#152 The Next Chapter of On The Fly

Welcome to our final edition of 2025.

It’s a major turning point for us, and not just because the calendar’s flipping. Just like many of us will attempt to change or improve ourselves in some way via New Year’s Resolutions, OTF is reinventing itself in 2026.

This entire edition is just a heads’ up on what to expect.

The Next Chapter of On The Fly

I worked in the financial services industry for seven years before launching this newsletter in 2022. It’s kind of a weird combo, full-time in insurance and side-hustling in a media space. I was a little nervous, worried about what judgment might come from friends and colleagues, but after months of planning and building courage and confidence, I decided to pull the trigger and bring OTF online.

Originally, my inspiration was I wanted to help people just entering the corporate world in ways I wish people had helped me when I first started. But my intentions weren’t totally selfless. I saw newsletters blowing up and getting sold all around me, most notably Morning Brew (sold for tens of millions with a $75M valuation to Business Insider in 2020). I remember thinking, “Two kids started a newsletter and sold it for how much? Why not give it a go myself?” (I had no delusions of achieving that sort of fortune, but maybe one day enough where it could replace my bi-weekly pay check?)

The goal was to balance business and personal growth, because that’s exactly what I wish I had at 22, a good balance of both. I wanted to stay informed on what was going on in my industry and the business world as a whole, and I wanted tips, hacks, and actionable advice to help me grow as a well-rounded human being. Typically, newsletters are one or the other, but I thought combining them made a ton of sense, and out of that OTF was born.

Over time, our content began to transition. Seeing the writing on the wall when it came to AI, we moved from the business-growth duo to our three pillars / focused editions: Growth (communication, learning, building your brand), Productivity (AI tools and news, plus human inspiration via sections like “Hustle Hub”), and Money (business, personal finance, and more). Then when the opportunity to start an Interview Edition presented itself, which would get perspective on all three from professionals across every industry, it was a no-brainer.

Now, however, despite how proud we are of the current product, we’ve decided once again to adjust our direction. Not a complete re-route; we’re not about to off-road from our current path to do something totally different.

We’ve simply decided to make some adjustments so that the product is more in line with who we are and who we want to be. Below you’ll find those adjustments, namely:

• What’s Leaving

• What’s Staying

• What’s Changing

What’s Leaving?

• Deep Dives Re: Personal Finance - This stuff is important, but we’re not experts on personal finance, and we want to focus on content where we have expertise rather than simply aggregating / curating.

  
  

• Interview Series - I could see this coming back in the future, but right now we don’t have the clout to secure these interviews with regularity. Maybe a reboot in 2027?

  
  

• Anything Else That’s Purely LINKS - If it’s valuable to you and we can offer some perspective on it, great. If not, it’s getting the axe🪓

What’s Staying?

• Communication / Networking Content - Prof Mike’s career is in teaching language, and anyone who works in corporate knows networking is a necessary part of the job. We will continue to bring these vastly different perspectives for both digital and in-person communication content.

  
  

• Productivity Content - AI trends, tutorials, and experiences, as well as other human productivity hacks.

  
  

• Miscellaneous Content Connecting to the 3 Pillars - Sections like The Search Bar, Hustle Hub, 2-Do, and more will remain as short-and-sweet sections that inspire both action and thought.

What’s CHANGING?

I am not a journalist and don’t see myself as an aggregator; I see myself as a creator at heart. But our content has never totally aligned with that self-image.

That changes now.

Moving forward, OTF will continue to bring info you value but in a more creative and personal way. What does that look like?

• Learning AI on the fly - There are so many self-proclaimed AI experts out there trying to teach the masses how to maximize their use of AI tools, but often it feels like a doctor using medical school jargon to try to teach me how to treat my cold. It’s hard to understand. It’s hard to relate to or even connect with!!
  
  I don’t have a degree in Computer Science, but I do have experience and knowledge courtesy of life’s best teacher: trial and error. I can reach people who might be intimidated by a developer or engineer through my experiences, successes, and failures as I learn about AI. And honestly, I’m more excited than ever to keep learning AI on the fly, and translating it into clear, no-tech-jargon copy so you can plug it directly into your work and life.

  
  

• Building on the fly - I don’t want to say too much here, but I’ve got a hustle in the works and figured, why not build it in public? Readers can follow me on this journey and learn from my trials and tribulations.

  
  

• Organic curation - We’re still gonna link to articles, but it’ll be less, and it’ll be different. In the past, putting together an edition involved Prof Mike and I scouring the internet looking for content that answers the question, “What might our readers find valuable?” It never mattered if we liked it or not.

  
  Now, that matters. We consume a lot of content during a given week. If and when we find something that moves us, we’ll share it with commentary.

All told, the essence of what you like about OTF will remain, but it’ll look and feel different, with some all-new content sections presenting valuable info in a more personal and entertaining way.

I’m so excited to show you what this will look like in January and hope you like it as much as I think you will.

Before You Go!

Next week, we’re taking our first week off since we launched! We’re gonna use that time to fine-tune our reboot and come back strong on the second Tuesday of 2026.

See you then.

Find Dan on LinkedIn

You are now On The Fly & In The Know.