How to Build Your First (or Next) Stream of Income
Why adding just one extra income stream can change your financial stability and future—no matter your age or income level.
“Any career that I’ve had, I’ve always had a second, third, fourth, or fifth stream of income. Some streams were just to give me seed money to invest in another business opportunity.”
— Ken Pressley, Tax Professional & Multi-Stream Income Builder
Watch the full episode on YouTube
How to Start Your First Extra Stream of Income
1. Start With What You Already Know & Enjoy
Before choosing a business or side income, identify the work you actually enjoy. If you don’t like it, you won’t stick with it—no matter how profitable it seems.
Ask yourself: What skills do I already use at work? What hobbies do I naturally gravitate toward?
Think about what’s accessible. You might love baking, but do you have the time? You might be great at organizing—could that turn into managing listings or assisting professionals?
The intersection of interest + accessibility is where your best opportunities live.
2. Research the Business Before You Jump In
Research isn’t optional—it’s the foundation of every successful income stream.
Look at:
The startup costs
Required skills or certifications
Time vs. payout
Profit margins
Competition
Your day-to-day responsibilities
Example: Ken’s clients researched the medical courier business and discovered it was perfect for them—they were already doing delivery work, but wanted more control over their income. Within months, they were earning more while keeping a bigger percentage of each earning.
3. Build Your Support System—Your “Income Team”
No stream of income scales without people. Consider:
Someone who has done it before (mentor)
People who can reduce your workload
A small circle of accountability
Ken shared that he could only handle 3 research assignments a week in college—until he added teammates. He grew his new business 4x simply by building a team.
4. Take Small, Immediate Action Steps
Once you know what you want to do and why, start small.
Send the first email
Research one platform
Watch one tutorial
Price your first offer
Momentum beats perfection every time.
🎯 Your Action Steps This Week
This Week
Identify 2 skills or interests you could monetize
Spend 30 minutes researching one related business model
Reach out to one mentor or peer already doing this work
Resource: Search “medical courier startup requirements [your state]”
Join The WISE Retirement Podcast Newsletter for more ideas
This Month
Test one micro-offer (e.g., service, product, gig)
Join a Facebook group or community in that industry
Set up a simple system: spreadsheet, business email, or booking page
Build a weekly habit of 2–3 hours dedicated to your new income stream
Track your: time spent, money earned, and lessons learned
✨ Questions for Reflection
Ask Yourself
What skills have people praised me for that I’m not monetizing yet?
What industry or income idea excites me—not just pays me?
What income stream could I build that still works even when I’m not working?
Discuss With Your Family/Partner
What time each week can I realistically commit to this?
What small financial investments are safe and reasonable for us right now?
Who can help hold me accountable?
Consider With Your Team/Community
What gaps exist in my network that I need to fill?
What industries are growing that match my skill set?
What do I need to prepare now for a long-term income plan?
📺 Upcoming Episode
Business Owner ups and downs, with a 800 credit score.