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
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,
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,
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 whatâs most important for you?
Get better as I go. And just keep on going, no matter what.
While it feels like Iâve lived several lives, all distinct from one another, theyâve all had this in commonâget better, keep going.
Iâm 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. Iâm so grateful that Iâve 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 ownâall things I didnât know enough about.
And to be honest, my heart wasnât 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 didnât 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, âwhat business do you have pretending to be a business owner,â and, âbest polish up that dusty resume, sonâ
I couldnât 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 anyoneâs 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 ârace to the bottom.â
Sometimes I move at the speed of desperation and this was one of those times. By the end of the day, Iâd 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 Iâve 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 didnât just change the game, it changed my life.
Now, itâs my turn to give back. I want to help othersâespecially freelancers and solosâfind their path, avoid the landmines, and create systems and processes that will deliver the freedom and stability theyâve always wanted.
If you had to choose a LONGTAIL SEO keyword for your life, what would it be?
âChaos to Clarityâ
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, itâs 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.
Iâm fascinated by human behaviorâwhy we do what we doâmy own included. I'm both inspired and troubled by our coping methods. Itâs crazy how often âcopingâ 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, Iâm passionate about solopreneurship because of the freedom itâs given me.
Having experienced the benefits firsthand, now I want to bring it to others.
Q: What is the most courageous thing youâve 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 lifeâeven 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 wasnât the example I wanted to set for our daughter. It was brutal, but necessary.
And it taught me something about courageâitâs not about being fearless. Itâs about making hard decisions, even when you're terrified.
Q: Why do you write on Substack?
There was so much I didnât 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 canât imagine this for themselves. Freelancers who donât see a path forward. Solos who are like I was: good at their thing but not as good at the business side of freelancing.
Thatâs 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 Iâm not adding value, Iâm 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. Itâs not about what I think they want; itâs about what they actually need right now.
Lastly, consistency. Show up, even when itâs 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. Thereâs 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 donât want to sugarcoat my story, because thatâs where the connection happens. When youâre transparent about your failures, shortcomings, and how youâve faced them, people relate to that.
Vulnerability is the glue that binds everything together. I canât ask people to trust me if Iâm not willing to put my own struggles and solutions out there.
I also use humor and snarkâbecause 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 youâre finding your voice in this way. Freelancing and solopreneurship can be a lonely life. But I didnât 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 Iâm at on my journey. Thatâs what I want to bring to mine, all those same things: empathy, relatability, and a clear sense of direction. Communities need clarity. Otherwise, weâre wasting everyoneâs time.
If you enjoyed this share and resonate with
way of being, subscribe and reach out! Heâd love to hear from you.
đ If you enjoy reading this post, feel free to share it with friends! Or feel free to click the â¤ď¸ button on this post so more people can discover it on Substack
I love âusing self - doubt as a motivatorâ. Itâs a fuel, that when topped up with its equally powerful, albeit potentially debilitating cousins âfearâ and âanxietyâ, that Iâve used to turbocharge me! When we learn to embrace and harness every part of our very human range of emotions, then maybe that even becomes a superpower. Congratulations on your progress and success Patrick O - that doesnât happen by accident, I acknowledge the âblood, sweat and tearsâ that goes into it. Keep thriving. Hereâs to your continued success. Huge thanks for sharing.
I shared that this is what happens when you make a real connection with someone. You learn about yourself. Several months ago, I was new here. Poking around, making mistakes, figuring things out.
Suddenly I met Magdalena, this lovely human who made me, a complete stranger, feel totally at home here. We made a connection. Thatâs when she hit me with something unexpected. And I almost said no. Scared Iâll say too much (happens a lot). Or that I donât have a story worth telling.
In doing this spotlight with Magdalena, I learned a lot about myself, my backstory and how vulnerable it feels to speak so freely about it.