Reinvention, Resilience, and the Power of Systems

The connection factor

Imagine this: As a single father navigating the aftermath of a divorce, you find yourself confronted with a failing business that you never truly desired. Your self-doubt echoes louder than ever, whispering insidious doubts about your abilities. This was the reality

Patrick O.

faced not so long ago.

But instead of succumbing to the chaos, he chose a different path. He chose courage. He chose reinvention.

In this candid interview,

Patrick O.

pulls back the curtain on his journey from the brink of despair to a thriving career as a sought-after freelancer. He shares how he harnessed the power of systems and processes to not only transform his business but his entire life. He reveals the unexpected joys of fatherhood, the challenges of ADHD, and the profound impact of embracing vulnerability.

With refreshing honesty and a touch of humor,

Patrick O.

offers a roadmap for anyone seeking clarity, reminding us that even when life throws its worst, the path to freedom and fulfillment is always within reach.

Q: Tell us a little bit about yourself, and what’s most important for you?

Get better as I go. And just keep on going, no matter what.

While it feels like I’ve lived several lives, all distinct from one another, they’ve all had this in common—get better, keep going.

I’m a dad to an amazing daughter who, at 10, is already maturing into a young woman faster than I can believe. Like so many parents, I selfishly wish I could freeze time. I’m so grateful that I’ve been able to work for myself for the last 15+ years, which has given me the freedom to be the type of parent I never had.

The entrepreneurial itch came in 2008 when I decided to launch an SEO agency. As a self-taught, college dropout with no experience working at any kind of agency, it was a bold move. Riding the wings of excitement and youthful ignorance felt like destiny, nothing could have convinced me otherwise.

Self-employment taught me quickly how much ADHD affected my ability to focus and stay organized. It also taught me how little I know about building a business. Through a series of partnerships, I no longer ran an SEO agency, but instead now owned half of a web design, development, and advertising agency. After a series of disappointments and breaches of trust that led to departnering, I was left running the web and ad agency on my own—all things I didn’t know enough about.

And to be honest, my heart wasn’t in it either.

Because in the midst of all this, my personal life was unraveling. I was going through a divorce. My daughter was 16 months old, and I found myself trying to keep afloat a business I didn’t care about. All while navigating fifty percent custody life and being newly single for the first time in 15 years.

If the military taught me anything about endurance, I knew I could push through.

But the imposter syndrome was real. I kept hearing a voice, “what business do you have pretending to be a business owner,” and, “best polish up that dusty resume, son”

I couldn’t bring myself to accept the defeat of applying for jobs. So I used self-doubt as a powerful motivator.

When I shut down the agency and ended my marriage all at once, it was devastating, but it felt like a clean slate. I had a lot of work to do, mostly on myself. I knew I needed to be solo for this part of the journey since I was not in a place to be anyone’s partner for anything, personally or professionally.

A therapist may have given me the business advice and kick in the pants I needed when he recommended I take work from the freelance website I use to hire freelancers. I thought he was nuts, no way was I about to put any effort in that “race to the bottom.”

Sometimes I move at the speed of desperation and this was one of those times. By the end of the day, I’d set up a freelancer profile. By the end of the first week, I got my first client and a 5-star review.

Then another. I bought courses, joined communities and got better at my craft. I was stacking up clients and glowing feedback faster than ever.

It felt like I was back. This time, I was on fire.

By now I’ve mastered quite a few subsets of B2B digital marketing. But the biggest breakthrough was learning how crucial systems and processes are to running a solo business.

It was like the clouds parted and angels sang when I finally figured that out. It didn’t just change the game, it changed my life.

Now, it’s my turn to give back. I want to help others—especially freelancers and solos—find their path, avoid the landmines, and create systems and processes that will deliver the freedom and stability they’ve always wanted.

If you had to choose a LONGTAIL SEO keyword for your life, what would it be?

Q: What are your hobbies, passions, obsessions, or what excites or inspires you? What sets your soul on fire?

Parenting, without a doubt. I never wanted kids so being a dad is my life's greatest unintended adventure. But, it’s also made me feel the most vulnerable. Watching my daughter grow up is bittersweet. I want her to stay little forever. But, I can't wait to see the woman she'll become.

