What My Late 30s Taught Me About Getting Paid

Data shows that baby boomers (our parents’ generation) tended to settle into their longest job stint in their late 30s and early 40s. The job they landed around that time was often the one: the role they stayed in for a decade or more, sometimes all the way to retirement.

Millennials, on the other hand, are still in the thick of figuring that out. We’re in our late 30s now, still shaping what stability even looks like. Will we have that “forever” job someday? Maybe. I know I’d love to think so.

I’d love for my next job to be that job. The one that offers everything I need and fits who I’ve become. But unlike our parents, we’ve job-hopped, shifted, and reinvented enough to know exactly what works and what doesn’t. 

And the biggest lesson I’ve learned is that it’s not all about the salary.

When “Good Money” Isn’t Good Enough

When I first graduated from college, the job market was bleak. It was the middle of a recession. I had a degree from a good school and a closet full of hope…and yet, no one was hiring. So I sat at home watching Living Single reruns and flipping through Vogue, convincing myself that networking meant emailing my résumé to every HR inbox in the county.

When a job finally came along, I didn’t ask a single question beyond, “What does it pay?” That was the entire bar.

Fast forward a few years and a divorce later, I was back on the job market with $7 to my name. My priorities hadn’t changed much: I just wanted a paycheck and basic health insurance.

A few years after that, I finally landed a role that checked every financial box. The budget of a lifetime! Bills paid, savings growing, debts gone, splurges plentiful. I was respected, valued, and surrounded by numerous opportunities for professional growth, including conferences, memberships, and more. It was lovely… until it wasn’t. The commute was brutal. I missed most of my daughter’s third-grade year! My coworkers were fine, but the culture was cold, and the politicking wore me down.

So, back on the job market I went.

This time, I prioritized commute and community. I found a job close to home, surrounded by good people, and for a while, it was perfect… until the bloom wore off. Suddenly, leadership was lacking, expectations were unrealistic, and the culture was greuling.

Eventually, I decided to pause. I stepped back to rest and recalibrate. But bills don’t pause, so I took a role that paid less but offered time freedom, a short commute, proximity to my mom and daughter, and healthcare that kept me steady.

That job taught me something the others hadn’t: the paycheck isn’t the only compensation that matters.

What Really Counts

As I prepare to take on one last role before stepping fully into entrepreneurship, I’ve realized that true compensation touches every corner of your life. So I made a list, my own personal “dream package.”

1. Time Freedom

Flexibility to come and go as needed. Autonomy over how and when I work. 

For some, that means hybrid or remote schedules. I actually like going into an office. But I want the freedom to move through my days without feeling chained to my desk.

2. Respect & Psychological Safety

Environments where you’re trusted, protected, and heard.

I learned this the hard way. At one job, I asked a colleague for help, which unknowingly triggered her workplace trauma. She became upset, and despite my efforts to repair it, she rallied others against me. My boss watched it unfold and did nothing.

At another job, when my dad passed away just before a major event, my boss called and texted through my bereavement leave. Then announced publicly that the event was canceled because of my father’s death. Neither workplace was safe.

Now, I value respect as much as I value pay.

3. Alignment

Doing work that aligns with your values and sense of purpose.

Early in my career, I worked in education, and I could see the impact. I can’t do work that doesn’t mean something. I want to know that what I do makes someone’s life a little better, not just someone’s profits a little higher.

4. Growth

Opportunities to learn, lead, and evolve.

I’m a nerd at heart. I thrive in places that encourage learning via professional memberships, conferences, training sessions, and data deep-dives. I’ve only had one job that offered this consistently, and I soaked it up. I want that again.

5. Support

Benefits that acknowledge real life.

Mental health coverage. Family leave. Reasonable workloads. I’m a woman of childbearing age, a mother, and a human who values therapy. I need healthcare that makes those realities possible, not punishable.

6. Fair Pay

Of course, compensation still matters. I’ve spent a decade honing my craft. I have two degrees, and I work hard. I want my salary to reflect that. And sure, if the job comes with a gym membership, tuition reimbursement, or equity options, I’ll take those, too!

A Quick Gut Check

If you’re wondering what the right compensation package looks like, here’s the truth: it’s deeply personal. It depends on your values, lifestyle, and stage of life. What you need in your 20s probably won’t match what you need in your 30s or 40s.

Here are a few questions to help you gauge if you’re truly well-compensated:

• Does your salary match your skill, experience, and effort?

• Does your workplace respect your time and boundaries?

• Do you feel emotionally safe and supported, or are you spending your evenings recovering from workplace stress?

• Does your job allow you to grow without burning you out?

If you can’t answer “yes” to most of these, it might be time to redefine what “enough” means for you.

Redefining ‘Enough’ On Your Own Terms

This next job search will be my first time intentionally negotiating beyond salary.

My first step is research. I’m digging into everything I can before even applying — salary ranges, benefits, scheduling, commute time, and healthcare. Then, in interviews, I’m asking the questions that matter most: What’s the culture like? How long has the team been together? How does leadership support growth?

No job will check every box. But I’ve learned that compromise should never come at the expense of your peace.

Sometimes the real negotiation isn’t at the offer stage, it’s with yourself. It’s deciding that you no longer need to settle for “good enough.”

The Real Reward

I genuinely love to work. But loving to work doesn’t mean doing it for free or at the cost of myself.

After eighteen years of education, experience, and growth, I finally know what it means to be paid in full. It’s not just about money. It’s about peace, respect, flexibility, and fulfillment.

So no, I don’t feel demanding for wanting it all anymore. I feel clear. Because at this stage, I’ve learned that the most valuable part of a job isn’t what hits my bank account; it’s how my work allows me to live the rest of my life.