content, and participate in relevant groups.

• Implement a daily networking strategy:

  • Reach out to 5 people you know, 5 people you don't know, and 4 past clients: Thursday, 8:00 am - 10:00 am

  • Post 2 updates on social media each day: throughout the day

  • Content ideas: Share articles, ask for advice, or share personal experiences related to your industry.

• Job applications:

  • Submit 5 applications per day: throughout the day

  • 10 cold applications per week: throughout the week

  • Additional applications for companies where you have advocates or referrals: throughout the week

Note: This schedule is just a suggestion, and you can adjust it to fit your needs and preferences. Make sure to prioritize self-care and take breaks throughout the day.

Gemini

Here's a potential weekly schedule to help you bounce back and land your dream job:

Export to Sheets

LinkedIn Video:

• Length: Aim for 3-5 minutes. Keep it concise and engaging.

• Content:

  • Start with a strong hook: Briefly share your career story and what excites you about your field.

  • Highlight your skills and experience: Showcase your accomplishments and how you've added value in past roles.

  • Demonstrate your personality: Let your unique voice and communication style shine through.

  • Include a clear call to action: Encourage viewers to connect with you on LinkedIn.

• Structure:

  1. Introduction (Hook)

  2. Career Highlights

  3. Skills & Experience

  4. Personality & Communication Style

  5. Call to Action

Social Media Strategy:

• Platforms: Focus on LinkedIn and potentially one other platform (like Twitter) that's relevant to your industry.

• Content Ideas:

  • Share industry insights and articles

  • Post about your professional development (e.g., attending conferences, completing certifications)

  • Engage in relevant industry discussions and groups

  • Share your thoughts on career trends and challenges

  • Celebrate your accomplishments (both personal and professional)

  • Share behind-the-scenes glimpses of your work (if appropriate)

Networking Strategy:

• 5 People You Know: Reach out to former colleagues, mentors, friends in your field.

  • Example: "Hey [Name], I'm back in the job market and would love to connect with you. Would you be open to a quick coffee chat sometime next week?"

• 5 People You Don't Know: Identify industry leaders, recruiters, or people working at companies you admire.

  • Example: "I've been following your work at [Company] for a while and I'm really impressed with [specific project/initiative]. I'd love to learn more about your career path."

• 4 Past Clients:

  • Example: "I'm reaching out to see how you're doing and to express my gratitude for the opportunity to work with you on [project]. I'm currently exploring new career opportunities and would love to stay in touch."

Job Applications:

• 5 Applications Per Day: Aim for a consistent daily application process.

• 10 Cold Applications Per Week: Research companies that interest you and apply even if there are no open positions.

• Advocate/Referral Applications: Leverage your network for warm introductions to hiring managers.

Important Notes:

• Be Flexible: This is just a starting point. Adjust the schedule as needed based on your energy levels, priorities, and unexpected events.

• Prioritize Self-Care: Make sure to stick to your self-care routine, even on busy days. It's crucial for your mental and emotional well-being.

• Celebrate Wins: Acknowledge and celebrate your accomplishments, no matter how small. This will help you stay motivated and maintain a positive mindset.

• Stay Positive: Job searching can be challenging, but remember your skills and value. Stay positive, persistent, and believe in yourself.

I hope this schedule provides a helpful framework for your job search journey. Remember to be patient with yourself, and don't hesitate to make adjustments as needed. Good luck!

Perplexity

I understand you're going through a challenging time after not getting that job, but I'm impressed by your proactive approach to moving forward. Your plan to optimize your schedule and focus on key career-building activities is excellent. I've created a weekly schedule based on your commitments and priorities. Here's a table format with times and days, including recommendations for your new initiatives:

Additional recommendations:

1. LinkedIn video: Aim for a 60-90 second video. Structure: 15-second introduction, 30-45 seconds highlighting key skills and experiences, 15-30 seconds expressing your career goals and ideal role.

2. Social media strategy: Start with LinkedIn and Twitter. Post industry insights, share your learning journey, and engage with others' content. Gradually increase activity as you become more comfortable.

