How My Inner Rebel Saved Me from Giving Up on Freelance

Late one bloodshot night I nearly threw in the freelance towel. I had become resentful of the self-employed life. I felt the inner rebel in me shouting out against the constant need to self-promote, the repetitive five-step webinars, and the ironic captivity of managing my own time. I found myself two hours into scrolling through LinkedIn job postings, wondering why I gave up the enticing stability of a nine to five job.

Then, I remembered a conversation I had five years ago. Being the hippie that my mom is, she was telling me about the four stages of the spiritual journey.

  • Blind Acceptance and Conformity to Status Quo
  • Questioning and Skepticism
  • Rebellion Against Status Quo
  • Rediscovering an Authentic Path

Cue my light-bulb moment.

The entrepreneur’s journey is a journey of the spirit.

The difference being that when I left the corporate world to pursue a career in coaching, I immediately entered stage one: Conformity. I conformed to the path my freelance mentors had taken. I copied their marketing strategies, their approach to coaching, and even their webinar templates.

After getting the hang of the coaching world’s status quo, I entered stage two: Questioning and Skepticism. Instead of blindly regurgitating my mentor’s scripts, I asked myself, “Is there a better way?” I questioned my routines and procedures, and created my own style of working with clients.

Conformity and questioning were both safe stages that couldn’t last too long. At some point last year, I slid, unprepared, into stage three: Rebellion. For the first time, I admitted every reason I was fed up with freelance life.


No, I don’t want to post spam-like Facebook ads.
No, I don’t want to offer another five-step webinar.
No, I don’t want to join one more cross-promotional Instagram opportunity.

While I was rebelling against my unfulfilling daily routines, I interpreted my frustration as a reason to quit the entrepreneurial journey all together. I worried: I am not cut out for freelance, I need to get a “real job.”

I almost threw in the towel because I believed I had tried and failed at pursuing my authentic path. I didn’t know that rebellion and frustration is a necessary step. I had left the corporate status quo for the freelance status quo, and now it was time to rebel and rediscover once again.

Eight years ago, I sat in a corporate office surrounded by successful Manhattanites, and I rebelled. I rebelled against the nine to five and the eighty-hour work week spent achieving goals that meant nothing to me. That initial rebellion instigated my search for a more authentic path.

Now, I’ve come full circle. Except, this time around, I’m rebelling against the status quo within an industry I love. I still have frustration, but I have my dream job. Instead of throwing in the towel because of social media pressures and the headache of paying for my own benefits, I’ll choose to notice what frustrates me and adjust accordingly.

I’m not going to lie to you. Some days I resent the wander. I pray to arrive at a destination, to have all my systems in place, and money flowing in. But the truth in me knows that when that day comes, it won’t last long. The creative in me will itch to rebel against my new norms. I’ll grow tired of the programs I sell and marketing campaigns I write.  I’ll begin the cycle again, questioning, rebelling, and launching into new phases of wandering and rediscovery.

When that day comes, I want to remember that the questions, frustrations, and belief that I am lost are all signs that I chose an authentic path, not a stagnant finish line.

For now, I feel privileged to follow a calling. I will honor my entrepreneurial journey, wandering into authentic expressions of norms that don’t resonate with me. For now, I will embrace the wander.

Photos by: Karen Hernandez


Jackie Viramontez

Jackie is a lover of mindfulness, healing, and Trader Joe’s dark chocolate. She wrote Amazon bestseller, I Can’t Believe I Dated Him, to help women own imperfections and embrace the true purpose of painful emotions. When she is not coaching, she is exploring Los Angeles with her filmmaker husband Jake.