My Struggle to Use My Hard Skills

I work all week using skills that I’ve spent years developing. Using those skills outside of my job, to grow, to become more self-sufficient, however, is a different monster. I’ve always wanted to work on side projects or make some extra money doing freelance gigs. Not to start a company. Not to become a founder. Just something that brings in a bit more income to help out with bills, debt, or add to the rainy-day fund.

Unfortunately, I haven’t quite figured it out yet. I have the skills and the motivation, at least in theory. But when it’s just me, no boss, no deadline, no roadmap, I’m at a standstill.

Side note: this is not going to be a list of tips or a guide for turning your hard skills into a side hustle or becoming a more productive self-starter. I don’t have that kind of advice; there are plenty of places you can go for that, but to quote the great poet Jay Jenkins, “That ain’t this and this ain’t that.” This is just me trying to understand my own roadblocks. These are just thoughts about how strange it feels to have useful skills but still struggle to use them to my benefit.

I know what I’m doing (Mostly). I work in email and automation marketing for a healthcare company. It’s been about four years since I started in this field. I have a background in full-stack web development, which makes me one of the few people on my team capable of working with dynamic templates, helping to bridge the gap between content, logic, and function. In short, I know how to build things. I know how to fix things. I know how to make digital experiences function and flow.

You’re probably thinking, “That field is endless with opportunities for freelance, consulting, or just building useful, self-driven projects.” And you would be absolutely right. It’s not a lack of knowledge or interest. I have the skills and I use them every day. However, when it comes time to put them into action for myself, there’s a clear disconnect.

Part of my hesitation is that I haven’t been in this field for very long. Four years is enough time to be good at what I do, sure, but not long enough to feel like I have every angle covered. I’m still learning what’s possible, still getting comfortable with the jargon, the frameworks, the full scope of what I could realistically offer clients in any variety of spaces that could use my services. Honestly, if someone asks about ROI on a campaign I built or wants to dig into strategy beyond anything I’ve handled before, then it will immediately feel like the jig is up! The guy you thought was an automation specialist is really just a bunch of kids stacked on top of one another in a trench coat.

At work, I have support for those kinds of questions, people who specialize in analytics, customer insights, branding, and the like. But on my own, there’s nowhere to pass the bill when it comes due. It’s all on me. And that “what if I don’t know enough?” fear is LOUD!

It’s like being a master chef who only cooks when someone hands me a recipe and the ingredients. Then I get home, stare at a box of dry pasta, and somehow forget how to boil water.

There is this trap that I and maybe many others fall into, believing that because we’re competent in one space, we should automatically be confident in all spaces. But confidence doesn’t just come from skill. It comes from repetition, from feedback, from navigating unknowns and realizing you can figure it out. I haven’t had enough of those reps outside of work yet to feel solid. And maybe that’s the issue.

Is it impostor syndrome? Even that term feels too broad to explain the weight of it. Because I’m seen as competent (at work). I’m often the go-to guy for certain problems. But when the structure and feedback loops fall away, I question everything. Is this good enough? Am I a fraud? Who am I to launch anything? The irony is not lost on me: I’ve got the tools. But outside the walls of my company, they most often sit untouched.

I don’t have a neat resolution, I’m still figuring it out. It’s not just about time or willpower, but about the mental space to feel capable outside of a structured environment, and the courage to take on entire projects alone.

Maybe other people feel this way. I certainly haven’t seen anything about this specific feeling. The feeling of being good at what you do, yet feeling inadequate to do it without the safety net of conventional structures. Maybe they call it something else. But if you are in that place, or somewhere nearby, I hope this reminds you that you’re not alone.

For now, I’m trying to be patient with myself, acknowledge the frustration, and keep showing up.