Tax Planning for Independent Contract Pilots | Aspen River Financial
Pilot cap, wings and epaulettes
Tax planning & preparation for contract pilots

Keep the turbulence in the air. Not in your taxes.

Fly the trip. Send the invoice. Get paid. Then come the quarterly estimates, payroll questions and operators who reimburse expenses three different ways. We put a year-round tax plan behind your contract flying.

Kia Smith, CPA, EA| Free 15-minute fit call| No documents. No pressure.

More contract work. More tax guesswork?

01

Quarterly taxes feel like a guess.

You're sending money. You're just not sure it's the right amount.

02

The state-tax question never feels settled.

You work across state lines. Which returns actually belong in your tax plan?

03

Your S corp came with homework.

Salary, distributions, payroll. Is someone checking how it all fits?

04

You get a return, but not much of a plan.

You want advice before the year ends, not a recap after it.

You already have recurrent training. You don't need a second specialty in tax law.

Kia Smith
Hi there!

Meet Kia

Kia Smith, CPA, EA and Certified Money Coach.

I'm the owner of Aspen River Financial. I help connect your income, payroll and tax planning so you know what needs attention — and when.

We help establish a usable system and provide the tax and payroll support agreed in your engagement.

You do not need a second career in Accounting and Tax.

Track It × Structure It × Plan It × Prepare It

A tax plan that keeps up with your flight schedule.

01

Structure It.

Make the business fit the work.

We review the setup behind your contract income:

  • Whether an S corporation makes sense
  • Salary, distributions and health insurance
  • Payroll setup and support on your platform

Your buddy's setup is a conversation starter. Not a tax plan.

02

Track It.

Get the numbers on the same page.

We help establish a practical system for:

  • Operator payments, invoices and 1099s
  • Expenses, receipts and reimbursements
  • Trip records and state work activity

Your camera roll should not be your accounting system.

03

Plan It.

Monthly or quarterly. Not just annually.

On your agreed planning schedule, we review:

  • Income changes and estimated payments
  • W-2 income and retirement contributions
  • State questions and year-end decisions

An extra busy month should update your tax plan, not ambush it.

04

Prepare It.

Finish with the returns, not a surprise.

We prepare the filings included in your engagement:

  • Your individual income tax return
  • Schedule C or your business return
  • Applicable state and nonresident returns

Tax season becomes the reporting stage. Not the opening investigation.

You cross state lines. Your tax plan needs more than a map.

Where you live, where you work and how you're paid all belong in the review. We sort through the facts before deciding which state filings are needed.

Flight logs, schedules and invoices can help document the year. They support the review; they are not an automatic tax-allocation formula.

Your residency and actual work locations
Employment versus independent contract arrangements
Individual and business filing requirements
State estimates and applicable credits

Hotel points: easy to count. State obligations: worth checking.

Making good money shouldn't mean guessing what you can keep.

Let's talk about your current setup and whether more proactive tax help makes sense.

Talk With Kia — Book a 15-Minute Fit Call →

The tax details that don't come with the day rate.

W-2 + Contract Flying

Two income streams. One overall tax picture.

We coordinate withholding, business income and retirement contributions instead of treating your side flying as an afterthought.

Travel & Reimbursements

Operator paid it? You paid it? Reimbursed three weeks later?

We help sort out the records, tax-home questions and potential deductions.

Training & Professional Expenses

Recurrent training, type-rating costs, insurance and equipment deserve a review.

Not an automatic yes, an automatic no, or a guess from the crew lounge.

What working together looks like.

1

Talk

A 15-minute conversation about your contract work, current setup and questions.

2

Review

After agreeing on scope, we review the relevant returns, records and business arrangements.

3

Plan

What needs to happen, who handles it and when.

4

Stay involved

Monthly or quarterly planning, payroll support and tax preparation, as agreed.

A few questions before we talk.

Still unsure? Book a fit call →
Who is this service for? +

Independent corporate and charter pilots with meaningful contract income, including pilots who also have a W-2 job. We look at your needs and complexity, not just your aircraft type.

Do I need to receive a 1099? +

No. Our focus is your independent flying business, whether you are paid personally or through an entity. We review your work arrangement and income, not just the forms you receive.

Do I need an S corporation? +

Not automatically. We evaluate your income, compensation, costs and circumstances before recommending a structure.

Are the tax returns included? +

Yes. The individual, business and state returns listed in your ongoing engagement are included. Additional filings or prior-year corrections are scoped separately before work begins.

Can you help with payroll and bookkeeping? +

We can help with payroll on your platform. You or your bookkeeper handle day-to-day records. We agree on the support included so nobody accidentally signs up for another full-time job.

What if I already have a CPA? +

We can discuss a combined planning-and-preparation relationship or, where appropriate, separate planning support. The first call is a conversation, not a commitment to switch.

Is this aircraft-owner or charter-operator tax advice? +

This service focuses on the pilot's individual and contract-business taxes. Aircraft purchases, ownership structures and charter-operator tax matters need separate review.

You handle the flight plan. Let's talk about the tax plan.

Stop saving your tax questions for the month your return is due.

In 15 minutes, we'll talk about your contract income, current setup and what feels unclear. I'll explain how our services work and whether a more detailed review makes sense.

Talk With Kia — Book a 15-Minute Fit Call →

Free introductory call. No documents. No pressure. An introductory conversation, not a detailed tax review or tax-advice session.