A Parent’s Guide to The Crossing
The Crossing is a mentorship experience designed to help boys and young men become stronger, more capable, more grounded, and more intentional about the direction of their lives.
It is built around a simple idea: growing into a capable man takes more than information. It takes experience, challenge, guidance, responsibility, and people willing to walk alongside you.
The Crossing provides a young man with another positive adult in his corner—someone who can listen, challenge him, provide perspective, teach practical skills, and help him turn what he knows into how he lives.
The Crossing is training, not therapy. The goal is not to diagnose, treat, or “fix” a young man. The goal is to help him develop the strength, discipline, judgment, confidence, and direction necessary to increasingly lead his own life.
What Is The Crossing?
Growing up comes with real challenges. Young men are learning how to handle pressure, responsibility, relationships, emotions, failure, independence, identity, work, goals, and the transition into adulthood.
There are things parents can teach that no one else can. There are also times when hearing something from another trusted adult—or experiencing a lesson for himself—can make it land differently.
The Crossing creates a space outside of home and school where a young man can talk openly, test himself, learn practical skills, take on challenges, make mistakes, reflect, and continue moving forward.
Depending on the participant and his goals, mentorship may include:
Conversation and reflection
Physical training
Outdoor experiences
Practical life skills
Goal-setting
Accountability
Leadership development
Real-world challenges
The experience is centered around three areas: Strength, Discipline, and Direction.
Strength
Strength is more than physical ability. It is learning how to remain steady under pressure, face discomfort, work through setbacks, develop confidence through action, and discover what you are capable of.
Physical challenges may be part of the process because the body is often one of the most direct places to practice perseverance, composure, discipline, and confidence.
Discipline
Discipline is learning to follow through. It means developing routines, responsibility, consistency, self-control, accountability, and the ability to make decisions based on what matters long-term rather than what feels easiest in the moment.
The goal is not perfection. It is learning how to make commitments, recover when you fall short, and keep moving forward.
Direction
Direction is learning to live intentionally. As a young man grows, questions naturally begin to emerge: Who am I becoming? What matters to me? What am I good at? What kind of life do I want? What responsibilities do I need to take on? What needs to change?
Mentorship creates space to explore those questions while helping turn ideas into practical goals and action.
Who Is The Crossing For?
The Crossing is primarily designed around the growth and developmental needs of boys and young men.
Some participants may need more confidence. Others may need accountability, structure, physical challenge, stronger habits, positive direction, or simply another trustworthy adult to talk with.
A young man does not need to be struggling or in crisis to benefit from mentorship. The Crossing can also serve young men who are already doing well and want to become stronger, more disciplined, more capable, or more prepared for adulthood.
The Crossing may be a strong fit for someone who could benefit from:
Greater confidence
More structure or accountability
Stronger habits and routines
A positive male role model
Physical activity and challenge
Greater responsibility
Practical preparation for adulthood
Help identifying goals or direction
Someone outside the immediate family to talk with
Leadership development
Better follow-through
A constructive outlet for his energy
Greater independence
A place to be challenged without being defined by his mistakes
While the program is primarily focused on boys and young men, mentorship may occasionally be available to others when the individual circumstances and mentorship relationship are a strong fit.
Mentorship Is Not Therapy
The Crossing is mentorship. It can provide encouragement, accountability, perspective, goal-setting, positive challenge, practical skill development, life experience, and a trusted adult relationship.
It is not psychotherapy, counseling, medical treatment, psychiatric care, addiction treatment, or crisis intervention.
There may be situations where a participant would benefit from professional mental-health or medical support in addition to mentorship. These roles do not have to compete with one another.
When something falls outside the appropriate role of mentorship, I will encourage the family to seek the appropriate professional support.
The Mentor, Parent & Young Man
I believe mentorship works best when everyone understands their role. The goal is not to replace the parent, take control of the young man's decisions, or make him dependent on a mentor. Instead, each person plays a different part in helping him grow.
The Young Man
The participant needs enough independence to develop trust, speak honestly, think through decisions, experience consequences, and begin taking greater responsibility for his own life.
He is not expected to have everything figured out. He is expected to participate.
Over time, the goal is for him to increasingly take ownership of his habits, decisions, goals, relationships, and direction.
The Parent
Parents remain the primary adults responsible for their child. The Crossing is not intended to replace parental leadership or compete with the family.
My role is to come alongside what parents are already trying to build and provide another source of guidance, accountability, perspective, experience, and support.
Parents often see parts of their son that a mentor may not see. A mentor may also see parts of a young man that do not always appear at home. When those perspectives work together appropriately, they can be powerful.
The Mentor
My role is not to control a young man's life or make his decisions for him. My job is to listen, ask good questions, challenge him when necessary, offer perspective, teach, encourage, create opportunities for growth, and hold him accountable to the commitments he makes.
Sometimes that means talking. Other times it may mean doing something difficult together or allowing him to make a decision, experience the result, and then helping him learn from it.
The goal is always growth—not dependence on the mentor.
Privacy & Communication With Parents
Trust is an important part of mentorship. A young man needs enough privacy to speak honestly, ask difficult questions, admit mistakes, and work through things without feeling that every conversation will immediately be repeated.
Parents also deserve appropriate communication regarding their child.
I do not believe either extreme works particularly well. Reporting every private conversation can prevent trust from developing, while completely excluding parents ignores their responsibility and involvement in their son's life.
Whenever possible, The Crossing aims for a healthy middle ground.
Parents may receive communication regarding areas such as:
Overall progress
Goals we are working toward
Habits and accountability
General patterns or challenges
Areas where support at home may be helpful
Significant concerns affecting the participant's wellbeing
Important changes in the direction of mentorship
I will generally avoid unnecessarily repeating private conversations word-for-word. When something important should be communicated at home, I may encourage the young man to have that conversation with his parent himself.
