I’m often asked how I made the switch from leading in an organization to starting my own leadership company.

I’m not sure there is an easy answer. Truthfully, the whole process felt squishy.

Yesterday morning I ran across an interview Anderson Cooper recently did with Fast Company Magazine. Cooper’s answer to one of the questions helped give language to my idea of squishy.

When faced with taking his own career risk Cooper said, I knew rationally that my fear of taking a step didn’t make sense. I had talked to enough successful people to know that the path to success is often meandering. It can appear to be a series of random events and only in retrospect can one look back and connect the dots.”

Looking back, my journey was not squishy. While there were times I was meandering, there were also concrete things I did to ultimately help me make the break. I can now even connect many of the dots.

If today finds you feeling unhappy and hopeless in your work, I believe the four things I did during my transition can help you with yours.

Four Steps to Help You Quit Your Job … 

1. Define. The first thing I had to do was define what it was I wanted to do. This was a process. A process that started with paying attention to who I am. “Defining Questions” like … Where is the energy? … Where is the effectiveness? … What is the need I can meet? … and Where is the affirmation? all helped me identify a preferred future.

FYW imageI wrestled with this for so long I literally was able to write a book with my friend Dan Webster to help others work through this process. If you need clarity on sorting out what YOU are born to do (or know someone who is drifting in their work), I highly suggest reading FINDING YOUR WAY: Discovering the Truth About You.

2. Align. The next thing I did was line my life up with what I had defined. I set my sights on building a company focused on encouraging, coaching, and speaking to leaders, teams, and organizations. I spent most of my time outside of my real job looking for opportunities to do those three things – it is the direction I pointed toward. I say it all the time, “Your direction always determines your destination.” It was certainly true for me. Every time I took a baby step I found myself closer to where I wanted to be.

Like me, you must align with your target. If you’re not willing to do whatever it takes to walk toward your dream, you likely have a lack of passion and subsequently the wrong target. I knew I had discovered my dream because my Defining Questions were answered. I was effective, energized, able to meet a need, and people kept encouraging (and even paying) me.

3. Refine. Step three was to keep refining. This included narrowing my focus and more importantly, working on myself. When I evaluated my definition I continually wondered, Is this really what I want to do with my life and is it the right fit for who I am and my skills?

compass-bw2As the process unfolded, I kept making adjustments. The challenge was that it required massive amounts of time, energy, thinking, questioning, and failing.

Believing I was planted instead of buried, helped me stay the course when others doubted me. Having a clear definition of what I wanted, served as my compass and helped me stay the course when I doubted myself.

Another part of the refining process was to listen to trusted counsel. More than once I asked those closest to me, Am I nuts or could you see me actually making a living at this?

Additionally, I refined by working on my skills and expanding my network. Every day I asked, How can I improve so people would be willing to pay me to do what I love? And, Who can I add value to today?

4. Resign. The last step was the hardest. I’m not sure why, but actually resigning was brutal. I think it was because I was so comfortable. I kept telling myself things like, “No one quits their job with three kids in college.” … “You’ll loose your health benefits.” … “What if you fail?”

All questions to be considered, but for me, indicators that I was a consumed with comfort. Ultimately, chasing comfort was killing me!

As a Bible-reading person of faith, I kept looking for a verse encouraging me to be comfortable (don’t waste your time, you won’t find it … at least it wasn’t in my Bible). And yet, over and over I discovered verses where God commands His children to be courageous. Ouch! … the opposite of comfortable.

As I played my life forward in my mind, I knew if I didn’t courageously go after my dream I would be disappointed in myself and ultimately end my life with uncomfortable regret. On the other hand, if I decided to go for it and failed, while I would be disappointed I wasn’t good enough, I would have no regret. 

The command to be courageous became my crisis point. Would I play it safe and grasp at security, or would I get-my-Cortez-on and burn my boats?

I struck a match and chose to resign.

Warning 1: Do not recklessly resign! Knowing I had thoroughly defined, aligned, and refined increased my courage and helped me surrender to what I needed to do.

Warning 2: Do not wait too long to resign! Go ahead and put your last day on the calendar and watch your urgency level increase – if you wait too long the moment will pass you by.

It has been over a year since I made the break, and I have never been happier in my work. But the fact is, it took me almost three decades to find my dream job.

I’m confident if you will define, align, refine, and resign you can land in your sweet spot much sooner.

Leadership Begins at Home,


What are the effects of choosing comfort over courage?

Comment Below …

Author: Randy

Randy is an author, speaker, executive coach, and the CEO of InteGREAT Leadership. He invests his time encouraging leaders around the world.