"How Do I Start?"

My Favorite Question High School Students Ask

When I begin working with high school students, conversations about activities and involvement can go in a few different directions.

Sometimes students ask, “What looks best for college?”

Sometimes they look at me with a completely blank expression.

Both reactions are normal. High school students are navigating a lot of expectations—school, friends, family, and the looming question of college. It can be hard to know where to start.

But every once in a while, a student asks a question that makes me smile.

“How do I start?”

It’s my favorite question.

Why That Question Matters

When a student asks “How do I start?” it tells me something important.

It means they’re curious.It means they’re motivated.And most importantly, it means they’re willing to try.

That willingness is incredibly valuable. Because the reality is that not every activity is going to be the right fit—and that’s okay. High school is a time for exploration. Trying something that doesn’t work out is often just as valuable as finding something that does.

Moving Beyond “What Looks Best”

One of the most common questions students ask is:

“What looks best for college?”

It’s an understandable question. Students want to make good choices and keep doors open. They are inundated with chatter about hacks and tricks to get in. But authenticity is critical. What matters is not what looks good, what matters is the student’s level of interest and commitment.

The truth is that the most meaningful activities don’t begin with strategy. They begin with curiosity. When students focus only on what they think colleges want to see, they miss the opportunity to explore what actually matters to them. And that’s the part that matters most.

My goal when working with students isn’t to tell them what I think they should do.

After all, I already went to college.

The goal is to help students think about what they want to do, to discover what they care about—and then encourage them to pursue it.

Starting Small Is the Real Strategy

When students ask how to start, the answer is usually simpler than they expect.

Start small. Attend the first meeting of a club. Volunteer for a local event. Send a cold email (or even make a phone call…gasp!) to a neighborhood organization.Ask a teacher about helping with a project.

It doesn’t need to be perfect, and it doesn’t need to last forever. The point is simply to begin.

Exploration Leads to Real Interests

Some students discover their interests quickly. Others need time to experiment. Both paths work. Navigating interests in high school is seldom a straight line. A student might try a club one semester and decide it isn’t for them. Another might volunteer somewhere once and discover something they genuinely enjoy. Those experiences—successful or not—help students build confidence, direction, and independence. And often, the activities that become the most meaningful start in the most ordinary ways.

The Value of Trying

One of the most important skills students can develop in high school is the willingness to try something new—even if it doesn’t work out. Whether the outcome is disinterest or discovery of a new passion, students learn when they get out of their comfort zone and try new things.

Learning that it’s okay to pivot, adjust, and try again is incredibly valuable.

In fact, the students who gain the most from their high school experiences are often the ones who are comfortable experimenting and figuring things out along the way. Tried something and failed? I’d argue that’s even more impactful than everything always going your way.

So… How Do You Start?

If you’re a student wondering where to begin, here’s the advice I share most often:

Start with curiosity.Start with something small.Start with something that interests you—even a little.

But most importantly, be willing to try.

Because that simple question—“How do I start?”—is often the first step toward discovering what really matters to you. 

And that discovery is far more meaningful than simply trying to build the “perfect” resume.

Get started by reaching out to Headed for College to learn more about our work and how we help students take the next step.