How as 28 Year Old I Quit Corporate To Become a Digital Entrepreneur

lessons from adventure Nov 19, 2021

The peaks and valleys of my professional life I’ve journeyed through over the last decade have brought me to not just believe in doing meaningful work, but also creating a career that brings me financial stability and supports my adventurous free-spirited lifestyle.

4 years ago, I was far from this world of doing meaningful work, in fact, I was clocking in for a paycheck at a job that was devoid of meaning. I was stuck in the traditional top down leadership architecture of a corporation that was owned by some private equity firm.

I was in an eCommerce marketing and operations role at a large outdoor company, and while the radness of the brand aligned with my lifestyle, working in the “office”, being bound to a desk, having to follow a traditional M-F, 9-5 and feeling stuck at the mercy of someone else’s orders did not align with my values, purpose, passions and free-spirited adventurous lifestyle.
I mean sure there were challenging projects that engaged my brain, but I saw the “ladder” I was climbing and it was not where I wanted to be going professionally.

Each day I clocked in my shoulders drooped a little lower, keystrokes got a little slower, and my ability to drop into a flow state while working on complex projects got harder…
Burnout was setting in, and it was affecting my professional performance, passion for life, and optimism about my dreams for the future.

No, the 9-5, corporate grind and building of someone else’s dream did not align with my vision of becoming a digital entrepreneur having a positive impact on thousands of people, while traveling the world, doing work I loved, and living the dream that most guys imagine in their 20’s and 30’s.

My job brought a steady paycheck, health benefits, and the perks of exciting new age corporate America; beer, ½ day summer Fridays, a community of outdoor enthusiasts…

It was literally everything that I had asked for 6-months prior, but it’s also the world that I previously left to pursue my dream of building a marketing agency that would bring with it financial stability, and lifestyle flexibility… the freedom to work where I wanted, with who I wanted.

That dream, manifested although not before floundering in fear and going back to the corporate world for a 6-month stint, resulting in the worst emotional, professional roller coaster of my life.

While there existed both lateral and vertical opportunities for growth, I was stuck in my own head, existing in a profession that did not align with my vision and life’s purpose that I created before leaving the last corporate job a year and a half prior.

The reality though, I’d been stuck for years, dreaming but not actually turning my dream into a reality. I was stuck in the fear of failure, the fear of rejection, the fear of not knowing exactly what steps to take to launch my dream into a successful orbit.

I’d falsely started several “side businesses” and managed to bring on several marketing clients throughout my 5+ year corporate career; I'd nearly replaced my salary twice, but never enough to feel safe quitting to go all in. With each passing month, and then year, I felt my dream of being a self-employed digital entrepreneur melting further and further away.

With each passing year, the voice of Warren Miller got louder and louder in my head. As he aged, so did I.

As winter set in each year I’d hear Warren whispering in my ears...

Hey kid,

𝑰𝒇 π’šπ’π’– 𝒅𝒐𝒏’𝒕 𝒅𝒐 π’Šπ’• π’•π’‰π’Šπ’” π’šπ’†π’‚π’“, π’šπ’π’–’𝒍𝒍 𝒃𝒆 𝒐𝒏𝒆 π’šπ’†π’‚π’“ 𝒐𝒍𝒅𝒆𝒓 π’˜π’‰π’†π’ π’šπ’π’– 𝒅𝒐. - 𝑾𝒂𝒓𝒓𝒆𝒏 π‘΄π’Šπ’π’π’†π’“

… sadly many of us never do, we reach our death bed with countless unfinished dreams. I did not want that to become my story, but I felt so damn stuck.

Slowly, I began to break down. One day at a time, going to work just became a total drag. I didn’t feel like I fit in, I was an outcast, with a dream that was just out of reach, a round peg jammed into a square hole.

This just made me feel more and more confused. I’d spend my days doodling, and daydreaming sometimes for hours, envisioning what it would be like to just save up enough money to quit, to get enough marketing clients to have some cash-flow, and then hit the road to the Teton Mountains, Wasatch Mountain Range, and the Swan Range in Colorado... I’d finally be free. I didn't need much, $4000 per month would be more than enough to thrive and feel stable.

