Top 3 Things I Wish I Knew When I Started Working as a 1099 Contractor

At Handmade our crafty professors are 1099 Contractors and it is important to me that they don’t have any surprises at tax time like I did my first year as a contractor.

When I first dipped my toes into the world of 1099 contracting, I thought I had it all figured out—freedom, flexibility, and finally getting paid what I was worth. But babyyyy, let me tell you—there were some behind-the-scenes truths I wish someone had sat me down and said “Sis, know this before you start!”

So if you’re new to the game (or thinking about making the leap), here are the top three things I wish I knew before I started signing contracts and submitting invoices.

1. You Have to Pay Estimated Taxes—Quarterly, Not Just at Tax Time

Let’s start with the big one. When you’re self-employed, no one’s taking taxes out of your paycheck for you. That means Uncle Sam still wants his cut—but it’s up to you to set it aside and pay it.

And not just once a year—every quarter.

I learned the hard way (read: a big, ugly tax bill + penalties) that the IRS expects estimated tax payments in April, June, September, and January. If you skip ’em or pay late, there’s a fee waiting with your name on it.

Pro Tip: Set aside at least 25-30% of every payment you receive into a separate savings account just for taxes. Use IRS Form 1040-ES or a good tax prep software to stay on track.

2. You Can’t Be Forced to Work Specific Hours—You’re Not an Employee

One of the biggest perks of being a 1099 contractor is control over your schedule. You are your own boss. So if a client is trying to tell you, “You must be available from 9 to 5,” that’s a red flag.

Legally, a client can request deadlines, deliverables, and quality—but they can’t treat you like an employee by controlling how or when you work. That’s the difference between a W-2 employee and a 1099 contractor.

Pro Tip: Set boundaries early. Be crystal clear in your contract about your availability and communication hours. If a client wants more control, that’s a conversation (and possibly a different type of contract).

3. Contracts Are Not Optional—They’re Your Safety Net

In the beginning, I took jobs on good faith—just a handshake and a few emails. Never again.

As a 1099 contractor, you need a contract for every project. Not only to protect your payment, but to outline your scope of work, payment terms, delivery timelines, and revision limits. A clear contract prevents confusion and protects both parties if things go left.

Pro Tip: Keep a simple contract template on hand. There are great tools like HelloSign or PandaDoc that let you send and sign contracts digitally in minutes. Also, don’t be afraid to walk away from clients who resist putting things in writing. That’s a red flag, too.

Final Thoughts: Know Your Worth, Know Your Role

Being a 1099 contractor is powerful—but it’s also a responsibility. You’re running a business, even if it’s just you. So treat yourself like a business from day one.

Get clear on taxes. Set healthy boundaries. And never start without a contract.

It’s not just about getting the gig—it’s about protecting your time, energy, and coin.

Now that you know better, you can do better. Go build the business you deserve—on your terms.

Stay Crafty,

Cheri