Money With a Side of Guilt

Photo credit: Stephan Kiessling, CC BY 2.0.

As I’ve been reading other Parents Month stories, it’s struck and impressed me how many of my fellow Billfolders, many younger than myself, are taking charge of their parents’ financial wellbeing. It’s also made me depressed.

Far from being my parents’ financial savior, I am a stone around their necks. Although they’ve worked their entire lives and saved wisely, the biggest drain on their resources isn’t poor health or recovering from the recession, it’s… me.

I’ve always marched to the beat of a different drummer, as my mom puts it. I’d prefer to say I’m independent, but really, I’m just brickheaded. I hate the idea of working a 9–5 job with regular hours and a regular salary, so I mostly subsist on freelance contracts and private tutoring. It’s a pretty good setup, until it isn’t. Most months, I can comfortably meet my expenses and may even be able to set a little aside in savings. But then come down months when a freelance payment is late or, worse, summer rolls around and my 15 weekly students dwindle to 2. That tends to wipe out my hard-earned rainy day fund and make me look longingly at my (not maxed-out, but still balance-carrying) credit cards. It’s not a good feeling.

My dad has a spidey-sense about when things are looking grim, and in his usual untacful manner will ask me if I need a loan. He is, however, always careful to phrase it that way, as a “loan,” even though we both know I have no way to pay it back at this point. It usually takes me a couple of days to swallow my pride and accept. And we’ve gone through this song and dance about once a year for the past seven years, ever since I decided to become self-employed. It’s embarrassing, frustrating, and demoralizing, and makes me wonder whether I should just give up and get a “real” job.

Even though they say differently, I’m afraid that I’m endangering my own parents’ financial security. I’m an only child, so my mom just keeps saying the money will be mine someday anyway. But at what point is it no longer a matter of “when” I can fully support myself, but rather “if?” What right do I have to drain their resources like this, even if they don’t see it that way?

I recognize how incredibly lucky I am to have them as a safety net. If not for their ability and willingness to help me out a little when I need it, I would have been forced into an ill-fitting but better-paying job long ago. I also recognize how lucky I am to have the education and contacts necessary to even get a job right now. I was raised Italian Catholic, so I can give and receive guilt with the best of them. But this self-inflicted sort is the worst. I know that while I’m not currently endangering my parents’ financial security, I am affecting their ability to live the life they want to in retirement. The longer I spend in this financial limbo, making greater financial gains only to suffer greater financial setbacks, the more selfish I feel in pursuing my path of self-employment.

One of the reasons this is so damn frustrating is that I’ve grown my career so much over the past seven years. In my quest to become, you know, financially independent, I’ve added a lot of skills to my repertoire. I started out just freelance writing and editing, and now I’m the managing editor of an online proofreading company. (We’re small, but mighty.) My tutoring sideline began as me helping out the son of a client, and now I’m so booked up at certain times of year, I subcontract other tutors to help with the load.

But I also had a major mortgage adjustment—thanks a lot, housing bubble loan—and had to buy a new (used car). See what I mean about greater gains and setbacks? It’s a never-ending cycle. I keep thinking that this next project, or that next side hustle, will be the one that turns the tide and puts me solidly on a path to stability. At some point, though, you’ve gotta ask yourself if it’s ever going to be enough.

Unless I’m thinking about money, I know I’m happier and more fulfilled with my current work situation than I could ever be in a steadier job. And I know my parents are perhaps not happy to help, but at least committed to getting me on an even footing. For now, anyway, happiness and the possibility of a more stable financial future (with a side of guilt) outweigh the alternatives. At some point a decision will have to be made, but at the moment for all the angst I feel over the situation, I’m simply thankful my parents have literally put their money where their mouths are to help me follow my dreams.

Anonymous is a freelance writer and tutor. She’s also a reader, a terrible cook, and an aspiring cat lady.

This story is part of The Billfold’s Parents Month series.

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