My Path to Financial Independence With a Sugar Daddy

I’ve never been very good with money. That’s not to say that I'm drowning in credit card debt or spending money I don’t have. But when it comes to financial goals and future planning, I just never learned how to do that, and worse, my palms get sweaty every time I think about it. So, for many years, I simply never did.

I’m sure a lot of it has to do with the fact that my family didn’t have a lot growing up. There were five of us siblings, and my dad had suffered an injury when I was a baby that kept him from being able to keep a steady job. He was on disability for most of my life, and while I have a lot of empathy for what he went through and how frustrated he was, I have to be honest that he was a financial strain on the family.

My mom worked two jobs and still barely had enough for rent, food, school supplies, and whatever else. We lived paycheck to paycheck, lived in hand-me-downs, and ate lots of casseroles at home. Things like going to the movies or having elaborate birthday parties were out of the question.

I’m actually grateful for the lessons that this kind of lifestyle taught me. Sure, I was super jealous of the girls in my grade who got new school clothes and went on family vacations. But I learned how to live with less. My sisters and I were experts at getting the very last of the makeup out of the tube while I watched my friends throw theirs away after a couple of months. I learned how to mend my own clothes and make my old shoes look new again. And to this day, I consider myself an excellent cook, because I can feed multiple people with a few cheap ingredients.

But there’s a lot of anxiety that comes with this kind of upbringing, too. And that’s something that I wasn’t really able to put into words until I met Simon.

Simon grew up in a family not so different from mine. Three brothers, blue-collar parents, a mostly empty fridge. There was no money for private school and even less for university, but he had managed to get noticed by a college football coach who advocated for him to get a full-ride. He was more strategic than a lot of his teammates, who had lofty and inflexible ideas about making it into the NFL. As those guys floated through their classes and spent all of their energy on practice and games, Simon studied economics with a minor in statistics. He never partied. His free time was spent in office hours or at the library. And although he didn’t get drafted into the NFL (and neither did anyone from his university), he did get a good job right out of school.

From there, Simon kept his nose to the grindstone for as long as he needed to to be able to retire early. At fifty, he was set up for life, and his parents were living in a comfortable assisted living facility nearby. He had investments and multiple properties. He kept himself busy by giving talks at universities and attending economics conferences. Whenever he was bored, he would take on a short-term consulting gig. He hadn’t taken a vacation in years, and sugaring was more about fulfilling a companionship need than actually enjoying having a companion.

But, while my anxiety about money manifested in not being able to focus on future financial planning, Simon’s version took the shape of being so focused on money that he forgot to have a social life. He never married. He didn’t have hobbies. He thought about life in terms of costs, investments, and efficiencies.

Until he met me, I think.

We butt heads a bit at the beginning over this big difference. He couldn’t imagine why I didn’t have any investments if I was so hell-bent on not ending up like my parents. And I couldn’t imagine why he couldn’t enjoy his free time without reading articles on economics or booking his next speaking engagement.

In sum, I felt like he was treating me like I was dumb and naive. And he felt like I was calling him boring and unfeeling.

During one of these conversations, something clicked for me.

“Maybe we’re in each other’s lives in order to teach each other something useful, something that’s lacking,” I suggested.

“Oh please, you know I don’t believe in that woo woo universe stuff,” he said.

I took a breath.

“Okay, maybe it wasn’t ‘meant to be,’ but that doesn't mean that we can’t take advantage of it, anyway. You’re right. It would be a good idea for me to start learning how to be a more financially responsible person. And I think it would be good for you to learn how to start actually enjoying the money you have instead of just thinking about how to make more. What do you think?”

And so we shook on it.

The deal we came up with was that my homework was going to be to start practicing keeping a monthly budget and setting up some kind of savings. Simon would help me make decisions about how to best invest the savings. He also wanted me to start thinking seriously about what kinds of things I would like to start working towards, like buying an apartment or getting a degree.

And Simon’s homework, which seemed a lot more fun to me, was to plan a vacation. I could be within the country if he wanted (but not within the state), and it had to be an actual vacation: no speaking gigs, no conferences, no consulting, no kind of financial gain. And of course, I would go with him as his “relaxation guide.”

Surprisingly, I had a much easier time with my homework than Simon had with his. I was actually enjoying keeping track of my spending and watching my investments grow little by little. Simon, on the other hand, kept procrastinating on planning the trip, and he rejected every one of my ideas for where we should go.

He was having a really hard time justifying the price of the plane tickets and the hotels, and in his home office, I found printed out menus of restaurants in the area we had talked about visiting, with the best deals highlighted. I realized that he was really obsessing over costs in a way that I had never noticed in him before.

Finally, I asked him to come clean.

“Look, I’m feeling so much better about things since you’ve started helping me,” I told him. “Let me help you. Give me a budget, and I promise you I will stick to it. But let me plan everything. All you have to do is show up and, for once in your life, not think about the money.”

It was like pulling teeth, but Simon finally agreed. And the budget he gave me was perfect for a romantic getaway up the coast. Even with first-class flights and an ocean-view suite at the hotel, we came in under budget.

I made sure to plan the trip for four days because I knew the first two would be him freaking out over how much everything was costing and getting used to not doing anything. If the trip dragged on too long, he would get bored and never want to take another vacation. I knew what I was doing.

And I was right. By the end of the second day, Simon seemed calmer. He paid for dinner without looking at the bill. He had us take a detour for ice cream as we walked home. He went to sleep without setting an alarm for the following morning.

The next day, I had scheduled for us to get a couple’s massage, on me. “Don’t worry,” I teased him, “I’m not taking this out of my savings. I made sure to adjust my budget and skip some unnecessary purchases this month. I’m holding up my end of the deal.”

He laughed, “I’m proud of you, but don’t be ridiculous. This entire weekend is on me. I can’t thank you enough for this. I’m having a great time.”

After our massage, we went for a stroll along the beach and played a game of which houses we thought were the prettiest.

“This is something that I think I would like,” I told him. “In the future. To have a house on the water. Not necessarily a beach, I think I’d prefer a lake, actually. But yeah, maybe I’ve found my financial goal.”

I was emotional, surprisingly. I realized that I had never thought that being a homeowner would even be possible for someone like me. Maybe it was just me, but I think Simon was also welling up. He gave my hand a squeeze, and we kept walking along the coast.

It’s been a couple of years since that first trip, and I’m closer to being able to put down a deposit on a home than I ever thought I would be. I’ve been looking at properties near creeks and lakes up in the mountains, and the idea is to continue living here and renting out the house until I’m ready to make a permanent move. Simon is still my sugar daddy/financial advisor. And I’m still his yearly vacation planner, although I’m trying to convince him to let me plan quarterly getaways. I think I’ll get him to come around.