Moving From Day Job to Dream Job (Without Going Insane)

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Moving From Day Job to Dream Job (Without Going Insane)
The world is out there waiting. You just have to take a flight.

For some time, I’ve toyed and stressed over when I’ll leave the 9-to-5 world to pursue my passions. Don’t get me wrong, the day job is great. But at the end of the day, my entrepreneurial spirit just won’t quit.


If you’re working the daily grind while side hustling, you know what I’m talking about. The thought of not getting a paycheck freezes us, though we know we could make it on our own. We want to not only take the leap but also do it the smart way.

Can we do this without completely losing our marbles? Yes—and here’s how.


The drudgery of the 9-to-5 grind makes it easy to complain, begrudge, and flat out hate our jobs. But this negatively affects our ability to perform in other aspects of our lives—namely, transitioning from the day job to dream job.

If you’re looking into entrepreneurship, you have to absolutely love your day job. Otherwise, you’ll be too miserable and unmotivated to make the jump. Marie Forleo discusses this concept in one of her most popular videos, How to Transition from Your Day Job to Your Dream Business.

One technique that works for me is to practice daily gratitude. By focusing on the great aspects of my day job, I don’t gripe as much, I stress less, and I produce better work on the side.


I recently expanded my side hustle, spreading my blog’s message at networking events and professional groups.

Why exactly am I doing this (besides to rock my business)? First, to practice self-promotion—something many of us aspiring entrepreneurs struggle with. Second, to test the market and see how people react to my side hustle (so far, so good). And third, to meet people who can guide and mentor me along this journey

As a result, I have joined an amazing group of professional women who spread positive vibes to Gen Y professionals. I’ve also got a partnership in the works to put together my first live event in 2013! Forming connections like these can seriously boost your confidence and take away a lot of stress because you’ll know you aren’t doing everything by yourself.


Use your day job to fund your side hustle. More importantly, use your day job to set up a hefty savings account so that you already have a cushion when you decide to work on your own stuff full time.

It’s much easier to work for yourself when you don’t have the insane amount of pressure from hustling to pay your bills. By having a financial safety net in place, the transition from employee to entrepreneur becomes a little less scary.

The Careful Cents blog explicitly details how one reader saved up enough money to quit his job and freelance full time. The Money Book for Freelancers, Part-Timers and the Self-Employed is also a fantastic resource for any of you who need help setting up a savings cushion.

Moving from your day job to your dream job doesn’t have to be completely overwhelming. By staying positive, surrounding yourself with great people, and doing your best to save money, you can make the transition less rocky.

Have you already let your inner entrepreneur out? Share how you did it in the comments.

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