Everyone has a version of this. A category of work that sits on the to-do list for weeks, then months, slowly accumulating guilt. For some founders it’s legal. For others it’s HR, compliance, or investor reporting. For me, it’s always been accounting.
Not because I can’t do math. Because every time I opened QuickBooks, I’d feel the weight of everything I didn’t understand, and I’d close the tab. There’s always something more urgent than confronting what you don’t know.
This week I finally sat down and did all of it. Reverse-engineered spreadsheets. Audited our QuickBooks accounts. Found missing payables. Fixed miscategorized transactions. Worked through international currency adjustments. Even handled an off-the-books equity correction I’d been dreading for longer than I’d like to admit.
And here’s the part I didn’t expect: it was actually kind of fun.
The difference wasn’t discipline. It was having AI as a collaborator. And the reason that mattered has nothing to do with accounting specifically.
The real barrier is shame
Think about the task you’ve been avoiding. Now think about why.
It’s probably not because the task itself is impossibly hard. It’s because there’s a gap between what you know and what you’d need to know to do it confidently, and closing that gap feels expensive. You’d have to ask someone. That someone is busy, or expensive, or both. And the questions you need to ask feel like they should be obvious.
That was my relationship with accounting for years. Accountants always seem busy. When I’d get on a call with mine, I’d feel the clock ticking. Every question felt like it should be obvious. Do I really need to ask what a trial balance is? Can I admit I don’t understand why this line item is negative? Is it okay to not know the difference between cash-basis and accrual?
So you nod along, say “makes sense,” and leave the call having learned nothing. Then you avoid the whole topic for another month.
This is the shame barrier. It’s not a knowledge problem. It’s a help-access problem. The help exists, but the social cost of accessing it is high enough that you just… don’t.
What happens when the shame disappears
When I sat down with Claude Code this week and started working through our financials, I could ask anything. Literally anything.
“What does this column mean?” No judgment. “Why is this number negative when we received money?” Clear explanation. “Walk me through how this journal entry should work.” Step by step, as many times as I needed.
I went deep on things I’d been skating past for years. The nuances of our P&L statement. How the balance sheet connects to the trial balance. Why certain transactions were showing up in the wrong categories. What our cash flow statement was actually telling me versus what I assumed it was telling me.
Each question led to a better question. And because I wasn’t worried about wasting someone’s time or looking dumb, I kept going. I’d ask a follow-up, then another, then branch into something related. It was the first time accounting felt like learning instead of an exam I was failing.
If you’ve ever had a mentor who made you feel safe asking the dumb questions, you know how much faster you learn in that environment. AI gives you that dynamic on demand, in any domain, at any hour.
The concrete results
This wasn’t a vague learning exercise. I worked through real problems in our actual books:
Reverse-engineered inherited spreadsheets. We had several financial spreadsheets maintained by different people over time. I fed them to Claude and asked it to explain what each one was tracking, how the formulas worked, and where there were inconsistencies. It found things that had been wrong for months. If you’ve ever inherited a spreadsheet from someone who left the company and spent hours trying to figure out what it was supposed to do, AI turns that from hours to minutes.
Audited QuickBooks categories. Transactions miscategorized across multiple accounts. Expenses in the wrong cost centers. Payables missing entirely. Claude walked me through each one, explained what the correct category should be and why, and helped me make the corrections.
Handled the stuff I’d been avoiding. International currency adjustments. An equity correction I didn’t fully understand the accounting treatment for. Reconciliation of accounts that hadn’t been reconciled in too long. These are the kinds of things where I’d normally email the accountant, wait three days, get an answer I half-understood, and still feel uncertain about whether it was done right.
Thought through the strategic questions. Beyond the bookkeeping, I used the conversation to think through bigger questions. I’ve thought about managing cash flow before, but this was different. What are our actual options right now? What interest rate is expensive versus reasonable for our situation? What are the trade-offs between different funding approaches? These aren’t strictly accounting questions, but they live in the same “financial stuff I’m uncomfortable with” bucket, and having a patient conversation partner made them approachable.
The pattern worth noticing
Here’s what I want you to take from this. It’s not “use AI for accounting,” although you should.
Every business owner has domains they understand well and domains where they’re faking it. For me, the product development, marketing, and technical infrastructure are comfortable territory. Finance has always been the thing I know I should understand better but never prioritize learning. It’s a version of the fear of the unfamiliar that I think most founders carry around quietly.
AI doesn’t replace the expert. I still need a CPA for tax strategy and compliance. But it fills the gap between “I know nothing” and “I know enough to have a productive conversation with my accountant.” That middle layer of competence is what most people skip, and it’s exactly where AI excels.
Before this week, my accounting approach was “send everything to the accountant and hope for the best.” Now I actually understand what’s in our books. I can read a P&L and know what I’m looking at. I can spot when something looks wrong. That upgrade happened because the learning barrier dropped to zero.
Apply this to your thing
This keeps happening. Tasks I’ve been dreading turn out to be approachable, even enjoyable, once I have a collaborator that’s patient, knowledgeable, and available whenever I’m ready to work. It happened with growth engineering. It happened with the small automations that add up. Now it’s happened with accounting.
The common thread is that the barrier was never ability. It was the friction of getting help. AI removes that friction, and suddenly the things you’ve been avoiding become the things you’re making progress on.
So here’s my challenge to you: think about the task that’s been sitting on your list the longest. The one you keep bumping to next week. Ask yourself whether the problem is really that the task is hard, or whether the problem is that you don’t have a safe, low-cost way to close your knowledge gap.
If it’s the second one, you might be surprised at what happens when you just start asking questions.