Selling herself

Jen wrote me this week. Her letter signed off with this: “From a single mom who never ever imagined selling herself on the internet just to make it in this world.”

Now 32, she’s been through a ‘toxic’ divorce. The house was sold. They fought in court. “In the end, the judge awarded me everything he could because he knew this was my ex’s doing. Although I was awarded everything, I owed my lawyer so much money I ended up walking away with nothing. I was desperate to survive.”

That’s when she went to OnlyFans. It’s a platform filled with content created by users and a robust preoccupation with, er, boobs. “I am not proud of this,” says Jen, “and would love more than anything to not have to do it.”

But the money’s good. Too good to give up, in fact.

Jen made $30,000 a year at first exposing herself, and “this year I project to make about $80,000- $100,000 from my much hated side hustle.” Meanwhile she has landed a normal job, paying $75,000.

“Since starting this side hustle, I have been paying debt off at a rapid rate, furnished my house and took my daughter to Disneyland,” she says. “Now, my plan is to save for a house. I read your blogs all the time. I watch the trends. I watch the interest rates and as housing prices go up and down. I am now in a relationship where he also makes good money. Not as good as me, but good money.”

She wants to get a place for about $800,000, and has a small amount of money saved. “When do you think I should buy? If at all?” she asks. “What other accounts should I open to offset this tax on my self employed income. I need to create a business and pay GST/ HST and pay myself as an employee. I can live of my actual income now, and I could potentially save all my income from my side hustle that I’m not proud of. Should I do some TFSAs and invest some of this money?”

My reply asked her for more information. How much cash is available for a downpayment? Is she buying solo or with a partner? Will they both be on title? On a mortgage? Is she square with the CRA? Does she have a loan preapproval? What’s she done about saving for her kid? What about the side hustle dependency when people get tired of ogling an aging thirtysomething? No pension there.

Well, dunno. She stopped writing me. So I wish Jen well.

A few thoughts occur now.

When her marriage fell apart it was, more than anything, the matrimonial home that caused the greatest angst. Jen says the sale was court-ordered, suggesting it was joint title and joint financing with one partner refusing to sell. At the end of the day, all equity was lost, likely the result of a big mortgage payout, with penalty, plus those legals.

Real estate can do that. So many people get marred, get pregnant and think they need a house – at any price because (a) properties always go up in value and (b) there’s always a lender around to shower you with debt.

Now she’s ready to jump in again. This time the relationship is more tenuous – no marriage – and her finances are dependant on a UK-based soft-porn platform with 220 million viewers and run-in with the US government for child exploitation. In other words, income might evaporate. Could Jen be left once again with real estate she can’t really afford, hooked in legally and financially to another person put on title?

If she stays an OnlyFans girl then trying to avoid taxation through incorporation is nuts. The accounting and regulatory burden is too high and the benefits nebulous. Besides, small-business owners taking dividends end up paying the same tax load as employees or sole proprietor producers. So Jen should claim it all, pay her share and use the take-home income to finance an RESP for her kid, invest in RRSPs plus a FHSA for future security and an immediate tax break, plus shovel any extra voyeur cash into a TFSA.

See if the new relationship holds, Jennifer. Don’t get into financing that requires a dubious side hustle. Stay flexible and stop thinking a deed and a mortgage will bring stability to your life. It could be the exact opposite. Like last time.

And ponder this: you’ve reached out to some dodgy, dog-loving dude on the net for personal life and financial help. Not good. Find a person IRL you can talk to about these things.

Mostly, if you’re doing something you hate, for money that you now could do without, stop. It matters not how your partner, your employer, the misfits in this blog’s comments section or society judge you. Only how you judge yourself.

About the picture: “Here’s a picture of Aero,” writes Charlie, celebrating his 13th birthday a few days ago. His brother, Reese, has graced yor blog in the past and also had his 13th on the same day. Feel free to use on your blog as you see fit. Thanks for all that you do!”

To be in touch or send a picture of your beast, email to ‘[email protected]’.

Source: https://www.greaterfool.ca/2025/05/08/selling-herself/