When to Pay a Professional (I'm Not Your Lawyer)
Last few lessons I walked you through the LLC stuff, the licensing, when it starts to matter. Now I want to say the thing underneath all of it, plainly, so nobody leaves this class thinking I know more than I do.
I'm not your lawyer. I'm not your accountant. I'm a caterer who figured out his own paperwork at the kitchen table after Jami went to bed, one Google search at a time. That worked for me. It might not be enough for you, and I'd rather tell you that now than have you find out the hard way.
The forty-minute wall that wasn't
I've told you about the business license already — how I went two years without one, built it up into this huge scary thing in my head, and then it took forty minutes online and cost less than a dinner out. That's real, and it's true for a lot of the paperwork in this module.
But there's a difference between paperwork that's a curb and paperwork that's actually a wall. A license application is a curb. Your tax situation once real money starts moving, or a contract dispute, or somebody getting hurt at an event you catered — those can be walls, and that's when you call somebody who does this for a living.
Where I'd actually spend the money
A few situations where I think paying a professional, even just for one conversation, is worth it:
- You're making real money and don't know what you owe. Not "sold some soap to your cousin" money. I mean if you're clearing a few thousand dollars a year and the tax questions are past what a spreadsheet and common sense can answer. An hour with a CPA, even just once a year around tax time, can save you way more than it costs.
- Somebody else's safety is in your hands. Food, kids, anything physical. I carry basic liability coverage for the catering because if someone gets sick at an event I worked, that's not a "we'll figure it out" moment. Talk to an insurance agent, not me, about what coverage actually makes sense for what you're doing.
- You're signing something you don't understand. A venue contract, a vendor agreement, anything with fine print and a signature line. If your gut says "I don't know what this means," that's the gut saying pay someone $150 to read it before you sign it.
- You're forming an actual LLC or partnership with another person. Two people splitting profits and nobody's written down who owns what — that's the kind of thing that ends friendships. A lawyer drawing up a simple operating agreement is cheap compared to what it costs when it goes sideways later.
None of that is exotic. It's mostly "pay a little now so you don't pay a lot later," which, if I'm honest, is the same lesson as the separate bank account and the spreadsheet. Different flavor, same idea.
The mistake I made instead of asking anybody
I never talked to a professional about the very first job I did — the wedding luncheon for my neighbor's daughter, back around 2015. Didn't occur to me. I didn't think of it as a business yet, I thought of it as doing a favor that happened to involve food.
I charged her $200. It cost me $340 in groceries and about eleven hours of my time, and I didn't tell her any of that. I just ate the loss, smiled, went home, and finally opened a spreadsheet because I couldn't keep doing math in my head at 11pm.
Nobody got hurt by that mistake except me and my own bank account. But it's the same root problem as the "do I need a professional" question — I hadn't decided yet whether this was a business or a nice thing I was doing for a neighbor. If I'd had that conversation with myself sooner, the money side wouldn't have been such a surprise, and I'd have known way earlier which questions were mine to answer and which ones needed somebody with an actual license to answer them.
Charge for your time or you don't have a business, you have an expensive way to be nice. I've said that before in this class and I'll keep saying it, because it's the thing that took me longest to learn and it colors this whole professional-help question too. If you're not charging enough to justify paying an accountant for an hour once a year, you're probably not at the size where you need one yet. That's fine. That's most of you, probably, and that's okay.
What this actually looks like at home
You don't need to hire anybody tonight. Here's what I'd do instead:
- Write down, honestly, how much money moved through your side thing last year — money in and money out.
- If that number makes you nervous or confused, that's your sign to call a CPA for one conversation, not a retainer.
- If you're about to sign anything with a venue, a vendor, or a partner, read it twice and if any sentence makes you squint, that's the sentence to ask a lawyer about, not guess at.
That's it. Most of you aren't there yet, and that's not a failure, that's just where you are.
Before next time: think about whether there's a contract, a partnership, or a tax question sitting in your business right now that you've been quietly ignoring. Write it down. We'll talk about it if you want.