Episode 54: Behind the Curtain: Our 2025 Lessons, Wins, and What’s Next for 2026
Before racing into another year of systems, funnels, offers, and scaling, Jessica Green and Natasha Roberson invite listeners into a rare behind-the-scenes look at what 2025 really looked like inside Self Made. This transparent Plan → Do → Review conversation pulls back the curtain on the lessons, mistakes, pivots, and wins that shaped their biggest year of clarity yet.
In Episode 54 of The Digital Shift™, Jess and Nat share the truth about joining a paid-ads mastermind, leveling up their sales skills in Sales Girl Bootcamp, hosting three virtual summits, building out their marketplace, and preparing for their first live event. Nothing is sugarcoated—because entrepreneurs don’t need filtered stories. They need the real ones.
This episode captures the heart of what Self Made was created for: empowering female entrepreneurs to master automation, mentorship, and simplicity. And in their reflection, they reveal how they re-centered their mission after a year of testing, building, breaking, and realigning.
It’s honest. It’s messy. And it’s exactly the kind of conversation founders wish more people had publicly.
The Big Shifts of 2025: From Build Mode to Refine Mode
2025 was the year Self Made built more than ever before—but it was also the year they realized that more wasn’t always better.
Jess and Nat revisit their original vision for Self Made and how easy it is for entrepreneurs to drift off-course while saying yes to opportunities that look good on paper but don’t align with the mission.
And as they walked through this year, they shifted from:
building everything
trying everything
saying yes to too much
…to refining, simplifying, and returning to what truly worked.
Because simplicity scales. And as they said in the episode—boring makes billions.
What Worked in 2025: The High-Impact Wins
2025 wasn’t all hard lessons. In fact, the wins were massive—and they came from alignment, clarity, and the right strategy.
🏆 1. Three Virtual Summits (January, May, September)
These summits brought in over 10,000 new leads, expanded their visibility, and solidified Self Made as a go-to resource for female entrepreneurs seeking systems, mentorship, and digital automation.
🏆 2. 52+ Weeks of The Digital Shift™ Podcast
Not a single week was missed—proving that consistency compounds faster than any hack or trend.
🏆 3. Workshops That Convert (and Actually Serve)
Workshops became their highest-impact format: simple, powerful, and transformational.
🏆 4. Tech Savvy School Officially Launched
A major milestone for the Self Made ecosystem—giving women the tech confidence needed to scale.
🏆 5. Team Clarity & Right-Seat Leadership
Finally putting the right people in the right roles created efficiency, reduced stress, and improved delivery.
🏆 6. Paid Ads & Sales Confidence Breakthroughs
Investing in a paid-ads mastermind and Sales Girl Bootcamp turned uncertainty into confidence—and gave them scalable acquisition channels.
🏆 7. The Digital Studio + Marketplace Growth
The Marketplace moved from idea to implementation, providing tools, templates, and resources for entrepreneurs who want plug-and-play systems.
🏆 8. The Digital Shift LIVE Coming to Atlanta in 2026
Their first live event is officially on the horizon—a pivotal moment in the brand’s evolution.
When Business Gets Messy: The Lessons That Hurt (and Helped)
Not every strategy sticks—and 2025 proved that truth more than once. Jess and Nat openly share the setbacks that gave them some of their most valuable clarity.
❌ Challenges & Webinars = Not Their Flow
What works for others didn’t work for them—and that’s okay.
❌ Overspending & Over-Hiring
Scaling too fast stretched the budget and the team in ways that didn’t align with their mission.
❌ Saying Yes to Too Many Done-For-You Projects
Hard lesson: just because you can do something doesn’t mean you should.
❌ Overcomplicating Offers & Launches
Complexity kills growth. Simplicity revives it.
❌ Chasing New Instead of Nurturing the Existing
A trap most entrepreneurs fall into—one they’re now committed to avoiding.
❌ Tech Meltdowns, Wrong Emails & Barking Dogs
Because entrepreneurship is rarely cute behind the scenes.
As they put it:
“We found out what wasn’t for us—and that clarity is the most profitable thing we gained all year.”
Plan → Do → Review: What’s Coming in 2026
After reviewing the year, Jess and Nat mapped out exactly what they’re keeping, starting, and stopping as they head into 2026.
KEEP
Workshops
Tech Savvy School
Mentorship-first community
Podcast consistency
START
Expanding the Marketplace
Growing podcast + social reach
Scaling paid ads across multiple platforms
Building Seasonal Labs
STOP
Overcomplicating offers
Saying yes when their gut says no
Anything that doesn’t align with the mission
Because 2026 isn’t about doing more—it’s about doing better.
Better systems. Better focus. Better impact.
Quote of the Episode
“Every season is feedback. The question is—are you listening, or are you taking action?”
Thank You, Self Made Community
2025 was a year of growth, alignment, and honesty—and none of it would matter without the women who walk this journey with them.
Your support fuels every summit, every episode, every workshop, and every next step.
Start Your Free Trial, Join a Live Event, or Explore the Marketplace
🚀 Start your 14-Day Free Trial inside the Self Made Hub → www.self-made.biz
🎟️ Grab your Atlanta Live Event Ticket → www.self-made.biz/atlanta
🛍️ Explore the Self Made Marketplace → www.self-made.biz/hub-marketplace
🔜 Teaser for Next Episode
Join Natasha next week for:
“You Don’t Need More Leads—You Need THIS: The Real Reason Your Sales Are Stuck.”
She’ll unpack what’s really breaking your conversions—and how to fix it fast.
