#117 Say It Better

Welcoming you back with a Wild Card Edition, which occurs only when there are 5 Tuesdays in a given month. Not quite as rare as a leap year, but pretty special nonetheless. And this Wild Card Edition is indeed special because today the vibes are shifting.

Since the beginning, each edition of OTF that you have been reading over the last two years, you’ve been hearing from me every week. But, behind the scenes, someone’s been sharpening the message — and pushing the ideas further.

It’s time you meet him.

He’s been involved as a consultant / part-time editor for a while now, but moving forward, he’ll be much more front-and-center.

It is my pleasure to pass this intro off to my good friend and writing coach, Professor Mike…

🧠 …I’m not gonna take up too much time here. First, I want to thank Dan for this opportunity. I’m excited to see what sorts of content we can cook up together.

Second, a little bit of background on me: I’m a tenured professor in NYC and have taught writing and public speaking all around the tri-state for almost fifteen years.

In my free time, for as long as I can remember, I’ve helped my more business-oriented friends in these same areas. Job applications, presentations, website copy, general sales / persuasive advice - you name it, I’ve advised on it.

So when Dan reached out years ago about this newsletter idea he had, I was thrilled to serve as both sounding board and advisor. Since then, I’ve helped in what little ways I could (you may have seen my influence in Cool Communicator), but with my schedule recently freeing up, the time is finally right to get more involved.

People say “money makes the world go ‘round,” but it’s really language that gets things moving. After all, you’ve got to convince someone to give you that money, no? So from the beginning, I’ve admired Dan’s idea to blend business news and concepts with personal growth content, especially the communication stuff.

Now, as the newsletter reaches the next stage in its evolution, my hope is that we can present more applicable, actionable content from two different perspectives: his, the business side, and mine, the language side.

But don’t worry - I’m not here to take you back to college pre-req English class. My goal is simply to answer your questions before you have to ask them, questions like “How does that work,” “Why that way instead of this way,” etc.

Thank you all for taking the time. Turning it back over to Dan…🧠

I’ve got nothing left except…

No Wild Cards In These Highlights…

FATTENING THE WALLET 💰️ 

•  Making Cents of our Interview Series’ Intent

ELEVATING YOUR BRAND 📈 

• The Introduction of Say It Better

• Expert Advice on Emotional Language

BOOSTING YOUR PRODUCTIVITY🚀 

• A Founder’s Note For The Rest of The Year

MAKING CENTS 💰️ 

How This Interview Series Brings Value

We’ve been teasing this for weeks now, but it’s so close we can taste it: the Behind the Grind Interview Series. Our first comes during May’s 4th edition and will continue like clockwork for every 4th edition after that. So far, our lineup already includes

• Finance Professionals.

• Savvy Investors.

• Business Owners.

• Entrepreneurs.

Let’s be real - I’m jacked up for this! But I wanted to take a moment to talk about why I’m so jacked up: it’s because I know that each and every one of you will get a lot out of it.

The best way I can put it is this: I see the Interview Series taking all the best that OTF has to offer - the educational, the actionable, the thought-provoking, the inspiring - and putting it all together from the perspective of real people sharing real (unfiltered, unedited) experiences.

Some of the Money Move questions you’ll get answers to include:

• How do you define a rich life — and what does that look like in real terms?

• What’s one money lesson you wish someone taught you sooner?

• What’s one money move you regret, and what did it cost you?

• What’s the best financial advice you’ve ever received?

• What’s an underrated money concept you swear by that others don’t think about?

And much, much more.

O.T.F
O.F.T: One Final Thought

I’m so excited to get answers to these questions and more from (have I stressed this enough?) REAL PEOPLE! We include interviews or similar content once in a while in sections like Hustle Hub, but when it’s other publications, we’re at the mercy of their “journalists.” Are they asking the questions people really want answers to?

Now, we’re in control, and it’s gonna be electric.

SAY IT BETTER 💯 

_{*This section is designed to help you sharpen your communication skills to make a stronger impact in your personal or professional life. Because when you say it better, you sell it better.} 

Recently while at work, I had these two separate encounters - both were with colleagues that are equals:

• I thanked one - let’s call her Mary - for her help with something we’d collaborated on, and she responded with “Happy to help.”
  

