Have you ever felt completely lost after a major life change? That's exactly where I found myself in 2022 when I left the military with no clear plan, no vision, and what felt like no real-world skills. In this article, I want to share how a series of uncertain leaps—some deliberate, some forced—ultimately led me to discover my path and develop skills I never knew I needed.
When Your Plan Falls Apart
I did technically have a plan when I left the military: rejoin a different branch and pursue a new military career. But that plan quickly fell apart.
My wife was understandably tired of the military lifestyle—constantly moving, being away from family, and dealing with my frequent absences. While I wasn't personally ready to leave that world behind, I understood her perspective. So, I got out.
The problem was figuring out what came next while I waited to potentially rejoin later.
The Job Search Trap
I applied for countless corporate positions, landing plenty of interviews thanks to a polished resume (shoutout to my mom, a professional resume writer). Despite getting offers from reputable companies, I fell into what I now recognize as a psychological trap: I couldn't bring myself to commit to a career I had zero passion for.
The idea of pouring my energy into something that wasn't aligned with my actual goals felt like a waste of my limited time on earth. This wasn't laziness—it was a fundamental mismatch between what my gut was telling me and what conventional wisdom suggested I should do.
Just Do Something: The FedEx Phase
Instead of forcing myself into a corporate job I'd resent, I took a position loading trucks at FedEx. It was simple, physical work that started at 4 AM. There wasn't even an interview—I applied and was told to show up at the warehouse on my start date.
This first leap taught me something crucial: Sometimes you just need to get moving. The job wasn't glamorous or aligned with my long-term goals, but it:
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Provided some income
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Didn't require a commitment I couldn't honestly give
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Most importantly, it broke my paralysis
It was action over planning, pragmatism over prestige. I was labeling my situation realistically: "I need income right now, and this works for now."
Recognizing the Wrong Fit: The Pool Manager Saga
My next leap came after I took what seemed like a "better" position managing a local pool. From military operations to supervising teenage lifeguards—quite the career pivot.
For a while, it worked well enough. There were the typical challenges—staffing shortages, unreliable high school employees, no-shows—but I adapted. I had plenty of overtime and enough flexibility to pursue my personal interests.
Then came the breaking point: the company moved my position to salary. What they framed as a 10% raise actually meant a $20,000 pay cut due to lost overtime—while simultaneously adding more responsibilities.
This moment crystallized something important: the deep dissatisfaction I was feeling wasn't just complaining—it was a signal. I was labeling myself as "stuck," and that identity wasn't one I could accept long-term.
Key insight: Pay attention to those moments of frustration or feeling undervalued. They aren't just complaints; they're signals defining what you don't want. Don't let a negative situation become your identity—use it as fuel to change.
Answering the Passion Pull: BJJ and the Coffee Spark
Around this same time, I discovered Brazilian Jiu-Jitsu (BJJ). It quickly became an obsession, gradually replacing my old military goals with new aspirations. This wasn't work—it was genuine passion.
This newfound enthusiasm, combined with my growing dissatisfaction at the pool job, sparked my biggest leap yet: "I want my own thing."
That's when I decided to start Wild Ridge Coffee. The fear was enormous—I had no business experience, minimal funding, and honestly no clue what I was doing. Starting a product-based business without an existing audience seemed borderline insane.
But when I looked at it from different time perspectives:
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In 10 weeks? Failing at the coffee business wouldn't be worse than staying miserable at the pool.
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In 10 months? I'd have learned valuable lessons even if it didn't work out.
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In 10 years? The real catastrophe would be having never tried at all.
Key insight: When passion pulls, listen. Reframe the risk: What's the real long-term cost of inaction versus the potential (even scary) upside of trying something new?
Starting Before You're Ready: Launching Wild Ridge
Looking back, launching a product business with zero audience or experience was probably the most naive thing I could have done. My confidence was non-existent, my perception of my abilities was rock-bottom, and my standards were basically "don't go bankrupt immediately."
But I did it anyway. The key was separating the feeling of confidence from the action of starting.
It took nearly three years to gain real traction. Financially speaking, it was rough going. But the learning? Immeasurable.
Key insight: Don't wait for confidence. You build confidence through action, not before it. Embrace the struggle, lower your initial bar if necessary, and just get the repetitions in. You will learn by doing what you could never learn by planning.
Focusing on Skills, Not Just Success: The Grind
Those first few years of entrepreneurship were a grind. I had to learn marketing, social media management, copywriting, web development, SEO, business funding, and product development—all through firsthand experience and plenty of mistakes.
When business growth is slow, it's easy to feel like a failure. To worry about what others think, whether you look legitimate, whether you're wasting your time.
The mindset shift that saved me was focusing on skill acquisition rather than external validation. The reality is, no one really cared if my first website was terrible, as long as I was learning and improving.
I wasn't just building a coffee company; I was building myself—my skillset, my capabilities, my resilience.
Key insight: Focus on the process and the skills you're gaining, especially in the early stages. The real win is developing capabilities no one can take away from you, regardless of whether this particular venture succeeds.
Leveraging Your Messy Journey: Helping Others
The final leap, which is ongoing: Realizing that my "messy" journey had created real value.
All those hard-won skills? It turns out other businesses need them too. I started writing for local businesses and offering consulting services based on what I'd learned through trial and error.
My credibility didn't come from formal education or corporate experience—it came from the fact that I actually did the work. I built websites, ran ad campaigns, wrote email sequences, created content, and solved real business problems.
Each new challenge expanded my skill set further—video editing, content strategy, copywriting—creating layers of expertise I could offer to others.
Key insight: Your unique struggles and the skills you built while overcoming them are valuable. Don't discount your journey. Find ways to leverage that experience—it might become the foundation for your next opportunity.
The Real Path Forward
Looking back on my journey from lost veteran to business owner, I've realized that it was never about having a perfect plan. It was about:
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Taking any action to break inertia (FedEx)
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Recognizing and leaving what wasn't right (Pool job)
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Following the pull of passion, even when scared (BJJ/Coffee)
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Starting before feeling ready and embracing the learning curve (Wild Ridge launch)
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Focusing on building skills over seeking validation (The grind)
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Leveraging the whole journey to create new opportunities (Consulting/Writing)
The point is: Taking leaps, even small ones, into the unknown is the path forward when you're stuck. It's how you develop yourself in ways you could never anticipate.
While I wouldn't consider Wild Ridge a massive financial success yet, the skills and experiences I've gained are invaluable. I've built marketing expertise, content creation abilities, business acumen, and problem-solving capabilities I never would have developed in a conventional job I was just tolerating.
Your Turn to Leap
This stuff isn't easy. If you're trying to figure out your own path or build your own thing, remember that the most important step is often just starting—even if the conditions aren't perfect.
Sometimes the best self-development doesn't come from careful planning, but from taking that first uncertain leap and figuring things out along the way.
So take the jump. Do the thing. It's entirely up to you.