It’s a good idea to occasionally take stock of where you are in your career. You probably have a gut feeling about your current job just from being there. If you’re in a place where office politics make it impossible to move up, or your manager clearly doesn’t care about your growth, it might be time to look for other jobs. That could mean a new role within the company or somewhere else entirely, but staying put means staying stagnant.

On the flip side, if you feel good about your prospects and are willing to work for them, don't just be a great employee—make sure your manager sees it. Go out of your way to make their job easier. A manager who values your work is like a cheat code for your career, but they can only champion you if they see your value and understand your goals. So, focus on excelling in your role (a good tip is to ask how you can help them look good to their own boss) and be open with them about your ambitions and needs. Ask for introductions to managers in other departments to expand your internal network. You can also use your manager as a resource to connect with employee groups, like an LGBTQ+ or Women’s Network.

The bottom line is to assess your current job with a simple green-light/red-light check. If you realize it’s a dead end, that list of skills and professional network you’ve been building will come in handy. But if you feel optimistic about where you are, it might be time to sit down with your manager and talk about your long-term goals—and maybe a raise.

How to Talk About More Money

What if I told you that you could earn $5,000 for about two hours of work? I’m serious, and no, this isn't a pitch for a pyramid scheme. It’s entirely possible through negotiation.

I get it—negotiating can be awkward. Many of us have been conditioned to feel that advocating for ourselves is rude or demanding. The thought of asking for more can be deeply uncomfortable, which is why so many people avoid it. That’s why I reframe it as an hourly rate. The prep, conversation, and follow-up for a raise negotiation might take two hours. If that nets you a $5,000 salary increase, you’ve effectively made $2,500 an hour. Would you ever turn down a job that pays that well? I certainly wouldn’t.

Since the potential return is so high, and since most people are working hard for less than they’re worth, everyone should ask for a raise. It’s not just about getting paid fairly for your current work; it’s the fastest way to boost your disposable income. It's much easier to ask for more money at work than it is to build a surplus by cutting out every little thing that brings you joy. You can’t just wait for a "Salary Fairy" to magically grant you more money; you have to ask for it.

Still, asking for a raise is terrifying for most people. Many can't remember the last time they tried, if ever. Those who have often recall it as an unsuccessful or distant memory. This is where a mindset shift comes in. Let’s break down the common fears and reframe them.

• The Fear: "I don't want to offend my manager. I like them, and this feels weird."
• The Reality: "Companies prioritize their own interests. The only way I get paid fairly is if I prioritize mine." The best career advice I ever received was that your company doesn’t care about you. Your coworkers might, and a good boss might, but the corporation itself is not your friend. A raise isn’t coming from your manager’s wallet; it’s coming from a corporate budget allocated for labor. For them, it’s a normal part of the job.
• The Fear: "If I ask for more money, they’ll get mad and fire me."
• The Reality: "The worst they can say is no. But if I don't ask, the answer is already no." Realistically, the worst-case scenario is that your manager says no, perhaps with feedback on what you need to improve. It can cost a company three to four times an employee's salary to replace them, so it makes no business sense to fire a capable employee over a simple request for more pay.
• The Fear: "I get a cost-of-living raise every year. I don’t want to seem greedy."
• The Reality: "That yearly 'raise' is likely not keeping up with inflation. I’m losing money if I don’t negotiate." Many of us become complacent with the standard two or three percent annual increase. In reality, with inflation often running higher, these raises mean your purchasing power is actually decreasing. You are effectively losing money year after year.
• The Fear: "Fine, I’ll ask... at my annual review in five months."
• The Reality: "Hey boss, can we schedule a meeting next week to discuss my performance and growth?" Waiting until your year-end review is a common mistake. By then, budget decisions were likely made months ago. People who are proactive ask regularly—every few months—to discuss their performance and goals. This keeps their request top-of-mind.
• The Fear: "I’m just grateful to have a job. They’re doing me a favor."
• The Reality: "I know my worth, and I can prove it." It's not sustainable to be undervalued long-term. If your job is taking advantage of you, they are not doing you a favor. You need to know the value you create in your role. This requires an honest self-assessment. Are you truly a top performer? If not, focus on improving first. But when you know your worth and have the evidence to back it up, you’re ready to ask for what you deserve.

Keep a "Brag Book" with Receipts

Knowing your worth is great, but having proof is even better. If you want a raise or promotion, you need a Brag Book. It’s a simple collection of evidence showcasing your accomplishments.

