JOSH: How did you strategically and responsibly make the jump from working a “dead-end job” to your dream job? What would you do differently knowing what you know now?

1. Validate Your Idea First

Work nights, weekends, lunch hours, and any other time you can to get enough of your product or service out there to see if people find it useful (ie. will pay money for). There is no better time than when you are working because then you have a constant stream of revenue to survive on. Once you quit your job, that revenue stops, so know where other revenue will come from before making any moves.
Nick Cronin, ExpertBids.com 
 

2. Quit Today!

Think of Steve Job’s commencement speech at Standford where he said “stay hungry, stay foolish.” He learned what he loved to do when he was young and never stopped doing it even after he was fired from Apple. Life is short and there is no time like the present to take action. Worst case you can always find another dead-end job if need be, but that will not happen. “Stay hungry, stay foolish.”
David Schnurman , Lawline 

 3. Lay a Foundation in Advance

I was able to line up some consulting work during the time that I was building our website and preparing to launch the service. This provided about 6 months worth of income which helped us keep more capital in the business to fund our growth.
Anderson Schoenrock , ScanDigital  

4. Sometimes You Leap First

I always knew I wanted to run my own business, and although I had worked at many companies during college internships… when it came time to graduate, I just turned down all my job offers and went straight into self-employment. I haven’t looked back! Luckily I had put away enough start up cash from those paid internships, so it wasn’t a totally reckless move.
Nathalie Lussier , Nathalie Lussier Media  

5. What is the worst case scenario?

If I had to go back I would have left sooner. I had the assessment of the risks all wrong. From the finances to my network to the support of my family, they all elevated once it was known that I was now on my own, trying to build a successful company that helped people. Now they now the long nights and no weekends were for a great cause. My worst case scenario never happened.
Greg Rollett , The ProductPros  

6. When It’s Time to Jump, You Have to Go

I didn’t take a particularly responsible approach to becoming an entrepreneur. I phoned in a resignation after a particularly bad day and decided that I’d better figure out how I was going to pay the rent. I’m all for saving up before you make the switch and putting together a good plan. But there has to be a point at which you leap.
Thursday Bram , Hyper Modern Consulting  

7. Go to school in the middle

If you don’t love your current job, go to grad school. Get an MBA, JD, or whatever interests you. While you’re there, you’ll meet people from all walks of life, and that will help you figure out if starting a business is the right path for you. It may not be the right time, or may be the perfect time, but school is a great way to smooth your transition from office to startup.
David Adelman , Reel Tributes  

8. Get a few clients–and get out!

I had clients, and I had savings–so my biggest mistake, and my only regret, was not leaving my various dead-end jobs to work full-time on MY business sooner. With some wise budgeting, a little savings cushion, and a final kick (losing a contract gig suddenly), my full-time transition was easy. If anything, I had more work than I could handle. If you know your idea works, don’t half-ass it!
Lindsey Donner, Well Versed Creative 

9. With My Back to the Wall

Luckily, I was abruptly laid off from my “dead-end job” I vowed that day to never put my career in someone else’s hands. Knowing what I know now, I should have jumped into the entrepreneurship waters sooner.
Anthony Saladino, Kitchen Cabinet Kings 
 

10. Just do it.

If you want to start a company you need to just make the jump into the cold water and follow your heart. I believe that it is in moments of distress, when you stand completely naked in front of the world, that great companies are built. Ideas change multiple times, so just quit your job and get started iterating your idea as often as possible.
Jean-Marc Freuler, Funding Gates 

11. One Thing Leads to Another

My passion actually grew from the line of things I did up to creating my business. Never underestimate what you’re doing at that moment because it could be preparing you for something bigger than you think. Be smart by being ready to make the jump and knowing what you’re getting yourself into before you do. Being an entrepreneur is freedom but also 24/7 hard work.
Ashley Bodi , Business Beware