The Great American Gig Shift: More Money. Fewer Hours. Better Life?

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Most mornings, Dave DeNard rolls out of bed around 9:00 am. He makes his coffee, scrolls social media, and then heads outside for a walk with his two beagles, Ruby and Nova. By 10:00(ish), he’s at his desk, ready to start his 4-hour work day. By many definitions, he’s retired. And he’s only 31.

“Working a 9-to-5 isn’t going to buy me a house and two cars, and support a few kids,” he says. ”Those days are long gone, unfortunately. Past generations could buy a home with a minimum wage job. My generation can’t afford rent.” 

So he decided to do things differently — by being his own boss.

According to our recent survey, DeNard isn’t alone. 43% of multi-job Americans say they’re working fewer hours and making more money than if they only had a single salaried job. If you look at Gen Z and millennials, that number is even higher, at 49%. 

In DeNard’s case, he’s earning more income selling his crafts on Etsy and coaching other Etsy sellers than he ever hoped to earn as a traditional W-2 employee. 

And while not everyone’s doing as well as DeNard, there’s a broader trend toward independent work that’s clearly on the upswing. According to a recent McKinsey survey, 36% of employed Americans now identify as independent workers. In 2016, that number was only 27%.

Could the gig economy be the next great land of opportunity?

When corporate salaries just aren’t enough

There’s no denying that economic pressure in the U.S. continues to rise. The median price of a single-family home in comparison to median household income is higher than at any point since the early 70’s. Health insurance premiums have increased 55% over the last decade. And let’s not get started on the price of groceries.

The result? According to a recent MarketWatch survey, 66% of Americans are living month to month, unable to save for the future or even for potential emergencies. 

Our survey backs this up. 39% of Americans with more than one job say they weren’t making enough money to meet their needs with a single income stream. And when we asked people why they started their side gig, 40% said they simply started it to pay for holiday gifts and expenses.

As concerning as that is, by adding a second income stream, 72% of our survey respondents say they feel more financially secure and 67% feel less stressed financially.

Not only that, they seem to be happier, too. 72% of multi-job Americans say they enjoy working for themselves rather than a corporation. And 66% say they are happier having multiple jobs than focusing all their energy into just one.

Gen Z and millennials want to do more of what they love

What arose from necessity for many Americans seems to be driving new opportunities for Gen Z and millennials. For them, moving away from single-salaried jobs is often more about pursuing goals than paying bills.

In fact, while 49% of our Boomer respondents said they weren’t making enough money on a single income, that number was only 30% for Gen Z, who were also 15% more likely than Boomers to say they picked up a second job simply because they had extra time. 

Other top reasons for getting a side hustle included more money for non-essential purchases, like travel or eating out, and a desire to pursue a passion project.

At 21, DeNard already knew he wasn’t cut out for corporate America. He had seen what his parents’ generation put into it and, by comparison, what his own generation was getting out of it. Instead, he chose to tour with a metal band that eventually got signed to a major label — one that had signed bands he listened to growing up. 

But even being a member of a rising band wasn’t the right fit. “I didn’t like the demanding lifestyle of always being on the road, enriching other people’s pockets,” DeNard says. He and his wife decided it was time for a change. 

They started selling crafts at every farmers market and music festival they could, paying upwards of $1,500 just for a spot and grinding all week to sell all weekend. 

There had to be another way to make it work.

“I was a hippie back then,” DeNard remembers, “and being on Etsy was the cool thing to do. If you had a successful handmade Etsy shop, you were ultra cool.” So he turned his sights online. 

A digital revolution?

The emergence of online marketplaces opened up a new business model — one that had never existed before. There was no need to pay for a spot at a fair, festival, or convention. Online business wasn’t limited to weekends. And platforms linked creators to customers across the country and even around the world without leaving home. Creators like DeNard only needed an Etsy page, a little marketing know-how, and a way to ship.

And the customers came to them… in droves.

For DeNard, what started as a side gig very quickly became a full-on hustle. Just three months after launching on Etsy, he had enough money saved to buy a house. “On the West Coast, mind you,” DeNard notes, “where prices are not friendly to a midwestern kid.” 

Since then, he’s turned that success to helping others.

In 2018, he launched his YouTube channel, AddToCart, where he started showing others how to make a living selling on Etsy, too. (One recent video is titled “I helped This Etsy Seller Get $1,000,000 Sales Her First Year.”) Not only does he find it extremely fulfilling to help others, but he’s been able to build a second income stream on his own terms. Now, he says he makes much more than people his own age and even more than many older than him.

Saying goodbye to corporate America

What DeNard and thousands of people like him have discovered as they built those multiple income streams is that once they reached a certain level, they could make more money and work less — the holy grail.

They no longer needed to depend on some larger entity for a salary — with increases doled out slowly in the form of incremental raises, promotions, or leaving one position for another. Increases that may barely keep up with inflation.

