Sippi's Advocacy Initiative & Leadership

Chart a new course. Sail into freedom.

We walk beside returning citizens on the journey home — from the first interview outfit to a résumé that opens doors, classes that build real skills, and mentors who stay the course.

Get Support Become a Mentor
  • Work Clothes
  • Résumés
  • Classes
  • Mentorship
Sippi's Advocacy Initiative & Leadership — S.A.I.L. Into Freedom logo
N E S W
Scroll
Your past may tell a story of where you've been, but your purpose is defined by what you do with what you learned — true redemption is returning with a heart to serve, a hand to lift others, and a commitment to help someone else find a better path.
Reentry Assistance with dignity & purpose

Our Mission

Everyone deserves a second wind.

Coming home after incarceration is one of the hardest voyages a person can make. Doors close, gaps show up on applications, and the path forward can feel like open water with no map.

Sail with Sippi exists to change that. We provide the practical tools and the human support people need to find meaningful work, grow their skills, and lead the lives they're capable of — because a past sentence should never be a life sentence.

S
Sippi's

Rooted in community, built on lived experience.

A
Advocacy

Standing up for fair chances and fair treatment.

I
Initiative

Hands-on programs that create real momentum.

L
Leadership

Helping people lead their families and communities.

Our Impact

Lives changed, one voyage at a time.

0+

Returning citizens served

0+

Résumés prepared

0+

Professional outfits provided

0+

Volunteer mentors

“When I came home, I didn't own a single thing to wear to an interview. Sail with Sippi got me dressed, got my résumé right, and three weeks later I was hired.”
Marcus T.Program participant
“My mentor never gave up on me — even on the days I wanted to give up on myself. I finished my GED and I'm now in a welding program.”
Denise R.Education & vocational student
“Mentoring with Sail with Sippi is the most meaningful thing I do each week. Watching someone find their footing again — there's nothing like it.”
James W.Volunteer mentor
Maurice Clifton Sr. at a Mississippi news-media interview
Maurice Clifton Sr. · Founder & CEO

In the News

A story of redemption & reform.

“Model Inmate”: Father Finally Has Crack Sentence Reduced as U.S. Senate Shelves Reform Bill

Our founder Maurice Clifton Sr. served more than two decades of a 33-year federal sentence before his release under the First Step Act in January 2020. Today he is a chaplain, advocate, and a voice for the people he calls the “left-behinds” — living proof that a past sentence should never be a life sentence.

Mississippi Free Press · Kayode Crown

Read the full story