Leader information

Challenge Day is a daylong experiential workshop for 7th-12th graders. Around 100 students and 20 adults come together in a big room for 6 ½ hours. 2 licensed Challenge Day leaders facilitate the group through a set of activities and experiences to support everyone in being real, connected and empowered. We lead high energy games and icebreakers and create a safe container. We teach about separation, compassion and power. We tell honest, often vulnerable stories from our lives. We make jokes, get silly and invite full self-expression. We model and demonstrate everything we teach. We foster connection across lines of difference, make room for amends and appreciations, welcome tears and laughter, give a whole lot of hugs. We actively love every person in the room.

Challenge Day workshops happen all over the US and sometimes internationally. Licensed Leaders travel 1-3 weeks a month about 9 months a year. We prefer to train people who are available to travel 3 weeks a month during our busy season, September-April.

You can live anywhere in the US near a major airport and do this work.

Usually a week of work means a travel day, 3-4 workshop days, and a travel day home.

Our licensing and training office is located in the San Francisco Bay area. All leaders come to the SF Bay for retreats together 3 times per year.

We don’t care about degrees or work/life history, we care very much about you being a heavyweight expert in a very particular set of skills:

You must be able to be real (honest, sincere, authentic) in a way that invites others toward the same, be able to genuinely connect (be loving, warm, open-hearted) in a way that guides others into connection, and be empowered in a way that leads others toward their power.
You must be able to compellingly engage large groups of adolescents. Teenagers are a tough audience! You must be able to win them over and be worthy of their trust.
You must be highly adept at big group co-facilitation - be able to "bring the party," lead activities gracefully, “read a room,” think on your feet, adapt in the moment and be a phenomenal partner to your co-leader.
You must be competent, mature and responsible. It’s essential in this work to get places on time, track time well during the workshop, be reliable, be able to fix things when you make mistakes, be professional and in integrity. All while also maintaining a sense of humor.
You must be able to guide people away from the superficial and toward the depths and lead people into profound, impactful experiences. It helps if you’ve done a lot of personal work, therapy, 12-step, etc or have your own faith background/connection to something higher. You need to be comfortable with full emotional expression. You need to know how to stay emotionally healthy and recharge in your downtime.
We are a non-partisan, secular organization holding a position of ideological neutrality in order to effectively serve a highly diverse population. You must agree to maintain a public identity that is politically and ideologically neutral.
You’ve got to understand teen issues, be able to play, laugh (sometimes at yourself) and meaningfully connect with students, adults and co-workers of all different ages, cultures, learning styles, races, identities, religions and abilities.

Be at least 25 years old, able to rent a car and drive.
Be able to lift/carry equipment up to 50 pounds per piece.
Maintain valid travel documents, including a valid passport.

Pass standard tests and background checks required to be certified to work with youth in schools:

Pass annual TB test
Pass fingerprinting for FBI and Department Of Justice (LiveScan) background checks.

We lead Challenge Days by and large during the academic school year, with summers and holidays often free for personal time or other endeavors.

Certified leaders give their availability to our booking office several months in advance, and we do our best to book days for you on the weeks you have made yourself available to work, with no guarantees.

For the first year after being certified, we find it best for new leaders to be available 3 weeks a month Sept-April for work. It ends up meaning leading around 75 Challenge Days that academic year. This helps cement the learning done during training and makes for stellar leaders. That said, exceptions can be made for exceptional candidates.

After the first year, you can choose to make yourself available 1-4 weeks a month.

Certified Leaders get paid per workshop day that they lead. Starting pay is $750 per day. Average pay is $1k per day. More details in our business model section below.

Leaders are independent contractors and are responsible for their own health care/benefits, etc. They are expected to buy and maintain all equipment, supplies, and apparel needed for the workshops they lead.

Flight, hotel and shared car rental costs for Challenge Day trips are covered by the schools.

After a thorough application process, if you are chosen to undergo training, you will be paired with a Lead Trainer. Together, the two of you will determine a plan to meet regularly (in person or on zoom) according to your schedules and locations. At least one trip for in-person training in the SF Bay area is required.

You will learn our program, practice delivering pieces and receive coaching. It's highly likely that several members of our team will be called upon by your lead trainer to work with you, for the best possible training. If there are other trainees learning at the same time as you, you may be paired or teamed up together, to enhance the learning.

Training will happen over the course of Spring 2024. It is unpaid, and doesn't cost anything (besides the cost of traveling to the SF Bay for an in-person intensive.)

When ready, trainees can get paid $250/day to apprentice (go with 2 Challenge Day leaders on trips and assist.) Certification happens whenever you are ready!

New leaders are expected to attend our all-staff retreat, August 8-10th and begin leading Challenge Days with a co-leader August/September 2024.

Duration and time-intensity of training are up to you, depending on you and your trainers' availability. You could dedicate full-time hours to training and be ready within a month or two, or dedicate 10 hours a week to training and do it over several months.

Feel free to look over our leader page for a deeper dive into our business model and agreements.