Plus, according to our survey, the people who have found this kind of success with more than one income stream are more likely to have built an emergency fund that can last them 4 months or more. Given the number of Americans eking out a living from one paycheck to the next, that’s a huge statement.

For independent workers who are truly thriving, retirement isn’t a goal anymore. It’s a reality. Working or not, they’re living their retirement dreams right now. Even workers as young as DeNard.

He and his wife have backpacked Columbia, Ecuador, Peru, and Argentina on their own dime and time. They just got back from a dream trip to the Greek island of Santorini. At one point, they even bought a massive class-A RV, drove it from Michigan to Nevada and back again, all over the course of three months — something he says they would never have been able to do with traditional 9-to-5 careers.

None of this, though, is to say that it all came easily. 

“There are times when you must hustle, yes,” DeNard says. “I’ve created something that works for me, and maintaining that is easy. But if you want to force growth, you do have to work hard. The only difference is that I am the boss.”

In pursuit of a better life

More money. Fewer hours. If 49% of Gen Z and millennial Americans with more than one job can claim this over a single-salaried job, that still means 51% aren’t there yet — but maybe they’re on the way. There seems to be a generational shift in that direction, with the end goal of finding happiness through financial independence.

So what defines the independent workers who make it? Is there a formula for success? “Develop a talent first,” DeNard says. “Develop it, and believe in it. That’s the thing with a lot of people. They don’t have faith or confidence in themselves. You have to make a decision that you will succeed.”

Is it really that simple? If the key to success is good old American grit, maybe things like inflation and housing prices aren’t as insurmountable as they seem. Maybe we’re still living in a land of opportunity, where a new way to make money pops up every other week. 

Maybe all we need is the courage to go after it.

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What Type of Business Structure Is Right for You?

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In many ways, the earliest stages of a new business are the most important. The decisions you make today can set your new venture on the path to success.

One of the first choices you’ll need to make is which business structure to use for your new organization.

Sole proprietorship

Partnership

Limited Liability Company (LLC)

S Corporation

Corporation

Each option has its own set of pros and cons. Let’s walk through them.

What is a business structure?

A business structure defines how your business is legally organized and operated, as well as its ownership, liability, governance (how it’s run), and taxation. 

Will the business be owned by one person, or will it be a partnership? Will the owner(s) pay taxes on the company’s profits, or will the company have to pay its own taxes?

The answers to these questions and more are determined by the business structure you pick.

Why does your business structure matter?

Most of the reasons why business structures matter come down to legal factors and tax implications.

Some business structures are only available to individual owners, not partners

Some structures make it easier to sell shares, offering more ways to get outside funding

Some offer you more personal protection for the company’s debts or potential mistakes

Some are taxed as businesses, while others pass the income to their owners, who are taxed personally  

Seeking advice from an expert can help you choose the right structure based on your personal situation and business objectives. This post walks you through the essentials, so when you do talk to a professional, you’ll be more prepared — and you’ll know what questions to ask.

Can you change business structures later?

Yes, but some changes are easier than others. It’s relatively easy to go from a less complicated structure to a more complicated structure. It’s harder to go backward. 

Many people start a business as a sole proprietorship or LLC and later incorporate, but changing from a corporation to a simpler structure is much more complicated, especially if you’ve sold shares of stock.

The common types of business structures

There are several business structures available in the US. Here’s a simple guide to help you understand the differences between them.

Sole proprietorships

Ownership: One owner

Sell shares: No

Personal protection: No

Taxation: You’re taxed personally; the company does not pay its own taxes

A sole proprietorship is an unincorporated business that you own and run by yourself.

That word “unincorporated” is important. Since the business is unincorporated, it’s not a separate legal entity from you. If someone sues the business, they’re suing you. And you’ll be personally responsible for the business’s debts too.

This is one of the simplest business “structures” because in many ways, it isn’t a business structure at all. It’s just you, doing business under a business name.

Pros:

Easy. A simple option with minimal formalities. 

If you’re going to run the business by yourself and you aren’t concerned about debt or liability, this could be a good way to get started.

Cons:

Provides no personal protection. You’ll be personally liable for business debts as well as any actions your business takes. Not recommended for high-liability industries.

You can’t sell shares to raise money, and banks are often reluctant to lend money to sole prorprietorships.

Partnerships

Ownership: Two or more owners

Sell shares: No

Personal protection: Yes, although it varies between LPs and LLPs

Taxation: Partners are taxed personally; the company does not pay its own taxes

Partnerships let two or more people own a business together. There are two common kinds: limited partnerships (LP) and limited liability partnerships (LLP).

In limited partnerships, one “general partner” has unlimited liability while all the other partners enjoy limited liability, but they also have limited control of the company. These limits are usually laid out in a partnership agreement. 

In limited liability partnerships, all partners are treated equally, with limited liability.

In both cases, profits are passed through to personal tax returns, meaning the partnership itself does not pay taxes. Instead, the taxes are paid by the partners as part of their personal taxes. In limited partnerships, the general partner also has to pay self-employment tax.

