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Should You Quit Your Job Before You Start a Side Hustle?

Entrepreneurship is reaching a tipping point. It’s a wave that will overtake your career in one way or another in the next five years. Why? Because the internet leveled the playing field. You can learn anything, anytime, anywhere, at any pace, and you have instant access to unlimited resources. Let me say that again — […]

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Entrepreneurship is reaching a tipping point.

It’s a wave that will overtake your career in one way or another in the next five years. Why? Because the internet leveled the playing field. You can learn anything, anytime, anywhere, at any pace, and you have instant access to unlimited resources.

Let me say that again — You can learn anything, anytime, anywhere, at any pace, and you have instant access to unlimited resources.

Photo by Kyle Glenn on Unsplash

Love it or hate it, Facebook changed the game when they created private networking groups, making it absurdly easy to connect with like-minded people. Now you can find someone who has done what you want to do to coach you through it. Or someone who is doing it now and go through it together. There’s no such thing as going at it alone anymore.

You want what you want, and maybe you didn’t know what you wanted before you started working from home. Still, now that you know you like collaborating without having to go to a physical location, contributing without having to work specified hours, creating without taking direction from an uninspiring boss, the limitations of a role that serves the company but not you aren’t tolerable.

If you’re determined to walk away from Corporate America, the trending advice is to start a side hustle, develop it, learn from it, and scale it until you achieve a “quit threshold,” and then you’re ready to walk. It’s excellent advice for a lot of reasons — meant to protect you from getting in over your head financially while uncovering essential truths about yourself and your business, but it’s asking a lot.

Yeah, it might work for a 20-something trading social time for their side hustle, but does it work for anyone else? Does it work for the parent who is trading family time? Or for the person who is trading self-care and wellbeing? Life is complicated, my friends. Work is only part of the equation.

Work is only part of the equation.

Let’s assume you already have a job and spend most of your waking hours at work. Does it make sense to pile more work into work/life balance?

If you’re already maxed out and/or need a change, perhaps a side hustle isn’t a good indicator of your potential entrepreneurial success. It may just lead to burnout. That doesn’t mean you’re not cut out for entrepreneurship. It may simply mean that you are choosing entrepreneurship for different reasons, like re-prioritizing or aligning your life. It’s not all hustle and scale.

As someone who’s been there, if you are serious about entrepreneurship, instead of investing every free moment in your side hustle, I’d rather see you fully fund your safety net, plan an exit strategy, and create a success plan. Then quit and go all-in.

Is it risky? Absolutely, but don’t let that stop you. Everything is risky. Your current corporate job is risky; you’ve just minimized the risk over the years by adapting to your organization’s culture.

Is it daunting? More daunting than risky. Making the transition from employee to entrepreneur is self-development in public. You don’t know what you don’t know; you start small, with no audience, and are 100% responsible for the results. Even on the most inspiring days, it is terrifying, but so is marriage, raising kids, all the good stuff. Shrug.

We enter those realms with a naïve hopefulness, with very little appreciation of how they will change us because we’re so focused on that outcome. We see the goal so clearly, but the day-to-day is a bit fuzzy because we can’t know until we are doing it. But the compromises and uncertainty, the roller coaster of emotions, aren’t just the symptoms; they’re the payoff. We are in it!

There’s a shift that happens when you go all-in on your dream.

It doesn’t necessarily make it happen any faster, but being fully present to the process is magic.

And that’s why you might need to quit before you’re ready — to commit on that level, making room to embrace the journey fully, letting go of the idea of going back, and advancing confidently in the direction of your dreams — pure magic.

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