Welcome Back, Future Funder!

What if staying at your current job is the biggest financial mistake you're making right now?

What if you're leaving $10,000+ per year on the table because you're too comfortable or too scared to make a change?

What if the "loyalty" you're showing your employer is actually keeping your family from getting ahead financially?

A lot of people stay in jobs that underpay them for years longer than they should. They convince themselves that job security matters more than fair compensation. They tell themselves that "it could be worse" while their income stagnates and their financial goals slip further away.

And maybe you’re in a great spot with your job and income. But if you aren’t, here’s the thing: you can't build wealth, pay off debt, or save for your kids' futures if your income isn't keeping up with your needs. And sometimes, the fastest path to financial stability isn't working harder at your current job. It's finding a better one.

In today's edition of Dinner Table Discussions:

✅ The three questions that tell you if it's time to leave
✅ How to know if you're actually underpaid (with real numbers)
✅ When side hustles make sense vs. when you just need a better job
✅ The self-employment trap that's keeping you broke

Bon appétit! 🧑‍🍳

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🍽️ Main Course: The Job Decision That Changes Everything

Let's be brutally honest about why we work. Yes, passion matters. Yes, finding meaning in your work is valuable. But none of that matters if you can't pay your bills or provide for your family.

The foundation has to be solid first: covering expenses, building wealth, paying off debt (here’s our guide to paying debt off), and creating a future for your children. Everything else is built on top of that foundation. If the foundation is cracked because your income isn't sufficient, no amount of "loving what you do" will fix your financial problems.

So the question isn't "Do you like your job?" The question is: "Is your current job serving your family's financial needs, or is it holding you back?"

Here's how to figure that out.

Question 1: Is Your Job Actually Paying the Bills?

This seems obvious, but you'd be shocked how many people stay in jobs that literally don't cover their monthly expenses. They're going into debt every month, rationalizing it as "temporary" while years pass.

If your job isn't paying the bills, you have exactly two options: increase income or decrease expenses. That's it. There's no third option.

Option 1: Increase Income

If you're making $20 per hour and it's not enough, you need to find a job that pays more. Period. This might mean switching careers, getting additional training, or taking a job you're overqualified for but that pays better.

Consider this: Servers at decent restaurants regularly make $30-40 per hour with tips. No degree required. No special training. Just the willingness to learn the job. If you're struggling at $20 per hour in an office, becoming a server might actually be the smarter financial move for your family right now. You can also always take more shifts as a server if you need more money, which you can’t do as a salaried office worker.

Don't let ego stop you from making more money. Your kids don't care if your LinkedIn profile is impressive, they care if you can afford groceries and keep the lights on 😬 

Option 2: Decrease Expenses

If you're making $30-40 per hour and it's still not enough to cover just your basic expenses, then your expenses are the problem, not your income.

Before you say "I can't cut anything," let me stop you. You can. There's always something to cut back on.

Food bill too high? Stop eating out. Cook at home. Meal prep. Buy store brands instead of name brands! Your grocery bill can probably drop 30-40% with intentional choices.

Rent too high? Move to a cheaper place. Yes, it's inconvenient. No, it might not be as nice. But if you're going into debt every month to afford where you live, you can't afford where you live. It’s probably time to move.

Car payment crushing you? Sell the car, buy something cheaper with cash. The lifestyle hit is temporary, but the debt is permanent until you deal with it.

Outside of extreme circumstances like catastrophic medical bills, you can find a way to make your income cover your expenses. It just might require choices you don't want to make.

Question 2: Do You Make Enough to Actually Get Ahead?

Okay, so your paycheck covers the bills. Great! Seriously, that’s a big deal. But are you swimming forward, or just treading water? (By the way, here’s why even a lot of six-figure earners live paycheck to paycheck.)

If you have nothing left over after expenses to invest, save for your kids' futures, pay off debt, or build toward a down payment on a house, you're stuck in financial neutral. You're surviving, not thriving.

Here's what to do about it.

Option 1: Ask for a Raise

Most people never ask for a raise. They just sit there waiting for their employer to notice their hard work and spontaneously offer more money. That almost never happens.

If you've been at your job for over a year, you're performing well, and you haven't gotten a meaningful raise (not just a 2% cost-of-living adjustment), it might be time to ask.

How to ask for a raise:

Do your research. Go to Glassdoor, Salary.com, and Payscale. Find out what people in your role, in your city, with your experience typically make. If you're being paid 10-20% below market rate, you have a strong case.

Document your value. Write down specific accomplishments, projects you've led, problems you've solved, revenue you've generated, or costs you've saved the company. You need evidence, not feelings.

Schedule a meeting. Don't ambush your boss. Say: "I'd like to schedule time to discuss my compensation and career growth here."

Make your case. Come in with your research and your documentation. And make sure to stay humble but clear. Say something like: "Based on market research, people in my role with my experience typically earn $X-Y. I've been here for Z years and have accomplished [specific things]. I'd like to discuss bringing my compensation in line with market rates."

Be prepared to negotiate. They might not give you everything you ask for. Be ready to discuss other benefits: more PTO, better 401(k) match, flexible work arrangements, professional development budget.

The worst they can say is no. And if they say no without good reason, that's valuable information about whether you should stay at your current company ⬇️ 

Option 2: Find a Better Job

If you can't get a raise, or if your current job has no room for growth, it's time to start looking.

