I had a conversation with a colleague last week that’s been weighing on me. She’s 67, one of the sharpest tax CPAs I know, and she casually mentioned her retirement plan: “Maybe two more busy seasons, then I’m done.”
My first thought was “congratulations!” My second thought was “wait, who’s going to know all the things only you know?”
The Numbers Are Sobering
According to the AICPA, 75% of current CPAs are Baby Boomers nearing retirement age. We’re talking about 136,400 annual job openings through 2034. This isn’t a gradual transition—this is what they’re calling the “Silver Tsunami.”
And here’s the kicker: accounting graduates are down 30% over the last decade. Only 1.4% of college students choose accounting anymore. The pipeline is broken at both ends.
What Actually Gets Lost
It’s not just the technical knowledge—that’s documented in tax code and GAAP standards. What leaves with retiring CPAs is:
- Judgment: When the rules don’t quite fit the situation, what do you do?
- Client relationships: The context behind why certain clients need certain approaches
- “How we really do it”: The gap between what the textbook says and what actually works
- Pattern recognition: Spotting the red flags that come from seeing 10,000 tax returns
- Institutional memory: Why we do things this way (usually because we learned the hard way)
Formal training teaches the rules. Veterans teach the nuance. And less than 50% of firms have any formal knowledge transfer programs.
I’m Becoming the Veteran (And It’s Scary)
At 15 years in practice, I’m suddenly one of the more experienced CPAs in my network. People ask ME the “stupid questions” now. And I realize: I don’t have great answers for a lot of things—I just remember what worked last time.
The weight of this hit me when a new associate asked me why we categorize certain expenses a particular way for a client. My honest answer? “Because that’s what Linda did before she retired, and it worked.” Not exactly transferable knowledge.
Can Plain Text Accounting Help?
This is where I think Beancount’s approach offers something unique. Instead of knowledge being trapped in someone’s head (or worse, in proprietary software), what if we could build knowledge INTO the ledger itself?
Transaction-level documentation:
2026-03-15 * "Office supplies - Staples"
Expenses:Office:Supplies 127.43 USD
Liabilities:CreditCard
; Classification note: Office supplies, not equipment, because under $200 threshold.
; Per client's capitalization policy (see policy-doc.md), expense immediately.
; Exception: If multi-year supply (check quantity), should spread over useful life.
Metadata for decision context:
2026-01-31 * "Quarterly estimated tax payment"
Assets:Checking -15000 USD
Liabilities:TaxesPayable
client: "ABC Corp"
reasoning: "Based on projected annual income $180K, but conservatively using $200K to avoid underpayment penalty"
tax-year: "2026"
calculation-date: "2026-01-15"
Tags for lessons learned:
2025-11-30 * "Correcting entry - duplicated expense"
Expenses:Travel -487.20 USD
Expenses:Corrections 487.20 USD
#lesson-learned
; MISTAKE: Failed to check if expense was already imported from credit card.
; Always reconcile imports against statement before month-end close.
What Should We Be Documenting?
I’m trying to be more intentional about what I document, both for my future self and for whoever might take over my clients someday. Here’s what I’m thinking:
- Client-specific policies: Why we handle certain things uniquely for this client
- Exception cases: When the standard rule didn’t apply and what we did instead
- Decision rationale: The “why” behind non-obvious categorizations
- Mistakes and corrections: What went wrong and how to avoid it
- Judgment calls: Where professional discretion was applied and the reasoning
But here’s my challenge: documenting takes time. Time I’m supposed to be billing. Time that feels like it’s slowing me down.
How do you balance “getting the work done” with “making sure someone can understand this work later”?
Questions for the Community
For those who’ve been mentored by retiring CPAs: What knowledge did you wish you’d captured before they left?
For self-taught folks: What gaps did you discover the hard way that proper mentorship might have filled?
For veterans considering retirement: What do you wish you could pass on but don’t know how?
And practically: How are you using Beancount (or any tools) to build institutional knowledge that outlasts individual practitioners?
I don’t want to be the person who retires someday and leaves behind a bunch of ledgers nobody can interpret because all the context was in my head.
Sources: Controllers Council: CPA Firms Face 75% Retirements, Eagle Rock CFO: The Accounting Talent Crisis 2026, CPA Journal: Intergenerational Solutions, Welcome to the Jungle: Retaining Critical Knowledge as Baby Boomers Retire