Wellness + Write-Offs: The Business Owner’s Guide + Tax Documentation Toolkit
You spend thousands on your health and wellness. But do you actually know which expenses could potentially be part of your tax strategy?
Botox. Massage. Red light therapy. Sauna. Therapy. Acupuncture. Nutrition. Fitness. Medical devices.
You’ve probably seen someone on Instagram tell you to “just write it off.”
And you’ve probably had someone else tell you absolutely none of it is deductible.
The real answer? It depends.
Your business structure matters. The purpose of the expense matters. Medical necessity can matter. How the expense is paid or reimbursed matters.
And documentation REALLY matters.
Wellness + Write-Offs was created to help business owners understand how wellness, self-care, health benefits, and tax strategy can intersect—without relying on sketchy internet tax advice.
This isn't a list of magical deductions.
It's a framework for figuring out what may apply to YOU, how to structure it, and what documentation you may need to back it up.
The guide is intentionally compliance-first: Kym explains that wellness expenses aren't automatically deductible and that the facts, structure, use, and supporting documentation have to be evaluated. ADS - Wellness + Write-offs E-B…
HERE’S WHAT YOU’LL LEARN
How to look at wellness expenses through a tax-strategy lens
Learn the questions that should be asked before assuming an expense is—or isn't—part of a legitimate strategy.
Which wellness categories may intersect with business or medical use
The guide explores areas including wellness and body maintenance, mental health and stress management, appearance and aesthetics, fitness and physical conditioning, and other wellness-related expenses where context matters. ADS - Wellness + Write-offs E-B…
Why some wellness strategies fall apart
No clear business explanation. Mixed personal and business use. No written justification. Inconsistent treatment. No documentation.
Because “everyone else is doing it” is not a tax strategy.
How medical intent changes the conversation
Learn how diagnosed conditions, provider-directed care, medical necessity, Letters of Medical Necessity, receipts, EOBs, treatment records, and outcomes tracking can become important pieces of substantiating an expense.
Why your business structure matters
A sole proprietor, S-Corp owner, C-Corp owner, and employer offering benefits don't necessarily play by the same rules.
The included toolkit specifically walks through considerations for HSA, FSA, HRA, MERP, ICHRA and QSEHRA arrangements, as well as special considerations for 2%+ S-Corp shareholders.
How to create a paper trail BEFORE you need one
Because the time to figure out why you claimed something isn't when someone asks you to prove it.
BUT THIS ISN’T JUST AN EBOOK.
You also get the Wellness + Write-Offs Template Bundle.
This is where you go from:
“Wait…could I potentially do this?”
to:
“Okay. What do I actually need to document?”
The included toolkit is designed to help you organize the strategy, supporting documentation, provider information, expenses, reimbursements, and outcomes that may be relevant to your situation.
YOUR DOWNLOAD INCLUDES:
WELLNESS BENEFITS STRATEGY MAP
Map out your entity type, health coverage, potential benefit structure, eligibility, implementation steps, documentation requirements, and advisor review in one place.
ELIGIBLE WELLNESS EXPENSES CHEAT SHEET
Evaluate expenses such as therapeutic Botox, red light therapy, sauna, medically directed massage, PEMF therapy, nutrition counseling, medically directed fitness, acupuncture, mental health care, sleep care, orthotics, diagnostics, OTC medications, supplements, and vision care.
You'll also have space to identify which plan may apply, whether an LMN may be needed, and what proof should be retained.
LETTER OF MEDICAL NECESSITY TEMPLATE
A structured LMN template your medical provider can complete when appropriate, including:
Diagnosis and ICD-10 information
Treatment, device, or service
Clinical rationale
Previous treatments
Expected outcomes
Frequency and duration
Provider attestation
Renewal dates
Supporting documentation
TREATMENT PLAN + OUTCOMES TRACKER
Track baseline metrics, frequency of treatment, adherence, results, side effects, and 30/60/90-day checkpoints.
Because buying something and calling it “medical” isn't documentation.
EXPENSE + SUBSTANTIATION LOG
Keep wellness-related purchases and their supporting evidence organized in one place.
Track receipts, EOBs, LMNs, plan type, reimbursement status, payment method, documentation, and other supporting records so you aren't trying to reconstruct everything months later. ADS - Wellness + Write-offs E-B…
REIMBURSEMENT CLAIM FORM
A structured claim form for MERP/HRA arrangements that helps organize eligible expenses, receipts, EOBs, LMNs, supporting documentation, reimbursement requests, and administrative approval.
MERP / ICHRA SETUP CHECKLIST
For business owners exploring employer-sponsored reimbursement strategies, this checklist covers areas including:
Eligibility
Employee classes
Allowances
Plan documents
Notices
Substantiation
Nondiscrimination considerations
Administration
Privacy
Payroll mapping
Reimbursements
Renewals
S-CORP OWNER HEALTH BENEFIT PLAYBOOK
S-Corp owners have additional rules to think about.
