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Should I Quit My Job and Start Chasing My Dream? Five Experts Weigh In

With socially conscious entrepreneurs everywhere, you're probably wondering if a 'regular' job is stifling your dreams.

Entrepreneurship seems like the cultural trend these days.

With the ability to create a website and the social media tools to advertise to the masses, being self-employed and building your own business is seemingly more simple than ever.

In addition, there’s an angst under the surface of society that breeds discomfort in this generation with the idea of doing anything other than what they want to do. If you’re not chasing your dream, it seems like you’re not fully living.

These advances in technology have made the question for many millennials, would-be entrepreneurs, activists and world-changers not, “Can I quit my job to pursue my dream,” but, “Should I?”

God has created everyone with dreams and plans buried deep within their hearts. The challenge is finding the right way to cultivate those dreams and to determine how, when and where to direct them.

So, are you supposed to work hard where you are, or are you called to step out to follow that God-given dream? If you stay put, are you being content or just lazy? If you follow your dream, how do you know it’s a calling and not wanderlust?

Thankfully, other people have been there before.

We talked with five experts to get their advice on how to know when (and if) you should quit your job and start chasing your dream.

Here are five things to think about before you decide:

1. Consider Your “Why.”

Paul Sohn, leadership coach and author of the book Quarter-Life Calling, is a brilliant young leader who from all appearances looks like he is wholeheartedly pursuing his dreams. But when I asked Paul if we should all quit our day jobs and start pursuing our dreams, he had this to share:

“Personally, I’ve asked myself this question countless times. Last year, I did the craziest thing an ambitious 28-year-old could do. I quit my high-paying Fortune 50 job in order to chase my dream. But honestly, my answer is ‘Yes and No.’ It depends. It depends on whether your dream is merely an expression of your self-serving ambition or an unmistakable call from God. If you find yourself in the former camp, I’d reassess your dream altogether. Start from ground zero and transform the intentions of your heart. If you know this is a profound sense of God’s calling, I say YES. Steward your time, talent and treasure and go all-in to pursue your dream. The world needs it.”

Why you’re chasing your dream is one of the most important questions for you to answer before you make a leap. Are you pursuing your dream because of deep conviction and passion that can withstand the challenges you’ll face or are you simply seeking a fast track to fame or success?

2. Consider What You Love.

What do you really love? “The biggest potential pitfall with quitting your job and launching your own business is the belief that because you loved doing one thing that you will love running a business about that thing you love,” says Alli Worthington, business coach and author of Breaking Busy. “This is where the ‘do what you love’ advice for potential entrepreneurs falls flat. Just because someone loves making graphics doesn’t mean that person would love running a graphic design business. Having passion for your business is fabulous, but don’t mistake loving watercolor painting to mean you’ll be great at running a watercolor painting business. A business needs a manager, a salesperson and someone who produces the product (or service). Sure, one person can do all three of those duties temporarily, but it’s not an optimal plan for long-term success.

“It’s very common for someone who loves doing something as part of a business to leave to start their own business, only to learn that the act of running their own business keeps them from doing the one thing they love.”

3. Consider Your Work Ethic.

Productivity expert and New York Times best-selling author Rory Vaden has some strong advice about evaluating our work ethic before chasing our dreams. He shares, “I actually think too many people today quit good jobs because it’s vogue to go after a ‘dream job.’ They think it’ll be easier to pursue their dream job but it’s not; it’s harder. You have to work harder, for longer, for less pay and less chances of being successful because most dream jobs are highly competitive. Even if it’s your own business, you’ll have a lot more work and headaches to manage.

“So do a check up from the neck up about how hard you’re really willing to work before you leave a great job in search of some fantasy. A good litmus test is how hard are you working now? You should always work hard. Crush it where you are. Succeed at the thing right in front of you. Experience all that your current opportunity has to offer. Perhaps it would be more of a dream job if you just worked a bit harder at it. If you’ve already proved you can work incredibly hard, and you’ve experienced most of what your current path has to offer, then sure, make the leap.”

4. Consider the Cost.

“I feel bad for my response because the traditional Instagram-type inspirational quote would say an emphatic ‘Yes!’” Casey Graham, CEO of 7 Figure CEO, says. “But after being in business for myself for a decade, I would say, you can’t buy a cheeseburger at McDonald’s with a dream. Real life costs real money. Real success requires real risk. Realizing dreams often times takes decades. So, yes, you should pursue your dream, but only if you have real money to pay your real bills and a real plan to actually sell something to real customers. I believe in your dream, but I also know it takes real dollars. Go for it! But only if you have real commitment.”

5. Consider Your Timing.

Creative director Stephen Brewster encourages people to dream for tomorrow while being a good steward of today.

“I love the dreamers. The truth is most of my life I have lived in a state of dreaming. I am a firm believer in the idea that God is aggressively planting dreams in His people! What comes with dreams is the responsibility for stewardship.

“God wants us to chase the dreams He is growing in us! But never let the excitement of your dream outpace the wisdom God has for how you get to your dream. God has given us a job and the Bible is clear at how we are to steward what God has given us. Chase your dreams! Chase them with passion and excitement. Chase them like crazy but never at the cost of stewarding what God has you to do today. Tomorrow is going to be amazing but not at the cost of today.”

Chasing your dreams is a sacred calling. As these experts share, there are some important considerations you need to process before you make a leap. Make sure your dream is really a burning passion. Take time to process, pray and seek counsel from people who know you well. How long have you had this dream? Is it today’s latest idea or is it something you’ve grown more passionate about over time?

Work on your dream while doing your day job. The best way to determine if your dream is worth the sacrifice is learning how much you’re willing to sacrifice for it now.

You’ll have a better understanding of the costs and the commitment necessary to ultimately help you succeed.

Chase your dream, definitely. Whether you quit your day job is worth the extra consideration.

Top Comments

Ashley Chelonis


Ashley Chelonis commented…

Jon Acuff's books go over the points made in more detail, if you would like more on this topic. Jon helps you take the above advice in a step-by-step approach. Get the book Quitter before you make a big leap, and then get the newer book, Do Over, while crafting your plan.


Ashley Chelonis


Ashley Chelonis commented…

Jon Acuff's books go over the points made in more detail, if you would like more on this topic. Jon helps you take the above advice in a step-by-step approach. Get the book Quitter before you make a big leap, and then get the newer book, Do Over, while crafting your plan.

Ema Cruz


Ema Cruz commented…

Yes, I agree. If you are not happy with what you are doing then you will always think about this as a burden and may also not feel good. so for all this, it is important we should do things we love to do.

Michael Johnson


Michael Johnson commented…

This article was so helpful to me! Read it in the old school magazine. Because I am old school.



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