Finding the Right Professional to Resolve 5 Years of ADHD-Related Bookkeeping Challenges

Dealing with the aftermath of five years of severe ADHD-related Bookkeeping avoidance? It’s overwhelming, and I’m unsure of what questions to ask when searching for someone to help straighten out this mess. Here’s what I’m considering:

Key Qualifications to Look For

Are there specific qualifications or educational backgrounds I should ensure a potential hire possesses?
Is it feasible to hire someone based outside of Canada?
How reliable are freelancers on platforms like Fiverr and Upwork?

I recognize that a CPA is essential for tax filing, but beyond that, I feel lost.

My Current Dilemma

My Bookkeeping situation is chaotic. I’ve been mixing business and personal finances in the same account, haven’t reconciled anything from my Airbnb endeavors (I run Airbnb Arbitrage), and lack a proper system to track different property incomes. I’ve relied on H&R Block for tax filing, which I regret deeply due to their mishandling. Unfortunately, every year I panic and end up returning to them.

I aim to re-file the last five years of taxes, but that’s a battle for another time!

Seeking Advice

I’m sorry if this inquiry seems out of place, but I’ve hit a wall with my Google searches, and while everyone claims to be an expert, the responses I receive are often automated or unhelpful.

Thank you for any guidance!

Personal Reflection

Through all this, I’m realizing my hesitation in getting help stems from embarrassment. I’m capable of fixing this with assistance, but the thought of someone seeing the chaos is daunting.

I’m incredibly grateful for the non-judgmental advice shared with me so far. Point me in the right direction, and I’m ready to move! If only I could trick my self-sabotaging brain into tackling these tasks as though they were for someone else’s benefit, I’d have fewer hurdles. If you know, you know!

It’s understandable that you’re feeling overwhelmed and unsure about where to start with cleaning up your Bookkeeping after five years of avoidance. Let’s break down the steps you can take and address your specific questions.

Qualifications to Look For

When searching for someone to assist with Bookkeeping and Accounting, here are some qualifications and aspects to consider:

Professional Credentials:
Bookkeepers typically have certifications such as Certified Bookkeeper (CB), or they might have completed Bookkeeping courses.
Accountants hold degrees in Accounting, and often have certifications such as Chartered Professional Accountant (CPA), Certified Management Accountant (CMA), or Certified General Accountant (CGA).
Experience with Small Businesses: Specifically, someone experienced with property management or Airbnb might be beneficial.
Software Expertise:
Look for someone who has experience with bookkeeping software that you plan to use, such as QuickBooks, Xero, or Wave. Proficiency in Excel is also a plus.
References and Reviews:
Ask for references from previous clients, and look for reviews online if they are available. This will help you gauge their reliability and professionalism.

Hiring Internationally

Hiring Outside of Canada: Yes, you can hire someone outside of Canada; however, be mindful of the following:
Understanding of Canadian Tax Laws: Ensure that the person is knowledgeable about Canadian tax laws if they need to provide Accounting advice or prepare taxes.
Communications: Consider time zone differences and language proficiency to ensure smooth communication.

Trustworthiness of Fiverr and Upwork

Platforms like Fiverr and Upwork can be useful tools for finding freelancers; however, exercise caution:
Check Reviews: Look at the profile reviews, ratings, and the history of completed jobs.
Detailed Proposals: Request detailed proposals for the work, including how they plan to approach your situation.
Trial Task: Consider starting with a small task to assess their work quality and reliability before committing to a larger project.

How to Move Forward

Initial Assessment:
Clearly define the scope of work: bookkeeping clean-up, system setup for future records, and possible tax re-filing.
Interview Potential Candidates:
Ask about their experience with similar cases.
Discuss their approach to organizing mixed personal and business expenses.
Assess their familiarity with Airbnb businesses.
**Non-Jud

One response

APAdmin

26 February 2025 at 2:49 PM
It’s understandable that you’re feeling overwhelmed and unsure about where to start with cleaning up your Bookkeeping after five years of avoidance. Let’s break down the steps you can take and address your specific questions.

Qualifications to Look For

When searching for someone to assist with Bookkeeping and Accounting, here are some qualifications and aspects to consider:
1. Professional Credentials:
2. Bookkeepers typically have certifications such as Certified Bookkeeper (CB), or they might have completed Bookkeeping courses.
3. Accountants hold degrees in Accounting, and often have certifications such as Chartered Professional Accountant (CPA), Certified Management Accountant (CMA), or Certified General Accountant (CGA).
4. Experience with Small Businesses: Specifically, someone experienced with property management or Airbnb might be beneficial.
5. Software Expertise:
6. Look for someone who has experience with bookkeeping software that you plan to use, such as QuickBooks, Xero, or Wave. Proficiency in Excel is also a plus.
7. References and Reviews:
8. Ask for references from previous clients, and look for reviews online if they are available. This will help you gauge their reliability and professionalism.
Hiring Internationally
- Hiring Outside of Canada: Yes, you can hire someone outside of Canada; however, be mindful of the following:
- Understanding of Canadian Tax Laws: Ensure that the person is knowledgeable about Canadian tax laws if they need to provide Accounting advice or prepare taxes.
- Communications: Consider time zone differences and language proficiency to ensure smooth communication.
Trustworthiness of Fiverr and Upwork
- Platforms like Fiverr and Upwork can be useful tools for finding freelancers; however, exercise caution:
- Check Reviews: Look at the profile reviews, ratings, and the history of completed jobs.
- Detailed Proposals: Request detailed proposals for the work, including how they plan to approach your situation.
- Trial Task: Consider starting with a small task to assess their work quality and reliability before committing to a larger project.
How to Move Forward
1. Initial Assessment:
2. Clearly define the scope of work: bookkeeping clean-up, system setup for future records, and possible tax re-filing.
3. Interview Potential Candidates:
4. Ask about their experience with similar cases.
5. Discuss their approach to organizing mixed personal and business expenses.
6. Assess their familiarity with Airbnb businesses.
7. **Non-Jud
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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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