This section helps you organize the questions surrounding 2%+ shareholder treatment, W-2 reporting, owner versus employee benefits, reimbursement arrangements, substantiation, and when alternative structures may warrant discussion with your professional advisors. ADS - Wellness + Write-offs E-B…
PROVIDER VISIT PREP + DOCUMENTATION PACK
Walk into your provider appointment prepared.
Track symptoms, functional impact, previous treatments, questions for your provider, treatment recommendations, supporting documentation, and—when appropriate—the information needed to request a Letter of Medical Necessity. ADS - Wellness + Write-offs E-B…
THIS IS FOR YOU IF…
You're a business owner who spends money on your health, wellness, appearance, or performance and keeps wondering:
“Can I write this off?”
“Is this actually legal?”
“Why did my CPA immediately tell me no?”
“Does medical necessity change anything?”
“What's an LMN and when would I need one?”
“Does being an S-Corp change this?”
“How the hell am I supposed to document all of this?”
Or maybe you already heard about one of these strategies online—but you'd rather understand the rules before throwing random expenses onto your P&L and hoping for the best.
This was made for you.
THIS IS NOT A “WRITE OFF EVERYTHING” GUIDE.
And that's exactly the point. Wellness strategy is not one-size-fits-all.
Whether an expense qualifies can depend on your entity, plan structure, type of work, medical circumstances, use of the expense, and supporting documentation. The guide repeatedly emphasizes that different entrepreneurs can have completely different outcomes based on their facts. ADS - Wellness + Write-offs E-B…
The goal isn't to get more aggressive.
The goal is to get more strategic.
Do the strategy. Document the strategy. Be able to explain the strategy.
MEET KYM
Kym Brake is a tax strategist and founder of OC Tax Brake with a BA in Accounting, an LLM in Tax Law, and more than 20 years of experience in the tax industry. ADS - Wellness + Write-offs E-B…
Her entire approach to tax strategy is built around one idea:
Stop waiting until tax season to find out what already happened.
Understand the rules. Plan ahead. Keep the documentation. And make smarter decisions while you can still do something about them.
No TikTok tax bullshit. No magical loopholes.
Just tax strategy explained like you're a normal human being.
STOP GUESSING ABOUT YOUR WELLNESS EXPENSES.
You already spend the money.
Now learn how to evaluate those expenses properly, understand what may apply to your situation, and build the documentation to support the strategies you implement.
GET WELLNESS + WRITE-OFFS
Instant digital download.
This product is for educational purposes only and is not legal, financial, medical, or tax advice. Eligibility, deductibility, reimbursement, and tax treatment depend on your individual circumstances, plan documents, entity structure, applicable law, and current regulations. Consult the appropriate tax, legal, benefits, and/or medical professionals before implementing any strategy
You spend thousands on your health and wellness. But do you actually know which expenses could potentially be part of your tax strategy?
Botox. Massage. Red light therapy. Sauna. Therapy. Acupuncture. Nutrition. Fitness. Medical devices.
You’ve probably seen someone on Instagram tell you to “just write it off.”
And you’ve probably had someone else tell you absolutely none of it is deductible.
The real answer? It depends.
Your business structure matters. The purpose of the expense matters. Medical necessity can matter. How the expense is paid or reimbursed matters.
And documentation REALLY matters.
Wellness + Write-Offs was created to help business owners understand how wellness, self-care, health benefits, and tax strategy can intersect—without relying on sketchy internet tax advice.
This isn't a list of magical deductions.
It's a framework for figuring out what may apply to YOU, how to structure it, and what documentation you may need to back it up.
The guide is intentionally compliance-first: Kym explains that wellness expenses aren't automatically deductible and that the facts, structure, use, and supporting documentation have to be evaluated. ADS - Wellness + Write-offs E-B…
HERE’S WHAT YOU’LL LEARN
How to look at wellness expenses through a tax-strategy lens
Learn the questions that should be asked before assuming an expense is—or isn't—part of a legitimate strategy.
Which wellness categories may intersect with business or medical use
The guide explores areas including wellness and body maintenance, mental health and stress management, appearance and aesthetics, fitness and physical conditioning, and other wellness-related expenses where context matters. ADS - Wellness + Write-offs E-B…
Why some wellness strategies fall apart
No clear business explanation. Mixed personal and business use. No written justification. Inconsistent treatment. No documentation.
Because “everyone else is doing it” is not a tax strategy.
How medical intent changes the conversation
Learn how diagnosed conditions, provider-directed care, medical necessity, Letters of Medical Necessity, receipts, EOBs, treatment records, and outcomes tracking can become important pieces of substantiating an expense.
Why your business structure matters
A sole proprietor, S-Corp owner, C-Corp owner, and employer offering benefits don't necessarily play by the same rules.
The included toolkit specifically walks through considerations for HSA, FSA, HRA, MERP, ICHRA and QSEHRA arrangements, as well as special considerations for 2%+ S-Corp shareholders.
How to create a paper trail BEFORE you need one
Because the time to figure out why you claimed something isn't when someone asks you to prove it.
BUT THIS ISN’T JUST AN EBOOK.
You also get the Wellness + Write-Offs Template Bundle.
This is where you go from:
“Wait…could I potentially do this?”
to:
“Okay. What do I actually need to document?”
