The Arena – Fork in the Road

Aug 16, 2015

August 6th, 2015 marks the last day of my “Arena Challenge”. I quit my job on May 8th, 2015 to spend more of my time, energy and focus on learning how to run an online business. Little did I know that it would not only be challenging in ways I wasn’t expecting, but I would accomplish more than I set out to do – including other areas of my life.

The decision enabled me to reclaim my time and I was rewarded with an ultimate level of freedom. I knew going in that it wouldn’t be without challenges, but I was mentally prepared to take them on. I willingly embraced it.

Experiencing it is something completely different and it challenged me in ways I wasn’t really prepared for.

The first day of the Arena started off on a good foot. I stepped out of my comfort zone by meeting a group of complete strangers to learn how to do something I always thought was “cool” but never believed that I could ever be capable of doing it. Under most circumstances, I would spend an incredible amount of time psyching myself up. This time around, I exchanged nothing more than a few messages with the group and then just … showed up. A year ago that kind of approach would have made me melt with anxiety.

And in a matter of hours, I had learned a few fundamentals of parkour.

I did my best to keep thoughts and worries away about how I was going to be perceived. I ended up having a blast. I wish I had gone back for their other sessions; but my scheduling didn’t quite pair up very well. Looking back, it’s still a pivotal moment for me.


I had finally stepped out of my social comfort zone and it paid off.


While I don’t remember every minor and even every major activity that I did during the past 90 days, there were quite a few highlights.

In my 90 Day Arena Challenge, I…

  • IMG_7563Conquered my year-long traveling goal of going to 6 out-of-town locations, 1 out-of-state location and at least one of those while 100% alone.
  • I ended up traveling to 3 of those locations while completely by myself, driving into unfamiliar territory.
  • Had the privilege of meeting close friends out of town completely on whim.
  • Already visited 4 different states with family.
  • Tennessee – Destination Imagination
    • Macy!
    • Pins!
    • Kelly’s Face Painting!
    • The DI Alumni!
    • Microsoft!
    • Dawn!
    • Quest of the Northern Star!
    • Boston Family!
    • You Are The Hero!
    • Maryland Flag!
    • So many experiences.
  • North Carolina
    • Stayed across the street from the ocean on Atlantic Beach.
    • Had a beer on the beach while skygazing at the most phenomenally moonlit clouds I’ve ever seen.
    • Visited an island and decided I’m going to own one some day.
  • Virginia
    • Seqkat!
  • Ohio
    • Family reunion.
  • Met one of my closest friends and biggest supporters for the first time ever in over 7 years. Seqkat. <3
  • Attended more family events, spent more time with family, family dinners, etc.
  • Police Reunion # 1
    • Reinforced that I have an amazing support system all around me, full of encouragement and even business advice. And not a bunch of naysayers.
    • Molly & Team Death Cup!
    • Deborah & Sarah!
    • Getting more comfortable about sharing Venture 15.
  • Pranger Reunion
    • Saw family that haven’t seen each-other in over a decade.
    • Got to talk about my business and ‘quest’ to a few that inquired.
    • Learned that some family had unexpectedly kept up on my progress via Facebook and this blog (this post is for you just as much as it is for me!).
  • Started a private online community to conquer another inner fear.
  • CoWork FTW

    Visited a co-working space in Fort Wayne for the first time.

  • Began livestreaming occasionally to work on social anxiety.
  • Have stuck with my mastermind from the beginning of the year. It keeps me grounded and inspired every week.
  • Got rid of more belongings that no longer offer anything to me beyond mental clutter. I’m learning to identify what is the most significant.
  • Have had coaching calls with a number of Rebels.
  • Have been reading more than I have in the past few years combined.
  • Have taken the first steps to learning how to cook and bake.
  • Continued with Operation Quickstep.
  • Continued to blog, albeit irregularly.
  • Have gotten more comfortable talking. Still a long road ahead of me.
  • And so much more.


I no longer had to ask for permission to do anything. Whatever I wanted, I could just DO. I was in complete control to seize any opportunity I wanted. And for many of them, I DID. And this was the whole goal of the challenge. While it was originally inspired by a business venture, it grew into something bigger – and better.

I wouldn’t have done it differently. Even the failures I would not change. I gladly accept my shortcomings because they show me where I can improve.

20150521_23444190 days later, I have an accurate perception of what I AM capable of and what I am NOT. I have a better vision of my future than I ever did before. I’m much more relaxed, I’m in much more control and I’m much more fine tuned with my own self and what my aspirations are.

Where do I go from here? Do I go back to find a job? Do I keep going with my freelance work and try to grow myself as an entrepreneur? My goals have changed over the past year-or-so. While the beginning half of this year was primarily focused on building a business, I’ve learned a great deal about both it and myself.

From this point forward, I will not only continue to grow my business full-time (90 days for another progress evaluation) but I will also keep my eyes open for opportunities. I know that by keeping my eyes and mind open, I may be better equipped to take on something exciting, challenging and fulfilling.

Will I remain a freelancer and business owner long term or will I find a blend between the two?

Time will tell.

Until then? It’s back into the Arena with me.


[ … ] the man who is actually in the arena, [ … ]
who at the best knows in the end the triumph of high achievement,
and who at the worst,
if he fails,
at least he fails while daring greatly [ … ]

– Theodore Roosevelt