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Farewell W-2, hello 1099

By Sunny Bonnell
Posted on 02/09/23
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Pardon our cynicism about the new year, but January 1 always comes with the same promise: “This is the year you do that thing you haven’t been able to do in past years, because reasons!” Often, that optimism ends with broken resolutions and frustration, because what motivates us isn’t strong enough to override our longstanding habits.

This brings us to a question first posed by The Clash: “Should I stay or should I go?” We’re referring to leaving the comfort of a full-time job and striking out independently as an independent contractor or freelancer. Going independent is in the air; where do you think all those workers went after they Great Resigned? They didn’t all go back into the workforce, because if they had, your local pub wouldn’t be closed Monday-Wednesday for lack of staff, and nurses wouldn’t be striking in New York. A bunch of them hung out their own shingles, and a lot more are planning to do the same: A 2021 Upwork survey found that 20% of current employees—about 10 million people—were considering the freelance life.

We get the attraction. We’ve run our branding agency Motto® going on 20 years, and we didn’t give up even back when we couldn’t get clients and had to sleep in our office. Why? Because controlling your time, and earning power and opportunities is intoxicating. You decide what you’re worth. You work where you want. You decide what values matter to you. You determine how to invest for retirement. Nobody can downsize you.

So why do so many gifted, ambitious professionals disinclined to take crap from a boss—talk yearningly about becoming indies but never pull the trigger? Entrepreneurship is hard. Freelance often equals instability, which means being unable to make a living, not having health insurance, missing office life, and not having a safety net, even if that net resembles a pair of handcuffs.

So we’re here with 6 facts about being an independent contractor that should give you a push if you’ve been standing in the doorway of the plane, so to speak, but haven’t quite been able to jump out.

Fact #1: You’re cost-effective when companies are laying people off.
As we were writing this, Microsoft announced it was laying off 5% of its workforce, the latest in a series of layoff announcements from Silicon Valley. That suggests companies all over the economy will be battening down the hatches in case of recession. But work still has to get done, so who will do it? You will. You’re less risky. You don’t get benefits, require expensive training, need office space, or force companies to pay for your worker’s comp, Social Security, or Medicare.

In fact, Hire finds that freelancers can be 20% to 30% cheaper for companies than full-time salaried staff. So as soon as you walk out of your Monday to Friday gig, there’s a good chance your now-former employer will want to contract with you to do the same work. Bingo. Instant client.

Fact #2: Non-competes may be going extinct.
In the past, employers could and did slip non-compete clauses into their employment contracts, stipulating that if you left the company, you couldn’t work for a competitor in the same industry for several years—including as a freelancer. That’s a dirty trick, and the Federal Trade Commission agrees. On January 5, the FTC proposed a new rule that would virtually ban the use of non-competes.  That’s a big deal because when you leave a company to become an indie, some of your most promising potential clients are other companies in the same line of work. You know their business, their market, their products, and maybe even their people. That’s useful for getting quick contracts so you can, you know, pay your mortgage while you’re building your portfolio. Pretty soon, if the FTC gets its way, employers won’t be able to stop you from doing that.

Fact #3: Broadband is getting faster and easier to find.
Wireless connectivity is the lifeblood of the freelance world. Whether you’re a designer, a coder, a writer, a consultant, or any one of 20 other specialties, you depend on cheap, accessible broadband to take meetings, send DMs, do research, send invoices, upload footage—pretty much everything. Plus, how will you spend a year working from the Marquesas in your converted Sprinter van and posting everything to your YouTube channel without the Internet?

Well, we have good news. The folks on the Forbes Technology Council have it. They predict that in 2023, the rollout of seventh-generation wi-fi and 5G will make the Internet much faster and bridge the digital divide. That also means you’ll need to pay greater attention to online security and privacy protection since more of your work and life will be online, but that’s a small price to pay for working from the beach, right?

Fact #4: There are some incredible software tools perfect for independents who want to run clean and stay healthy.
Once upon a time, software for indies pretty much came down to QuickBooks and…QuickBooks. Yeah. Let’s just say that now, software developers have decided there are profits to be made off helping people like us run efficiently, pay our taxes on time, stay organized, and keep minds and bodies fine-tuned. From project management to help you eat better, there are great tools everywhere.


  • Harlow, a suite of tools that lets freelancers handle everything from invoicing to proposals and contracts from one place;
  • WorkFrom, an app that lets you locate ideal worksites, whether that means a coffeehouse in a strange city to a coworking space in a strange city;
  • Calendly, an application you may already know about that’s amazingly great for scheduling everything from Zoom calls to vacations;
  • Noizio, an app that helps users design work-friendly personal soundscapes, and on and on.

Fact #5: You can outmaneuver climate change.
This one might seem like a stretch, but is it? After the devastation of atmospheric rivers in California and blizzards smashing upstate New York, where you choose to set up shop—and if that location puts you in harm’s way from fires, floods, or heat waves—have become topics worth thinking about.

When you’re bound to a company, you’re pretty much bound to a city, come literal hell or high water. But when you’re an independent contractor and floodwaters or wildfire smoke become too much to take, you can at least pack up and move somewhere safer while keeping your client base. Maybe that doesn’t seem like a big deal now, but unfortunately, it’s likely to become more and more relevant in 2023, 2024, and 2025.

Fact #6: You’re recession-proof.
No one seems to know if an economic downturn is in the cards for 2023, but if it is, you can be sure that many more people will lose their jobs as businesses slash costs. Not you. You’re immune. As a freelancer, you can do what intelligent Wall Street investors do: Diversify. Instead of depending on one employer for all your income, you can take on as many clients as you have the bandwidth. Even if a handful of your clients are hurting and don’t have work for you, some inevitably will. That evens out the income volatility of a churning economy and lets you sleep better at night.

Sunny Bonnell profile picture
By Sunny Bonnell
Founder & CEO Motto®