Chapter 10
Finding My Niche
May 26, 2015
I had been freelancing full-time now for over a year, but I hadn’t made any money in months. My wife, exhausted and frustrated, returned to work while I stayed at home with our one-year-old, trying to figure things out. The tension in our home was palpable. Every day felt like a ticking time bomb, and I could see the worry etched on my wife’s face as she headed off to a job she didn’t exactly care for, leaving me behind to care for our child and chase a dream that seemed more elusive by the day.
One day, she texted me from work, “Your mom’s calling. What should I tell her? I don’t get paid until next Friday.”
I stared at the message, a knot forming in my stomach. No one understood why I’d left a good-paying career in engineering to become what they saw as a cruff—a man with no direction, dragging his family into financial instability. But I wasn’t ready to explain myself or justify my vision to nonbelievers. All I knew was that the beliefs that had gotten me where I was no longer served me. I couldn’t follow those voices to get to where I wanted to be.
My vision was clear—I knew what I wanted to build, what I wanted to achieve—but I couldn’t shake the fear that I was failing those who depended on me. It was a lonely place, trying to build something new while the world around me, including those closest to me, questioned, “what are you doing?”
My only comforts were the books and stories I read about people who had turned their thoughts and dreams into reality. I clung to them as lifelines, hoping that by internalizing their wisdom, I could manifest the success I so desperately sought. I followed these with a non-stop stream of articles, videos, and webinars about making money online, diving into anything that promised a way out of the financial hole I had dug for myself.
One day, I’d be going back and forth with a client over a $50 flyer; the next, I’d be editing video for a political campaign. Then I’d be tutoring high school students for $15 an hour. I was all over the place, chasing dollars instead of building a business. But I was determined not to get a job.
Then I got an email from my boy Nael:
"Here’s what I want to know from you. Because I know how great you can be. Some others know. But I don’t think most have that one thing they can grab on and say they know you can do this very well. There’s video and websites, but what’s the thing people can hold on to? What is your biggest professional win? Don’t worry about how big you think it is. Just scan everything you’ve done and pick out a few so I’m aware, and maybe it’ll jog some ideas inside you too.
Whatever those are, do people know? Why not? I’ve probably said this to you, but absolutely no one would know about my TV stuff except for the people who actually picked my music to be on those shows unless I put it out there. And now it’s the thing that people spread to others.
What’s the most amount of money you’ve been paid for your services? And what did you get paid for? What’s the biggest result someone has had because of you? Another great question to ask is: Why haven’t things worked out with clients? If you zoom out and are critical of yourself, how can you fix those things? But yeah, overall, what has been your biggest win? And what is your next biggest win?"
I stared at the screen, my heart sinking. What was my biggest win? I scrolled through my mental Rolodex, but nothing stood out. Sure, I had a good education, and I’d been through a high-profile training program, but those weren’t my wins—they were steps on a path I hadn’t fully chosen.
Nael’s questions forced me to confront a truth I’d been avoiding. For the past 18 months, I’d been on a relentless journey—finding my way, making money, raising my son, nurturing my marriage, and chasing dreams. But I hadn’t truly won anything of my own. The biggest win wasn’t financial or professional; it was the journey itself, the struggles, the minor victories, the ammunition I’d gained along the way.
But then Nael asked the question that changed everything:
"If you could do one thing right now that someone would pay you for, that you know you could keep your enthusiasm high for and not get bored with, what skill would you be using? I’m asking so that I can actively look out and try to create that specific kind of scenario. And then what proof do you have that shows you can do that thing?"
A lightbulb flickered to life in my mind. I knew the answer, but it had been buried under layers of doubt and distraction.
I replied, "Ok, perfect. I left it out, but it’s Squarespace. I genuinely love crafting this stuff—getting paid would be a bonus, especially when it’s in the $1,500–$3,000 range. I found an untapped market today on Craigslist of people looking specifically for Squarespace web experts. It took me a couple of hours to work my way around the country and reply to all those emails, but it gave me two ideas:
I can cherry-pick these as a daily routine. I used to do it occasionally to get a video job here and there (it’s how I scooped up DLS).
If I can figure out a way to just get these Craigslist posts directly in my inbox every morning, I win. With this focus, I know I’m going to make bread. I have a place to focus my content marketing efforts. I can easily pull in IM stuff as needed, etc."
With this realization, I knew I could focus on finding work related to this platform. Squarespace wasn’t just a tool; it was something I genuinely enjoyed working with. The simplicity, the creativity, the ability to help people bring their ideas to life on a digital canvas—it all resonated with me deeply. And for the first time in months, I felt a spark of excitement about the direction I was heading.
I set up alerts on Craigslist for every major metropolitan area in the country. Anytime "Squarespace" was mentioned in a job post, I would be notified. That first week, I started receiving alerts every morning in my inbox—someone in Arizona looking for a Squarespace web designer, someone in California, and so on. It felt like the beginnings of a lead-generating system, all from these alerts.
Once that was in motion, I wondered where else I could find people seeking Squarespace web design help. I turned to Upwork, where I had previously tried to find designers and developers. Despite hearing negative things about Upwork—like it being a freelance marketplace with less-than-ideal clients—I decided to give it a try as a freelancer. I set up RSS feeds to notify me whenever a new Squarespace web design job was posted, allowing me to respond quickly. I didn’t stay on Upwork for long, but I was there long enough to recognize patterns in what people were looking for—customizations and tweaks. They were attempting to do it themselves but needed extra help with the development side of things. I saw an opportunity to fill that gap.
In 30 days, I’d gone from waking up depressed to waking up to leads wanting to work with me. With this boost of confidence, my mind was ripe to take it to the next level. I was no longer chasing every opportunity that came my way. I had found my niche, my focus, and it was beginning to pay off.