How I Finally (Mostly) Mastered Tax Season
After Years of Trial and Error
Let’s talk about tax season. More specifically, let’s talk about surviving tax season with your sanity intact.
Before we get to that though, I want to give you some context about who we are so you can better understand how this process fits within our firm.
At Nicholynn Advisors, we focus on serving small business owners, entrepreneurs, and individuals who value structure and proactive financial planning. We provide traditional bookkeeping and tax prep services, but we also provide tax planning and strategic CFO services. We’re a boutique firm, which means we don’t take on hundreds of tax clients and we prioritize quality over volume. Because of this, we’ve developed a tax prep system that works for us - one that might not fit every firm, but can certainly be adapted. (And yes, if you have multiple tax preparers, our appointment booking software, Acuity Scheduling, allows for multiple staff calendars!)
I’ve been having our clients schedule their tax prep for the past four years, and I have learned a lot. Mostly about all the things that didn’t work.
But after years of fine-tuning, I’ve finally built a system that keeps things running (mostly) smoothly. If you’re a tax preparer, an entrepreneur, or just someone who appreciates a well-oiled process, buckle up.
I’m taking you behind the scenes of how we do things at Nicholynn Advisors and why we’ve made certain rules non-negotiable.
Opening the Tax Season Gates
Every January (usually by the 5th), we send out an email to all our clients letting them know that our tax schedule is officially open. We also let them know when we will actually start processing returns, which is typically February 5th.
Why the wait? Because January is already chaos. Between year-end financials, 1099 filings, and the general madness of business accounting, February 5th is the earliest I can start without losing my mind.
In that initial email, we provide details for the entire tax prep process and any updates we've made for the current year. Clients also get a link to schedule their Tax Designation Date™ (TDD), which is my fancy name for “the day I actually sit down and work on your return.”
And yes, I took the time to trademark that term.
While these are appointments, I don’t meet with the client during these TDDs. You’ll see why…
There are two separate links - one for business tax returns (S Corps, Partnerships, and C Corps) and one for individual tax returns (with or without a Schedule C business).
As I mentioned, we use Acuity Scheduling, which gives us the ability to take a payment and require certain questions to be answered before someone can book an appointment.
So in order to schedule a TDD, clients must pay the following deposit amount based on the type of return they’re scheduling and answer a short questionnaire. For exactly what we ask on the questionnaire, read to the bottom.
$100 for personal returns
$200 for business returns
This deposit is nonrefundable.
Why? Because a few years ago, I had a client book their appointment, fill out all the tax organizers, and then, on the day of their appointment, tell me, “Never mind, my wife says she can do the taxes herself.” I was not amused. Lesson learned.
Now if a client doesn’t follow through, we keep the deposit. Simple as that.
Getting the Paperwork in Order
By mid-January, we send out electronic tax organizers and engagement letters to everyone who has scheduled their TDD. If someone books after mid-January, we send their materials within two business days.
And by “we,” I mostly mean my part-time admin assistant, who is a lifesaver. Get yourself one.
Once clients complete their organizers and sign their engagement letters, my assistant:
Downloads and organizes all their documents into our secure storage
Renames all the files (because most clients upload things like “Scan123456.pdf”)
Checks that all documents are legible and complete
If something is missing or unreadable, she follows up with the client. And trust me, this is necessary because some people really will upload a W-2 that looks like it was crumpled, stomped on, and left in the rain. Or is not from the year we’re working on.
We also tell clients - multiple times - that everything must be uploaded at least two days before their TDD. If they miss the deadline, we reschedule their appointment to our next available timeslot. No exceptions.
After two reschedules, they’ll get an email cancelling their appointment altogether until they contact us. This hasn’t happened yet, but it’s in the fine print.
Balancing Tax Prep with Ongoing Client Work
Tax season doesn’t mean my other client work stops.
While TDDs are a huge part of my schedule, I’ve structured my calendar to ensure I still have time for other commitments. And life.
I also heavily rely on the settings in Acuity Scheduling to help me set up the parameters of how I’ve structured the TDDs so I don’t have to manually adjust much.
Before I share all the parameters I have on my schedule, you need to know something very important. Don’t open your calendar to allow clients to pick any time they please.
Set specific times that you will allow the appointments to happen at.
My clients choose from appointment times of 8:30am, 1:00pm and 4:30pm (when I offer a 3rd appointment). And that’s it.
Since I don’t actually meet with the client during this appointment, the timing of it doesn’t matter to them - it only matters to ME. The first year I let clients schedule whenever, and then my calendar was shit. I almost gave up on the whole process and went back to the FIFO method.
