From Food Stamps to Six Figures: Beth Ann Hart’s No-Tradeoffs Path to Building a Business

Beth Ann Hart, founder of Hart Health Consulting, on anxiety, single motherhood at 19, and the phone-calculator moment that tripled her income. From Chronic Boss Unfiltered.

A little over a year ago, over dinner at Lolita in Boston, Beth Ann Hart told Lilly Stairs the number she’d been carrying around for years: $100,000 a year by the time she turned 30. She also wanted to meet her daughter at the bus stop and be there for her son while her husband, an active duty Air Force pilot, is gone roughly 70% of the year. In her head, the only road to that number ran through a full-time executive director role, and that meant giving up the flexibility she needed most.

Lilly pulled out her phone calculator. They raised Beth Ann’s hourly rate (she had been undercharging), added two or three more clients, and watched the total land above six figures right there at the table.

“I’m like, it’s not that easy. There’s no way. I think for the first time it felt possible.”

Here’s what has happened since that dinner:

• About four months later, she launched Hart Health Consulting
• She has tripled her income
• She’s on track to make multiple six figures in 2027, and she isn’t 30 yet

What you’ll hear in this episode

• How a single mom at 19 finished her degree on schedule and bought her first house at 21
• Why Upwork was a slog until it wasn’t, plus how Lilly hires through it
• What finally pushed Beth Ann to treat the anxiety she’d lived with since childhood
• The confidence shift that happens once you’re in rooms with C-suite executives
• The money question her almost-nine-year-old still asks

Where the grit started

Beth Ann got pregnant with her daughter at 19, as a college sophomore, and became a single mom. She moved back home to Oklahoma and made herself one promise, which was that she would not take a semester off. She kept it.

• She wrote a paper while she was in labor
• She went back to work when her daughter was three weeks old, at a job where she could strap her baby to her chest for a full eight-hour day
• She finished her bachelor’s degree by the time her daughter was about two
• At 21, she bought her first house with money she earned herself

“I say all the time that we kind of grew up together.”

That house was small, and it was hers. She still drives past it when she visits Oklahoma, and she fully plans to buy it back someday.

The Upwork chapter

The Air Force brought the family to Charleston, where Beth Ann landed at a free healthcare clinic and kept side gigs going the way she always had (back in Oklahoma it was bartending, waiting tables, and teaching ballet). When she and her husband were ready to grow their family, she went looking for remote work on Upwork so she could be home after her son was born.

The early stretch was a grind. She applied to role after role, and plenty never turned into an interview. “Once you get one good hit on Upwork, things just started falling in place,” she says. One of those hits was Chronic Boss.

Lilly’s take on hiring through Upwork

• It works. She found Beth Ann, our former social media lead Liz, and her event planner Jess there.
• Learn to interview first. Her early hires didn’t all work out.
• Know the qualities you’re hiring for. Once you do, the talent is there.

Anxiety, and the year she stopped handling it alone

Beth Ann has lived with anxiety since childhood and didn’t start treating it until last year. For a long time she managed it the way she managed everything else, by pushing through with exercise, meditation, sunlight, and books. As a single mom there was never room to slow down long enough to notice.

What it looked like for her

• Alone with her thoughts more often after she married and had her son, with her husband away so much
• Irrational fears about her kids being at school, things completely outside her control
• A fear of flying that could keep her off planes and away from opportunities

“I can’t miss out on opportunities. I can’t miss out on my children’s excitement about things.”

What changed

People she trusted told her this was a chemical imbalance, and no amount of exercise was going to fix it. So she made three changes:

• Medication. She started Lexapro, now permanently nicknamed Sexy Lexi (a Lilly original).
• Therapy. She started going, and she says it has changed her life.
• The gym, every day. It has nothing to do with physique. “It’s the only hour of the day that I don’t think about work or anything else.”

Lilly shared her side of that conversation on the episode too. A couple of years ago, feeling outside pressure to prove she didn’t need medication, she tried coming off hers, and it went badly. She’s back on it and glad she is. Her word to anyone carrying guilt about it is simple: if you need it, it’s okay to need it.

Beth Ann protects her care because her health and her wealth sit on the same ledger.

“If I’m not taking care of myself, I’m not taking care of my children. I’m not taking care of my clients.”

From yes year to choosing her clients

Beth Ann declared 2026 her yes year, and those yeses added up. She’s now in a position to be selective about who she works with, and she knows exactly who to avoid because she’s worked for them. Right before her son was born, a boss told her she couldn’t work full time with a baby.

“I know you didn’t just say that to my face, ’cause now I have to prove to you that I can.”

Beth Ann’s rules for walking into any room

• Be the dumbest person there. Go in to learn and soak up everything you can.
• Be easy to work with. Communicate well and listen. This came from her brother-in-law when she was 17, and she calls it the best advice she’s ever gotten.
• Let the work back the confidence. Lilly’s addition, and the reason Beth Ann’s confidence holds up.

These days she’s often in rooms with C-suite executives. “You go in feeling insecure and you leave thinking, wait, maybe they didn’t know more than me. Maybe I did belong in there,” she says.

Built around her family, on purpose

Yes, her husband is gone most of the year. Yes, anxiety has been part of her life since she was a kid. AND that is exactly the life that taught her to build a business around her family instead of the other way around. Some days she works at 5 a.m. and again at 10 p.m. so the middle of the day belongs to her kids.

“Being a single mom makes me a killer military spouse, and being a military spouse makes me a killer business owner. I couldn’t have one without the other.”

The question her daughter still asks

Her daughter is almost nine and still assumes dad makes more money. When she wants to buy something, she asks whether Beth Ann checked with him first.

“I told her, you don’t have to ask a man to buy anything. Go out there and make your own money, girl.”

Asked what she’d tell the version of herself sitting at Lolita, Beth Ann says that woman already knew she could do it. She needed someone she trusted to say it out loud and run the numbers with her, and now she wants to be that person for other women.

Listen to the full episode

If you’re the founder with a number in your head and a list of reasons it only works in a corner office, this one’s for you. The full conversation between Beth Ann and Lilly is on Chronic Boss Unfiltered on Spotify, Apple Podcasts, and YouTube, so press play and keep your phone calculator close.