As I gained more clarity of what this would look like, my desire to take action and finally turn my vision into a reality burned hotter and hotter each day. I started to pick up some more clients outside of my corporate job, 1, then 3, then 5. I had replaced my salary once again entirely outside of work, and from a cash perspective felt prepared to bounce from corporate once and for all.

I still remember the day I walked into my boss's office, riddled in fear but fueled by excitement to give my notice… what would she think of me? How let down would she feel having just hired me 6-months ago? Would my plan really work out? I just leaned in with faith that it would all work out.

2-weeks later I celebrated my last corporate day and drove straight to Jackson Hole Wyoming to shred pow with my good buddy Drew. And, that was just the beginning of a new life, freedom and the manifestation of some of my wildest dreams. This was about 4 years ago.

My notebook doodles turned into…

  • Living a true nomadic lifestyle for 2 years, I skied, I worked, I lived life. I was free and happier than ever.
  • Peak Prosper (a men’s performance and transformation coaching company) became a reality that is now impacting 1000’s of men on every continent, giving them the guidance and resources to find meaningful work aligned with their authentic skillset that brings financial stability with the freedom to pursue their dreams.
    I met and married the woman of my dreams and we’ve shared some of the most epic adventures I’ll ever experience in this lifetime.
  • I turned a childhood dream into a reality and trekked to Everest Basecamp and all throughout the Sagarmatha Region for a month's time.

Now, I ski powder more days than I can count and have no one to ask if I can take a morning off to go energize my soul with some fresh mountain air, and cold powder snow. I work with some of the most inspiring clients that I could ever ask for… men who are building their dream businesses that are abundantly prosperous and purpose aligned (multiple 6-figures), creating epic relationships, and taking care of their minds and body.

All of these external manifestations in my life unfolded because I’ve transformed my inner world, letting go of the fear that once paralyzed me, and filling that hole with unwavering faith. Entrusting the guidance from mentors who have created the results that I wanted in my life, and taking actions aligned with the person I always wanted to be.

Daydreaming got me nowhere but stuck in a life of comparison between where I was and where I wanted to be.

When I look back on my life and all those years that I spent stuck, I see three apparent things that were totally missing in my life...


𝟏. Clarity;
I did not really know who I was. I was smart and driven but lacked clarity around what my values, skills, strengths, weaknesses, purpose, and passions really were and how these details of my personality could intersect to create a business that supported my dream.


𝟐. Vision;
I lacked a crystal clear vision for my business and life that energetically charged me… a vision that represented “why” the work that I wanted to be doing mattered to me and what it would actually look and “feel” like to be living a lifestyle of freedom in the pursuit of my wildest dreams.


πŸ‘. Goals;
My goals were not much beyond, make $4000 from 4 clients. They lacked three critical elements to successful goal setting, they were not vision aligned, they had no plan of action (POA) and I did not have a mentor to help guide me on my path.
But when I finally cracked the code and got these three key things in my life right (Clarity, Vision, and Goals), everything changed, and quickly.

These three elements have become the foundation of our method that we now teach to 100’s men to help them find meaningful purpose aligned work, and I want to share this method with you for free in a short training video I've put together.

Over the course of this short 20-minute video...

we’re going to help you understand

how you can find meaningful work that supports the adventurous lifestyle you love with one of the most powerful career and business transformation methodologies on the planet…

and ensure you leave with a plan you can implement...

You'll Discover How To...

βœ… Confidently clarify your path forward.
βœ… Find work that impacts others using your authentic skillset.
βœ… Create financial stability to live the life you love.

Learn more and sign up for the free training below, I’m stoked to meet you and help you crush your professional goals.

Watch the Training Here ---> https://www.peakprosper.com/path-to-peace

PS; never give up on the life you truly desire to lead. - Scott