TDD appointments are 3 hours long and I allow scheduling a max of 3 per day. Most days, though, I only do 2. This constraint is a feature that Acuity allows.
No TDDs are scheduled during the week leading up to either the March 15th deadline or the April 15th deadline. This gives me the ability to follow up with anyone who was already in process to get done before the deadline, while setting the expectation that if you didn't schedule your TDD for at least the week before the deadline, I'm not rushing to get it done on time.
I have the option to open up additional appointments. So for example, on days where I only have 2 appointments, if I know the 2 I have will be super easy, I open up a third slot to allow another client to schedule then.
Tuesdays are reserved for ongoing client work. No TDDs are scheduled on Tuesdays, giving me a dedicated day to focus on advisory services, financial reviews, and ongoing engagements.
I schedule client calls (including tax review appointments) before, between, and after TDDs. This allows me to maintain relationships and ensure my other clients don’t feel neglected during tax season.
Boundaries prevent burnout. My TDD schedule is strict, but that’s what allows me to stay on top of everything without running myself into the ground.
I am also completely off on Sundays and only have a maximum of two TDDs (and no other work) on Saturdays. This way I know I can go out Saturday night and enjoy myself without stressing and also have one full day of rest. Also, I don’t work every Saturday - just the ones when I have nothing else going on.
For anyone who goes on extension, we won’t work on their returns until June 1st. I’m taking my daughter to Europe in May for a couple of weeks and I’ve set the expectation now that I’m not available in May so don’t ask.
Likewise, all extended returns must be completed by September 1st. My birthday is September 12th and I have never been able to celebrate my birthday until after October 15th. Not this year! If the returns don’t get done by 9/1, clients still have time to find someone else to do them, but it won’t be me.
It’s a balancing act and it may seem like a lot, but having this structure in place makes tax season manageable without sacrificing the quality of my ongoing work.
Also, most tax returns do not take me 3 hours to complete. But having that time blocked allows me to have a large enough window to still get the taxes done if something crazy pops up.
Conceptually, what does all of this look like? Here’s a snapshot of this week’s calendar so you can see it in action:
Thursday looks a little messy, but that S Corp reasonable comp call that’s overlapping was supposed to be in that open space on Wednesday. The client needed to reschedule, but I knew that first appointment would be an easy one so I happily rescheduled the client.
Reminders, Reminders, Reminders
I like to think that my clients read every single word on every single email and post. But I’m not naive.
So that is why Acuity also sends reminders that say the same thing that I’ve already told the clients in my pre-tax season email, my intial confirmation email when they choose their TDD, and their engagement letter.
Clients get two reminder emails - 7 days and 3 days before their appointment. Both of these reminder emails say the following:
You do NOT need to be present or available during this time slot and we will NOT be calling you. If we have questions or need additional information, we will email you at the end of your appointment day.
If you have not completed your tax questionnaires and submitted your documents to us, you still have plenty of time to finish.
If you have 90% of your information ready but are waiting on a form that may not come in time, keep your TDD slot anyway. Just be sure to submit your questionnaires and all of the documents you do have before the TDD. We will prepare your returns with the information we have and will wait to complete your drafts once you provide the final information.
If you need to change your appointment, you can do so by clicking the button below. Once we are within 48 hours of your scheduled time, you will not be able to change/cancel your appointment yourself and will need to email/call us for assistance.
Business Owners, Please Have Your Books Done
This one was new for 2024 because, again, a hard lesson was learned.
If a client owns a business, their bookkeeping MUST be done before their TDD.
For our bookkeeping clients, this isn’t an issue since we close their books at the end of January. But for everyone else, we give them two choices:
They need to get their books done before their TDD.
They pay us to do a bookkeeping review/clean-up before their TDD (booked separately).
This one change alone has saved me so much frustration this year.
I was surprised by how many clients actually opted to get their books in order themselves, even some who hadn’t done so in past years!
If they ignore both options, we *may* use their TDD appointment to do the bookkeeping review, and their tax prep gets rescheduled for a later date.
I actually did this today with a client. We switched today’s previously scheduled TDD appointment to a bookkeeping review appointment (at a whopping $397/hour for 3 hours) and I added a third TDD appointment to next Wednesday because the other two tax appointments that day are relatively simple. The client was happy and I’m not behind.