You don't need to double your income overnight. A 15-20% salary increase can be completely game-changing for most families. That's the difference between barely scraping by and actually building wealth.

Example: If you're making $50,000 and you find a new job paying $57,500 (15% increase), that's an extra $7,500 per year. After taxes, that's roughly $5,000 more annually, or about $416 per month. That $416 per month could:

• Put $5,000 into your Roth IRA

• Pay off a credit card in months instead of years

• Fund a 529 plan for your kid's college

• Build a 6-month emergency fund in 1 year

Even just a 10% raise with a better 401(k) match could be enough to completely change your financial trajectory.

How to find a better job:

Update your resume and LinkedIn. Make them reflect your actual accomplishments and value, not just job duties.

Network. Tell people you know that you're open to new opportunities. Many of the best jobs are never publicly posted, they're just filled through referrals. Seriously, do not sleep on the networking bit.

Send in applications strategically. Don't just spray and pray. Target companies and roles where you could genuinely add value and grow.

Interview while employed. AKA, don’t quit your current job while you’re searching for the next one. You have way more negotiating power when you're not desperate. You can walk away from lowball offers.

Don't feel guilty. You owe your employer good work while you're there, not lifelong loyalty while being underpaid.

Option 3: Add a Side Hustle (BUT Be Smart About It)

If you can't get a raise and don't see immediate opportunities for a better job, a side hustle might make sense. But (and this is critical) most side hustles are terrible financial decisions when you do the real math.

Here's what I mean. Let's say you pick up DoorDash as a side hustle. You make $17.50 per hour. You work 10 hours per week, earning $700 per month. Sounds decent, right?

Wrong. Let's do the actual math:

DoorDash Reality Check:

• Gross income: $700/month

• Taxes (25% self-employment + income): -$175

• Gas costs: -$200

• Increased car maintenance and depreciation: -$100

• Net income: $225/month

You're working 40 hours per month for $225. That's $5.63 per hour. You'd literally make more money working one extra shift per week at your regular job.

The side hustle rule: If your side hustle doesn't pay at least 75% of your regular hourly rate after all costs and taxes, it's not worth your time. You're better off asking for overtime at your main job or spending that time job hunting for a better position.

Side hustles that might actually be worth it:

• Freelancing in your professional field ($50-100+/hour)

• Tutoring if you have expertise ($40-80/hour)

• Skilled trades work (plumbing, electrical, handyman at $50-100/hour)

• Selling high-value items you already own (one-time boost, not recurring)

• Things like DoorDash IF you can make a worthwhile amount (after expenses)

Side hustles to avoid:

• Any gig work that pays under ~$25/hour before expenses (DoorDash, Uber, Instacart)

• MLM schemes (you'll lose money, not make it)

• Anything requiring significant upfront investment

• Anything that doesn't scale or build equity

The Self-Employment Trap

If you're self-employed or freelancing and struggling to get ahead financially, your problem might not be your skills or your work ethic. It might be the structure itself.

Self-employment sounds amazing: freedom, flexibility, unlimited income potential. But here's what nobody tells you about the financial reality.

The hidden costs of self-employment:

• Self-employment tax: 15.3% on top of regular income tax

• Health insurance: $400-1,200+ per month for a family

• Dental and vision insurance: $100-300 per month

• No paid time off (sick days cost you money)

• No employer 401(k) match (that's free money you're missing)

• Inconsistent income (feast or famine cash flow)

• You're doing admin, marketing, and accounting instead of earning

I was a freelancer for four years. I thought I valued freedom above all else. Then I did the math and realized I would make more at a salaried job with benefits AND not have to remember to save up for taxes throughout the year.

When I switched to full-time employment, my income went up by about 33% (including benefits). Plus I got health insurance, a 401(k) match, paid vacation, and the mental relief of steady income for my family. Huge!

Ask yourself honestly:

• Are you self-employed because it's actually more profitable, or because you're afraid of traditional employment?

• If you added up all your self-employment costs and taxes, are you really making more than you would at a salaried position?

• Is the "freedom" worth the financial stress and instability?

If you're struggling to achieve your financial goals because you're paying thousands per month in health insurance and self-employment taxes, getting a full-time job might be the smartest move for your family right now.

You can always return to self-employment later when you're financially stable. But building wealth is nearly impossible when your income is inconsistent and your costs are astronomical.

Bottom Line

Staying at a job that doesn't serve your family's financial needs isn't loyalty—it's inertia. And inertia doesn't pay off debt, build wealth, or fund your kids' futures.

If your job isn't paying the bills, find a better one or cut your expenses until it does. If your job pays the bills but leaves nothing for getting ahead, ask for a raise, find a better job, or add income strategically through a side hustle that actually makes financial sense.

And if you're self-employed and struggling, be honest about whether the "freedom" is worth the financial burden. Sometimes the most liberating thing you can do is get a steady paycheck with benefits.

Your family's financial stability matters more than your comfort zone. Make the hard decision if you need to. Your future self will thank you.

Cheers to getting 1% better each week! 🥂

👂 We’d love to hear from you

👂 Have you left a job for better pay?

We’d love to hear about it! And your story could inspire someone else to do the same.
Just hit reply and share.

Thanks for reading,
—Your friends @ Future Funders 🍽️

P.S. Forward this to a friend who's been complaining about their paycheck for two years but hasn't applied anywhere else. 😬