The Path From Fortune 500 To Freelancer

Our guest author, Jim Karwisch makes lives better through Improvisation. He offers Leadership Skills Training as a Speaker and Coach. You can learn more about Jim and the powerful work he does at DuMoreImprov.com

Note: Jason’s perspective is shared in this blockquote format.

So there I was, sitting next to my five colleagues. Our department was shutting down and leadership was offering a severance package. The decision I pondered for some time was finally forced front and center. Would I stay in corporate America, or would I take this opportunity and make the leap into freelancing? Let me rewind just a bit and tell you how I ended up here.

From 1997 to 2001 I worked for seven companies and temp agencies and as I traveled  across the United States acting, directing, and studying improv theatre.  It was a grand adventure.

When I moved back home to Atlanta in 2001, I was offered a  permanent administrative assistant position at a Fortune five hundred company. This was my opportunity for a steady day job while I created and ran my theatre company in the evenings. The stability obviously worked for me because thirteen years later I was still working the same day job. By this point, I had moved up in the company from an assistant to working in communications and innovation in the downtown offices. Then it hit me, would I ever be able to break this routine and forge my own path?

In  the fall of 2014, on a seemingly normal day, I arrived at the office and was ushered into a conference room with the rest of my Readiness and Engagement team. In front of each of us was placed a packet of paper by a representative of HR. It was clear what was happening. There was a reduction in force occurring and we were that reduction. I saw in the faces of my colleagues varying forms of anger, sadness, and frustration. It was difficult to maintain the proper somber attitude in support of my coworkers  because as we turned to the details of our severance packages, I saw something wonderful. I had been given enough money to make the break from my nine to five job and pursue my dream of going out on my own.

Are you someone who wants to make the same transition? Are you facing  your own severance package opportunity? Have you saved money in your attempt to make a leap but something is holding you back? You might very well be asking yourself “can I really do this?”

The answer I found was “Yes you can, but you will need a plan.”  You will need a guide to help maneuver around pitfalls so things don’t dry up before you strike oil.

At the time I was attending Watermarke Church pastored by Andy Stanley. As a way to practice and showcase my craft, I doodled an infographic of his sermon. It turns out it got noticed by Jason Montoya who then favorited the tweet. Wondering who this person was, I clicked through to the profile page of the young man that would soon change my way of thinking about this perfectly timed opportunity.

I messaged him immediately and we soon grabbed hot drinks which lead to an extended lunch. We could see right away we were like minded and a friendship was quickly forming.

“As a futurist, I anticipate how things could unfold for the good and the bad. When Jim told me he’d be leaving his corporate career and launching into freelancing, I immediately saw all of the potential positive and negative outcomes he would face on his journey. I was immediately compelled to share insights that would allow him to replace the structure he lost from his company and prevent the many hardships he would likely endure.” - Jason

As Jason listened to my story, he shared practical and valuable advice. Jason encouraged me to focus on understanding how committed I was to freelancing In a kind and non-insulting way, he challenged my commitment. I had signed my severance agreement and was out the door of my old job, so I wondered how much more committed I am? As it turns out, the action of starting did not necessarily equate to a commitment to finishing. Jason helped me see how difficult the life was if I was not fully committed with eyes wide open. (Jason added this same information as Achievement #1 of his book.) 

Clear and focused, my time with Jason was appreciated and memorable.  Our recurring meals at Willy’s Mexican Cantina led to numerous helpful discussions on what I was offering in my package (Achievement #2) revenue streams (Achievement #3), marketing, networking, maximizing my existing clients (Achievement #4) and my most sales friendly skills. My Journey was beginning and I wasn’t doing it alone.

“As a freelancer, we’re technically on our own and making choices that help and hurt us. This is why it’s vital we build deep relationships to form a community that helps us endure and progress. Jim became a great friend and support during my freelancing journey and someone who helped encouraged and share ideas. The burden was lightened by his companionship. ” -Jason

“Finishing is never easy. Imagine running a marathon. At the end of a marathon, a crowd is waiting to cheer us on, hand us water and pick us up when we fall. When we buckle down, take responsibility and lead courageously through the difficult and unknown, we elevate to the highest level of freelance flourishing.” -Jason

(Since then Jason has shared with me Achievements #7 and #8 which make an incredibly well-rounded course in freelance success.)

When I started this journey, my income was entirely sourced from a fortune five hundred company. Today my income is one hundred percent from coaching, speaking, writing and training others to improve their communication, collaboration, and leadership. A huge thank you goes out to Jason Montoya and his insights in Path Of The Freelancer. Without this guidance, I most certainly would not have made it this far.

Through Path Of The Freelancer, you have the opportunity to receive this insight and support. Please check out the resource section to help you in your freelancing journey. -Jason