How to Find the Right Professional to Tackle My Five-Year ADHD Bookkeeping Neglect

I’ve found myself in a predicament with my Bookkeeping due to severe ADHD, resulting in five years of avoidance. Now, I’m seeking someone to help clear up this mess, but I’m unsure of what to look for or ask during this process.

Key Considerations

Qualifications and Education:
What specific credentials or educational background should I focus on when selecting a Bookkeeping professional?

International Hiring:
Is it advisable or permissible to engage someone from outside of Canada?

Online Platforms:
Are freelancers on platforms like Fiverr and Upwork typically reliable for such tasks?

While I am aware that employing a CPA is essential for filing taxes, I’m at a loss for all other aspects of managing this situation. I’ve mixed business and personal funds, failed to reconcile Airbnb accounts (as I operate an Airbnb Arbitrage business), and lack a system for tracking income across various properties. Furthermore, my decision to use H&R Block for tax filings has not served me well and I regret that choice deeply. I panicked and turned to them, thinking it was my only option.

I also hope to re-file my taxes for the past five years, but I’ll address that once I’ve handled this initial challenge.

Apologies if this inquiry feels out of place, but I’ve exhausted search engines, and while many people appear to be experts, the responses I receive are lackluster or automated.

Thank you for your patience and understanding!

Edited to Add:
I’ve realized my procrastination stems partly from embarrassment. The thought of exposing my disorganized records to someone else is daunting, even though I know I’m capable of managing it. I appreciate any non-judgmental advice—just point me in the right direction, and I’ll follow it. If I could trick my self-sabotaging mind into believing this effort benefits someone else, perhaps it would be easier to tackle. If you know, you know.

Finding the right person to help you organize and rectify your Bookkeeping situation is a great step toward gaining control over your financial affairs. Here’s a comprehensive guide to help you navigate this process:

Qualifications to Look For

Educational Background:
A degree in Accounting or finance can be a strong indicator of a professional’s ability to handle Bookkeeping tasks.
Certifications:
CPA (Certified Public Accountant): Although more relevant for tax filing and complex financial advice, a CPA may still have the skills needed for thorough Bookkeeping.
CB (Certified Bookkeeper): This certification, offered by organizations like the American Institute of Professional Bookkeepers, shows that the individual has met a national standard.
Experience:
Previous experience with small business bookkeeping, especially in hospitality or real estate (like Airbnb arbitrage), could be highly beneficial.
An understanding of Canadian tax laws if you’re looking to re-file your taxes, although this might require a tax specialist eventually.

Hiring Considerations

Can I hire someone outside of Canada?

Yes, but be aware of the implications:
You may face challenges related to understanding specific Canadian tax regulations and compliance requirements. If you choose to hire someone outside Canada, ensure they are familiar with Canadian laws or limit their work to organizing your records.

Trustworthiness of Online Platforms (Fiverr, Upwork)

Reputation: On platforms like Fiverr and Upwork, always check the provider’s reviews and ratings.
Portfolio: Review their portfolio and past work examples to ensure they have handled similar tasks.
Trial Assignment: Consider giving a small task to assess their capabilities before committing to bigger assignments.

Steps to Take

Initial Assessment:
Ask for a consultation to discuss your needs. See if they offer an assessment period to evaluate your current situation.
Communication:
Open and clear communication is key. Ensure they understand your unique business, particularly the mix of personal and business accounts.
Bookkeeping System Setup:
Discuss what bookkeeping software you could use (e.g., QuickBooks, Xero) to keep track of income and expenses systematically.
You might benefit from a more defined system for reconciling Airbnb income, categorizing expenses, and setting up accounts separated for personal and business use.
Reconciliation and Cleanup:
Plan

One response

APAdmin

25 February 2025 at 8:14 PM
Finding the right person to help you organize and rectify your Bookkeeping situation is a great step toward gaining control over your financial affairs. Here’s a comprehensive guide to help you navigate this process:

Qualifications to Look For
1. Educational Background:
2. A degree in Accounting or finance can be a strong indicator of a professional’s ability to handle Bookkeeping tasks.
3. Certifications:
4. CPA (Certified Public Accountant): Although more relevant for tax filing and complex financial advice, a CPA may still have the skills needed for thorough Bookkeeping.
5. CB (Certified Bookkeeper): This certification, offered by organizations like the American Institute of Professional Bookkeepers, shows that the individual has met a national standard.
6. Experience:
7. Previous experience with small business bookkeeping, especially in hospitality or real estate (like Airbnb arbitrage), could be highly beneficial.
8. An understanding of Canadian tax laws if you’re looking to re-file your taxes, although this might require a tax specialist eventually.
Hiring Considerations

Can I hire someone outside of Canada?
- Yes, but be aware of the implications:
- You may face challenges related to understanding specific Canadian tax regulations and compliance requirements. If you choose to hire someone outside Canada, ensure they are familiar with Canadian laws or limit their work to organizing your records.
Trustworthiness of Online Platforms (Fiverr, Upwork)
- Reputation: On platforms like Fiverr and Upwork, always check the provider’s reviews and ratings.
- Portfolio: Review their portfolio and past work examples to ensure they have handled similar tasks.
- Trial Assignment: Consider giving a small task to assess their capabilities before committing to bigger assignments.
Steps to Take
1. Initial Assessment:
  Ask for a consultation to discuss your needs. See if they offer an assessment period to evaluate your current situation.
2. Communication:
  Open and clear communication is key. Ensure they understand your unique business, particularly the mix of personal and business accounts.
3. Bookkeeping System Setup:
4. Discuss what bookkeeping software you could use (e.g., QuickBooks, Xero) to keep track of income and expenses systematically.
5. You might benefit from a more defined system for reconciling Airbnb income, categorizing expenses, and setting up accounts separated for personal and business use.
6. Reconciliation and Cleanup:
  Plan
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What should I expect/look for when finding someone to rectify my 5yrs of severe adhd bookkeeping avoidance?

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