Every few months, Jenny Castillo packs her bags and jets off to another country.

She’s leaving to go meet up with friends, attend wellness retreats, and satisfy a gnawing urge to travel.

The 32-year-old attorney is a self-proclaimed HENRY (high earner, not rich yet). The term, coined by Fortune Magazine in 2003, originally described families with incomes between $250,000 to $500,000.

On the outside, these high-earners appeared on par with America’s markedly wealthy. But the truth is they are taxed heavily and tend to fall easily into the “lifestyle creep” trap.

Today, the term HENRY has expanded to include earners who’ve cracked the six-figure mark. The Census Bureau shows just “8.5% of the income-earning, non-student population makes $100,000 or more per year. Ninety-one percent of the same population makes less.”

Castillo counts herself among this group. Originally from the Dominican Republic, she was raised by a single mother in Lawrence, MA.

“I come from modest means,” says Castillo. I didn’t come from people who have 401k’s and savings.”

Today, she serves as an Associate for a D.C. based law firm. She lives in Washington’s Trinidad neighborhood with her real estate developer husband. And individually, she earns just over $100,000 a year.

Castillo is not rich. But she revels in her title of HENRY, and even blogs about it on her aptly titled blog, Jenny the Henry.

We caught up with Castillo for a look at her work, how she spends her money, and her personal finance philosophy.

Jenny Castillo

What changed when you went from 5 to 6 figures?

“It’s not as life changing as people think. It’s very easy for your expenses to grow with your income. For example, when I first started my career as a young clerk, I was eligible for certain student loan benefits that my current income makes me ineligible for. You’re also in a different tax bracket, so you may see more money going out.”

“When I was clerking, I thought ‘if I could just make 6 figures I would be good.’ But now that I’m there, life has changed and I’m not satisfied. I thought it would be enough but it is still not enough. I want more. And I’m not just talking about material goods. I’m talking about feeling secure and not worrying.”

How does someone get to the next level?


“I think of mentorship like a spice rack. You have to gather people from all across the spectrum. Different people add different flavors to your life.”

“I’m transitioning from one job to another right now and ran the scenario by my mentors. They each gave me advice that was tailored to me. These people help me make hard choices. They have the foresight to see if a hard choice will propel me to the next level.

On operating in the workplace

Be intentional. Always take time to think through what you are good at. What are the qualities that attract people to you? Do you enjoy talking to people? Do you enjoy teaching people? Then match those specific skills with what a job can look like.”

What are some of your financial goals?

Successful people today have 3 or more streams of income. And the thinking is you need 7 streams to reach financial freedom.”

What Is Your Personal Finance Philosophy?

“I think it’s important to be transparent with one another. We need more tools to be able to advocate for ourselves or know when we deserve more. But the more knowledge we have the better our position in life can be. There is enough for all of us.”

“Also, save more than you spend and pay yourself first. It sounds basic, but a lot of people don’t do it.”

What Are Your Spending Habits?


“I have a separate account just for fun things like travel and going out to eat. I think it helps you stay on track so you’re not always saying no to yourself.”

Luxury Travel

“I love to travel. I recently went on a luxury retreat through a company called Pangea Dreams. It’s an organization for bloggers and women entrepreneurs and teaches the fundamentals of the social media world. I started my blog in January and was overwhelmed by the technicalities of it. The goal of the retreat was to teach the minutiae.”

Fixed Expenses

“Things like taxes, mortgage payments, utilities and other bills make up most of my expenses and claim almost half of my income.”


“With the remaining half a good chunk of that goes to my savings account, my 401k, and investment properties.”

Save Like a HENRY

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Featured Photography by Morgan Murray