Pros:

Partnerships allow you to own a business together. They’re popular among groups of professionals like lawyers, accountants, or consultants who want to pool their resources, sharing the risks and responsibilities of owning a business. 

Cons:

May be limited to certain types of professionals, depending on your state. May be required to file annual reports. Often have more formal obligations for filings and paperwork than LLCs.

Limited liability company (LLC) 

Ownership: One or more members

Sell shares: No

Personal protection: Yes, your personal assets are generally protected from business debts and legal liabilities

Taxation: LLC members are taxed personally; the company does not pay its own taxes

A limited liability company (LLC) can be owned by one person (a sole-member LLC) or by two or more people together (a partnership LLC). It provides protection for your personal assets against business lawsuits and creditors.

Like sole proprietorships and partnerships, LLCs don’t pay taxes as corporate entities. Their profits pass through to the individual members, who pay taxes as part of their personal income taxes. That’s why sole proprietorships, partnerships, and LLCs are sometimes called “pass-through entities.” 

Pros:

LLCs offer significant benefits for those who want to enjoy pass-through tax advantages and protection from personal liabilities without the full regulatory burden of corporations. They’re a popular choice among entrepreneurs, freelancers, small business owners, and real estate investors. 

Cons:

One of the biggest trade-offs of choosing an LLC is that you generally can’t sell shares. If you want to raise funds through equity financing or pursuing an IPO, the LLC structure usually won’t let you do that.

LLC rules, like other business entity rules, also vary by state. Depending on where you live, LLCs may only be allowed for more than one member, may have a limited lifespan, or may be required to dissolve and reform if there’s a change in ownership. 

S Corporation

Ownership: 1-100 shareholders

Sell shares: Yes

Personal protection: Yes, your personal assets are generally protected from business debts and legal liabilities

Taxation: Shareholders are taxed personally; the company does not pay its own taxes

An S Corporation (S Corp) allows for shareholders while still passing income, losses, deductions, and credits through to those shareholders for federal tax purposes. This helps the shareholders avoid double taxation in the same way an LLC does. 

This structure is a good option for small to medium-sized businesses looking to limit their liability and benefit from pass-through taxation while still allowing for the possibility of shareholders. To qualify, a business must have a limited number of shareholders, all of whom must be U.S. citizens or residents.

Pros:

S corporations offer liability protection as well as the tax advantages of a pass-through entity, while also allowing for shares that can be transferred. The S corp structure may also enhance credibility with customers and investors due to its formalized structure.

Cons: 

On the downside, S corps face limitations on the number and type of shareholders, which can restrict fundraising efforts and the potential for growth. There are also stricter operational processes and compliance requirements, such as holding regular meetings and maintaining detailed records. 

Corporation

Ownership: Ownership in a corporation is divided into shares held by shareholders

Sell shares: Yes

Personal protection: Provides the strongest shield in protecting personal assets from business liabilities

Taxation: Taxed as separate entities, paying corporate income tax

A corporation is a legal entity that exists independently of its owners. It provides the strongest liability protection for its shareholders, meaning their personal assets are typically protected from the corporation’s debts and liabilities. However, corporations are taxed separately from their owners, leading to the potential for double taxation on income—the corporation pays income tax, and shareholders may also pay personal income tax on their net gains.

This business structure is suitable for larger businesses or those seeking to raise funds through the sale of stock, as it allows for an unlimited number of shareholders and greater access to investment capital.

Pros:

This structure offers the strongerst liability protection to shareholders, which can encourage investment and limit personal financial risk. Corporations can also raise capital more easily through the sale of stock, they may benefit from a wider range of tax deductions and incentives, and they have perpetual existence, meaning they can continue operating independently of changes in ownership or management.

Cons: 

Small businesses or individual entrepreneurs might face challenges due to complicated regulations, high administrative costs, and the risk of double taxation on earnings when choosing this business structure.

How to pick a business structure for your business

Following these steps can help you navigate the issues and choose the best fit for your business.

Step 1 – Review your needs

Decide how many owners your business will have, whether you want to sell shares, how much you care about personal protection against business debts & liabilities, and how much formality you’re prepared to manage (including the possibility of corporate taxes.)

Step 2 – Weigh each structure against those needs

With those factors in mind, consider the legal and tax implications of each structure. As a business owner, you’ll need to weigh the liability protection of each entity, the administrative requirements that will have to be met, and the potential tax advantages.

Step 3 – Seek professional advice

Consult with a lawyer and/or tax advisor, especially regarding the specific rules for each structure in your state. Make sure you understand the local nuances of each business structure before you make a final decision. 

Step 4 – Revisit your options as your business grows

Regularly review and reevaluate your business structure as your company grows and evolves. You’ll want to make sure your business structure still meets your objectives and that you stay compliant with regulatory agencies and tax authorities.

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