OG Tuesday Issue #193

The Assist Newsletter
June 3, 2024
A motivational quote in bold white text on a blue background reads, "I am grateful for my progress, no matter how small." The background features colorful abstract shapes in teal, yellow, pink, and red on the left side.

Today’s checklist: 

  • Get more done with an assist from AI
  • Deciding between entrepreneurship and employment
  • TA reader Annie on recording wins

🤔 Riddle me this: We share a name but are quite distinct, one a boy with blue hair and the other a nostalgic blink. Our adventures are weird, from dreams to the absurd, aired on Nickelodeon, we once were heard. Who are we? (Find the answer on the bottom).


💼 Entrepreneurship: How Melda Akin turned a dream into a lucrative AI consultancy.

💡 Juneteenth: Year-round commemoration ideas for higher ed.

💭 Organization: Lifestyle tips and tools based on your Meyers-Briggs personality type.

💰 Business Budgeting: What budgeting and financial planning looks like with AI flare.

🏳️‍🌈 Pride Month: Haters gonna hate. Remember what really matters during Pride Month.


A modern cartoon illustration shows various people using AI-powered tools for productivity in a vibrant, high-tech office. One person is on a computer with a robot assistant on the screen, another is scheduling meetings with an AI tool, and a third is watching a video to learn about technical things.

AI Powered Productivity Hacks


1. Ask ChatGPT for feedback on something you’ve written. This tip comes from Adriana Fernandes via Medium, who also offers this prompt template to help you get started:

I need your feedback on my (TEXT TYPE).

It’s aimed toward (TARGET AUDIENCE) and its big promise is that it (WHAT YOU WANT TO ACHIEVE WITH THE TEXT).

I want you to look for logical fallacies and bad writing primarily, but also point out excessively long or detailed sentences or paragraphs.

2. Add AI tool Clara to your meeting request emails to streamline scheduling.

3. Leverage AI to quickly learn about technical things. Tiff In Tech provides simple instructions in her 12-minute Youtube video.

4. Switch from catch-all search engines to AI powered niche engines to find what you need faster.

For example…

  • Use Consensus to find peer-reviewed research and publications
  • Use Exa to find knowledge relevant to complex queries
  • Use Andi when you want answers instead of links to pages where you hope to find answers

5. Use ChatGPT to prepare for interviews. You can ask it to generate sample questions or even use it to conduct a mock interview. See Teal’s 7 Ways to Use ChatGPT to Prepare for a Job Interview for all the details.

6. Let a tool like Welltory learn about and predict your stress patterns.

7. Let Motion, a work planning tool, learn from your behaviors and optimize your schedule.

What should you do next? First? Let data-based guidance make these choices for you.



GroupTogether makes it easy to give office gifts from the whole team.

Make Work Fun with Office Gifts Your Team Will Cherish 💗


Summer’s upon us, and your employees may be wishing they were on the beach instead of staring at a computer screen 😵‍💫.

Boost morale and reward high performers with a thoughtful gift and a card from the team.

GroupTogether makes it easy to put together a gift for any occasion including:

  • 🏆 Job Well Done
  • 👶 New Baby
  • 💍 Weddings
  • 🎖️ Work Anniversaries
  • 🎉 Birthdays

Use company funds, or let the team pitch in for big milestones.

It’s simple, meaningful, and free 😎.

Try GroupTogether today!


A split-screen illustration showing two scenes. On the left, a woman is with coworkers around a water cooler, representing her role as an employee in an office setting. On the right, the same woman is sitting at her desk in a cozy, personalized home office, representing her role as a business owner.

Employee or Entrepreneur? How to Make an Informed Decision


One TA Subscriber wants help shaping their career:

The biggest challenge I’m currently facing is choosing between becoming a full-time entrepreneur or returning to corporate America as an employee.

We wish we could tell you the right choice. We wish we could say confidently that there even is one right choice.

Since we can’t do that, we’re offering the next best thing: A framework that can help you arrive at a sound, well-considered decision.

The PrOACT Decision Making Framework

This framework, outlined in Smart Choices: A Practical Guide to Making Better Decisions, is especially helpful for considering complicated decisions with unpredictable, but long-lasting, implications.

Step 1: Define the outcome you hope your decision leads to.

This is often referred to as “defining the problem,” and it parallels the first step in many problem-solving approaches.

The goal? Define your ideal future state—where you want to end up, what you want to achieve, etc.

The more specific your definition, the more grounded you can make your decision.

Step 2: Determine measurable objectives.

Answer the following questions:

  • What important factors does this decision influence?
  • How would I like my decision to influence these factors?
  • How will I measure progress or success in this area?


Income might be a factor when choosing between starting a business or becoming an employee.

A fully developed objective might read: Increase take-home pay as measured by my weekly net income.

Step 3: Brainstorm alternative approaches to meeting your objectives.

Consider all the possible avenues you might take to fulfill your objectives.

Include the options framed in your original decision statement as well as others you may not have considered.

This step gets around the inconvenient truth that sometimes, the way we frame our decisions can inadvertently limit our options.

For example, there might be viable ways to approach your objectives beyond being an entrepreneur or an employee.

Step 4: Layer on consequences for each alternative.

Limit your thinking to consequences that directly affect your core objectives.

Step 5: Weigh tradeoffs and make a decision.

Start by eliminating alternatives that come with the most or the most significant consequences.

When you have a short list of final options, consider the tradeoffs involved with each:

  • What do you gain?
  • What do you lose?
  • Which objectives can this option potentially advance?

A clear winner should emerge as you complete this final step.

We hope it helps you take your next steps with confidence.

PS: Any systematic approach to making choices could be considered a decision making framework.

We chose the PrOACT framework based on the complexity and scale of your decision, but there are many more frameworks in the sea if you want more help with this or any future decision.

Other decision-making frameworks include:


ClickUp’s free 1:1 meeting template

My 1:1 Meetings Used to Suck — Then I Did This 


A great way to foster better relationships between you and your boss or direct report is through one-on-one meetings.

The perfect 1:1 meeting template keeps all of your agendas and action items—tailored for each individual—in one organized place.

This template does just that by laying out roles, expectations, and how to best implement a feedback cycle.

📄 Get the 1:1 meeting template free here.

*Presented by ClickUp.


Record Your Wins


Maintain a detailed record of your achievements, new responsibilities, revenue contributions, and positive feedback throughout the year.

This comprehensive list will serve as a valuable tool during your annual review, showcasing your accomplishments and strengthening your case for a raise.

Photo of Annie Sragner (Chief of Staff) Annie Sragner (Chief of Staff)

⭐️ Want to be featured? Share your best career advice here.


Stuff We’re Loving This Week


🌍 Manage all your company’s business travel in one place.

📚 Dive into the suspenseful and gripping mystery of A Flicker in the Dark by Stacy Willingham.

🍷 This free app arms you with user reviews and ratings to help you make quicker decisions when you’re shopping for wine.

🖊️ Upgrade your writing game with these premium gel pens.


A person is lying in bed, looking at the camera with a playful expression. The overlaid text reads, "Millennials, have we decided what our midlife crisis stereotype is going to be?”


🚨 Job Alerts



Before you go…


Answer to the riddle.

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