Why Your DIY Legal Work Is Costing You More Than You Think

I found the proof in my freezer, and it changed how I think about getting professional help

There Was a Mysterious Ziploc Bag In My Freezer

I recently learned I’m becoming the age of a woman who finds things in her freezer that she has no idea where they came from. I was digging through mine last week, looking for smoothie fruit, when my hand pulled out a large, frost-covered Ziploc baggie.

I shook it, then poked at it, wondering if this was the moment I’d look back on as the one where I finally lost my mind. There was no note taped to it, no date scrawled anywhere, nothing to explain what was inside or how long it had been sitting there, and I had no memory of where it had come from.

I peeled the stiff plastic zipper apart, praying to the goddess of peri-menopause, bracing for the worst. To make myself feel better, I tried to convince myself someone must have snuck into my house and planted rotten goat-brain nuggets. Instead, thirty flat rectangles lay inside. I pushed the bag as far away from me as I could, closed my eyes, and reached in to bravely inspect the home invaders with my fingertips.

After a minute of caressing them, it all came back to me. These were my homemade cherry Pop-Tarts, made back in November. Nine months ago.

How a Pie Turned Into a Full-Day Hundred-Dollar Pastry Project

My little brother turned forty last fall and was hosting an intimate party at his place with a small crowd of friends and family. Always wanting to be more than just a party-goer, I volunteered to make the dessert. My brother didn’t want a cake, so I offered to make a pie. After all, I was pretty sure I could recall Julia Child’s never-fail killer pastry recipe off by heart.

Then I found out the party was standing-room-only, with finger foods and no forks or knives in sight. So, in an expert problem-solving way, I, and Pinterest, of course, came up with the perfect solution. I let go of Julia’s pastry and turned my pie idea into adorable handheld pastries, homemade and healthier versions of Pop-Tarts, instead. Genius!

Handhelds meant puff pastry, an egg wash, and enough cherries for forty plump pockets, which also meant forty individual pastries, each one rolled, filled, folded, and sealed by hand.

Excited to take on such a rewarding venture for my brother, I went to my favourite spot for flash-frozen fruit and bought two industrial-sized bags of tart cherries for over forty dollars each, then bought puff pastry, lemon, sugar, and eggs on top of that. The whole project landed well over a hundred dollars.

My niece, who was basically born holding a golden spatula, came over because I needed someone who actually knew what she was doing. Even with the two of us working side by side for hours, my kitchen wasn’t equipped for a project like this, and we didn’t have enough counter space to roll out that many individual pastries at once. We ended up baking in batches, tray after tray, waiting for the oven to free up between rounds. What should have been a short afternoon of kitchen calm turned into most of a day, the two of us standing at that counter hot and sweaty and tired, egg wash caked on our hands long into the evening.

Thirty Pop-Tarts Nobody Wanted

I’m not sharing any of this to tell you how great a sister or a baker I am. Sure, I’m a lady with good ideas and good intentions. The truth about the Pop-Tarts is they came out, let’s say, fine. Not amazing, not Pinterest-worthy, just fine. The evidence was clear: this wasn’t the hit I was hoping for, because I still had thirty of them sitting in my freezer nine months later, completely forgotten until I went looking for smoothie fruit again.

These sad, grey homemade Pop-Tarts, which I put back in my freezer, by the way, because I don’t want to admit total defeat, remind me a lot of my work.

You see, I keep running into the exact same situation with clients, just with contracts instead of cherries.

Your Cheap Template Is Never Actually Free

A contract someone pulled together themselves, without knowing what should actually be in it, ends up the same way those Pop-Tarts did.

I have clients come to me frequently with a similar story.

They know they need their clients to sign a legal document before they get started, so they Google “client service agreement.” They find a budget-friendly template online, spend a few hours customizing it late at night, and feel good about having “handled” the legal side of their business.

Then they suspect they know better than the template, because they can just throw it into ChatGPT and let the AI clean it up, and it never seems like it could be that hard, since the AI spits out a fancier version of the contract, full of legal-sounding words that feels way more legit.

Then, just to be completely sure, they send it to their cousin’s ex-wife, who happens to be a retired tax lawyer, to look it over.

All in all, the simple DIY legal project takes far more time and money than they expected. Then they send it to their client to sign, and the client comes back with concerns about what happens if they need to cancel partway through, something the agreement never actually spells out. Instead of working it through, the client walks away.

After that, taking on a new client starts to feel risky, because now there’s a real fear of landing right back inside another agreement that’s just as unclear, with someone else walking away next time too.

The real cost shows up later, in the client who left, the work that went with her, and the hesitation that shows up every time someone new asks for a contract after that.

Why I’m Not Baking These Again

Looking at the sad, hard desserts in my freezer solidified my stance on DIY. This well-meaning project cost me so much more than just money. It cost me a lost afternoon, messy kitchen, sticky cookie sheets and a disappointing birthday dessert. Worse, my good intentions and my strong can-do attitude low-key sabotaged the exact celebration I was trying to make special.

I could have bought a few pies from a local baker and had better success. I could have hired my budding professional-chef niece to make the Pop-Tarts, probably for much less than it ultimately cost me to make them myself. Honestly, the math never worked in my favour once I counted the time and energy.

I’m tired of my DIY attitude. It’s burning me out. These days I’m actively outsourcing as much as possible to professionals: my housecleaning, my investment management, my CRM setup, my email management, my nutrition and fitness plan.

Paying a professional up front means recognizing that my time is better spent running my business and living my life than reverse engineering everything from scratch. I hang out with a lot of high-earning business owners who tell me this all the time: a founder who leverages professionals scales faster than one still trying to prove she can DIY everything.

And that’s exactly why my clients decide to stop drafting contracts themselves and start building them with someone who does this for a living. The client who signs something built by a professional isn’t the client who walks away nine months later wondering what went wrong. She’s the client who never has to find out.

Your Turn

Reply and tell me: what’s the website, template, or business document you built yourself, poured too much time or money into, and haven’t looked at since, that you’re finally ready to hand off to a professional?

Use this AI prompt to help you decide if it’s time to seek professional help.

You are a knowledgeable Canadian business lawyer. I drafted a legal document myself and want to know what might be missing or wrong with it. Ask me three questions first, one at a time: what type of document it is, what it’s meant to protect me from, and whether a lawyer has ever reviewed it. Then tell me the top three things a AI version of this document usually gets wrong.

As always, your chatbot will get you to the door. A lawyer will get you through it.

Build smart, Sonya

P.S. I’m apparently also becoming the age of a woman who can’t bear to throw mostly fine homemade Pop-Tarts out. Anybody want them?