Pros and Cons of Being an Entrepreneur Vs. Working a 9-To-5


  • People on Twitter have been debating what’s better: a nine-to-five or entrepreneurship.
  • Insider spoke with nine-to-fivers, entrepreneurs, and work coaches to gather insight into the topic.
  • Two experts said work burnout is on the rise, and that the future of work will change post-pandemic.
  • See more stories on Insider’s business page.

On March 29, Tino Masaya posted a tweet that sparked a debate on Twitter.

“A 9-to-5 job is not slavery. Leave us alone. Not everybody wants or can be an entrepreneur,” the 30-year-old UK native tweeted.

Masaya, who works for her local city council, told Insider that she tweeted her statement because she was tired of the narrative, especially peddled on social media, that everyone has to be an entrepreneurial “hustler” with multiple streams of income.

It got over 11,000 likes, nearly 2,500 retweets, and over 200 comments. “Somebody had to say it,” one person replied. “Entrepreneurship isn’t for everyone.”

“When entrepreneurs say this, it tells me a lot about how they treat their own employees,” another commented.

Weeks later, the conversation was sparked again by an April 17 video in which a group of people debated which was better: a more traditional job or the path of entrepreneurship. “Your nine-to-five cannot sustain you,” one person said in the clip.

But Masaya said her nine-to-five does sustain her. She’s fine with having a boss and waking up at 8 a.m.

So is Simone Noble, who ran her own consulting company for about a year before moving to it part time. She loved the freedom it gave her, allowing her to set her own schedule and spend more time with her family.

But she didn’t like having to chase down money from her clients to pay the bills. Relying on this income, she was plagued by anxiety: Would she be able to pay for food, for her car, for her home? Eventually, she decided it was too much.

“Having to run around looking for ways to make money — that’s not for me,” she said. Noble went back into the full-time flow of a nine-to-five, where she has a boss and a more reliable income. Her business partner still runs the consultancy full time.

Entrepreneurship is glamorized on social media, where a crop of self-made creators document their lifestyles and career successes in real time. To the outsider, they appear to make quick money from their endeavors, but social media paints an overly rosy portrait of the true entrepreneurial experience, which is often gritty and unrewarding. Almost half of entrepreneurs reported struggling with mental health — and the true number is likely much higher.

Current and former entrepreneurs, as well as work coaches, told Insider that social media places undue pressure on people to become self-made by pursuing their passion. They agreed that a nine-to-five can provide a stable career path and also be rewarding, despite the online narrative. They added that the pandemic is redefining traditional work to be more flexible for employees, thanks to a widespread desire for a more entrepreneurial life and changes in work life.

Social media glamorizes what the life of an entrepreneur is like

There are some days Robreuana Ruiz wishes she worked a nine-to-five.

Ruiz, an entrepreneur in Atlanta, makes six figures a year from her cosmetic companies Fash N’ Lash and Curl Candi, which she started at the age of 24. But these days, she’s dealing with what she calls “entrepreneurial depression” from trying to keep up with supply and demand, and from the pressures of running her own company. “It’s an emotional roller coaster,” Ruiz said.

“Social media can make everyone feel like they have to be this boss entrepreneur, but businesses are not for everybody,” she said.

Ruiz is referring to messaging from groups such as “LLC Twitter” or “Roc Nation Brunch Twitter,” where a flood of followers — many of whom were inspired by the success of the mogul Jay Z — encourages others to chase an entrepreneurial life and invest any gains for the chance to seek higher returns. But it takes courage and patience to launch a business, Ruiz said — not to mention capital.

“Social media can make everyone feel like they have to be this boss entrepreneur, but businesses are not for everybody,” she said.

 

As her own employer, Ruiz has no fixed schedule, and making payroll is solely dependent upon customers, rather than a corporate enterprise. This means there are good months, but there are also months where she’s left worrying.

Entrepreneurial depression is “real, and it’s not talked about enough,” Ruiz said.

Despite this, she has been earning six figures. But social media makes that success feel inadequate. “It makes us feel like we aren’t doing enough,” Ruiz said. “I’ve been an entrepreneur for three years, and I haven’t made a million dollars yet.”