Leader Levels

Experience

Knows both roles

Supports Leader 1

Pay per Day

Level 3 Room

Trainee

N/A

Apprentice

$250

N/A

Leader 1

20 days

$750

Needs a Level 3 Leader

Leader 2

75 days

$1000

Needs a Level 2 Leader

Leader 3

150 days

$1000

Can support a Level 1

Leader 4

300 days

$1000

Can support a Level 1

Extras

Pay

Pay Terms

Leader Level

Air Travel

100

per day led on trip

Level 1 and above

Travel Booking

$100

per trip

Level 1 and above

Client Coaching

$150

per trip

Level 2 and above

Mentoring Leader 1

$250

per day

Level 3 and above

Solo Day

$500

extra per day

Level 3 and above

Training

$5000

per trainee

Level 4

New Leader Referral

$1000

per trainee

Apprentice and above

New Client Referral

$1000

per client

Apprentice and above

Overview of our Business Model

In the past, Challenge Day leaders were either independent contractors or employees of the 501c3 (formerly Challenge Day, now called Challenge Day Fundraising).

Going forward, Toward the Real LLC (now doing business as Challenge Day) will be moving to a licensing model with Leaders instead of an employment model.

This means we will be responsible for training and certifying leaders on the skills they need to lead challenge days.

Once you are certified as Challenge Day Leader, you are licensed to lead days under our licensing agreement. You are neither a contractor or employee, but a licensed sole proprietor.

This means you set your own schedule, purchase and maintain your own equipment, supplies, and uniform, and whatever health insurance needs you have. You are essentially running your own business, as a licensee.

Challenge Day Office and Training will handle training and certification, establishing and maintaining relationships with clients, booking, scheduling, billing and liability insurance.

Keep your explicit agreements with Challenge Day Office and Training
Participate fully in the three annual leader retreats
Lead at least 20 days per school year

Our goal is to support all Challenge Day Leaders in performing at that level. If you fall below it, we'll work hard together to get you back there.

Meet minimum days experience
Get training on new responsibilities / skills for that level.
Ask Certification for a level up.
Certification will interview you, leaders you've lead with, ask them for feedback on your skills, and decide wether or not to level you up.
All these interviews will be recorded and made available for anyone to review.

As a licensed Challenge Day Leader, you may charge up to a certain amount per day (see table below), depending on your leader level.

Challenge Day will handle all invoicing and billing for our clients, and wire you your pay within 3 days of the day being delivered, or when our clients pays whichever comes later.

You are free (and encouraged) to work on your own terms, anywhere, for anyone. However, you may not use the Challenge Day intellectual property or brand unless your day is booked through a licensed Challenge Day Office.

Right now, the US office is the only licensed office. We are working on licensing offices in Belgium, New Zealand and the Netherlands over this next year.

Starting 2024/2025 we will be encouraging existing leaders who are not on the west coast to open Licensed Challenge Day offices in different locations.

The vision is for multiple licensed independent businesses to be coordinating work for leaders around the world, all working towards a shared purpose, with an impeccable set of shared standards and practices.

Three times a year, we gather in person in the San Francisco Bay Area for three days and two nights.

We use this time to:

Create a cohesive, unified field between us
Practice our tools
Continually improve our program and sharpen our skills
Replenish, nourish, and support each other where needed

Retreats are usually held:

Mid August
Late December / Early January
Mid May

Leaders are expected to pay for their own travel expenses. Food (and a couch to sleep on if you want) will be provided at the retreat.

Please do your best to be there, barring matters of life / death or important travel.

Because of summers, other school breaks and holidays, the work is seasonal and there isn't work available all times of the year. In general you can expect to lead days from late August to early May.

Number of days you're schedule will depends on how many weeks per month (on average) you make yourself available:

If you're available 1 week per month: you'll lead around 25 Challenge Days per year
If you're yourself available 2 weeks per month: you'll lead around 50 Challenge Days per year
If you're available 3 weeks per month: you'll lead around 75 Challenge Days per year
If you're available 4 week per month: you'll lead around 100 Challenge Days per year

Ongoing Agreements for Maintaining Certification

We expect Challenge Day Leaders to be professional:

1. Punctuality: Arriving on time for work, meetings, and appointments.

2. Dependability: Following through on commitments and taking full responsibility for getting it done.

3. Effective communication: Communicating clearly, concisely, and respectfully.

4. Dress and grooming: Maintaining a neat and clean appearance appropriate to the setting.

5. Respect and courtesy: Treating everyone with respect and consideration, regardless of their background, position, or opinions.

6. Ethical conduct: Acting with integrity, honesty, and maintaining confidentiality when required.

7. Collaboration and teamwork: Cooperating with colleagues, sharing knowledge, and working together to achieve common goals.

8. Adaptability: Being reasonably open to change, embracing new ideas, and adjusting to shifting priorities and circumstances.

9. Emotional intelligence: Demonstrating self-awareness, empathy, and the ability to work with emotions without acting out.

10. Law Abiding: Maintain a clean legal record.

We have three main goals for a Challenge Day:

First, we make the room safe enough for participants to be real. They experience the impact of authentic sharing and making it safe for others to share.

Second, we bring enough love and clarity to break down the walls of separation. Participants experience that they are not alone, and that we have way more in common than what divides us.

