Personal Bookkeeper Needed — Organize 5 Years of Personal Finances: Hands-On, Accountability-Focused

Project Overview I’m a business owner with multiple companies across several jurisdictions and a fairly complex overall financial picture. My business side is well-handled — I have bookkeepers, CPAs, and a part-time CFO for that. This project is different: it’s about getting my personal finances organized. I have roughly five years of personal transactions (bank accounts, credit cards) that have never been properly categorized. I need someone to work hand-in-hand with me to go through it all, get it categorized and organized, and build a clean picture of where things stand. This is not a “send me your files and disappear” job. I work best with someone alongside me — someone who will show up consistently, keep the project moving, and isn’t afraid to push me when I let it slip down my priority list. The work itself is something I’ll be heavily involved in (a lot of the categorization decisions are mine to make), but I need a structured partner and a steady cadence to actually get it done. Goal: Fully categorized and organized by end of year — sooner if we can move faster. How This Will Work • Weekly live working session (video call, screen-share) — this is the core of the engagement. We’ll work through transactions together in real time. • A few hours of independent work between sessions — you’ll prep, organize, flag questions, and chip away at categorization so we’re not starting from zero each week. • Proactive follow-up — if I go quiet or miss a deadline between sessions, I want you to chase me down. That accountability is a big part of what I’m hiring for. Logistics • Type: Part-time, hourly, short-term project • Hours: 10–15 hrs/week • Rate: $14–25/hr (based on experience) • Timeline: Now through end of year, ideally faster • Tools: Open to your preferred system (spreadsheets, QuickBooks, Quicken, etc.) — we’ll agree on one together in week one • Confidentiality: This involves sensitive personal financial data. A signed NDA will be required before we begin. Responsibilities & Tasks • Review and categorize ~5 years of personal bank and credit card transactions • Set up (or help me choose) a clean categorization structure for personal finances • Reconcile transactions across multiple personal accounts and cards • Identify gaps — missing statements, unclear transactions, records that need to be tracked down • Maintain a running list of open questions/decisions that need my input, rather than guessing on ambiguous items • Lead our weekly working sessions with a clear agenda and a sense of where we left off • Proactively follow up between sessions — flag overdue items, keep me on schedule, hold me to deadlines • Track overall progress against the end-of-year goal and flag early if we’re falling behind What I’m Looking For • Solid experience with personal bookkeeping or transaction categorization (not just business books) • Comfortable handling sensitive financial information with discretion • A direct communicator who will push back and ask pointed questions — not someone who waits passively for instructions • Highly organized, detail-oriented, comfortable with years of backlog and some ambiguity • Available for consistent weekly hours over several months • Bonus: experience working with business owners or individuals with complex, multi-account financial lives How to Apply Please include: 1. A bit about your experience with personal (not just business) bookkeeping/categorization 2. How you’d approach a client who’s behind on a project they know is important — how do you keep them accountable without being annoying about it? 3. Your availability for a recurring weekly time slot 4. Your hourly rate within (or near) the stated range I’m looking to start soon and would love to find someone I can build a steady weekly rhythm with.