Money Woes

Hi HENRYs! This week we are delving deeper into the HENRY lifestyle and discussing a HENRY low, money woes.

At first blush, it may seem that my blog/Instagram are about lavish living, but they ain’t. Lavish means sumptuously rich or luxurious, and my lifestyle is anything but that. HENRY stands for high earners not rich yet, and the NOT RICH part deserves some attention.  

NOT Rich

Not Rich is the most fundamental part of understanding my HENRY lifestyle because in reality, as a HENRY I work hard and enjoy the fruits of my labor, only sometimes. Meaning, I can’t always afford a trip with friends or a luxury accessory even if I put in the work at my job and my check suggests that I can afford it. I am not financially free, despite what my 20-year-old self had planned. I have student loans, 401K payments, a home, other annoying bills, and a little sister in college. In other words, my income doesn’t exclusively get stashed into the “for fun” bucket, and this bucket sometimes runs low.

I was painfully reminded of my financial limitations a few weeks ago when friends invited me on a trip to Colombia, one of my favorite destinations. Upon receiving the invite, I instantly began to plan what outfits I wanted to bring and noteworthy sites within Colombia to explore. And the arepas!! My mouth watered at the thought of all the arepas I would devour.  

The initial bout of elation quickly dissipated when I realized…crappppppp I can’t afford this. The trip was scheduled for a few weeks after the holidays and I had already stretched my budget during that time. Going on the trip would have been financially irresponsible. The size of my workload also jostled me back into reality. How could I travel and still get everything completed?

Eventually, I came to the realization that I couldn’t go. Sadly, this isn’t the first time I’ve had to make a choice like this, so below I am sharing the factors I took into account when reaching my decision.  Keep in mind that these aren’t hard fast rules (remember we are trying to get away from that in 2019), instead regard them as guidelines.  Also, note that these guidelines only come into play when I am considering decisions involving my “for fun” money. Different pots of money have different guidelines (maybe we can talk about that in a different post).

Guiding Questions

  1. Is it on the List?
  2. I consider whether the particular experience or item under consideration has been on my bucket list, or for big ticket items, on my wish list. OR do I simply want this because the opportunity presented itself? For the Colombia trip, I considered that it wasn’t the first or second time I would be visiting the country and even though I love Colombia, it wasn’t a country I needed to go back to January 2019.

  3. What do the numbers say?
  4. The numbers don’t lie. Is there even “for fun” money available? Sometimes, this is the hardest question to answer because even if something is on my list it can be financially out of reach at that time. The answer can also be humbling. As someone that works so hard and enjoys nice things, this time around I had to admit to myself “hey girl, you can’t afford this.” That, my friends, was heart-wrenching.

  5. Does the price justify the experience?
  6. Basically, how fun will this be and can I defend this decision to my future self? In other words, how much will I have to spend to extract the benefit from this activity or thing? What kind of memories will I build? Can I visualize myself enjoying the experience or with the item, or am I just letting FOMO rule me. In the instant case, I knew the trip would be memorable. Plus, it was an opportunity to reconnect with friends I hadn’t seen in a while, so the answer to this question was yes.

  7. Work Schedule?
  8. Ahhh work, can’t live with it, can’t live without it. This one is usually pretty easy. Either I am swamped and can barely breathe or I have time to play. Right now, I am currently busy and beyond stressed, so thinking about taking time off was overwhelming me.

  9. What does your partner say?
  10. This one may be controversial because I do ask my husband before I make a big purchase. Before you judge me, hear me out. I don’t ask him for permission, I ask for his opinion. He knows me so well that he can usually tell if I really want something or if I am talking myself into it. Additionally, because we share a household, what I do with my money impacts him, so it would be selfish of me not to ask him to opine. For this dilemma, he said “have you looked at the flights? They are over $1K.” WELP. That answered it.

Saying No

As I indicated before, I decided not to join my friends. I considered the above questions and ultimately decided that there were too many N0s to justify the expense. I am currently battling FOMO every time they post pretty pictures; however, I know my future self and bank account will appreciate my prudence.  

Ugh. Being responsible is hard.

As my decision revealed, the HENRY lifestyle isn’t all sunshine and rainbows. I still have to prioritize spending and decide if a particular item/experience fits my budget. If not, I have to enjoy it vicariously through Instagram stalking. Successful HENRYing means having sufficient self awareness to realize when something is out of reach, at that time. This doesn’t mean that I can never have it, it’s just not the right time.

Has anyone ever been in this position?  Let’s commiserate together.


Hi! I’m Jenny, a millennial HENRY. I practice law in Washington, D.C. where I live with my husband. Like most HENRYs, when I am not at toiling away at work, I enjoy travel, new experiences, and a good outfit. My obsession with all the above led me to create this blog. I yearned for a creative outlet to air out my thoughts on the HENRY lifestyle, and the headaches that sometimes accompany it. I invite you all to join the conversation with me! Sit down, scroll, and let’s discuss HENRYing it up, the Jenny way.

Leave a Reply

Your email address will not be published.