6d (edited) • General discussion
📖 I Did Everything Right — And It Still Wasn’t Enough
Here’s what I figured out after, and why I’m building this community.
I had always grown up knowing how to approach work the right way — working hard for every minute I was on the clock, taking care of the company’s resources as if they were my own, aligning to and embodying the mission and vision of the organization. That was just how I was wired, and for a long time I believed that if you did those things consistently, the financial rewards would follow naturally.
The reality I ran into was different. I was making just under $50,000 a year, and as our family grew and costs kept rising, we reached a point where the math genuinely didn’t work anymore. Between 25 and 30% of my income was going toward health insurance and out-of-pocket medical expenses alone. We had sat down together and reviewed our budget meticulously, cutting every additional expense we could find. There wasn’t much left to cut. The final straw was when we had to go on state-assisted medical insurance, which I believe serves a real purpose and I’m glad it existed — but I also knew I was capable of more and didn’t want to accept that as our permanent situation.
# The Five-Year Plan
So I did what felt natural to me. I built a plan. I put together an aggressive five-year roadmap with specific goals and targets — not just for my own growth but for what I could deliver for the company — and I brought it to my VP. I asked him directly: if I hit these goals aggressively, what would it take to get to $70,000?
He was genuinely a good person who cared about me, and he also had the interests of the company in mind, as he rightfully should. His answer was a walkthrough of the standard progression — slow, incremental raises over a much longer timeline than I had in mind. I understood why that was his answer. That’s how the system was designed to work. But I was feeling the financial squeeze in that moment, not years down the road, and I knew I needed to make a change more immediately than that process would allow.
That was the point where I updated my LinkedIn profile to be visible to recruiters and started actively looking at other roles.
# What I Actually Learned
The thing I hadn’t understood before that conversation was something that sounds simple in hindsight but genuinely wasn’t obvious to me at the time. In most organizations, the behaviors I had built my professional identity around — hard work, loyalty, ownership, mission alignment — are incentivized with recognition like awards or public praise, but they don’t typically translate into significant financial compensation unless your role is specifically tied to revenue generation, like sales.
I felt genuinely disappointed when I realized that. Everything I had poured into that role, the sense of ownership I felt over the work, the belief that I had earned something real through years of showing up that way — and it hadn’t paid off the way I expected. It felt like I had been handed an incomplete set of rules for navigating professional life, and I was only now finding out what was missing.
What I also came to understand, though, was that my VP wasn’t the problem. Everyone operates from a framework, and that framework makes us blind to certain things — in his case, the current cost of raising a family, the current market value for specific skills, and the way that technology has completely shifted things like remote work and what geography means for income potential. He wasn’t withholding anything. He just couldn’t see what I could see from where I was standing.
# Choosing Differently
At that point I made a decision that felt uncomfortable in a way I didn’t fully expect. I stopped filtering job opportunities based on the difference I could make or the mission I could align with, and started looking purely at income and benefits. That felt like a compromise of something, and I want to be honest about that because I think a lot of dads in this position feel the same tension.
But looking back, it was the right call. Providing for your family isn’t a lesser purpose — it is the purpose. And I had to get clear on that before I could move forward without second-guessing myself.
My wife knew everything that was happening during this time. We were in it together, which I think made a real difference. Carrying that kind of pressure alone would have been harder in ways that are hard to fully explain.
# What Happened Next
Within a few months, a recruiter I had been working with closely brought me two options. The first role I interviewed for was the smoothest interview process I had ever been through — the second and third rounds went just as well, and it was clear to both sides that it was a strong fit, even though I had gone into the search with nothing more than income and benefits as my criteria. My income increased by 80% in that role, and within two years, through further promotions, I had more than doubled what I was earning when I sat across from my VP with that five-year plan.
The relief that came with that change is hard to overstate. The financial pressure that had been a constant background noise in our lives just lifted. That move I made reluctantly, the one that felt like a compromise, turned out to be the most important professional decision I had made up to that point.
# Why I’m Sharing This
I’m building this community for dads who are working hard, who are committed to their families, and who are running into the same wall I ran into — where the effort is real but the income isn’t reflecting it, and the gap between what you’re earning and what your family needs keeps getting harder to ignore.
The things I wish someone had told me earlier are pretty straightforward in hindsight: hard work still matters, but it has to be aimed at the right target. Your market value and your employer’s compensation structure are two different things, and it’s worth understanding that difference clearly. The people around you — even the ones who genuinely care about you — are working from their own frameworks and can’t always see what your family’s situation actually requires. And sometimes the move that feels uncomfortable or even like a step away from who you are is the one that actually gets your family where they need to be.
That’s what I want to work through together here. I don’t have all the answers, but I’ve lived through some of the hard parts, and I think there’s real value in figuring this out in community with other dads who are trying to do the same thing.
If any part of this resonates with where you are right now, you’re in the right place.
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📖 I Did Everything Right — And It Still Wasn’t Enough
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