Two years ago, I had just returned from a 15-month trek around the world, and I was crashing at my parents’ house in North Carolina, trying to determine my next move. Though I had called New York City home for seven years prior, I didn’t want to return to the same ‘ole, same ‘ole, and I craved a different city. I had a few friends who lived in Los Angeles and another group in Boston, so I decided to spend one month in each place to test it out. So, as any single gal would do, I paid $10 to swipe on Tinder in both locations to check out the dating scene. That $10 became the very best money I ever spent since two weeks later, I matched with my now-husband in Boston.
That money might not seem like much, but it changed the course of my life forever: I moved to Boston, we spent a year going on trips and falling in love, moved in together, tackled the pandemic together, got engaged and adopted a puppy. While many people think about spending as a negative, making investments in yourself and your future can be beneficial and impactful. In addition to that $10, there have been other expenses that have made a difference in my personal and professional journey: $180 for a one-way flight to NYC after college, a $5,000 down payment to go on Remote Year, and even that $1,000 spent to buy a MacBook Air for my writings.
It’s essential to think critically about those purchases that you’ve been thinking about forever but haven’t made. Perhaps it’s remodeling a part of your home, finally getting an at-home office set-up, or taking that week-long vacation. Chances are high you won’t regret it once you finally spend it. Here, eight women share the stories behind the best money they’ve ever spent:
“I had built-in bookshelves installed.”
Two years ago, Christina Nicholson, a blogger, podcaster, and content creator, had built-in shelves installed on the main wall in her house, complete with a sliding ladder.
What she spent: $5,000
Why it was worth it: “I love to read, so much so that I even started doing video book reviews and launched a book review podcast. This is something I’ve always wanted — ever since I started buying books in high school. It’s my favorite part of the house. When I started my own business in 2015, making money was motivated by me getting this wall put in my house. For some people, it’s fancy houses, luxury cars, and expensive bags. For me, it’s a pretty place to put lots of books.”
“I went to the airport and went on a spontaneous solo vacation.”
Gwen Jimmere, the CEO and founder of Naturalicious, did what everyone has thought about doing at one point or another: she went to the airport and asked for a roundtrip ticket to the first warm location they were flying to. She didn’t know where she would end up, but she was feeling depleted and exhausted as an entrepreneur and working mother. So she woke up, decided enough was enough and packed four outfits and two bikinis. She ended up in Phoenix, AZ.
What she spent: $1,700
Why it was worth it: “I learned so much about myself on that trip. And I realized it was something I desperately needed. I’m so glad I went. I’m a person who craves adventure and spontaneity, but as I’ve gotten older and added more and more responsibilities to my plate — I’ve created a fast-growing company, I have employees, I’m a mom and a life partner, in addition to tons of other things — I have far less opportunity for spontaneity to occur. I also learned how to unplug. There was zero cell service on Route 66 and while at the Grand Canyon. That was an all-day trip by itself. So I had to live in the moment, which is something I didn’t know how to do prior to this trip. I was gone for only four days, but I came back home refreshed and replenished. It was the best.”
“I hired a house cleaning team to come in once a week.”
The best money Rachael Pontillo, the CEO of Holistically Haute Inc. and the president of The Nutritional Aesthetics Alliance, has ever spent is an ongoing expense: a bi-weekly house cleaning service. As someone who was always stressed about the clutter in her home, she tried everything, including decluttering consultant Marie Kondo-ing her space, blocking 15 minutes a day to put things away, and so on, but nothing ever stuck. After all, since both she and her husband work full-time jobs and they have two teenagers, it’s tough to stay on top of the house. So, after much struggle, she finally gave in and invested in long-term service.
What she spends: $240 a month.
Why it’s worth it: “What it did was not just clean the house, but it also forced us all into a better routine of putting things away and tidying more often so that the cleaning team would actually have space to clean. Since we have had the housecleaning team, our house has been clutter-free, which has helped me enjoy being in my home more and has helped me feel more creative and productive. It seems like a trivial thing, but I am shocked at how much taking housecleaning off my plate has improved my family’s lives. The first day the housecleaners were cleaning while I was working in my office — and I came out of the office, and the house was sparkling. I breathed such a sigh of relief. It was like I could finally exhale and let go of all those negative feelings I had been holding in.”
“I hire a babysitter on the weekends.”
Since launching Casa Blanca, a Bumble-like real estate platform for finding and buying a home in October, Hannah Bomze and her husband had very little time to disconnect. When you add in a global pandemic and the need to care for children while working at home, it’s stressful, to say the least. So, they decided to hire a babysitter for a few hours every weekend for some peace and quiet.