The included toolkit is designed to help you organize the strategy, supporting documentation, provider information, expenses, reimbursements, and outcomes that may be relevant to your situation.
YOUR DOWNLOAD INCLUDES:
WELLNESS BENEFITS STRATEGY MAP
Map out your entity type, health coverage, potential benefit structure, eligibility, implementation steps, documentation requirements, and advisor review in one place.
ELIGIBLE WELLNESS EXPENSES CHEAT SHEET
Evaluate expenses such as therapeutic Botox, red light therapy, sauna, medically directed massage, PEMF therapy, nutrition counseling, medically directed fitness, acupuncture, mental health care, sleep care, orthotics, diagnostics, OTC medications, supplements, and vision care.
You'll also have space to identify which plan may apply, whether an LMN may be needed, and what proof should be retained.
LETTER OF MEDICAL NECESSITY TEMPLATE
A structured LMN template your medical provider can complete when appropriate, including:
Diagnosis and ICD-10 information
Treatment, device, or service
Clinical rationale
Previous treatments
Expected outcomes
Frequency and duration
Provider attestation
Renewal dates
Supporting documentation
TREATMENT PLAN + OUTCOMES TRACKER
Track baseline metrics, frequency of treatment, adherence, results, side effects, and 30/60/90-day checkpoints.
Because buying something and calling it “medical” isn't documentation.
EXPENSE + SUBSTANTIATION LOG
Keep wellness-related purchases and their supporting evidence organized in one place.
Track receipts, EOBs, LMNs, plan type, reimbursement status, payment method, documentation, and other supporting records so you aren't trying to reconstruct everything months later. ADS - Wellness + Write-offs E-B…
REIMBURSEMENT CLAIM FORM
A structured claim form for MERP/HRA arrangements that helps organize eligible expenses, receipts, EOBs, LMNs, supporting documentation, reimbursement requests, and administrative approval.
MERP / ICHRA SETUP CHECKLIST
For business owners exploring employer-sponsored reimbursement strategies, this checklist covers areas including:
Eligibility
Employee classes
Allowances
Plan documents
Notices
Substantiation
Nondiscrimination considerations
Administration
Privacy
Payroll mapping
Reimbursements
Renewals
S-CORP OWNER HEALTH BENEFIT PLAYBOOK
S-Corp owners have additional rules to think about.
This section helps you organize the questions surrounding 2%+ shareholder treatment, W-2 reporting, owner versus employee benefits, reimbursement arrangements, substantiation, and when alternative structures may warrant discussion with your professional advisors. ADS - Wellness + Write-offs E-B…
PROVIDER VISIT PREP + DOCUMENTATION PACK
Walk into your provider appointment prepared.
Track symptoms, functional impact, previous treatments, questions for your provider, treatment recommendations, supporting documentation, and—when appropriate—the information needed to request a Letter of Medical Necessity. ADS - Wellness + Write-offs E-B…
THIS IS FOR YOU IF…
You're a business owner who spends money on your health, wellness, appearance, or performance and keeps wondering:
“Can I write this off?”
“Is this actually legal?”
“Why did my CPA immediately tell me no?”
“Does medical necessity change anything?”
“What's an LMN and when would I need one?”
“Does being an S-Corp change this?”
“How the hell am I supposed to document all of this?”
Or maybe you already heard about one of these strategies online—but you'd rather understand the rules before throwing random expenses onto your P&L and hoping for the best.
This was made for you.
THIS IS NOT A “WRITE OFF EVERYTHING” GUIDE.
And that's exactly the point. Wellness strategy is not one-size-fits-all.
Whether an expense qualifies can depend on your entity, plan structure, type of work, medical circumstances, use of the expense, and supporting documentation. The guide repeatedly emphasizes that different entrepreneurs can have completely different outcomes based on their facts. ADS - Wellness + Write-offs E-B…
The goal isn't to get more aggressive.
The goal is to get more strategic.
Do the strategy. Document the strategy. Be able to explain the strategy.
MEET KYM
Kym Brake is a tax strategist and founder of OC Tax Brake with a BA in Accounting, an LLM in Tax Law, and more than 20 years of experience in the tax industry. ADS - Wellness + Write-offs E-B…
Her entire approach to tax strategy is built around one idea:
Stop waiting until tax season to find out what already happened.
Understand the rules. Plan ahead. Keep the documentation. And make smarter decisions while you can still do something about them.
No TikTok tax bullshit. No magical loopholes.
Just tax strategy explained like you're a normal human being.
STOP GUESSING ABOUT YOUR WELLNESS EXPENSES.
You already spend the money.
Now learn how to evaluate those expenses properly, understand what may apply to your situation, and build the documentation to support the strategies you implement.
GET WELLNESS + WRITE-OFFS
Instant digital download.
This product is for educational purposes only and is not legal, financial, medical, or tax advice. Eligibility, deductibility, reimbursement, and tax treatment depend on your individual circumstances, plan documents, entity structure, applicable law, and current regulations. Consult the appropriate tax, legal, benefits, and/or medical professionals before implementing any strategy