I hope you’re making it through holiday chaos with minimal glitter-related injuries! 

A few weeks ago, I asked you to send your end-of-year questions. You had a lot of good ones, so today I’m answering a few that come up the most.

P.S. Don’t forget to get your health insurance by December 15. 

“I’m about to get married, and I own a business. Is there anything I need to do?”

First of all, congratulations! This is an exciting moment, and I do get this question a lot. 

Let’s start with the wedding veiled elephant in the room. A legal name change creates a paperwork avalanche. 

If you change your name, you have to update your Social Security card before you can get a new driver’s license or REAL ID, before you can get a new passport, before you can update your business filings. Then your signature on bank accounts. Then anything tied to your ID. It’s a whole change-management process, but it’s a critical one. 

Next, let’s talk about ownership. 

Legally, everything in your business up to the day you get married is yours. Everything after becomes “ours” unless you carve it out in writing. You can write a document that you both acknowledge, or you can work with a lawyer on a full-blown prenup. The important thing is that you have a document to point to that is clear about who owns what and has financial responsibility. 

Of course, there are upsides to shared ownership too. 

If you’re both pursuing aggressive financial goals, your spouse can participate in your retirement plan as an owner, or you can distribute profit to them in ways you can’t when unmarried. Just remember, if you ever part ways, all income, profit, and intellectual property created after the wedding date is fair game in a split unless you’ve documented otherwise.

My one piece of real advice? Have a tax planning call. Once you’re married, your business earnings affect your household income, your partner’s financial picture, and your shared tax strategy. Even if your spouse never touches the business, your numbers now belong to both of you.

“I’m moving to a different state. What does this mean for my business?”

People usually ask me this because they’re excited. Either they’re heading to a lower-tax state, or they think they’ve found some clever loophole where their business “stays” behind. 

Let me save you some time: you can’t game this. This isn’t like keeping your car registration at your mom’s house to get cheaper insurance. Your business lives where you live. Not where your P.O. box lives. Where you physically do the work most of the time. 

If you’re moving from a high-tax state to a low-tax one, just know the old state will try to keep you on the books as long as possible, especially California. It can take up to two years to fully close down an LLC. 

If you’re moving from a low-tax state to a high-tax one, all you need to know is that the new state will want their money. You’ll file your state tax return with your new home address, and you’ll eventually get a letter saying you have business income but no registration. Penalty city. 

The moral of the story here is,  within the first 90 days of actually living in your new state, talk to a trusted business advisor about your options.

The other thing you need to take care of is your bank. If you’re with a national bank, you’ll likely be fine. They’ll update your address and you’re done. But if you love your little local credit union in Arizona and you move to Washington, you may have to physically fly back to close that account. Ask yourself how many times you’re willing to go back to the old state to mop things up.

Finally, make sure your business name is available in the new state if you need to re-register. It’s annoying to arrive somewhere new and find out someone else already grabbed it.

“I don’t want to delegate, but I’m overwhelmed. How do I know if it’s actually time to delegate?”

Hello, you’re me.

I know exactly how you’re feeling: overwhelmed, barely treading water… but also confused. Are you overwhelmed because you’re doing the wrong work, or because you’re doing too much of the right work? 

Here’s how to think about it:

Are you starting to resent some of the work you have to do?

This is the big one. If the work has to get done, doesn’t have to be done by you, can’t be removed without breaking your business model, and you feel dread every time it hits your desk, there’s your answer. It’s time to delegate.

Has your pricing outgrown parts of your workload?

As you raise your prices, clients start noticing when you’re doing $50/hour work inside a $400/hour relationship. They won’t say it that bluntly, but it shows up in questions like, “Do you really need to be the one doing this?” Delegation protects your value, and investing in lower-cost support can keep you focused on delivering the work only you can do.

Have your clients told you to get help?

The reason I hired my first assistant was because three clients said, “You need an assistant. Please stop doing everything yourself.” That kind of feedback isn’t a joke after the second time. If the people who pay you are saying it, listen.

Finally, here’s tough love you need to hear: you can’t control everything.

I know, I don’t like that either. Delegation forces you to let go of a little control, and it brings up every feeling you’ve been ignoring. Sometimes people make messes that you have to clean up. That’s business adulting.

“How do I tell if something is actually wrong in my business, or if I’m just panicking?”

For me, this is a facts versus feelings question. I can factually tell you what’s going on. It might not alleviate your feeling of panic. 

Start with the facts. Look at your books. Ask a trusted business advisor to walk you through what they see. Don’t go to Threads, Reddit, or ChatGPT. Strangers online don’t know your margins, your industry, your cash flow, or your risk tolerance. 

Thirty minutes with someone who understands your numbers will tell you if the business is the right level of healthy, or if there’s a real problem developing. That part is straightforward, because it’s math.

Then look at your feelings. Your numbers might be great, but you still feel terrible. There might be a people or support issue. Or you might be having a human response to stress, exhaustion, or uncertainty. You might be tired, lonely, worn out, or scared of making a mistake, and your brain translates that into, “My business is failing.”

Your feelings don’t always follow the spreadsheets. And that’s OK. 

You’re a human being, and you’re definitely not alone. It’s been a hard year, especially so for small businesses. The world is chaotic. And you’re doing something difficult.

So, if you’ve looked at the facts, and you still feel heavy or panicky? Or you’re too panicked to even consider looking? Don’t ignore that. Talk to someone.  If you don’t know who to talk to, call the national 988 Helpline (available 24/7). If you have health insurance, most carriers offer a free, confidential behavioral health hotline. If you’re looking for a community of entrepreneurs, The REAL Mental Health Foundation is a great resource. 

Don’t worry about finding your forever therapist or the optimal approach. Pick up the phone and talk to someone. 

We’re down to the last two critical weeks in our end-of-year checklist. Let’s do a quick roundup of the most important dates:

• This week: Small group open enrollment deadline (yours may be earlier)

• December 15: Deadline for marketplace open enrollment for January 1 (plus first premium payment) 

• December 19: Last day to expect professional partners to be in the office

• December 25: Christmas Day federal holiday

• December 26: Last day for most payroll runs with direct deposit

• December 31: Last day to open a 401(k) retirement account or make purchases for 2025 qualified expense deductions

• January 1: New Year’s Day federal holiday

I listened to a podcast interview with UCLA women’s basketball coach Cori Close last week. She said her goal as a leader is to “be transformational in a transactional world.”  Immediately, I scrawled it on a Post-it and it’s now on my kitchen wall. If you’re reading this newsletter, you probably have the same goal. Yes, we need to sell things and make money, but we’re also trying to lead in a way that changes something for the better. If this is on your mind, give this interview a listen.

Gusto’s new report recognizes something important: even though small business health insurance has gotten a lot more expensive, most of you decided to offer it anyway. As small business owners, we’re not required to do this. If you are offering health benefits next year, please accept this hearty cheer for you.

Yes, a drunk raccoon was found passed out in a Virginia liquor store. Look, the world is in a weird place right now. This year has been a decade. I appreciate that you trust me with hard questions. But I want you to know, I’m also a person you can ask, “Hey, did you see that drunk raccoon?” Yes. Yes, I did. And it was amazing.