For The Win

Today’s Topics

• Fuel for the Driven Mind ⛽

• The Climb 🗻

  5 Mins Read Time

Fuel for the Driven Mind ⛽
By Jo

Small wins add up, buddy.

When you’re truly driven, a lot of things that should feel significant end up passing you by. You’re laser-focused on a goal—trying to shatter it—and in that pursuit, the attempts, the failures, the stumbles… they all blur together. And honestly? They don’t matter as much as we think they do.

People don’t care how much you win by. Not really. And if they do, it’s usually because it reflects something back at them—how far they feel they have to go, how much harder they might need to work, how close they are to their own breakthrough.

But a win is a win. Big or small, loud or quiet—it counts. And you deserve to celebrate it.

The funny thing about driven people (myself included) is that we don’t always know how to celebrate. We hit a milestone, nod at it for half a second, and immediately move to the next hurdle. It’s how we’re wired… and honestly, I wouldn’t change it. That pace keeps me humble. It keeps me grounded. It keeps me hungry.

Are you the same way? Because if you are—welcome to the club. This mindset isn’t for the weak. I admire folks who know how to let loose and enjoy the moment, but I also know myself better than anyone. When I let my guard down for too long, the vision gets blurry.

Take college, for example. I went all in—locked into school mode like it was a cage I wasn’t allowed to step out of. And that cage got me a master’s degree. I overshot the original goal by miles. Could I go further? Sure. But the cost-to-benefit ratio isn’t there for me right now. Everything in life is case-by-case. And at that point, I was ready to leave that college town, ready to catch up with my peers, ready to step into real life with momentum.

Looking back, I thank my former self for that push, because the old me almost couldn’t handle it. But he did. And because he did, I walk differently today—more aware that there truly are no boundaries you can’t push when you’re committed to bettering yourself.

Especially when part of you is moving forward out of fear—fear of being unsuccessful, of being stuck, of falling short. That fear can paralyze you… or it can turn you into something unstoppable.

The Golden Rule
So here’s the reminder: It never hurts to celebrate your wins—even the ones where the reward hasn’t fully shown up yet. Sometimes the win is just knowing you kept going.

The Climb 🗻

By Marcus

Do you ever get tired of people sharing their prescription for success from the mountaintop, like it’s really that easy?

Over the past several years, I’ve had the opportunity to work with hundreds of entrepreneurs on both ends of the spectrum. Some were extremely successful. Others were completely new to entrepreneurship, bringing their hopes, dreams, lived experiences, nervousness, and commitment into a new venture.

I’ve witnessed life-changing success and transformations in people who didn’t think it was possible. I’ve seen success arrive after ten years when someone expected it to take one year, and I’ve seen people win within a few months when they thought it would take much longer.

And although I’ve experienced my fair share of negatives as an entrepreneur, it’s rewarding to help people avoid similar mistakes, mindset challenges, and roadblocks along the way.

The part that catches most people off guard is what the grind of reaching success really looks like. The uncertainty, failures, finances, challenges, setbacks, doubt, fear, and everything in between. People don’t seem to care about any of that until you’re successful.

Sometimes there’s real value in hearing what it looks like when you haven’t reached the peak of the mountain.

Your climb to success is a huge part of the journey.

An Uphill Battle

For the past couple of years, I’ve been working to get more involved with AI and tech in general. I’ve been trying to build a portfolio: AI certifications, IT skills, courses, and more. This was before AI became the unavoidable force it is now.

Long story short, I realized that AI tools were advancing too quickly, and I didn’t have enough time with my other responsibilities to keep up. I’d learn something only to have a new advancement appear that made the previous information less relevant.

So about seven or eight months ago, I decided to start building AI automations with the knowledge I had. If this is what the market wanted, I’d figure it out. I started simple: an automated daily email update of NBA news stories. It sounds basic now, but at the time, I didn’t know what I was doing and it took a while.

Around four or five months ago, I decided to go deeper and build a conversational AI agent. This meant learning coding fundamentals, logic, workflows, creating a knowledge base, training prompts, debugging, and more. There were days I was completely stuck and frustrated, and I’d have to walk away and come back later when the solution finally clicked.

As I continued building, every step required learning something new. I’d wait for tech support only to find out I was the issue, spend more money on resources, rebuild workflows from scratch, then have something break again.

At the same time, I was writing a script and preparing my first tech demo—more things I had never done that took longer than expected. I think it took fifty attempts to get the demo video right, and even now I don’t think it’s great, but perfection is the enemy of good.

Now, as of this week, after two years, I finally have something tangible to add to my tech portfolio. Something I can present and continue to develop for real-world use. There was no celebration. It doesn’t feel like a win. It feels like a milestone that needed to be reached so I could move on to the next set of challenges.

About Your Progress

The idea behind “Winning in the Weeds” is that if you’re actively making an effort, you might be doing better than you think. It may not be obvious now, but if you stay the course, your efforts can lead to the actual win you’re seeking.

When you keep your head down and do the work, you evolve. You solve problems, learn lessons, and develop skills that will help you in the future.

It’s hard to track your progress in real time. It’s usually only when you reflect that you see how far you’ve come.

Yes, it’s difficult to stay motivated and positive when you know how far you still have to go, but motivation and positivity are nice bonuses when they’re available. Don’t count on them.

What will likely fuel your success is a combination of commitment, consistency, and resilience.

What have you been working toward that feels slow or stagnant? What have you learned, and what does that mean for your next steps?

If your goal is taking longer than expected, how can you begin building positive momentum toward your bigger picture?

Keep climbing.

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