The Other Side of the Equation: How to Increase Your Income
There's no limit to what you can earn
Why We Started with Expenses
We've spent most of our time talking about reducing expenses, and there's a good reason for that. When you cut $100 from your monthly spending, you get a double benefit: $100 more to invest each month AND $30,000 less needed for your FI number.
When you earn an extra $100, you only get the first benefit. Plus, that extra $100 is taxed, so you might only keep $65-75 of it depending on your tax bracket.
But here's the thing: there's a limit to how much you can cut expenses. There's no limit to how much you can earn.
You can only reduce your housing costs so far before you're living in a van. But you can potentially double, triple, or even 10x your income with the right strategies and effort.
Today we're going to explore every realistic way to increase your income, from quick wins to long-term career transformations.
Keep in mind, I still think expense reduction is more important since it is directly within your control. That said, let’s cover some ideas to bring in more cash.
The Income Optimization Mindset
Before diving into tactics, let's talk mindset. Most people think about income wrong:
Traditional thinking: "I have a job that pays X. That's my income."
FI thinking: "I have skills, knowledge, and time that can be monetized in multiple ways. My current job is just one income stream."
The goal isn't just to make more money at your current job (though that's part of it). It's to think strategically about all the ways you can create value and get paid for it.
Category 1: Optimize Your Current Job
Start with low-hanging fruit: maximizing what you earn from your existing work.
Salary Negotiation
When to negotiate:
During annual reviews
After completing major projects
When taking on new responsibilities
When you receive a job offer from elsewhere
How to negotiate effectively:
Research market rates for your position and location
Document your achievements and value-add to the company
Practice your pitch beforehand
Ask for specific amounts, not vague raises
Consider the total compensation package (benefits, vacation, flexibility)
Common mistakes:
Waiting for your boss to offer a raise
Negotiating based on personal needs rather than professional value
Accepting the first counteroffer without discussion
Let’s recap this! You should be making more money from your existing job every single year. Why? Because you’re presumably getting better at it every single year. Over time you learn to do the same task faster and better with the same or lower cost. That should be valuable to your employer. If it isn’t, you need to consider who might find it more valuable.
I will make an entire post on how to do this because I have repeatedly done it during my career. I received a raise every single time.
Maximize Employer Benefits
Many people leave money on the table by not fully utilizing employer benefits:
401(k) matching: This is free money. Always contribute enough to get the full match.
HSA contributions: If available, max out HSA contributions (triple tax advantage). This money can be taken out tax free for medical expenses, but it can also be taken out after 65 without penalty like a regular retirement account. These accounts are great!
Professional development: Use tuition reimbursement, conference attendance, and training budgets. This is like getting to go to school for free. Why pay for your own classes?
Flexible benefits: Choose the most valuable options during open enrollment. Read the entire list. I once worked for an employer with five free days of emergency daycare coverage.
Stock options/ESPP: Understand and optimize any equity compensation. We’ll go deeper on this later, but often an ESPP will allow you to purchase stock at a set discount. At one of my jobs, I was able to use my salary to buy stock for 10% less than the market price. Then I turned around and immediately sold the stock at full price each month. Free money!
Performance Optimization
Become indispensable:
Take on high-visibility projects
Develop skills that directly impact company profits
Become the go-to person for specific expertise
Build relationships across departments
Document and share your wins
Position for promotion:
Understand the requirements for the next level
Start doing that job before you have the title
Find a mentor or sponsor in leadership
Communicate your career goals clearly
Potential Income Increase: 10-50% depending on your current situation and negotiation success
I know this is high-level advice and we’ll do some examples later, but it’s good advice! You should be a better employee every single day. It may be 1% better, but that eventually adds up to a promotion.
Category 2: Side Hustles and Freelancing
This is where many people start when they want extra income. The key is choosing something that aligns with your skills and schedule.
Service-Based Side Hustles
Consulting/Freelancing in your field:
Use your professional skills for other companies
Often pays 2-3x your hourly rate as an employee
Can be done evenings/weekends
Builds network and credibility
Online services:
Writing/copywriting
Graphic design
Web development
Virtual assistant work
Online tutoring or coaching
Local services:
Handyman work
Pet sitting/dog walking
House cleaning
Personal training
Photography
Gig Economy
Delivery/rideshare:
Uber, Lyft, DoorDash, Instacart
Flexible schedule
Low barrier to entry
Income varies significantly by location and time
Task-based work:
TaskRabbit, Handy, Thumbtack
Use specific skills (assembly, repairs, cleaning)
Higher hourly rates than basic delivery
Digital Side Hustles
E-commerce:
Amazon FBA (Fulfillment by Amazon)
Dropshipping
Print-on-demand (t-shirts, mugs, etc.)
eBay/Facebook Marketplace flipping
Content creation:
YouTube channel monetization
Podcast sponsorships
Newsletter subscriptions
Online course creation
The Reality Check: Most side hustles start slow and require significant time investment. Be realistic about the time-to-income ratio.
Potential Income Increase: $200-2,000+/month depending on time investment and chosen hustle
Let’s pause for a second. You are not going to make a fortune with Uber, eBay, dog walking, or cleaning. These jobs have a low barrier to entry which means you will have plenty of competition. That said, the miracle of compound interest means money earned today is worth far more in the future.
As long as you approach these with the right mindset and are encouraged every time that extra $100 comes in, you’ll do okay. These are ideas to augment your income, not replace it. I have tried a few of these in the past and can tell you about my experience.
