50 Bosses DEEP – 75 Day Boss Up Challenge

A Wellness + Accountability Fundraiser for Entrepreneurs

Entrepreneurs spend so much time building businesses, solving problems, and showing up for everyone else that they often neglect themselves in the process.

The 75 Day Boss Up Challenge was created to change that.

Hosted by 50 Bosses DEEP through our Boss Walks wellness initiative, this challenge is focused on helping entrepreneurs reset mentally, physically, emotionally, and professionally while supporting a meaningful community movement centered around total wellness and economic prosperity.

Starting June 1st, 2026, participants will commit to 75 days of intentional growth, discipline, movement, accountability, and impact.

This is more than fitness. This is about becoming a healthier leader, a stronger entrepreneur, and a more intentional person.

The Challenge Includes These Commitments:

MOVE YOUR BODY DAILY
You don't have to become a bodybuilder
Walk. Stretch. Dance. Lift weights. Ride a bike. Do something.
Your business needs a healthy CEO. Your body carries your vision every day. Give it the attention it deserves.
Minimum goal: 30 minutes a day.
READ 1 BOOK

Your business will only grow as much as you do.

Read one book during the challenge on:

Leadership
Business
Finance
Mindset
Wellness

75 days from now you'll either have more excuses or more knowledge. The choice is yours.

GIVE BACK

Success isn't just about what you gain. It's about what you give.

Donate money.
Volunteer.
Mentor someone.
Support a cause.

The goal is simple: make someone's life better because you showed up.

RESET YOUR MIND DAILY

Entrepreneurs carry a lot.

Take 15-20 minutes each day to:

Pray
Meditate
Journal
Reflect
Practice gratitude

A busy mind needs maintenance too.

PROTECT YOUR HEALTH

This challenge isn't about perfection.

It's about making better choices.

Drink more water.
Get more sleep.
Eat a little better.
Log off sometimes.

Your body is your first business partner. Treat it like one.

BONUS CHALLENGE
Find an accountability partner.
Someone who will encourage you, challenge you, and remind you why you started.
Entrepreneurship can be lonely.
This challenge doesn't have to be.

Participants will also share progress, wellness wins, lessons learned, and community impact moments throughout the challenge.

Donation & Sponsorship Options

Supporters can participate or sponsor the movement through:

- $1 per day pledge = $75 donation

- $2 per day pledge = $150 donation

- Additional sponsorship amounts are welcomed

Funds raised help support:

- Boss Walks wellness programming

- Entrepreneur wellness initiatives

- Community impact efforts

- 50 Bosses DEEP programming and outreach

Why This Matters

At 50 Bosses DEEP, we believe entrepreneurship should not cost you your health, peace, purpose, or well-being.

Too many leaders are burned out, overwhelmed, unhealthy, and disconnected while trying to build success.

This challenge is about changing that narrative.

We are D.E.E.P.

Dedicated to Elevating Economic Prosperity.

Join us as we commit to becoming healthier entrepreneurs, stronger leaders, and better versions of ourselves for 75 days.

Challenge Starts:

June 1st, 2026

Join the Movement

Commit. Transform. Give Back. Grow.