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Transition Night | From Middle to High School

From Middle School to High School

Many cultures, religions, and social groups mark the transition from middle school to high school with some type of event, celebration, or activity.

For my two sons, I decided to make up my own transition event. I wanted it to be fun, significant, and memorable.

The Search for Advice

I started by soliciting advice from trusted friends and family members about their personal experiences with this transition as well as anything they learned from ushering their own children through this phase of life.

I received a ton of exceptional advice.

The hard part was parsing it down into something that was accessible and not overwhelming.

I boiled down pages of input into 11 Key Words. These words, in my opinion, represent some of the most important aspects of life that a rising high schooler will face.

There are no right or wrong answers to this puzzle, but here are my 11 Key Words:

  1. Relationships
  2. Preparation
  3. "Good"
  4. Discipline
  5. Fun/Not Folly
  6. Patience
  7. Struggle
  8. Problem-Solve
  9. Learn
  10. Dream
  11. Work Hard

Anchor Moments

I wanted our event to be special, memorable, and unique. I wanted to "anchor" this night in their minds.

My first decision was to include two of my best friends, who were close mentors to my sons since their birth.  They represent two incredible male role models in my sons' lives that they could lean on in my absence.

Unfortunately, one of these friends was out of the country when the event went down. Luckily, my other friend not only showed up, but helped tremendously with the logistics and planning.

We started off the night with a fun, memorable, and unexpected jump from a 20' bridge into a river below. This got everyone's attention and put us into a high state of awareness.

We then paddled down this brackish river on our surfboards and standup paddleboards to the river mouth, which emptied into the ocean. This was quite a unique experience that was new to us.

Standup paddling and surfing commenced, and a great afternoon was had by all.

After a few hours of offshore wind-aided surfing, we quickly rinsed off in an outdoor shower and got dressed for dinner.

Here is my Facebook Live post moments before leaving for dinner (wetsuits still on).

Dinner and Dialogue

It was just the four of us - my two sons, Coach Reilly, and me. I had texted my sons the 11 Key Words over the prior 11 days (one every day) and asked them to pick their Top 5.

It was a joy to hear them talk about what these words meant to them in the context of their lives. There was some overlap in the words they both chose, but not as much as you might guess with identical twins. This was interesting.

We had some great laughs during dinner, too. At one point, our server suggested that the twins might struggle to finish the "large" surf and turf platter. She said most people had to "share it". That was a challenge that my sons couldn't pass up. Needless to say, the boys polished off the platter with room to spare. 

Coach Reilly and I exchanged stories from our lives, our wins and losses during high school, and how things have changed.

We laid it all on the line. We talked about sex, alcohol, social media, drugs, peer pressure, competitive sports, teen driving, expectations, conformity, and discipline.


One big takeaway was the suggestion for the twins to enter high school with a strong mindset already in place when it comes to dealing with tough issues like sex, alcohol, and drugs. Decision-making under stress becomes a lot easier when you know where you stand on these issues before they arrive. The typical "tough decisions" faced by teens become non-factors (in theory).


We presented the boys with a few symbolic gifts to reinforce the significance of the night:

  • Surfing Tidal watches - which suggested that "now was the time to take control of their lives"
  • The Startup of You - a book by LinkedIn Founder, Reid Hoffman, that teaches students how to develop a portfolio of skills and knowledge that will make them immune to changes in industries, technologies, and job markets.
  • Custom anvil - the anvil is the symbol of PrepWell Academy and represents the constant shaping and re-shaping we experience in our lives. How we all live through "dips in the fire" where the struggle can seem overwhelming. With patience and persistence, we can see our way clear, but not without getting bumped, bruised, and hammered along the way. In the end, a beautiful tool, weapon, or piece of art remains - only to experience yet another "dip in the fire". The top of the anvil contains an inscription of the 11 Key Words as a constant reminder of the highs and lows of life.
  • Discipline = Freedom t-shirt - a phrase we discussed at length during dinner. Each boy had his own "take" on what this phrase meant to him.

No guarantees

The event went off without a hitch and exceeded all of my expectations. Of course, there are no guarantees that these two young men will make all the right choices - no one is perfect. In fact, it's a fact that they will make mistakes.

I summed up the night by telling them that if they remember only one thing from the whole night - it should be that we love them unconditionally - no matter what.

I felt good about sitting down with my sons - free from the typical distractions, rushing around, and commitments - to put it all out on the table. We held nothing back - and it got uncomfortable at times - but we pushed through.

I said my piece - and now I am at peace.

Without any doubt, my sons now know where Coach Reilly and I stand on some of most important issues they will face over the next four years.

We're already brainstorming about where we will go and what we will do four years from now - when the boys transition from high school to college.

Have you had a similar experience?

There are certain themes that this particular transition event didn't address fully - like community, faith, and family - but I have plans to address these separately.

I'd love to hear your experiences or if you've done something similar to acknowledge this transition from middle school to high school. Please share feedback in the comments sections below.

I'd especially love to hear how anyone has handled this transition with girls.  The concept of "transition" is certainly universal, but the tone and content may differ with girls.

Prep On,

Author: PrepWell Academy's Founder, Phil Black, has spent a lifetime cracking the code on the world's most competitive programs: Yale University, Harvard Business School, Navy SEALs, Goldman Sachs, Entrepreneurship, Shark Tank, etc.

Inside PrepWell Academy, Black teaches students everything they need to know about the college admissions process in a series of expertly-timed, 3-5-minute, weekly training videos starting in 9th grade and continuing through 12th grade [Note: this program can only be joined in 9th or 10th grade]. My specialties include military service academies, ROTC scholarships, Ivy League, and student-athletes.

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