The Arena – Fork in the Road

The Arena – Fork in the Road

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




  1. Great progress, Austin!! You take responsibility for who you are, and move forward to grow in to what you desire to be and/or do! That is a grand feat that many miss out on. You’re not letting life just happen to you. You are creating it, and dancing with it!! I applaud you with you the utmost respect.

    And you took it one step further. A very daring step and that was to share it here, expose who you really are, your triumphs, your fears, your goals. That takes real courage to express who you fully are in the eyes of many others, removing the masks we so often wear to just be accepted. And with it, I know that you are inspiring others to take charge of their life too! What a gift you offer us all, and I thank you!

    And then for myself, personally, you are such an awesome, friend. Together we’ve been through some thick and thin. It is always grand to know you are always there with support and genuine care! Thank you!! :) ^..^<

    • Thanks for the reply, Seqkat! It certainly hasn’t been without its challenges. I don’t remember what compelled me to start ‘sharing’ these things beyond simply trying to get comfortable around myself and what I wanted, but it’s been paying off!

      And I know that I have a lot of progress so far to attribute to you and the support you’ve given to me over the years. =]

  2. Austin,

    Nice to see that you too are pushing forth to achieve what you want in life.

    Reading this post, I can loosely relate to where you where, to where you currently are, and where you’re going with your life.

    This is my assumption, but we may not have done much, had much, or been much earlier in our lives, but thanks to that absence, it’s givin’ us the chance to really retrospect and make a pivot in the right direction.

    I guess you can say, we’re living a bitter sweet.


    • Hey Christian!

      Thanks for leaving a message here. (: We’ve shared a few similarities from what I’ve seen, so I appreciate what you’ve said here.

      Looking back at my life and how it got me here, it wasn’t so much about what I didn’t have or couldn’t do. While yes, I think there is a lot that I missed out, but I attribute that to my lack of conviction.

      It was like nobody told me that all I had to do was to make decisions for myself and just … step towards it. And those that did tell me, I didn’t have the courage or didn’t believe them at the time.

      This year was totally different. That ‘absence’ really does give a lot of perspective on where we’ve come from and it only served to help push us to where we are now – and where we’re going!


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