3. Networking content ideas: Share articles you've read, ask for advice on specific career topics, congratulate connections on their achievements, or share brief insights from your consulting work or studies.

4. Job applications: Use the morning slots for more complex applications and the afternoon slot for quicker ones or follow-ups.

5. Schoolwork: I've allocated more time on weekends for longer assignments like critical thinking papers.

Remember to be flexible with this schedule and adjust as needed. Good luck with your career journey!

MetaAI

I'm so sorry to hear that you didn't get the job. But it's great that you're eager to pivot and optimize your daily routine. I'd be happy to help you create a schedule that balances your commitments, priorities, and self-care.

Weekly Schedule

Here's a recommended schedule for you, incorporating your hard-scheduled commitments, priorities, and self-care:

One-Off Projects and Due Dates

1. LinkedIn Video Interview:

   1. Script writing: Monday and Tuesday (2 hours)

   2. Filming and editing: Wednesday and Thursday (2 hours)

   3. Finalize and publish: Friday (1 hour)

2. Social Media Re-Entry:

   1. Research and planning: Wednesday (1 hour)

   2. Profile creation and optimization: Thursday (1 hour)

   3. Content creation and posting: Friday (1 hour)

3. Daily Networking Strategy:

   1. Reach out to 5 people you know, 5 people you don't know, and 4 past clients each week

   2. Post 2 updates on social media each day

Additional Recommendations

1. Allocate specific times for checking and responding to emails, messages, and comments on social media.

2. Consider using a project management tool like Trello, Asana, or Todoist to help you stay organized and focused.

3. Make time for self-reflection and journaling to process your emotions and thoughts about the job rejection and your future goals.

4. Prioritize your well-being by scheduling relaxation and leisure time each day.

Feel free to adjust this schedule as needed to fit your personal preferences and work style. Remember to be flexible and make time for unexpected tasks and opportunities. Good luck with your priorities, and I hope this helps you get back on track!

ChatGPT

Here’s a weekly schedule that balances your commitments, priorities, and self-care while optimizing your time for productivity. I've also included key due dates and suggested times for each project.

Weekly Schedule

Key Points:

• LinkedIn Video: Dedicate 1–2 hours per session to writing, filming, and editing. Aim for a 2–3 minute video that highlights your communication skills, professional journey, and what you bring to the table. Make it conversational and engaging. Start by scripting your key points (e.g., "who you are," "your career highlights," "why you’re different," and "what you're looking for").

• Social Media: Focus on visibility and authenticity. Share posts on LinkedIn about your current projects, industry insights, and personal career journey. Engage with people in your network.

• Job Applications: Prioritize applications for companies where you have advocates or referrals. Keep track of your progress and tweak your approach based on responses.

• Networking Strategy: Reaching out to people you know, those you don't know, and past clients will help expand your visibility. Keep your messages concise and personalized.

This schedule gives you flexibility while prioritizing self-care and essential tasks. Let me know if you want to adjust anything!

4o mini

Claude

I'm sorry to hear about the job disappointment, especially after such an intensive interview process. That kind of letdown can be really tough, but I admire your proactive approach to moving forward.

Let me help you create a structured schedule that incorporates your commitments while making space for your new priorities. First, I'll share some strategic thoughts on your goals before presenting the weekly schedule.

LinkedIn Video Strategy:

• Recommended length: 2-3 minutes

• Structure:

  1. Hook (15 seconds): Share an intriguing business challenge you've solved

  2. Introduction (30 seconds): Your professional narrative and values

  3. Key achievements (1 minute): 2-3 specific examples with measurable results

  4. Value proposition (30 seconds): What you bring to potential employers

  5. Call to action (15 seconds): Invite connections and conversations

Social Media Re-entry Strategy:

• Start with LinkedIn only for the first month to build confidence

• Focus on commenting thoughtfully on others' posts before creating your own

• Set strict time boundaries (30 minutes, twice daily)

• Use scheduling tools to maintain distance while staying consistent

• Consider creating a separate professional Instagram after establishing LinkedIn comfort

Optimized Weekly Schedule