Third, we guide them towards their agency. Participants understand that they are not victims, and experience the power of making a choice and acting on it.

That's at the heart of our day, and the gift we hope to bring. Many of us have received various other precious teachings and insights in our lives. It is natural that we would want to share them when we have the opportunity. Challenge Day Leaders commit to resisting that temptation.

It's important that there's consistency in the programs we deliver, because we are in the business of shifting culture. Culture, in part, is created through shared language, practices, and shared experience.

If the day changes too much from leader to leader we water down the signal, and reduce the chance of a new culture taking hold.

Also, the more we talk, the less students get a chance to speak.

Challenge Day Leaders agree to cover all of the core teachings, and not add any of their own. They do so in their own style, and their own words, in a way that's authentic to them. They make sure to include shared metaphors and language so students across schools and within have a shared culture.

They don't need to be on script, but they need to be on point.

In addition it's important to maintain a non-partisan, non-activist public image

We deeply respect your right to free speech and honor your commitment to political causes and religious view points that matter to you.

However, we live in a world that's getting more and more polarized. Unfortunately, in such a polarized world, any overt public display of activism or political affiliation can get in the way of us reaching youth and communities that disagree such views.

Challenge Day must be politically and ideologically neutral to get into to the room. Our goal is to deliver an inclusive, non-partisan, secular workshop that wouldn't offend 80% of the citizens of the country we're in.

Central to our work is the ability to find common ground, and to speak to the common humanity that unites us. Challenge Day Leaders agree to keep their public image in alignment with this.

1. Being real and leading others to do so.

2. Being connected and leading others to do so.

3. Being empowered and leading others to do so.

Nitty Gritty Details

At the annual January retreat, we'll ask you for your general availability for the fall.

At the end of spring retreat, we'll ask you for your general availability for the spring.

Once we have your general availability, we will generate all the placeholders and put them up on the Calendar.

We expect you to:

- Let us know the moment you're not available for a placeholder, so we don't book it. Changing your mind / schedule around placeholders is fine. You're only responsible to give us a heads up when it changes.

- Once a placeholder becomes tentative, you are committed to that day. If you need to change it for a non-emergency (health, death...etc.) then we expect you to coordinate finding a sub with another leader. If we can't find a sub, you need to do the day. We don't have travel or hotels booked yet for a tentative day, so if you find a sub it won't cost you anything.

- Once a tentative day becomes confirmed, you're responsible for travel switching costs with your sub. Again, this is for non-emergency changes to your schedule.

If any of the changes are due to an emergency, we will cover the costs of travel switching and/or cancel the day.

Historically, each day costs the office an average of $20 to $30 in equipment maintenance and supplies.

We'll charge the school upfront for air travel, hotel, and car rental. If you book these things yourself, you'll use a company account, and won't need to provide receipts. If we book them for you, there's no paperwork needed on your end.

Company credit cards are going away. When you're on the road, all incidentals are on you. This includes things like food, gas, and extra luggage charges.

Yes. Everyone leading Challenge Days needs to get certified to do so. But if you already have experience as a leader you skip all the check offs and training. All we do is have a conversation to make sure this new system is clear and understood and you get your certification.

You are responsible for purchasing and maintaining your own equipment. However, leaders previously employed by the 501c3 who want to get certified and are committed to working at least one week a month for the next year will be gifted the equipment they are currently using.

No. Because other leaders will be sharing the use of your equipment (depending on role) we need to make sure there isn't a learning curve for every partner you have.

For now, your equipment needs to match the ones we traditionally used. If you have a line on better, lighter, cheaper, or in any way more superior equipment let us know, and we'll add it to the list of approved equipment.

We will gift you what we have in storage and supply. Once we run out, you'll need to buy your own. For things like T-shirts, posters and validation cards, we will provide you with contact info for the supplier, and you'll need to purchase from them.

We don't make a profit off any supplies.

In addition to facilitating the day, we expect you to:

- Call the coordinator the night before and double check details of the day.

- Record the day and upload recordings by the end of the trip (ideally end of the day)

- Submit an EOD by the end of the trip (ideally and of the day)

If we charge the school for any cancellation or rescheduling will pass on half of that deposit to you.

If we charge them full price for cancelled day, we will pay you in full for that day.

If your partner cancelled for a non-emergency, or cancelled for an emergency and didn't make it on the trip you'll get paid the Solo rate.

If it's an emergency that happened on the road, you and your partner will get paid the normal rate for your day.

If someone needs to be swapped out on a trip for an emergency, we will cover the extra travel and hotel costs.

Leader Portal

Interested in Being a Challenge Day Leader?

Feel free to look over our leader page for a deeper dive into our business model and agreements.

Leader Levels & Certification

Overview of our Business Model

Ongoing Agreements for Maintaining Certification

Nitty Gritty Details

Get regular updates from us

Leader Portal

Interested in Being a Challenge Day Leader?

Feel free to look over our leader page for a deeper dive into our business model and agreements.

Leader Levels & Certification

Overview of our Business Model

Ongoing Agreements for Maintaining Certification

Nitty Gritty Details

Get regular updates from us

Let's get started