Handling Last-Minute Requests
I handle last-minute client requests with a firm but fair approach that prioritizes both my sanity and client expectations:
Reinforce Boundaries Early & Often – My process is structured for a reason. Clients are informed multiple times about deadlines, expectations, and the need to schedule their TDD in advance. This significantly reduces last-minute surprises.
Late Requests? Here’s the Deal.
If I have capacity, they pay a Last-Minute Rush Fee to secure an emergency spot. This fee is steep enough to discourage procrastination but fair for my time.
If I’m fully booked, they go on extension and I handle their return after June 1st. No exceptions.
The One-Star Review from the Perpetual Last-Minute Client
The only negative review I’ve ever received is from someone who, for three years in a row, waited until the last minute. The final year, they reached out two days before April 15th, and when I didn’t immediately respond, they left me a bad review.
My response to their review was: "Our policy has changed, and we no longer work with businesses that don’t respect our time."
And let me tell you, it felt good.
The Bottom Line
This system is working well for me, now that I’ve completely overhauled it from the process I started with four years ago. But I’m also at a different place in my life than you may be. My daughter is 19 and in college now. I’m not chasing after little ones, or involved in a bunch of other things that require my time.
Will this exact process work for you? Probably not.
But you can absolutely adapt it to work around your schedule and the clients you work with. Do whatever you can to protect your time, stick to your system, and offer clear, structured alternatives for last-minute requests.
By maintaining structure, setting firm boundaries, and ensuring expectations are met in advance, I’ve been able to run an efficient and predictable tax season without burning out.
This keeps me sane and helps my clients plan better. (Well, most of them.)
Here are the exact questions we ask during TDD scheduling.
And when I say exact, I literally copy and pasted. You’re welcome.
Individual Tax Return TDD Questions
The following is a Form in Acuity Scheduling that the client must read and complete before they can schedule their TDD for their individual tax returns.
This is the header of the Form:
If you have a Schedule C business (sole proprietorship, single-member LLC), your business books must be up to date before your Tax Designation Date™ (TDD) since your business and personal returns are prepared at the same time.
As part of booking this appointment, you will pay a $100 nonrefundable deposit to hold your TDD. This will be applied to your final invoice once your drafts have been completed. Within 2 business days (or as early as January 15th), you will receive a follow-up email with your engagement letter and tax questionnaires.
If you aren't ready by the date you've chosen, simply reschedule and pick a different date. However, be aware that this means it may be a while before you can pick a new date if other slots have started filling up.
Here are the questions on that Form:
Which type of return is this for?
Individual Returns (Personal only - no business)
Individual Returns (with Schedule C business OR rental property)
Enter the NAME and EMAIL ADDRESS of the person responsible for completing the tax questionnaires.
If you are making this appointment for someone else (like a child or parent), enter their name here.
Do you expect to have any of the following items? (Check all that apply)
Education expenses and credits
Investment Property (long-term rental; short-term rental; etc.)
Filing as Head of Household (requires a Due Diligence form)
None of the above
If you have a Schedule C business, what is the name of your business? (List all applicable businesses)
Are your business books reconciled through the end of the year? Yes or No.
If you answered No above, do you need assistance from Nicholynn?
Yes - Bookkeeping Review Session ($397/hr)
Yes - VIP Accounting Overhaul ($1250 for a half day)
No - I will have the bookkeeping done before my TDD
Maybe - I will let you know
Business Tax Return TDD Questions
Again, this Form is specifically for Partnership, S Corp, or C Corp returns.
This is the header of the Form:
If you have a Partnership, S Corp, or C Corp return prepared ahead of your personal return, you will need TWO separate Tax Designation Dates™ (TDD)—one for business and one for personal. If you only need a business return, no personal TDD is required. Multiple businesses require separate TDDs for each entity.
As part of booking this appointment, you will pay a $200 nonrefundable deposit to hold your TDD. This will be applied to your final invoice once your drafts have been completed. Within 2 business days (or as early as January 15th), you will receive a follow-up email with your engagement letter and tax questionnaires.
If you aren't ready by the date you've chosen, simply reschedule and pick a different date. However, be aware that this means it may be a while before you can pick a new date if other slots have started filling up.
Here are the questions on that Form:
What is the name of your business?
Are your business books currently reconciled through the end of the year? Yes or No.
If you answered No above, do you need assistance from Nicholynn?
Yes - Bookkeeping Review Session ($397/hr)
Yes - VIP Accounting Overhaul ($1250 for a half day)
No - I will have the bookkeeping done before my TDD
Maybe - I will let you know
What is your 2024 business return type?
S Corporation
Partnership
C Corporation