I’m fascinated by human behavior–why we do what we do—my own included. I'm both inspired and troubled by our coping methods. It’s crazy how often ‘coping’ leads to self-sabotage. Understanding our behavior has been crucial to improving not just my business, but my relationships too.

I also love new business ideas and being a solopreneur, but ADHD brings with it a set of challenges. I spent years thinking I could lead a team and build a business when managing myself has been one of the hardest parts.

The chaos is tough. But, I’m passionate about solopreneurship because of the freedom it’s given me.

Having experienced the benefits firsthand, now I want to bring it to others.

Q: What is the most courageous thing you’ve ever done?

Asking for a divorce. We were both miserable.

It was like ripping the band-aid off the only thing that felt stable in my life—even though it was by no means stable. I felt isolated.

After the divorce, I was at my lowest, both personally and professionally. I had lost multiple long-held identities for who I was anymore. I was completely unmoored, living 400 miles away from my hometown and family and instead the shadow of my old life but now without any kind of support system.

But I knew I couldn't let the fear of uncertainty stop me from making the right choice. I knew staying in an unhappy marriage wasn’t the example I wanted to set for our daughter. It was brutal, but necessary.

And it taught me something about courage—it’s not about being fearless. It’s about making hard decisions, even when you're terrified.

Q: Why do you write on Substack?

There was so much I didn’t know about freelancing when I got started. I saw other freelancers charging $100/hour, $125, $150 or more and glowing reviews. I remember thinking about what they could possibly be doing, how they do it, what they were offering. How could they consistently deliver excellence in results and customer experiences?

Systems? Processes? I had none of those. Worse still, I had no degree, direction, or boundaries with clients. I'd take any work, even if it meant undervaluing what I had to offer.

Not anymore. Now I charge more than most freelancers and often have to put new clients on a wait list.

Today I'm known for enterprise B2B tech sales and marketing, but mostly unknown to the people I feel called to help the most.

I want to reach the freelancers who can’t imagine this for themselves. Freelancers who don’t see a path forward. Solos who are like I was: good at their thing but not as good at the business side of freelancing.

That’s why I write on Substack: to show freelancers that the road from chaos to clarity is here. And help them avoid making the same mistakes I did.

Q: What are your values as a writer/creator/leader?

Be helpful. Always. If I’m not adding value, I’m wasting time. I want to inspire action, no more delays. I can help people find their own path to freedom, both personal and professional.

Authenticity is another must for me. If I'm not transparent with my audience about my struggles and how I've overcome (or am still overcoming) them, I won't build real trust.

I also believe in staying focused. I know how hard that is for me, and I assume many of my readers struggle with it too. So, I try to keep things clear, concise, and actionable. Listen to your audience. It’s not about what I think they want; it’s about what they actually need right now.

Lastly, consistency. Show up, even when it’s hard.

Q: How do you connect with your readers?

Too many wide-eyed freelancers get started like I did: with no path forward living an unsustainable life of financial uncertainty. There’s more to becoming a successful solo than just setting up a freelance profile.

I offer the systems and shortcuts I use through workshops, bootcamps and accelerators.

I connect with these solos through shared experiences. I don’t want to sugarcoat my story, because that’s where the connection happens. When you’re transparent about your failures, shortcomings, and how you’ve faced them, people relate to that.

Vulnerability is the glue that binds everything together. I can’t ask people to trust me if I’m not willing to put my own struggles and solutions out there.

I also use humor and snark—because freelancing is hard enough, why not make it fun where we can?

Q: What do you look for in a community, and what is your secret ingredient in building your community?

Honestly, building a community scares me a bit. It feels like this big responsibility to lead or even participate in one, especially while you’re finding your voice in this way. Freelancing and solopreneurship can be a lonely life. But I didn’t go it alone. And neither should anyone. So in a community I seek: relatability. They should understand the struggle and have been in the trenches too. I like to see empathy and intuition, especially when it comes to meeting me where I’m at on my journey. That’s what I want to bring to mine, all those same things: empathy, relatability, and a clear sense of direction. Communities need clarity. Otherwise, we’re wasting everyone’s time.

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Patrick O.

way of being, subscribe and reach out! He’d love to hear from you.

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