We recently had the chance to connect with Tiffany Coles and have shared our conversation below.
Good morning Tiffany, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: Are you walking a path—or wandering?
Ooooh! I love this question as an introductory icebreaker into who I am. I strive to walk in God’s path for my life rather than wander. I truly believe we are all predestined for a purpose, and it’s up to us to humble ourselves, surrender, and follow the plan God wrote for us long before we ever arrived here.
I know I’m walking His path because my life looks nothing like what I once imagined — and I say that with a laugh and a lot of gratitude. I recently shared with my therapist that, for a long time, I only envisioned myself as a mother, and maybe working in the music industry, which was the career path I was originally on.
While I still get to weave the arts into my work from time to time, it’s become clear to me that my true purpose is simply to help people. That’s what I strive to do every day. Scripture tells us to “give cheerfully, not out of compulsion” (2 Corinthians 9:7–8), and that principle grounds how I move through the world. Serving others brings me joy and fulfills my soul — and that confirmation lets me know I’m exactly where I’m supposed to be.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Tiffany — also known as Tiffany Alana — and I’m a self-proclaimed social socialist, as well as the Founder and CEO of Bosses Give Back, a community service organization rooted in accessibility, collaboration, and heart-led service.
Bosses Give Back was born in 2019 during my junior year at Temple University after I participated in a Study Away program in Los Angeles. Seeing extreme wealth in the Hills and, just miles away, unhoused communities struggling to survive on Skid Row shifted my perspective forever. It reminded me of home in Philadelphia — places like Kensington and inner-Center City — and I found myself asking hard questions about injustice and what responsibility I had, even without wealth, but with passion.
When I returned home, I felt an undeniable urgency to create change. Bosses Give Back started in my college apartment over brunch with a few close friends who shared the same heart for service. What makes BGB unique is that there’s no exclusivity — if you have a heart to serve, you belong here. We believe that to be a boss, you must give back.
Since our founding, we’ve grown through meaningful partnerships and collaborations both locally and nationally, and we continue to build community by meeting people where they are — with dignity, compassion, and consistency.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What part of you has served its purpose and must now be released?
I’m currently learning how to release parts of my relationship with chronic illness — specifically my Complex Regional Pain Syndrome (CRPS), which I’ve lived with since 2014. It’s been one of the most frustrating and emotionally complex aspects of my health journey, but I’m realizing it’s also something that deserves space and visibility.
I created a separate platform, @alanasjournal_, with the intention of sharing that journey, though I haven’t always shown up consistently. Moving forward, I envision sharing my story more openly — especially on stages — because one of the most powerful things I’ve ever heard a mentor say is, “Sharing stories saves lives,” and I truly believe that.
Chronic pain intersects with so many parts of life — identity, worth, productivity, and community. I often speak privately with others navigating chronic illness, and we discuss dynamic disability — the reality that symptoms and capacity can shift day by day, minute by minute. Releasing the need to hide that truth feels necessary.
I try to remind myself and others that our worth is not tied to productivity. I am enough simply because I exist. And while what I contribute to my community matters deeply, it doesn’t define my value. Sharing that truth — and eventually releasing the weight of carrying it alone — feels like part of my purpose.
Was there ever a time you almost gave up?
Yes — there were moments when I felt very close to giving up. One of the most difficult periods was during the transition from high school to college, when I was overwhelmed, exhausted, and emotionally depleted.
What stopped me was love — specifically, a moment when my play brother said, “You wouldn’t want your mom to come home and find you like that.” That sentence stayed with me. From a young age, I carried a lot of pressure, much of it self-imposed after internalizing the voices of people whose opinions ultimately didn’t matter.
Therapy has been a major part of my healing, and since giving my life to Christ and being baptized, I no longer struggle with dark or self-harm thoughts. My heart, however, remains deeply tender toward anyone still navigating that journey. No one should feel alone in their pain — and I hope my story reminds people that help, hope, and healing are possible.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What are the biggest lies your industry tells itself?
One of the most harmful misconceptions in the philanthropic space is the quiet belief that people who need help somehow deserve or chose their circumstances. The truth is, we are all one moment away from our lives changing forever.
While it’s not always spoken aloud, you can feel it in the energy sometimes — and that matters. How we show up while serving is just as important as the service itself. Compassion, humility, and respect should always lead during service.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. What is the story you hope people tell about you when you’re gone?
I hope people say, “She treated people kindly.”
In everything I do, I strive to lead with kindness, honesty, and respect — values that were poured into me by my village. I pray that Bosses Give Back becomes part of my legacy for my children and community, long after I’m gone.
What began as a passion project quickly became purpose. And no matter where life takes me, I know I will always be helping people along the way. I see Bosses Give Back as my love child — something I’ll continue to nurture for as long as God appoints me to.
I want to be remembered as a woman who delighted in the Lord and lived with intention — patient, gracious, humble, forgiving, loyal, and grounded in love.
Contact Info:
- Other: instagram.com/bossesgiveback
instagram.com/alanasjournal_
Image Credits
Darrien Johnson-DeVose @thecommunitycurator on IG
Barry Miller @limitlessbmedia on IG