• Later in the day, I thanked John for doing me a work-related favor, and he said, “No problem.”

Both people were happy during the encounters, and both were perfectly sociable before and after my thank-you. And each answer essentially means the same thing; they’re just different versions of “You’re welcome.”

So why am I still thinking about it?

Because despite the fact that I consider communication a strength of mine, I’m always thinking about whether or not there’s a way to say it better. In this newsletter alone, I’ve gone through idk how many variations of a greeting and a closing because I’m constantly looking to improve.

And in this particular example, I felt better after hearing “Happy to help” than after hearing “no problem,” which then led me down a rabbit hole since I say “no problem” most times. Was it more about the people behind the words, or do these seemingly-minor words matter?

Enter…🧠 Professor Mike’s POV

The short answer is: it could be both, but without knowing the context of your relationships, I’ll lean toward the words mattering more than we think.

The way you say “You’re welcome” may not ever hurt you in the long run, but it could HELP you. First, let’s break down both phrases from the anecdote:

Is this overanalyzing something that most people don’t ever think about? Of course. But that’s the point.

Phrases like “No problem” have become so common-place that it’s almost like we don’t hear them. They barely register. Now I ask you: why would you ever want to say something that doesn’t register? 

Going an alternative route, however, gives the speaker an opportunity to benefit from the exchange. In this case, “Happy to help” may give the listener a positive emotional response (rather than feeling guilt about the favor, for example), may make the listener more willing to reach out again in the future (which benefits anyone interacting with a current or future boss, an important networking contact, etc.), and may strengthen the relationship overall.

So does “No problem” hurt you in the eyes of the listener? I don’t think so. But to me, it’s a missed opportunity to present yourself in a more positive, memorable light, and how you present yourself in these small moments can have a BIG impact down the road. 🧠 

EXPERT ADVICE 💭

On The Importance of Emotional Language

In this space, we usually focus on the source’s credibility and stats, but today, with our own in-house language expert in tow, we can just focus on the quality of the content. And this video hits the nail on the head - the perfect complement to why “Happy to help” is better than “No problem.”

(Also: this creator, “TolentinoTeaching,” has almost 46K subs, which is pretty damn good.)

TL;DW Takeaways

1. Creating an emotional response in your reader / listener puts you in great position to be a successful persuader.
   

2. In Say It Better, the underlying message was about choosing words that fit the mood or emotion you want to create. A more involved and (usually) more effective way to accomplish this? Storytelling.

FOUNDER’S NOTE 💭 

I wanted to close with a little more about this partnership with 🧠 Professor Mike and why I think you’re really going to love it.

In my 10 years working in corporate at one of the largest financial service companies in the world, along with building this newsletter and my own personal brand on the side, one truth has never changed:

Business = Communication.

Whether you’re negotiating deals, keeping customers happy, sending emails or leading a team, communication is everything. Even with AI changing the game, your ability to communicate clearly, confidently, and persuasively becomes your superpower.

If you can sharpen how you say things, how you pitch yourself, and how you sell ideas? You’ll stay ahead — no matter how fast the tools change.

And that’s what Professor Mike brings to the table:

A sharper edge.
A deeper understanding.
A real advantage.

Together, our promise to you is simple:

We’ll keep giving 110% to make sure every edition leaves you sharper, that way you can future-proof your skills.

Thank you for trusting us with your time and attention. We don’t take that lightly — and we never will.

With great care,

Dan 🤝 

Before You Go

Next week, we’ll be back with our Growth Edition, which will feature Hustle Hub, a 2-Do for May, and a brand new piece of interactive content I am so damn excited for!

In the meantime, if you have a quick second, please let us hear from you in our exit poll. It always means a lot to us.

Community Poll 📊 

Last Week’s Poll Results:

What do you value most in the content you consume? (3,665 subscribers)

• Teach me something new. 📚 (Accurate info FTW) - 50%

• Make it original, or I’m out. 🎨 (Style + Vibes) - 10%

• Give me tips I can actually use.💡 (Actionable stuff)- 40%

As always, see you next Tuesday 🤝 

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