Wingspan Authors

Lee @ Wingspan

For Contractors

Why Location Matters for Freelancers Working In These States

Some states are not like the others.

For Contractors

What Freelancers Need to Know About State Contracting Laws

Let’s learn the basics.

For Contractors

How Occupational Accident Insurance (OAI) Can Protect You

Expect the unexpected.

For Contractors

When Are Estimated Taxes Due in 2026?

The next payment is due sooner than you might think.

Why Contractors Will Be Essential to Your Company in 2026

These highly skilled professionals are the future of the modern workforce.

For Contractors

Why Contract Work Is Perfect for This Moment

Your next side hustle could start today.

For Contractors

Got Questions About Your 1099? We’ve Got Answers.

There are no dumb questions here.

For Contractors

The 1099 Checklist You Need for Tax Season

‘Tis the season.

For Contractors

This Is How to Get Your Small Business Ready for 2026

It’s time to separate your business and personal bank accounts.

For Contractors

Confused About Your Freelance Taxes? Start Here.

Yeah, it’s tax time already. Again.

For Contractors

What Contractors Need to Know About the 1099-K

Heads up: the reporting threshold is changing for 2025 and 2026.

For Contractors

How New Changes to the 1099-NEC Will Affect Contractors

Are you a contractor earning more than $600 per year? This affects you.

These Are the Biggest 1099-NEC Filing Challenges (And How to Solve Them)

Hint: the solution involves automation.

For Contractors

Why Liability Insurance Is Worth Buying for Claims Adjusters

It’s always good to have back-up.

For Contractors

Why Contractors Should Consider Accident Insurance

Reason #1: Occupational Accident Insurance can reimburse lost income