Qualified, Broke & Tired—Part II: When the Dead End Finally Ends

Actually, I really do.

A lot has happened in the months since I wrote about how deeply dissatisfied I was with my income level and how much I felt it had begun to define me. It felt like it defined too much of who I was, simply because I literally could not afford myself. Living pay cheque to pay cheque and sometimes less than that—can be both daunting and deeply discouraging.

When your survival feels uncertain, it starts to bleed into everything. It reshapes how you see yourself. It dictates what you say yes to, what you delay, what you deny yourself. It shrinks your sense of possibility. And slowly, quietly, you begin to confuse your financial reality with your worth.

I felt like I was in a space I had long outgrown. I was drowning in it, unsure of what was next, unsure of how to move forward, unsure of whether there was a forward. It genuinely felt like a dead end. And after spending over JMD $1.5 million to acquire a Master’s degree, the last thing you want is for your job—the very thing shaping your career—to feel like a ceiling instead of a ladder.

So I went job hunting. Not casually. Intentionally. Desperately. Prayerfully.

I sent out close to 100 résumés over a two-month period. I told anyone within my professional space that I was looking for something new. I even told my Director. Because a big part of moving on professionally is knowing when something no longer serves you, even when you are grateful for where it started.

I prayed over every application before submitting. But there was one position I truly wanted. The job description aligned exactly with where I felt I was heading. I had no idea what the salary was and it didn’t matter. I was familiar with the organization, and based on what they needed, I knew I could bring value and more.

So I applied. And I prayed. And I told God that regardless of what came from the other applications, this was where I genuinely desired to be.

Within a month, I was interviewed. A month later, I received the offer.

Manager.

I cried. I called my sister. I cried again. I felt something shift inside my body—like my shoulders finally exhaled. Like my spirit had been holding its breath for years without realizing it.

This was not just a new job. It was a release.

It has now been just over three months since I stepped into this new role. A role that has not only provided me with an increase in income, but also managerial responsibility and creative oversight, something I had been yearning for, even before I had the words for it.

But has my mentality shifted?

Not entirely.

Yes, I am earning more now. But the millennial dream still feels elusive—especially when you are building your life largely on your own, without generational safety nets, inherited property, or financial cushions to fall back on.

I am not raking in major cash, but at this phase of my life, the professional growth I am experiencing is currently worth more to me than the dollar value of my salary. So I am willing to look past that—for now.

Still, I know myself well enough to know that eventually, the desire for more will return. And when it does, it will become both my ambition and my next internal war.

Because the millennial struggle isn’t just personal—it’s structural.

That feeling of being qualified, broke, and tired isn’t unique to me. Never was. It reflects a broader generational reality shaped by systems that were never designed to support us in the way they supported those before us. Some of us, no matter how hard we work, will never fully meet the expectations we set for ourselves, or those imposed on us by arbitrary societal timelines and definitions of success.

So at what point do we learn to be content?

At what point do we start redefining what success means—outside of salaries, square footage, and comparison?

I don’t have the answer. It would be dishonest to pretend that I do.

I see value in succeeding because it brings me closer to the life I want. But my dilemma remains:

• How much of myself am I willing to give up right now to get there?

• How much am I willing to live without?

• Is this leading me closer to the freedom I desire?

  
  

And maybe the real millennial dream isn’t about arriving at all—maybe it’s about deciding what we refuse to sacrifice on the way. Time? Health? Money? Relationships? The beauty of life is that you get to decide.