Sometimes it feels like you’re doing everything right—working hard, staying healthy, checking all the boxes—and yet, you’re still stuck.

You’re not earning what you deserve. You’re stressed about money.

And even your self-care routine is draining your wallet. These are the real-life dilemmas a lot of people face, and Kevin O’Leary is here to give it to us straight.

Let’s dive into two questions from readers trying to figure out how to take back control—both financially and professionally.

“I’m Overworked, Underpaid, and Not Sure How to Ask for More”

Dear Kevin,
I’m in my mid-thirties and have been with the same events company—about 100 employees—for over three years now.

I was brought on to help organize corporate events and swanky birthday parties.

But only six months into the job, my manager quit, and suddenly I found myself doing their job too… without the promotion or the paycheck.

The company’s struggling a bit—our events calendar isn’t as packed anymore—but I’m still outperforming my goals.

And yet, my raises have barely budged: 2% for the past two years.

I’ve got lingering credit card debt from my twenties that I’m slowly paying off, but I could really use a bigger paycheck.

The problem? I’m exhausted. I don’t have the energy to look for another job, and I’m nervous that asking for a raise might backfire. What should I do?

—Raise Ready

Kevin’s Take: Own Your Value—Then Prove It

Kevin says: Let’s tackle the first red flag—your credit card debt.

This may sound harsh, but if you’re paying 23% interest, that’s on you.

Credit card companies thrive off people making that mistake. So first thing’s first: keep grinding to get that balance down. Every dollar you throw at it helps.

Now, let’s talk about the money you should be making.

If you’re doing the work of two people, it’s time to stop asking whether you deserve a raise—you already know you do.

But here’s the catch: your boss doesn’t need a buddy.

They need someone who makes their job easier.

That’s your leverage. When you become the person who helps your boss shine, that’s when they realize your worth.

So, how do you approach the conversation?

Get your numbers in order – Track your wins. Come armed with proof of how you’ve exceeded expectations.
Do a quiet job hunt – Even if you’re not ready to leave, start exploring other opportunities. Get an offer. That’s your power.
Use your annual review wisely – Present your case professionally. Don’t threaten, but do be ready to walk if they say no.

If you really are the asset you claim to be, another company will want you.

And if your current company doesn’t recognize that, it’s time to leave anyway.

“Staying Healthy Is Making Me Broke—How Do I Cut Costs Without Sacrificing My Wellness?”

Dear Kevin,
A few years ago, I heard someone on a podcast say, “health is wealth.” It really stuck with me.

I’ve since made wellness my top priority—I’ve got the gym membership, I eat clean, I take my supplements, and I stay on top of doctor visits and therapy. Honestly? I’ve never felt better.

But here’s the issue: when I crunched the numbers, I realized I’m spending over $2,000 a month just to stay healthy.

I want to keep this lifestyle up, but I need to find a way to spend less. What can I cut without hurting my health?

—Happy, Healthy, Broke

Kevin’s Take: Yes, Health Is Wealth—But You’re Probably Overspending

Kevin says: You’re absolutely right—investing in your health is worth it.

But you’re also not wrong to feel like it’s getting expensive.

Staying healthy can cost a lot, but there are smarter, more efficient ways to do it.

First off, let’s talk food. If you’re spending tons on restaurants or food delivery, cut that out immediately.

Not only is it pricey, but restaurants load your meals with sugar, fat, and salt.

Cooking at home is cheaper and better for you. Just doing that could cut 20% off your monthly spend.

Next up: supplements. This is where a lot of people waste money. You might be taking vitamins you don’t even need because a blog or influencer said you should.

Instead, go to a trusted wellness clinic and get a proper blood test.

Find out exactly what you’re deficient in—maybe it’s vitamin D or B12—and only buy what’s necessary.

Also, there are amazing free apps out there to help you monitor your diet and fitness goals. Kevin personally uses one called “Lose It.”

It tracks calories, breaks down nutrients, and keeps you accountable—without costing a cent.

Bottom line? You don’t need to stop investing in your health, but you do need to get smart about it.

Final Word from Kevin

Whether it’s asking for a raise or managing your wellness budget, it comes down to one thing: know your worth and act accordingly.

Don’t expect anyone else to manage your money, your health, or your career for you.

Take the reins—and don’t be afraid to ask for more, but only after you’ve earned it.

If you’ve got questions like these, send them Kevin’s way at askkevin@mailonline.com.

Because let’s be honest—life doesn’t come with a playbook, but solid advice helps.