#147: THREE MAJOR LESSONS FROM OTF

Welcome back and Happy Thanksgiving week!

It’s been a hectic year, so me and Prof have decided to take some much-needed R&R to focus on spending time with loved ones this week.

But before you go do the same, I wanted to share a quick note:

First, I want to thank you for taking the time out of your day to read this newsletter. I am forever grateful for the continued support. I never take it for granted and it means the world to me.

Now, I use this time of year to reflect on the year that was, and it got me thinking about what I’ve learned while issuing this newsletter for the last three years.

While I could list out 100+ lessons, I’m going to break it down to 3. Why only 3? Because as I thought about all of the lessons, these are the 3 I will take with me into the future. They’re mission critical and hopefully what I share can somehow help you in your current or future endeavors - whatever that might entail.

Lesson #1 Staying Informed is MASSIVELY Underrated!

Here is how I stay informed on topics I am interested in. I don’t rely on one medium. I choose different mediums to consume.

I like having the ability to learn visually through a video. Or by reading other newsletters through different styles of writing. Or even letting my ears do the work, where I throw on a podcast and just listen to someone share their story. Choosing different mediums helps keep the content interesting and engaging for my brain.

Now, whether you choose one or multiple mediums to stay informed on the topics you’re interested in, it doesn’t really matter. What matters are the benefits from staying informed.

Here are my Core 4.

• 1) I make better decisions. When I know what’s happening in the industries I work in (Financial Services, Media, AI), it becomes easier to judge what’s risky and what’s worth understanding further. My decisions become less emotional and far more calculated hopefully leading to stronger outcomes for me in the future.

• 2) I spot opportunities. I don’t like being late to the party. Staying informed helps me see the bigger picture to jump on opportunities. For example with AI, it makes me say: “Man, this new AI tool is sick, BUT what are the opportunities that can come with it? Maybe I share about it internally at the company I work for and become a subject matter expert? Maybe I create a product from it and make additional income? Maybe I dive into it so deeply where I become an expert to help others learn how it works so it can benefit them.” Moral of the story: You can create more opportunities for yourself by staying informed.

• 3) I become a stronger conversationalist. Whether I am at work, out with friends or chillin with family - having context, stories, and insights makes me participate in conversations better. It’s nice to contribute conversations with specifics. It gets the other party more engaged too.

• 4) I avoid getting blindsided. The economy, AI, and the business world move fast. The last thing I want to do is be uninformed and miss the next investment window, the next AI breakthrough or the latest going on in my industry. No one likes to be blindsided. The solution? Stay informed.

So, as we head towards 2026 and beyond, continue to stay informed…(cough* like by reading OTF, cough*)

Lesson #2 Ownership

Here is my definition of ownership after thinking about it for awhile this past weekend.

Ownership is taking responsibility for the direction of your life, not waiting for someone else to draw the map for you.

Look, I will be honest, I’ve always had career aspirations at the company I work for, and I still do. I care about my work, especially the people I work with and those I help serve. I bring my best foot forward each day and work so dam hard. I’ve done this since Day 1.

But one day, after working 7 years with the company, I thought about how hard I worked during that time for someone else. I then had this realization that I didn’t actually own anything by working for someone else. That hit me hard. Because in a career, and from my experience, you’re always moving in the direction that someone else sets for you.

With OTF, I suddenly had something that moved in the direction I set for myself. I’m able to take responsibility for the vision I have for OTF and bring it to life at the pace I want. I am able to move at my own speed, at all times. I have no one drawing the map for me, I am choosing the direction and it feels special AF. That’s the magical lesson of ownership to me.

Lesson #3 The Art of Risk

As I reflect, life has felt like a series of risks.

• Asking for a raise is a risk.

• Moving to a new city is a risk.

• Implementing something new at work is a risk.

• Sharing your ideas publicly is a risk.

• Negotiating deals and your POV are a risk.

• Starting something new is a risk

• Deciding to change is a risk.

I could list out 4,807 more things, but I believe you get the point.

However, the part that I wish someone taught me sooner was this, it’s not only about taking risk, it’s also about how to think about risk and to me, this is the difference maker.

For me, I can’t make a big decision without assessing it and breaking it down in questions. I need to zoom out and be like okay, “what questions need answers here?” For example:

• Does this make sense? Why does it make sense?

• What’s the upside? What’s the downside?

• Will I regret this 30 years from now if I don’t try it?

• Do I do it now or wait 6 more months?

• The list goes on and on.

I begin to play 21 questions with myself, not to second-guess my decision, but to not act irrational and think that it’s all going to work out because I say it will. I’ve learned that’s not how life works. I have responsibilities for a family now. I need to act smart, not stupid.

So when thinking about these lessons, I believe they intertwine with one another where risk could be the bridge between staying informed and taking ownership. Hear me out.

Staying informed helps you understand what’s going in the world to create opportunity. Ownership helps you build something within the world to create direction for yourself. Risk helps you get from the former to the ladder.

Before You Go!

Thank YOU again for joining us for another edition of OTF! I hope you and your family enjoy some R&R like the OTF team this week.

We will see you next Tuesday to reel in December! There’s a lot in store as we head towards year end.

Let’s go!

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