1. Create a folder in your email inbox and name it "Brag Book" or "Raise Receipts."
2. Save everything. Every time a client praises your work, a colleague thanks you, or you’re mentioned positively in an email chain, drop it in the folder.
3. Quantify your success. Did you increase revenue by a certain percentage? Grow a social media account by X followers? Numbers are hard to argue with.

This folder isn't just for your ego; it's your secret weapon for performance reviews. You’ll have a year’s worth of successes ready to go, making it easy to justify your ask.

The Script for Asking for More Money

Step 1: Get Prepared Before the conversation, know what you’re asking for (more pay, a new title?), understand your market value (use sites like Glassdoor), and organize your wins from your Brag Book. Practice the conversation with a friend to get comfortable saying the words out loud.

Step 2: Set the Meeting Keep it simple. Send a message like, "Hey [Boss's Name], could I put 30 minutes on your calendar this week? I'd love to discuss my growth at the company."

Step 3: Start Strong Be direct. "Thanks for meeting with me. I'm excited to share some recent accomplishments, and I'd also like to discuss my salary for the upcoming year."

Step 4: Make Your Case Share two or three of your biggest wins. "Over the last two years, my work has grown our e-commerce business by 25% and I've also grown the Instagram account to 50,000 followers. I’ve also trained two new coordinators."

Step 5: Make the Ask Transition quickly to money. "With that in mind, I’d like to discuss my compensation. Based on my research and accomplishments here, a raise of X dollars would be appropriate."

Step 6: Stop and Wait This is the hard part. After you make your ask, stop talking. Let the silence hang. Your boss will respond. If they say yes, fantastic! If it's a no, don't panic. Ask, "I understand. What skills or accomplishments would you need to see from me before we can revisit my pay?" This turns a "no" into a roadmap for the future.

Beyond a Paycheck: What Else to Negotiate

Compensation is more than just salary. If cash is tight, consider asking for other valuable perks.

• Equity (RSUs and ISOs): Shares of company stock that can become very valuable as the company grows.
• Paid Time Off (PTO): More vacation days give you more paid time away from work.
• Flexible Work: Negotiate your hours or the ability to work from home.
• Signing Bonuses: A one-time payment when you sign a new job contract.
• Job Titles: A better title is free for the company to give and can position you for higher pay at your next job.

Why You Might Need a Side Hustle

You might think wealthy people don’t have side hustles, but you’d be surprised. I used to work with a guy on Wall Street I’ll call Jerry. He made a high six-figure salary, but he also had a side hustle business: buying and flipping rare sneakers. He wasn't making a fortune from it, but he loved the thrill. To him, it was "free money." Jerry’s story shows that if there’s a hustle to be had, people who are smart about money want in. This can be one of those money hustles that adds a nice stream of income.

I’m not a fan of hustle culture, and if you’re already overworked, the advice to "get a side hustle" can feel dismissive. However, a side hustle can be a powerful way to boost your income and create financial breathing room. It gives you choices. With the rise of remote work, it’s easier than ever to find side jobs for extra income without them taking over your life, and it's a great way to handle starting a side hustle while working full time.

What to Look For in a Side Gig

• It Doesn't Have to Be Your Passion: I distinguish between a side hustle (done for quick money) and a passion project (done for creative fulfillment). It’s okay to have hobbies that don’t make money. Turning something you love into a job can sometimes suck the joy out of it.
• It Should Be Low-Risk: Look for low cost side hustles with minimal startup costs. Walking dogs on Wag costs you nothing to start. You want to be able to test an idea without a big financial commitment. A buying and selling side hustle, like Jerry’s sneakers, can be a great option if you know the market.
• It Should Actually Make You Money: That "free money" feeling disappears when you account for hidden costs. If you drive for Uber, factor in gas and insurance. Keep a close eye on your net profit to make sure your gig is worthwhile. And don’t forget to set aside 30-40% of your earnings for taxes.
• It Should Fit Your Life: The best side gig is one that fits into your existing schedule. If you’re an office worker, a physical side job like assembling furniture can be a nice change of pace. If you have a long commute, online freelance work could be perfect.

A quick word of warning about Multi-Level Marketing companies (MLMs). They’re often pitched as easy side hustles, but the business model is based on recruiting others, not selling products. A Federal Trade Commission report found that at least 99% of people who join MLMs lose money. If it seems too good to be true, it probably is. This is not the type of freelance business you want to start. If you're looking for real opportunities by starting a side hustle while working full time, focus on building skills that can lead to a side hustle to full time career.