Category 3: Skill Development and Career Changes
Sometimes the biggest income increases come from leveling up your skills or changing career paths entirely.
High-Value Skills to Develop
Technology skills:
Programming/software development
Data analysis/data science
Digital marketing
Cybersecurity
Cloud computing (AWS, Azure)
Business skills:
Sales (highest ROI skill for income growth)
Project management
Financial analysis
Strategic planning
Communication skills:
Public speaking
Writing
Leadership
Negotiation
Career Transition Strategies
Industry switching:
Research high-paying industries in your area
Identify transferable skills
Network with people in target industries
Consider additional certifications or education
Remote work opportunities:
Can access higher-paying markets regardless of location
Often 20-50% salary increases possible
Reduces transportation costs
Better work-life balance potential
Entrepreneurship:
Starting your own business
Highest income potential but also highest risk
Requires significant time and often capital investment
Consider starting as a side business first
Potential Income Increase: 25-200%+ depending on the career change
This is where the real money is made. You probably can’t career switch into being a neurosurgeon or a celebrity attorney. The good news is you don’t have to. In 2025, many of the most in-demand skills can be learned for free. It won’t be easy, but a college degree is not the obstacle it used to be.
Category 4: Investment and Passive Income
True passive income takes time to build, but it's the ultimate goal for FI.
We’ll go over this when we talk about how to invest. For now, just know there are multiple options. Real estate, stocks, private business ownership, and lending are all possibilities for earning passive income.
The Psychology of Income Increases
Most people I encounter are able to take steps towards cutting their spending. However, those same people are often unable to work towards more income.
Common Mental Barriers
Impostor syndrome: Feeling like you don't deserve higher pay or better opportunities
Comfort zone addiction: Staying in familiar situations even when they limit growth
Perfectionism: Waiting until you're "ready" instead of taking action
Analysis paralysis: Researching options endlessly without taking action
Every year you don’t take action is time that can never be recovered. You need time on your side for compound interest to work its magic!
Overcoming Income Plateaus
Lifestyle inflation trap: As income increases, spending often increases proportionally
Golden handcuffs: High salaries that make it hard to leave even if you're unhappy
Specialization vs. diversification: Whether to go deep in one skill or develop multiple income streams
My Personal Income Journey
I'll make a more detailed post with all my numbers, but I’ve had a three-phase journey:
2008-2012: Traditional employee mindset
Single income source (day job)
Annual raises of 3-5%
No negotiation or optimization
Income: $57k → $71k over 4 years
2012-2014: No income! (went back to school)
2014-2022: FIRE awakening and optimization
Started negotiating aggressively
Developed high-value skills (data analysis, project management)
Began consulting on the side
Changed jobs for 20-30% pay increases
Income: $71k → $250k (Yes, that is an absolutely crazy amount of money. No, that is not how I reached FIRE.)
2022-Present: Multiple income streams
Consulting business grew to significant income
Doubled-down on stock investments
Occasional speaking engagements
Total income: $250k → $500k+
Key insights:
Biggest income jumps came from job changes, not annual raises
Developing in-demand skills was more valuable than an advanced degree
Network building was crucial for opportunities
Multiple income streams provided security and acceleration
Strategy by Career Stage
Early Career (typically 20s-early 30s)
Focus: Skill development and rapid advancement
Change jobs every 2-3 years for salary jumps
Invest heavily in learning high-value skills
Build professional network aggressively
Consider higher-risk, higher-reward opportunities
Mid-Career (typically 30s-40s)
Focus: Optimization and diversification
Negotiate aggressively at current job
Develop side income streams
Consider leadership positions
Balance income growth with family obligations
Late Career (typically 40s-50s+)
Focus: Passive income and wealth preservation
Transition to more passive income sources
Mentor others (paid consulting/coaching)
Consider entrepreneurship with accumulated capital
Focus on tax-efficient income strategies
Notice I said typically. I was able to accelerate the timeline and you can too.
Action Plan by Time Investment
1 Hour Tasks
Negotiate current salary annually
Optimize employer benefits
Track industry salary trends
Build LinkedIn network
5 Hour Tasks
Develop one high-value skill
Start a simple side hustle
Apply to higher-paying positions
Create content in your expertise area
10+ Hour Tasks
Build serious side business
Major skill development (coding, certifications)
Active real estate investing
Launch online course or product
Common Income Increase Mistakes
Lifestyle inflation: Spending increases match income increases, negating FI benefits
Tax optimization ignorance: Not understanding how additional income affects tax liability
Time vs. money miscalculation: Choosing low-hourly-rate activities when higher-value options exist
Burnout from over-commitment: Taking on too much additional work and affecting primary job performance
Neglecting the downside: Not considering risks of side businesses or career changes
The Bottom Line
Increasing income is a powerful FI accelerator, but it requires strategic thinking and sustained effort. The best approach combines:
Maximizing your current position through negotiation and performance
Developing high-value skills that command market premiums
Creating multiple income streams for diversification and acceleration
Building long-term passive income for eventual work-optional status
Remember: every extra $100/month you earn (and save) accelerates your FI timeline by reducing the time needed to accumulate your target amount.
Next time, we'll go deeper on how to increase income at your current job.
Until then, your homework: Pick one income optimization strategy from this post and take action on it this week. Whether it's researching salary data, starting a skill development course, or having a conversation with your boss about advancement opportunities.
Here's to earning what you're worth (and then some),
Max
Remember: The goal isn't just to make more money. It's to increase the gap between what you earn and what you spend so you can invest the difference and reach FI faster.