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Welcome to “On the Couch” — a series of Q&A sessions where you get to know the human side of our amazing staff at Well Clinic.

This week, we chatted with Isaiah E. Bailey, Director of Finance and Justice, Equality, Diversity, and Inclusion (JEDI) Strategies at Well Clinic in San Francisco.

On the Couch with Isaiah E. Bailey


What is your favorite part about your work?

I’ve always enjoyed the problem solving nature of being an accountant along with the responsibility to communicate numbers in plain language. I’m motivated by the challenge to interpret complex business transactions, uncover solutions and process efficiencies, and foresee risks and opportunities for continued business growth.

What’s even more rewarding is the impact I have through my continued commitment to social responsibility, hybrid work cultures, authentic relationships, resilient leadership, and always putting people first. Justice, equity, diversity, and inclusion are the driving force behind all of my decision making.


What is your favorite thing about San Francisco?

My favorite thing about San Francisco so far is you all. I have never been to San Francisco, but if everyone is as warm and welcoming as you all have been then I’m sure it’s a great place.

My favorite thing about New York is the diversity. I grew up and still live in a melting pot. I was always exposed to all kinds of people. I didn’t realize until I became much older that not everyone has this privilege.


What is your favorite place you’ve ever been?

A few years ago I got to visit a side of my family I never knew. After all these years my grandmother, Lottie Williams, had 2 sisters living in South Carolina with all these houses and land. They had so many stories to tell me about grandma and how they grew up in the South.

My grandma’s cousin Paul, now in his 80s, even remembered walking down the dirt road with grandma to school. I was blown away. Tucked away in the low country of South Carolina sits a small restaurant named after Mae Williams, my grandmother’s sister. I never met Mae, but I got to visit and see Mae’s son (a cousin I never met) at the counter taking orders.

I remember walking in saying wow, someone in my family has a business and I have all this family with all this land and houses. It was a world away from the apartment building nickel-and-diming I was used to in the Bronx, NY. It gave me a sense of self and family. So I love to visit South Carolina where I get to learn more of who I am.


Name five things that are on your bucket list (things to do before you die).

  1. I have to go to Africa. I have to see where I come from.
  2. I have to buy my mom a house. You know the story of the single Black mom raising 3 boys in poverty with no support? That’s my mom who has overcome so much. While pregnant with me for example, my mom lived in a homeless shelter so she deserves it.
  3. I actually really want to skydive one day. I’d have to do some research on things like the death rate or something but I can see myself now jumping out of a plane and falling from the sky. I think that’s pretty cool.
  4. I always wanted to adopt a child, or two. Some of my family members went through foster care and adoption systems and I know it’s a terrible thing. I always wanted, since I’ve been so blessed, to help just one brother and sister stay together. To lose your parents is terrible but then to be split from your siblings on top of that is just something no one should bear.
  5. I always wanted to make one of those top lists. You know, like Forbes 30 under 30 or top 100 accountants. One of those lists. Or maybe even Times top 100 influential people. Wishful thinking maybe. I think that’s pretty cool. Not as cool as jumping out of a plane though.


What is your favorite memory ever?

If I had to nail it down to one, it would be making sweet potato pies with grandma during Thanksgiving. My grandma was in charge of pies for the entire family and everyone would stop by and pick up pies for friends. I tried grandma’s recipe from memory last Thanksgiving and let’s just say I need help.


Where did you grow up?

I grew up in the Bronx, NY. I was actually born in a 4th floor apartment as my mom didn’t make it to the hospital. So every family gathering I have to hear everyone tell the story of how they saw me born lol.

Please don’t read this with any sympathy, but I grew up very poor. As a kid, I didn’t realize it as much as momma always made sure we had. As I got older though, I realized we were barely getting by. I joke all the time and say we played all the poor people games like tag where all you need is basically anything designated as “base” to play. We played steal-the-bacon with a plastic bottle. Then there was mother-may-I. All these games required no equipment, just a bunch of kids. This was all in front of the building on the concrete sidewalk since parks were few and far in between.

The fire hydrant was our waterpark during the hot summers. The fire department would come and shut it off and then minutes later we had it back on. Everyone on the block knew each other. Your mother was allowed to reprimand me and then tell my mother who would then reprimand me too. It was a village kind of thing.

If it wasn’t for the owner of the neighborhood deli who would let grandma run up a tab each month and pay it back the first of the next month when her fixed income arrived, we wouldn’t have made it. But we had a blast. I wouldn’t change a thang.


What is your favorite quote?

“Be curious, not judgmental.” By Walt Whitman.

I think if we live this way we can find more solutions than problems. In every interaction, if you try to be just a little more curious and empathetic rather than judgmental and pessimistic, things turn out better. It’s great for communication, learning, conflict resolution, workplace strategies, etc.


In your free time, what are you most likely doing?

More than likely I’m either hanging out with one of my cousins somewhere in Harlem, NY, shopping and out to eat, or making some type of digital content (editing photos, videos, presentations, etc.). I’m trying to read more books.


What are five albums you’d want with you if you were stuck on a deserted island?

