Self Made

How to know when to make a side hustle a main gig

These signs will show you that you're read to switch from full-time employee to entrepreneur.
By Tara Tadlock  on 
When to leave your job for your side hustle
Credit: Ian Moore / Mashable

In 2021, nearly 50 million Americans quit their jobs, setting a record for resignation rates. Experts call this mass exodus of the workforce "The Great Resignation." This phenomenon of employees leaving their positions shows no signs of slowing. This year in just March alone, over 4 million American workers said sayonara to traditional 9-5 roles for various reasons. It's not just U.S. offices that are taking a hit. Globally, there is a movement to be your own boss and lean into your side hustle as a primary source of income. 

The COVID-19 pandemic has taught us that life is too short to be unhappy, underpaid, unappreciated, or uninspired. Those who have been balancing working a 9-5 position and a side hustle, listen up! It may be time to pursue your passions and leave your desk behind. If you're looking for a sign to delve into the world of side-hustles-turned-main-income-stream, here are ten:  

1. You feel comfortable with the financial risk

For many, the only thing holding them back from pursuing their side hustles full-time is financial fear. "My biggest fear was that I wouldn't be able to make enough money to fund my travel," Alexx Hayward, now a freelance marketing consultant and travel blogger, says of leaving her traditional office job. "But I also knew that the worst-case scenario was that I wouldn't bring in enough income, in which case I would just go get another 9-5 job again. At least I could say I gave it a go." Calculate your savings, know your expenses, and if you feel comfortable with the risk, all signs point to "go for it"!

2. Your side hustle feels more aligned with your passions

Office jobs have become synonymous with boredom, monotony, and a general lack of passion. Millions of young people are resigning to pursue the thing they really love. Hayward echoes this sentiment, "Many of us became self-employed because we were more passionate about our side hustle than our 9-5 job."  

woman climbing the corporate ladder
Credit: Bob Al-Greene / Mashable

3. You spend your work days thinking about your side hustle

If you are constantly thinking and talking about your side hustle at your desk job, it may be time to take the leap. Luke Tavener, the owner of Orange Robe Tours, left a high-paying role working in China to start his own profit-for-purpose social enterprise in Luang Prabang, Laos. "I realized I kept thinking about starting a social enterprise at work. I talked about it for years," Tavener says. "Something just clicked, and I realized that I needed to go for it instead of sitting at my desk talking about it." 

4. You picture yourself thriving outside of your cubicle

Ask yourself what you envision for your future. If the honest answer doesn't involve your current company or a desk job, it may be time to resign and lean into your big dream. "When my supervisor mentioned that I could be placed in a manager position in five years," Tavener reflects, "At that moment, it hit home that that role wasn't what I wanted to do. I couldn't picture it at all. When I thought about the future, all I could see was me in Laos working on my own business." 

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5. Your work environment is toxic

Your workplace being toxic is more than enough reason to leave. Nothing is worth your mental health and inner peace.

"For me, it was the combination of a bad boss and an expiring work visa," says Hayward. "I had to decide whether I wanted to commit to my 9-5 job and toxic work situation for another three years, move home to New Zealand to keep climbing the corporate ladder, or wing it and take a leap of faith into freelance work. I chose the latter!"

woman drowning in email
Credit: Vicky Leta / Mashable

6. You lack freedom

Feeling chained to your desk is a sure indicator that it's time to make a move. It can be frustrating to arrange your entire life around a job, from where you live to how many vacation days you get (and when you can use them). The freedom to travel and live abroad is a massive draw for workers. 

"This frustration and desire for more freedom in my life led me down the road of figuring out what skill I could monetize to ditch my desk," Lauren Melnick remembers. Melnick left her 9-5 in November 2016 and has been a successful freelance travel and SaaS content writer ever since. She also runs a successful travel blog, YouTube channel, and has over 20,000 followers on Instagram. "[The decision to leave my job] has given me the thing I value the most: freedom. I've had the freedom to travel to 40 countries in six years. I've had the freedom to quadruple my 9-to-5 salary. I've had the freedom to cherry-pick my projects. I've had the freedom to level up my life because it's a major personal development project when you start a business," she says. 

7. You feel a sense of dread at work

Lola Méndez, a freelance journalist, realized it was time to quit her fancy 9-5 role as a Senior Manager at a New York City branding agency when she felt dread in place of excitement. "When I was told I'd be promoted to Director in 2015. I should have been thrilled, but I felt doomed," Lola says. "I was 25 and felt like there had to be more to life than working at my desk all day." 

8. You feel empowered make it work

Take the skills you have acquired in your 9-5 position and apply the same time, energy, and work ethic to your side hustle. Transferring your skills and feeling empowered to put your time and energy into your side hustle is how passion projects become full-blown businesses that thrive. Méndez believes that time management, ambition, and dedication are key to success in your side hustle.

9. You're looking for a challenge

There is typically a ceiling to what you can earn and a pentacle position or title you can achieve in corporate jobs. If you have "climbed the ladder" and there are no more opportunities available, it may be time to set yourself a new challenge– growing your side hustle into a full-time business of your own. 

10. You're earning more on the side

Is it a "side hustle" if you're out-earning your 9-5 wage? Be it an Etsy store, content creation, or freelance writing– once you can live off your side hustle profits, there should be no more room for doubt left.  

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Tara Tadlock

Tara Tadlock is a freelance contributor for Mashable.


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