There are benefits to having a 9-to-5

Michael Greenberg, a serial entrepreneur in Denver, said social media has made it easier than ever to make money by equating an online persona with a moneymaking business.

“There’s a media machine built around the idea that you have to be hyperproductive to succeed, and that if you’re not hyperproductive, you’re somehow falling behind,” Greenberg said. “We are productivity-obsessed in the worst possible way.”

“We are productivity-obsessed in the worst possible way.”

Greenberg has never worked a traditional nine-to-five, but he’s now on the hunt for a more stable gig as he continues to run his side hustles. Specifically, he wants his baseline income to be handled by a job that takes “between 25 to 40 hours a week.”

In his own Twitter thread, Greenberg called entrepreneurship lonely and hard. He loved being able to work everywhere, but didn’t like not having a team of peers. He loved having control over the budget and hiring, but not that he had to often pay for mentorship opportunities. “Don’t let the entrepreneurship, startup, hustle porn fool you,” Greenberg tweeted. “The only right choice is the one you choose to make.”

After all, working a nine-to-five has its perks and practicalities. Masaya, the UK native who tweeted about the pressure of entrepreneurship, said paid sick leave and maternity leave were two major benefits to working a traditional job. Noble, who gave up her own consulting business for a nine-to-five, liked knowing that there would be money for the bills each month.

In the United States, healthcare benefits — as well as dental, vision, and retirement — are tied to employment. In 2011, the Employee Benefit Research Institute found that there were over 20 million self-employed people in the US, 30% of whom lacked health insurance. And a study published in November of last year, by Agnieszka Kwapisz of Montana State University, found self-employed men were 62% less likely to be insured, and self-employed women 83% less likely, compared to the general public.

Heaven Williams

Heaven Williams and her candles.

Heaven Williams


Paid sick leave and disability benefits are also tied to employment. Even to qualify for unemployment benefits — as over 50 million Americans did during the height of the pandemic last year — one must prove they had been employed recently.

Up until the pandemic, the self-employed didn’t count.

“There are certain companies out there that do care about their employees and have amazing benefits,” said Heaven Williams, who works for a Sacramento homeless shelter during the day and runs a candle business on the side. “If you find something that you love to do and it’s a nine-to-five, there is nothing wrong with it.”

The structure of day jobs can learn a thing or two from entrepreneurship

One main part of entrepreneurship that most people like is flexibility and having agency over their time. Over 40% of those surveyed in 2017 for a report done by the accounting organization FreshBooks said becoming self-employed had given them better working hours, improved the quality of their childcare, and allowed them to spend more time with their families.

This is a trend that is looking more likely to be adopted into the traditional working environment, especially in a post-pandemic world. Insider’s reporting on the future of work has suggested the nine-to-five may not be the same after the crisis passes. Ashley Whillans, a professor at Harvard Business School, believed the traditional workweek could become more flexible, where workers come to the office three days a week, spend two days at home, and have two days off.

Microsoft is now allowing employees to work from home for less than 50% of their workweek. Both Twitter and Spotify are allowing employees to work from anywhere.

What’s more, Greenberg believed most people don’t even want to be entrepreneurs — they just hate the jobs they’re in. Matching workers with jobs they like could see an increase in employee satisfaction.

Joe Sanok, a podcast host and the author of the professional help book “Thursday Is the New Friday,” said he was a supporter of the four-day workweek, and that the concept of “summer Fridays” — the practice of giving employees part or full time off to enjoy the warmer months — should be more prevalent in modern workplaces.

Meanwhile, Paula Davis, a burnout consultant, said workplaces will be able to attract more people by offering more flexibility, such as the option for remote work and giving employees more free time.

“I also think a sense of meaning, impact, and purpose is something companies are really going to have to step their game up,” said Davis, who experienced burnout both as an entrepreneur and as a commercial lawyer. “You’re going to have to explain to people how this is changing the greater good.”

Even if the workweek is redefined and social media gets the story straight on entrepreneurship, society is still playing a dangerous game with productivity as more people seek to monetize their time and personas.

Burnout is at an all-time high, along with the number of side hustles. said she knew of many people who had started to work traditional jobs alongside side hustles, seeking to juggle both on their quests for uncertain success.

“That’s not productivity,” she said. “More, exhaustion.”





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