Sometimes helping him find the courage and words to communicate directly is part of the mentorship.
Safety Comes Before Privacy
Privacy has limits, and I will never promise a participant absolute secrecy.
If I believe a participant may be in serious danger, intends to seriously harm himself or another person, may be experiencing abuse or exploitation, or another significant safety concern arises, I may need to involve a parent, guardian, emergency resource, or other appropriate person.
The wellbeing and safety of the participant comes first.
What Can Mentorship Look Like?
Not every meaningful conversation needs to happen sitting across a table. Depending on the participant, his interests, and the goals we are working toward, mentorship may take place through conversation, activity, challenge, or a combination of all three.
A session might include:
Physical training
A hike or outdoor challenge
Fishing or another shared activity
Working through a difficult decision
Setting goals for the next month
Building a morning or evening routine
Practicing communication
Discussing friendships, dating, school, work, family, confidence, responsibility, or the future
Learning practical life skills
Working on leadership
Reviewing something that went wrong and figuring out what could be done differently
Completing a challenge that requires patience, effort, or problem-solving
Creating a plan and then putting that plan into action
The environment may change, but the purpose remains consistent:
Learn. Practice. Reflect. Grow.
Why Challenge Matters
The Crossing intentionally includes appropriate challenge because confidence rarely comes from simply being told that you are capable. It grows when you experience yourself doing difficult things.
That challenge might look like completing a hard workout, finishing a long hike, speaking honestly when it would be easier to stay quiet, following through on a commitment, taking responsibility after making a mistake, trying something unfamiliar, or finishing something you wanted to quit.
Those experiences create evidence. Over time, a young man begins to realize: I can handle more than I thought I could.
Challenge within The Crossing is never intended to humiliate, punish, intimidate, or recklessly push someone beyond appropriate limits. Challenge should have a purpose.
The objective is to gradually expand a participant's confidence, capability, judgment, resilience, and willingness to engage with difficult things.
What Parents Can Expect
Parents should not expect an overnight transformation. Meaningful growth is usually cumulative, and it often begins with small changes that may not seem dramatic on their own.
You may begin to notice that he:
Wakes up when he said he would
Begins exercising consistently
Handles a disagreement differently
Tells the truth when it would have been easier to hide something
Takes ownership instead of immediately making an excuse
Starts thinking more seriously about his future
Helps without always being asked
Becomes more willing to attempt difficult things
Communicates more directly
Recovers faster after a setback
Starts keeping promises to himself
One change may seem small. Over time, however, small decisions begin forming habits, habits begin forming character, and character begins shaping the direction of his life.
What I Ask From Parents
Parents are an important part of the mentorship process, and there are a few things that can make the experience significantly more effective.
Allow the Process Time
Not every meaningful conversation creates an immediate visible change. Sometimes an idea needs time before a young man understands it, accepts it, or begins applying it for himself.
Growth is rarely perfectly linear.
Avoid Using Mentorship as Punishment
The Crossing should not become somewhere a young man is “sent” every time he gets in trouble.
Accountability matters, but the mentorship relationship works best when the participant understands that I am in his corner—not simply another person waiting to punish him.
Support Accountability at Home
If we develop a goal, routine, responsibility, or challenge, support from home can make a major difference.
The goal is not for parents to constantly monitor everything he does. It is to create an environment where responsibility is expected and growth is supported.
Communicate Important Changes
Major changes involving home, school, relationships, behavior, health, or significant life circumstances may provide important context for mentorship.
Parents do not need to report every detail, but meaningful changes can help me better understand what a participant may be navigating.
Let Him Own His Victories
One of the most important parts of becoming a capable man is developing internal ownership.
When he succeeds, let the victory belong to him. When he struggles, give him opportunities to problem-solve. When appropriate, allow him to experience the natural results of his decisions.
The goal is not simply to produce better behavior while adults are watching. It is to help him develop the ability to lead himself when no one is watching.
The Goal Is Independence
Successful mentorship should not make a young man dependent on his mentor. It should gradually make the mentor less necessary.
The long-term goal is to help develop a young man who can:
Regulate himself when emotions are high
Think before acting
Make thoughtful decisions
Handle discomfort
Communicate directly
Take responsibility for mistakes
Ask for help when he genuinely needs it
Keep commitments
Recover from setbacks
Recognize unhealthy influences
Develop meaningful goals
Follow through without someone constantly pushing him
Eventually, the lessons should become his own.
That is the point.
Starting The Crossing
Before mentorship begins, I want to understand both the parent's perspective and the young man's perspective.
An initial conversation gives us the opportunity to discuss:
What you have been noticing
Where he seems to be doing well
Where he may be struggling
What he wants for himself
What you hope mentorship might provide
Any important circumstances I should understand
Whether The Crossing genuinely feels like the right fit
The young man's willingness matters. He does not need to arrive excited about every part of the process, but meaningful mentorship requires at least some willingness to participate, engage, and grow.
There does not have to be a crisis before mentorship begins. Sometimes the right time is simply when a young man reaches a point where he is ready for more responsibility, more challenge, and more direction.
A Final Note to Parents
Raising a young man means preparing him for a day when you will no longer be able to make every decision for him.
Eventually, he will need to decide for himself how he responds to pressure, who he surrounds himself with, how he treats people, how he handles failure, whether he keeps his word, what he does when nobody is watching, and ultimately what kind of man he becomes.
The purpose of The Crossing is to help strengthen him for that transition.
Not by giving him every answer, but by giving him opportunities to think, act, struggle, learn, build confidence, accept responsibility, and discover that he is capable of carrying more of his own life.
He will eventually have to make the crossing himself. The role of mentorship is to help prepare him for it.
The Crossing
Strength · Discipline · Direction