What she spends: $20 an hour
Why it’s worth it: “There’s not a lot of time on the weekdays for me to decompress, so the best thing I did was get a few hours of help on the weekends. Sometimes I use the time to take a nap or watch ‘The Crown’, or do things that are just harder to do with kids in tow, like holiday shopping. Just having those few hours to myself gives me time to relax and recharge.”
“I incorporated my business.”
Though she was technically ‘in business’ before, it wasn’t until she paid the $125 LLC certificate fee in Pennsylvania that Beau Wangtrakuldee truly felt like an entrepreneur. Once this was complete, it clicked for her: her clothing company, AmorSui is real, and her time, commitment and resources are worth it.
What she spent: $125
Why it was worth it: “Incorporating AmorSui as an LLC solidified my commitment to make the idea and mission to make greener and safer personal protective equipment available for everyone a reality. I had the initial idea of products that would become the lines of AmorSui’s protective wear in 2013 when I was burned in a chemical spill because my lab coat failed to protect me. I could not find inclusive protective apparel options for women after this accident. I did not pursue the idea as a business for many years because I didn’t know how and was afraid the idea might not be well-received by others. During my postdoc fellowship tenure at the University of Pennsylvania, I was exposed to the entrepreneurship community of founders and startups there, which encouraged me to explore multiple business ideas I had, and AmorSui received the most interest from others. This gave me the courage to start this business and hence the LLC incorporation.”
“I bought the black Prada pumps I always wanted.”
Many people have the dream item they’ll purchase once they reach a certain income or savings level. Maybe it’s a car, a watch, or if you’re like Jacqueline Berchielli, it’s a pair of shoes. In 2011, at the age of 27, she landed her first six-figure salary but still suffered from severe imposter syndrome. She always felt like she had to prove her worth and capabilities, even though it was a moment she dreamt of since childhood. She was wearing a tailored suit and a high-end, black pair of designer heels in that vision. Two weeks into the job, she decided she had the suit, but she needed the heels. A week later, she brought home black Prada pumps. Today, she’s the founder and CEO of her own company, Meetnorth — where she still wears those pivotal heels.
What she spent: $525
Why it was worth it: “Once I got the shoes, I started feeling more confident — like I deserved to be where I was. I had earned this. Even though they are just shoes, they were a strong symbol that ultimately shifted my perspective and perception that I was as capable as I always imagined I would be. I didn’t just buy these shoes — I earned them, and being successful is my new normal.”
“I signed up for a coding boot camp class.”
When Samantha Dong, the founder and CEO of ALLY Shoes, decided to sign up for an ‘Intro to Coding’ boot camp course at General Assembly, she didn’t expect it would change her life so much. At the time, she was a management consultant in New York but interested in the tech startup world. She had regretted not taking a computer science class in college and figured the boot camp could be the first-step into her dream industry. She was right.
What she spent: $560
Why it was worth it: “I realized programming isn’t hard or intimidating. In fact, it’s a lot of fun, and it’s possible to learn on your own. This gave me the confidence to look into new languages such as Java and Python in the future. Then, I found a job. Coincidentally, I was sitting next to another former management consultant who pivoted to tech. We bonded, and I helped him with questions during the session. A few weeks later, he reached out because he knew a tech startup that was hiring. He put us in touch, and a few months later, I packed up my bags and joined a Series-A tech startup in San Francisco. Eventually, I founded ALLY, and the rest is history.”
“I bought a six-pack of beer.”
At the age of 18, Barb Stegemann left her life in poverty by jumping a bus to attend college. She had $5 in her pocket and no sheets for her bed when she showed up at the University of King’s College. Her roommate loaned her sheets, and she spent those last five dollars on a six-pack of beer to share with new friends. She then landed two part-time jobs, took out student loans, and thus, her career began. Today, she’s the founder of The 7 Virtues.
What she spent: $5
Why it was worth it: “If I had bought into the myths that being of humble roots was a barrier, I would still be back in my trailer clutching my five dollars. I made this investment because I saw my mom’s power taken from her when she and my father divorced. She was not well and could not work. My sister and I had part-time jobs during high school to bring food home and buy our clothes and have dignity and take care of our mom. I knew I could not live that way, being dependent on a man. It gave me the courage to show up. Share everything you have in life, and the world showers you with more. Then, continue to share that out with others for the rest of your life.”
