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Swipe Right On Your Dream Accountant

Hi! I'm Caitlin.

I'm a business strategist for creative freelancers, here to help you find a calmer & more strategic way of doing business.


Finding the right accountant for your freelance business can be almost as daunting as finding your soulmate on Tinder.

But I did, and you can do it too

(I really did meet my husband on Tinder. Not my accountant though. That would be weird.)

I know you didn’t choose entrepreneurship because you’re excited about bookkeeping or reading tax code changes for fun. 

That’s what you need a tax pro for: keeping you on the IRS’ “nice” list, helping to maximize your return (or minimize what you owe), and guiding you out of trouble if you’ve f’ed up in the past (I’ve been there!). 

They can also advise on questions such as “Should I file as an LLC or Scorp”,  “What estimated taxes should I be paying” and “Help, I’ve made a disaster of my bookkeeping and I don’t know what to do.”

In my search for The One, I swiped left on…

…H&R Block. It was so expensive and impersonal that I left in tears.

…A little old lady with a little old dog to match. Her living room displayed copious amounts of doilies and doubled as her office. She shamed me for running behind on my tax payments instead of educating or supporting me.

…A local guy who filed my taxes late and didn’t tell me. When I got a letter stating I owed a $60 penalty I was pissed.

Then I met Lynn, the accountant of my dreams. She taught me so much about how freelance taxes work, patiently answered all of my questions, and double checked everything with me to make sure it was correct. I bought her wine last year. Good stuff. Two bottles. 

My years of searching taught me that I need an accountant who:

  1. Explains things clearly and takes the time to make sure I understand.
  2. Is willing to answer questions throughout the year as they come up. (It’s so much easier to do things correctly the first time than try to fix mistakes a year later!)
  3. Asks clarifying questions that show they understand my business and don’t just put my return through on auto pilot.
  4. Doesn’t cut corners. I’m a risk averse person. I like rules, structure, and not getting audited. (Some tax professionals are more flexible than others.)
  5. Has rates that fit the budget of my teeny-tiny microbusiness.

You’ll have your own unique non-negotiables, but outlining what you need from an accountant before booking that appointment will save you time, money, and frustration.

Finding The Accountant of Your Dreams:

Do you need an Accountant or CPA? (Also, what’s a CPA?)

All CPA’s are accountants, but not all accountants are CPA’s. CPA stands for “Certified Public Accountant” and designates someone who pursued specialized education and passed the state CPA exam.

CPA is a state license that must be renewed annually and requires continuing education.

Non-licensed accountants must register for a Preparer Tax ID Number with the IRS in order to file your taxes, but if the IRS audits you, they are not allowed to represent you in the process like a CPA could.

You may pay a bit more for someone with a CPA license, just make sure the tradeoff is one you’re comfortable with.

Where To Find An Accountant

The internet can be your best friend or worst enemy when it comes to finding your person. While I personally love that I don’t have to lug out the yellow pages or even make phone calls to inquire about accounting services any more, searching online can be incredibly overwhelming. Here are a few places to look first.

  • Check out these hashtags on Instagram #(yourstate)accountant #freelanceaccountant #accountantforcreatives #smallbizaccountant
  • Ask your sole proprietor or single owner LLC  friends. Personal references are some of the strongest, and if your other entrepreneurial friends have someone they love, it might be a match made in heaven.
  • Search “small business accountant” on Google Maps to find someone local.
  • If you use bookkeeping software like Quickbooks or Wave, many now have features built in that help you find an accountant.
  • Your states CPA organization
  • The IRS’ directory
  • If you have a spouse or family member working in corporate, they may have access to something called an “Employee Assistance Program”, which offers consultations for financial services (among many other things!)

Pro tip: Look specifically for a tax professional who is a solo practitioner or works for a small firm. You can build rapport with any accountant, but often solo practitioners have a better understanding of what your needs are as an entrepreneur, because they’re entrepreneurs too.

Questions to Ask Before Hiring An Accountant

If you’re prone to first date nerves, let me be your wing-woman. Here’s a cheat sheet of talking points.

First, share a little about yourself. You’re a small business owner, a sole proprietor or LLC, based in (location), and you do (insert products or services here.)

Then, let them know what you’re looking for: You’re looking for an (accountant / bookkeeper / CPA) that (insert your non negotiables) and you have a few questions to see if you’re a good fit.

You’re doing great. Now ask about them

  1. Are you taking new clients right now?
  2. Do you have any specialties?
  3. Are you a CPA?
  4. What is your rate?
  5. Do you have a process for consultations or quick questions through the year?
  6. What is the best way to contact you and send you documents? (they should have an online portal for your sensitive documents!)
  7. What can I do to help keep fees low?
  8. How early should I send you my annual tax documents?
  9. Do you have a checklist or something to help make sure I send everything?
  10. Have you ever had a client get audited? Can you help me if I get audited?

How to Choose The One

Everything is going well, and you’re wondering if it’s time to get serious. 

  • Do you like them? Your accountant should set you at ease and build a natural rapport. Taxes are already frustrating enough, you need someone who makes the process easier not harder.

  • Are they responsive? How quickly do they get back to you when you reach out to them or do you have to send follow up inquiries to get answers to your questions?

  • Is this someone you want to build a long term business relationship with?

  • Do they have reviews or references? What are the themes their clients bring up about their experiences?

  • Are they local? Make sure they’re familiar with your state specific tax laws.

  • Check their credentials. Your accountant will be dealing with a lot of your personal information, so it’s wise to check their credentials before you begin work. Every accountant using the CPA title is required to keep their license up to date. You can look up a CPA’s name online through your state’s accountancy board to make sure their license is still active. Look them up on the Better Business Bureau and using this tool on the IRS website.

If you need an accountant, don’t wait!

Accountants are humans who get slammed during tax season. Contacting them early – better yet, off season – is the best way to get their full attention. 

Check out these Cool AF Accountants:

*Pssst! I follow all of these people and think they are pretty cool. But please do your own homework before hiring!


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Hi! I'm Caitlin.

Hi! I'm Caitlin.

I’m a business strategist for creative freelancers.

I'm here to help you escape the trap of "hustle culture" and find a calmer, more strategic way of doing business.