Chicago, Illinois
Professional accounting & bookkeeping support in Chicago
Watson Me Accounting LLC keeps the books of owner-operated Chicago businesses accurate, reconciled and closed on schedule — at a flat monthly fee agreed in writing before the first month begins.
- Service area
- Chicago & Cook County
- Fees
- Flat monthly, in writing
- Commitment
- Month to month
- Reply time
- One business day
Built around your needs
Accounting support built around your needs
No two small businesses keep records the same way. Some arrive with three years in a spreadsheet, some with a bookkeeping file nobody has reconciled, some with nothing but a bank feed. The work starts where you actually are.
We scope the engagement to the volume and complexity in front of us, put the number in writing, and keep it steady. If the business changes shape, we talk about it before anything on the invoice changes.
Bookkeeping and accounting support only. We coordinate with your tax preparer and do not provide tax, legal, audit or investment services.
Who we help
Owner-operated businesses across the city
- 01
Individuals
People with side income, a rental unit, or a household that runs like a small operation, whose records have outgrown the shoebox.
- 02
Independent contractors
Tradespeople, drivers, and field workers paid per job, with income from several sources and expenses piling up between them.
- 03
Freelancers
Designers, writers, developers, and creatives billing a handful of clients, where irregular income makes the bank balance a poor guide.
- 04
Entrepreneurs
Owners launching or running a first venture, often funding it personally and learning the recordkeeping side as they go.
- 05
Startups
Early-stage companies spending ahead of revenue, with founders who need burn and runway visibility long before they need a finance department.
- 06
Small businesses
Established shops, restaurants, and local services with steady activity, a few employees, and books that need to simply be right every month.
Featured services
The monthly work, done properly
Recordkeeping, reconciliation and reporting, handled on a fixed schedule.
All services- 01
Monthly Bookkeeping
Every transaction categorized and every account reconciled, closed on a fixed schedule each month.
- 02
General Ledger Maintenance
Ongoing review of the ledger itself — mis-postings, stale balances and orphaned accounts found and fixed.
- 03
Transaction Categorization
High-volume transaction coding done consistently, against a chart of accounts built for your business.
- 04
Accounts Payable Support
Bills entered, due dates tracked, and a weekly view of what you owe and when.
Why it matters
Why organized accounting matters
Decisions stop being guesses
Hiring, pricing and equipment decisions get made against real numbers instead of the balance in the operating account.
Year-end becomes a handoff
When the books are already reconciled, your tax preparer receives a clean file instead of twelve months of untangling.
Lenders and landlords get answers
Loan applications, leases and license renewals ask for statements on short notice. Current books mean you can send them.
Problems surface early
A duplicated vendor charge or an unpaid invoice shows up during reconciliation, not months later.
Our approach
Five steps, in the same order, every time
- 01
Understand
A short conversation about how the business actually runs — accounts, tools, who touches what, and what you need to see each month.
- 02
Organize
Chart of accounts, bank and processor feeds, and document handling set up so records arrive in one place instead of five.
- 03
Reconcile
Every account matched to statements each month, with questions grouped into one list rather than sent to you piecemeal.
- 04
Report
A consistent monthly report pack — profit and loss, balance sheet, and cash summary — delivered on a fixed date.
- 05
Maintain
The same close, the same date, every month, so year-end is a handoff to your tax preparer instead of a scramble.
Service packages
Published fees, quoted in writing
Cleanup and setup projects are scoped and priced separately, never added to a monthly invoice as a surprise.
- Ledger
- $700
- per month, starting
- Solo owners and single-entity businesses with straightforward books.
- Operating
- $1,050
- per month, starting
- Growing businesses with employees, multiple accounts, or a payment processor.
- Controller
- $1,450
- per month, starting
- Multi-location, multi-entity, or high-volume operations that need closer attention.
Local
Chicago-focused accounting support
We work with businesses across Chicago and Cook County — storefronts on commercial strips, trades running jobs across the metro, and service businesses operating from a home office. Working locally means we understand the city and county paperwork small businesses run into, and we can meet in person when a records handoff calls for it.
Most of the month-to-month work happens over shared files and a scheduled call, so your location inside the county matters less than how your records arrive.
- Service area
- Chicago, IL · Cook County, IL
- Hours
- Monday–Friday, 9:00am–5:00pm CT
- Phone
- 701 518-4751
- watson@watsonmeaccounting.com
Questions
Asked before we start
- How much does monthly bookkeeping cost?
- Flat monthly fees start at $700 for straightforward, low-volume books and rise with transaction volume, number of accounts, and payroll. Most Chicago small businesses land between $700 and $1,450 a month. You receive an exact number in writing before any work begins.
- What do the monthly packages include?
- Each package combines monthly bookkeeping and reconciliation with a report pack on a fixed schedule. Larger packages add payables and receivables tracking, payroll recording, multi-entity support, and scheduled review calls. Every package is month to month, with the fee agreed in writing before the first month.
- What does catch-up work cost if I am behind?
- Catch-up is quoted separately from ongoing bookkeeping because it is a repair job, not late monthly work. Six to twelve months behind typically runs $950 to $2,500 depending on volume and record condition. We review your records first and give you a fixed number before starting — the quote does not change mid-project.
- Why might my final price differ from the advertised starting price?
- Starting prices assume a typical scope. Your written quote reflects your actual transaction volume, account count, record condition, reporting frequency, and any added work like payables or payroll. The starting price is real — simpler books genuinely start there — but we confirm your number in writing before you commit to anything.
Next step
Tell us how your books look right now
A short intake — software, volume, how far behind you are, if at all. You get a written flat-fee quote back, and we reply to every message within one business day.