  • The Best of Aretha Franklin
  • The Best of Luther Vandross
  • The Best of Bob Marley
  • The Best of Al Green
  • The Best of James Cleveland


Where was your last vacation?

Sad to say I don’t go on vacation much. I honestly don’t even remember. I’m making an effort to change this.


What cause(s) are you most passionate about?

If it has to do with uplifting and/or supporting Black people, that’s where my heart is.


Do you have any talents that few people know about? If so, what are they?

Most people don’t know I spent a few years producing New York Fashion Week shows, doing portrait photography, and managing fashion, media, and entertainment talent. I’ve worked with America’s Next Top Model, Bravo’s Project Runway, and Dove as well for example.


What is your favorite sports team?

I actually have never been too big on sports, but I grew up very close to Yankee Stadium in the Bronx so they are like rooted in my heart. Every New Yorker rocks a Yankee hat as standard fashion in my neighborhood.


What is your favorite food?

Veggie Lasagna (must have zucchini)


What is your favorite book?

A Raisin in the Sun by Lorraine Hansburry.

A book about a poor Black family with each family member having their own plans for a $10,000 insurance check coming to the family from the father’s death – this is the surface level plot, of course it’s much deeper than this.


What is your favorite movie?

Friday by Ice Cube.

A movie about two friends from Compton who got into trouble for smoking the weed they were supposed to sell for someone else. I watch this movie at least 25 times a year. It’s a classic for sure.


What was your favorite toy as a child?

I don’t remember playing with toys as a kid. We grew up outside. I do remember a Mr. Potato head though as I type this that I loved dearly.


Do you have any pets? Please introduce them to us.

I had two dogs a few years back but had to give them to a cousin. My new complex didn’t allow pets. Dior and Dog (pronounced dee-oh-gee) were brothers, Maltese. I miss them so much.


When are you at your most creative?

I’m most creative either in the shower or after 1am. I guess it’s something about water and/or the time when everyone else is asleep and the world seems still that gets me going.


What motivates you?

I’m motivated by the word no and wait. Tell me either of these two things without a reason and I’m fired up ready to get it done.


Name one guilty pleasure, past or present.

Shopping. All my life. Since I started my first summer youth employment job at 14 years old. As many years as I’ve spent advising people and businesses on money, I suck at keeping my own books in order. I’ll look at something I want, know very well I shouldn’t buy it, and say welp, you only live once and can’t take this money with you when you go. I’ve gotten much better over the years and much more responsible but the general theme of YOLO creeps up every now and then. I think not having a spouse or any children at 29 years old allows for flexibility.


Describe one of your first few jobs.

My first job, which now that I think of it was probably illegal, was a 4 day gig at 13 years old in Baltimore, MD. My uncle worked at a mattress store that was running a sale. He said I’ll pay you $100 a day to hold this sign outside for a full 8 hours a day for 4 days. I jumped at the money making opportunity. Of course I only worked maybe 3-4 hours a day before uncle said come on inside and relax the rest of the day (and only did 3 days), but he paid me a full $400. He wanted to show me money doesn’t come free. Uncle was always a teacher that way knowing I was living up in NY without my own father present.

My next few jobs from 14-18 years old were always during the summer months via the NY Summer Youth Employment Program where I would serve as a youth counselor for summer camps across the Bronx, NY.


What’s one fun thing you wish you could do more of?

I wish I was a more fun person as odd as that sounds. I see my college friends always traveling and doing things while I foolishly try to hang on to the friends from my neighborhood growing up who don’t know as much about the world. I’m trying to keep one foot in two worlds and I think now is the time to focus on me and embrace me and reward me with the life I worked hard to build. I like to fish, hike, ski, road trips, etc. but no one in my neighborhood likes those things so I never do them. Silly me.


What makes Well Clinic different?

I could literally write a book on this question. Well Clinic is the complete opposite of the CPA firm culture I just left. You’ll probably even notice in my communications it’s very CPA firm/corporate America-ish which I actually hate. I want to rid myself of that unnecessary baggage.


What is a “Director of Finance and Justice, Equality, Diversity, and Inclusion (JEDI)?”

As a servant leader, it is my natural desire and conscious decision to get to know each of you as individuals and implement justice, equity, diversity, and inclusion strategies that encourage and support your uniqueness. This is in addition to my primary responsibility of providing all of the support and resources you’d normally expect from someone in a finance capacity.

With a focus on workforce strategies, employee engagement, and digital transformation, I look forward to working with you all to build the future of Well Clinic.



  • I absolutely love Well Clinic! From the beginning, my husband and I felt like we were in a comfortable and safe space.

    Our couple’s therapy bridged gaps in our relationship and helped us understand each other that much more.

    Ivette B

  • Well Clinic is an oasis, especially for busy professionals like me.

    It’s a relaxing and safe space, nothing like the stuffy or drab offices you’d expect when going to a therapist.

    Brianna S

  • Well Clinic’s inviting and professional design makes me feel comfortable and at ease, which probably benefits the work I am doing.

    In fact, it doesn’t really feel like a therapy clinic at all, which I find awesome.

    Jim M


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