Questions I Asked Myself Before Leaving My Job - Rolling Stone
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Questions I Asked Myself Before Leaving My Full-Time Job in Pursuit of My Side Hustle

Spend time carefully thinking through your options and don’t rush the process.  

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Johnstocker — stock.adobe.com

Many people are tempted by the prospect of starting their own company. Entrepreneurship brings the opportunity to be your own boss, solve your own problems and create your own rules. Entrepreneurship can also be a very lucrative career choice — just look at companies like WeWork, Instagram and Slack, which all started as side hustles. On the flip side, however, pursuing entrepreneurship can be one of the most challenging and risky decisions you can make, especially if you already have a stable corporate job.

In 2019, I made the leap from working on my side hustle part time to making it my full-time job. After eight years working for companies like Google and YouTube and juggling running my own company with my co-founder Warren Jones, I found myself walking away from a steady six-figure job, endless options of free campus food and a slew of other perks that have become the norm in Silicon Valley.

Most people would call you crazy for stepping away from so much, especially when there are so many people who only dream of working at a tech giant. The idea of leaving such a stable environment and entering a world of so much uncertainty may leave some people scratching their heads.

Even though this idea would perplex many, it had been a vision of mine to one day work for myself. Fast forward to today, and I run a dynamic events and marketing company called Toasted Life that builds experiences and events for young multicultural professionals in markets such as L.A., New York, San Francisco, Chicago and Atlanta. From curating private dinners with celebrities to chartering boats off the coast of Zanzibar to coordinating panels with platinum-selling artists, my company is a lifestyle and leisure brand that cultivates community and champions celebration through events and experiences. In 2018, we expanded internationally and produced events in Kenya, Ghana, Tanzania and Canada. We’ve also had the opportunity to work with some very notable brands, including Nestle, Hennessy and Under Armour, as well as some very prestigious universities.

I wanted to share some questions I asked myself while considering whether to go all-in on my side hustle. Here are four questions to ask yourself before leaving your full-time job in pursuit of full-time entrepreneurship:

Am I ready to put it all on the line?

Entrepreneurship is a gambling game and easily one of the riskiest professions you can pursue. I feel that for an entrepreneur, it is entirely your responsibility to make your dreams come true. Your company’s failures are your failures, and when things get tough, it is up to you to pick yourself back up. As an entrepreneur, you own your fate, and you own the decisions you make. At the same time, however, the idea of failure shouldn’t be a deterrent from chasing what you believe in because failure is often a prerequisite for success. Successful entrepreneurs learn from adversity, grow from mistakes and know how to adapt quickly.

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What is my gut telling me?

Before I took that big leap, I really had to make sure I was listening to myself and trusting my instincts. As an entrepreneur, you have lots of people in your ear sharing what they think is best for you, but what is your gut telling you? Some people will push you to jump early, but these people don’t have to deal with the consequences of being an entrepreneur, like the financial risk, the lack of sleep, and the ups and downs. For those on the other side of things, they may just not see what you see. Maybe they don’t think you have it in you because they don’t how this business idea has fully consumed you, from your thoughts to your dreams at night. They might think the idea is a bad one, but maybe they don’t understand the problem you are setting out to solve. Also, it is very likely they aren’t even your target audience.

Have I timed this right?

Timing can be everything. Waiting too long to go full time could cause you to miss your window, but jumping too early without truly testing the viability of your business or service can be just as detrimental. I spent about five years growing and studying our business before I was comfortable enough to go full time. I needed to study our revenue year over year and understand our baseline. I needed to see our scalability potential. I needed to be confident that freeing up my workload would immediately drive revenue for the business.

Do I understand what my new life will look like?

To me, the most exciting part of being an entrepreneur is being able to engineer my version of my dream job and, in some ways, turn something that is almost a hobby into a full-time job. However, entrepreneurship isn’t just fun and games. Entrepreneurship can be stressful, and when you are relying on its success to eat, you may be forced to miss out on some important moments. I personally have had to sacrifice a lot of time with my friends and family. It’s not a good feeling to miss birthdays and weddings or cancel dinner plans with a friend, but it can come with the territory. Visionaries often have to sacrifice a part of themselves to make their ideas come to life, and an entrepreneur needs to have a firm understanding of how to balance their personal needs as a human being.

The survival mentality of being an entrepreneur can be daunting, but staying in a comfortable full-time job may not allow you to fully invest in taking your passion project to the next level. Spend time carefully thinking through your options and don’t rush the process.

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