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Going & Growing Guide
to the High School Experience


Empowering students and families to thrive through their high school experiences with self-awareness and college admissions strategy


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What are the conversations and topics that need to be addressed each season of every year in high school for students to grow in self-awareness while developing their personal strategic edge in the college admissions process? This annual guide to growing and going through the high school experience helps you navigate what’s next with confidence, intentionality, and organization.

We recommend students and parents/mentors come together at least four times a year and make room for a reflective hour to discuss the seasonal checklist questions. Taking time to work through each question by writing first and discussing second, will create deeper connections in awareness and actions. In our practice, we encourage this process occur with parents and mentors also answering the questions from their perspective. This invites multiple viewpoints to inform the conversation. In between these intentional conversations, it’s important to set smaller goals and follow-up conversations for accountability on a weekly and monthly basis.

Finally, at Cultivate., we know there is usually not one right answer to a question. The answer to, “What is the best school?” is “How do you define best?” These questions are designed to help students and families take ownership of their growth and mindsets, so that you are empowered to chart your own course forward. We wish you the best in going and growing through your high school experiences.


Guiding Question: How am I building my confidence and what role does reflection play in helping me do this? 

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Summer Freshman Year


  • What am I looking forward to in the upcoming high school experience? What do I know about the high school I am attending and how it aligns with who I am and what I value about learning?
  • What will a successful start to freshman year look like? Sound like? Feel like?
  • What are the expectations I need to define for personal, academic, family, and social success?
  • What kinds of classes am I taking, and how will the level of rigor and my grade affect my future plans? What are extracurricular goals I want to make for service/athletics/arts/clubs & organizations? Where do I want to spend my time and energy beyond the classroom? What do I want to know more about?

Fall Freshman Year


  • How am I following up with the goals and expectations from summer?
  • How am I spending my time before, after school, and on weekends? If how I spend my time is who I am, what does my schedule say about me? 
  • In what ways am I developing the skills of communication, collaboration, creativity, and problem-solving through what I am learning in school? 
  • What has been the experience so far that has really made me excited, feel alive? Who and what was involved? What does this help me understand about who I am and what I value? 
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Winter Freshman Year


  • What is working best for me as a learner? What would I like to see improve? Why?
  • What am I learning about myself as I progress into the second semester of freshman year? What have I succeeded in? What has been most challenging? Why?
  • What does it mean to practice educational self-advocacy? When was there a time where I asked for help or expressed I needed something explained in a different way?
  • Summer is coming sooner than I might think. When I think of how I spend my time, what could I do to explore interests, deepen passions, and create meaningful balance? Are there formal summer programs I might apply to?

Spring Freshman Year


  • What kinds of college conversations have you been a part of over the course of freshman year? What colleges do you know about or would you like to know more about?
  • What kinds of courses will I take sophomore year to challenge myself intellectually and prepare academically for as many future options as possible? What does the right kind of schedule look like and feel like for me?
  • Am I applying to a summer program or working with my family to craft an intentional use of my summer time? What would I like to gain from my experience/s?
  • What am I planning to read to explore new ideas and ways of seeing?
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