For more than 15 years, I worked with a CPA I truly trusted. She worked from home, we handled almost everything digitally, and she made a stressful part of life feel manageable. She retired a few years ago, and ever since, I've been trying to find that same kind of working relationship again.
I haven't found it. That's what this post is about.
I'm writing this partly to clarify what I'm looking for, and partly because I'd genuinely like to find the right CPA. If you're a CPA yourself, or know someone who might be a good fit, this should give you a pretty clear picture of whether we'd work well together.
My Taxes Are More Complex Than Average — But They're Organized
My taxes have been more complex than the average person's for over 20 years. That said, I don't think they're unusually exotic or hard to understand. Relative to what I have going on, they're actually pretty straightforward. The bigger issue has always been organization and pulling everything together properly.
About 20 years ago, just preparing the raw materials for my CPA was a major project. I'm not exaggerating when I say I used to take an entire week off work just to get everything together. I'd go somewhere, sit down, and prepare a complete zip file of documents and notes to hand over.
Thankfully, technology has improved that process a lot. What used to take me a full week eventually became a long weekend. These days, I can usually get everything together in about a day.
I'm methodical about it. I organize everything into clearly labeled folders, bundle it into a well-organized zip file, and send it over.
I know I do a good job because my CPAs rarely come back asking for missing items. I'm not dropping off a pile of random documents and hoping for the best. I'm careful, organized, and pretty tax-fluent.
The one thing I'm not especially good at is getting everything over super early. I usually deliver my materials around April 1, which obviously is not ideal timing. But because the zip file is complete and well organized, I've always felt it should still be very workable with the right CPA.
The Kind of Working Relationship I Value
One thing I want to make very clear: I highly value working digitally.
I am not looking for a CPA who needs lots of meetings, office visits, or phone calls. With my longtime CPA, I probably spoke on the phone with her three times in fifteen years. We did almost everything by email.
That worked perfectly for me.
I like asynchronous communication. I like being able to send a thoughtful question, include documentation if needed, and get a clear response back. I like keeping things organized and documented. I like being able to work efficiently without having to schedule time on the calendar for every little thing.
But asynchronous should not mean slow, vague, or incomplete.
Digital communication only works when the CPA on the other end is responsive, organized, and willing to actually answer questions. I do not need constant contact. I do need timely and useful contact.
That distinction matters a lot to me.
What I've Experienced Since My Longtime CPA Retired
After my longtime CPA retired, I first went with a medium-sized firm. I paid quite a bit more, and I assumed that higher cost would come with better service. It didn't. They prepared the return, but communication was lacking. Questions were difficult to get answered. The relationship felt transactional. I was paying a premium and still not getting the level of support I wanted.
After that, I intentionally shopped around for someone smaller. My thinking was simple: someone working from home or running a leaner practice might have lower overhead, better systems, and more room to provide personalized service. That seemed like the right fit for someone like me, especially since I prefer a digital-first working style.
But over the last few years, I've still felt like I'm just one more return moving through a system. I upload the files. I wait. Eventually I get the return back. If I ask questions, the answers are often delayed or incomplete. The process feels like a black box.
That's the part I'm tired of.
I'm Not Just Handling My Own Taxes Anymore
Another factor is that I'm now also helping prepare my mother's taxes. I organize her materials in a very similar way to how I organize mine. She also has a somewhat more-complex-than-average situation, including rental properties and related documentation, so there are really two tax workflows I'm managing now.
That makes the need for a good CPA relationship even more important. I'm looking for someone who can work with me in an organized digital way across both fronts. Someone who can handle a clean process, keep things moving, and communicate clearly when questions come up.
I'm not looking to create chaos for anyone. In fact, I think I'm bringing a very orderly process to the table. I just want a CPA who can meet me there.
What This Tax Season Made Clear to Me
This year, I did something interesting.
I took the raw materials I normally provide to my CPA, along with prior-year returns and prior-year tax materials, and uploaded them into Claude. In about 45 minutes, it produced a tax return draft for me.
Meanwhile, I was still waiting for my CPA's version, which took about a week and a half.
When the CPA's return finally came back, the two were nearly identical.
That really drove something home for me: the role of the CPA is changing.
To be clear, I am not looking to replace my CPA with AI. I still think there is real value in having a professional prepare and sign a return. There is value in judgment, experience, accountability, and reducing audit risk.
But this experience did sharpen something for me. If AI can get very close on the mechanical side of preparing a return, then the value of a CPA is no longer just the final output. The value is the relationship, the judgment, the responsiveness, and the support around the work.
That is the part I'm looking for.
What I Actually Want From a CPA
I want a CPA who provides confidence.
I want someone who can answer questions during tax season and throughout the year. Someone who can help me think through planning questions when they come up. Someone who understands that tax preparation is not just about filling out forms correctly, but also about helping a client feel informed and supported.
For me, tax season is never pleasant. It means pulling time out of an already busy life, organizing documents, double-checking details, wondering whether I missed something, and then usually writing a painful check at the end of it all.
What makes that process bearable is having someone I trust on the other side.
That's what my longtime CPA gave me. She made me feel taken care of. She reduced stress. She helped me feel confident that things were being done correctly. She answered questions clearly, even though we did almost everything asynchronously.
That's the standard I know is possible, because I already had it for 15 years.
The Kind of CPA I'm Looking For Now
At this point, I'm looking for a CPA relationship that feels organized, digital, responsive, and professional. Here's what I value:
Comfortable Working Digitally
Asynchronous by default. Files, notes, and questions flow over email or a portal — not over scheduled meetings.
Clear and Timely Communication
When I ask a question, I get a real answer in a reasonable window. Async doesn't mean slow.
Works Well With an Organized Client
I'm bringing a clean, well-labeled zip file to the table. I want a CPA who can use that to move faster, not one who re-asks for everything.
Handles Two Returns Gracefully
Mine and my mother's — including rental properties — in a structured way.
Answers Planning Questions
Not just processes forms in April. I want a thinking partner when a decision has tax implications.
Understands the Real Product
The deliverable isn't just a completed return. It's confidence and clarity.
I'm not looking for hand-holding in the sense of constant meetings or endless calls. I'm actually pretty low-maintenance in how I like to work. But I do want thoughtful support when it matters.
Why I'm Writing This Publicly
I'm writing this because I'd genuinely like to find the right person.
Maybe that person is a solo CPA. Maybe it's a small firm. Maybe it's someone who has embraced AI and automation, not as a threat, but as a way to spend less time on data entry and more time advising clients and communicating well.
That feels like the future to me.
Not a world where a CPA charges a premium to act as a human wrapper around tax software — but a world where good tools free up time for better service.
That's what I'm looking for.
So if you're a CPA, or know one, and this sounds aligned with how they work, feel free to reach out.
I'm shopping for a new CPA.
I'm looking for someone who understands that in a world where the mechanical side of tax prep is getting easier, the human side matters more than ever.
