What Parents Teach Us About Little Leagues: From Struggle to Strength

Youth softball thrives not because of fancy facilities or big-name coaches, but because of the passion and dedication of parents who care. While hiring a professional coach can be helpful, the heart of any successful league or travel organization lies in the hands of parents—those who organize, communicate, cheer, and show up every week because they genuinely want their daughters to grow, improve, and have fun. It’s not about being an expert; it’s about being invested. The most effective programs I’ve seen aren’t run like corporations—they’re run like communities, led by parents who love the game and want to build something meaningful for their kids.

In 2012, I was working as an office manager at a local real estate company when a co-worker asked if I could teach his daughter how to pitch. Her team couldn’t throw a strike, and the games were dragging. Soon, other parents started asking me for help too. But at the time, I saw myself as a future executive, not a coach. The idea of working with kids—besides my sweet, forgiving nieces—felt foreign. What do you even say to a 9-year-old? Still, my co-worker was persistent, and I could use the extra cash, so I said yes.

Fast forward to today—I now own and operate a pitching school with over 160 students. I’m regularly asked to help little leagues improve their pitching because it truly is the foundation of the game. When pitchers throw strikes, batters get to hit and fielders get to field. That’s when the game becomes exciting and developmental for everyone. To support these leagues, I began reaching out to successful coaches and league leaders to learn how they built their programs, what they wish they’d done differently, and their best advice for others.

The leagues I spoke with varied widely. Some had well-established programs with most pitchers receiving instruction, while others had more recreational play with enthusiastic, hands-on parents. One thing they all had in common? They learned through trial and error—and now, I hope to pass on some of their hard-earned insights so you don’t have to learn everything the hard way.

We all want more opportunities for girls, no matter their goals—whether it's high-level travel, high school, college ball, or simply having fun with friends as an 11-year-old. No matter the destination, every journey begins in little league.

And every thriving little league starts with a handful of passionate leaders. One woman I spoke with joked that she stays up at night thinking about softball—she called herself “obsessed.” But not in the way you might expect. She’s not pushing her daughter toward college ball or national titles. She just loves watching her improve and have fun. That was eye-opening. I used to associate the word “obsessed” with the hyper-competitive dad who overcoaches and favors his kid. But this was different. This was love for the game. I think I can finally call myself obsessed, too.

This same leader rented out local public schools in the winter after doing her own research to find affordable space. She held open practices for all players in the league—and the turnout was fantastic. Parents trusted her because she wasn’t part of a business; she was part of their community. Another league did something similar with open pitching practices led by high school players. Their only challenge was low turnout in December and January—possibly due to poor communication, or maybe just a lack of awareness that pitching is a year-round commitment.

One coach told me his team used to lose every game to a rival who had great pitching. Once he learned that the rival team worked with a professional pitching instructor, he did the same—and now his team is competitive. He made an important point: even after watching dozens of lessons, he still doesn’t feel confident teaching his daughter the way a trained coach can. Another echoed that sentiment, adding that if he could do it again, he’d have his players start lessons at age 7 or 8—before they begin player pitch, not after. Pitching, in both baseball and softball, is a team’s backbone. Without it, you simply can’t compete.

So why don’t more players get formal instruction? There are many reasons—some rooted in ego or misinformation, others in logistics or finances. A common misconception among baseball dads is that windmill pitching is just like overhand baseball pitching. Once they realize it’s a completely different skill set, they hit new roadblocks: cost, time, and access.

One mom who helps run a growing, lower-level league told me her biggest struggle is getting families to commit to instruction. Local options are limited and far away. It’s hard to convince parents to drive 25+ minutes and pay $80 an hour when they’re not even sure their 8-year-old will stick with it. Add in busy schedules and long commutes, and it becomes a non-starter. So they struggle—and stay stuck.

Another mom noted how parents today don’t play catch with their kids like they used to. With both parents working, they’re more likely to outsource instruction. That shifts the responsibility to coaches and leagues, which means leaders have to adapt—and step up.

In addition to pitching, there were a few other points that came up repeatedly. As girls grow older and look toward high school or travel ball, movement pitches become essential. A local high school coach told me he often sees players claiming to have five different pitches—but none of them actually work. He prioritizes spin and effectiveness, especially if a pitcher lacks top-end speed.

Overhand throwing is another area of concern. Whether it’s because of the size of the ball, societal expectations, or lack of practice at home, many girls are falling behind in this basic skill. And it matters.

With all this focus on skill development, it’s easy to forget that great coaching isn’t just about the mechanics. In a powerful article by John O’Sullivan, thousands of coaches were asked what makes a great coach. Over 80% of their answers pointed to emotional intelligence—not tactics. Great coaches inspire, connect, and believe in their players—even more than the players believe in themselves.

If that’s the job of a coach, then isn’t it the job of a league leader to believe in their coaches the same way?

We ask our kids to push through challenges and “figure it out.” Maybe it’s time we held ourselves to the same standard. League leaders face endless obstacles—budgets, gym access, weather cancellations, inconsistent instruction, motivation. But the most committed ones find a way through. As O’Sullivan puts it: “Improvement in any achievement activity does not come without struggle, without times of discomfort and difficulty.”

There’s no one-person solution. But when parents and coaches step up and lead, they inspire others to follow—and that’s how the future of your softball organization takes shape.