Founder: Rachel Ritlop 
Business: The Confused Millennial, now 'Confidently Mom' 
Revenue/Month: $250K 
Founders: 1 
Employees: 1 
Website: theconfusedmillennial.com now confidentlymom.com 
Location: United States (operates remotely) 
Founded: 2016 

The Confused Millennial isn’t just another personal development blog—it’s a lifeline for young professionals and new parents trying to make sense of life’s constant transitions. Covering everything from career moves to financial uncertainty to the complexities of raising a family, the platform has struck a balance between practical advice and real, unfiltered storytelling. It’s the brainchild of Rachel Ritlop, an entrepreneur and consultant who has turned her own winding career path into a roadmap for others looking to create a life and business on their own terms. 

For Ritlop, the journey to entrepreneurship wasn’t linear. “I got fired from my first job out of grad school,” she says bluntly. That experience set off a chain reaction—one that led her to launch The Confused Millennial in 2016. What started as a space to document her own career struggles and lessons quickly became something much bigger. “I realized so many people were feeling lost, not just in their jobs but in adulthood in general. I wanted to create a place where we could figure it out together.” 

That sense of authenticity resonated. Within three years, Ritlop had transformed her blog into a multi-six-figure business, attracting more than two million readers. Unlike many digital entrepreneurs who rely on a single revenue stream, she built a model that combined sponsored content, digital products, consulting, and brand collaborations. “I never wanted to be at the mercy of one algorithm or platform,” she explains. “Diversification was key.” 

Her business savvy caught the attention of major companies. Soon, Ritlop found herself consulting for brands like Coca-Cola, helping them understand and engage with millennial consumers. “Brands were struggling to connect with my generation in a way that felt real,” she says. “They wanted to know how to cut through the noise and actually resonate.” Her insights, rooted in both personal experience and analytics, proved invaluable. 

Despite the impressive numbers and high-profile partnerships, Ritlop remains deeply connected to her audience. She isn’t just offering polished success stories—she’s talking about the parts of life that often go unspoken. “There’s this pressure to have everything figured out, but the truth is, none of us do,” she says. Whether discussing the identity shift that comes with parenthood, the mental toll of entrepreneurship, or the reality of financial instability, she approaches each topic with a mix of honesty and actionable advice. 

That transparency extends to the financial side of things as well. Ritlop doesn’t just share vague encouragement about making money online—she breaks down exactly how she built her business, from the mechanics of SEO to negotiating five-figure brand deals. “I always tell people, blogging isn’t dead—you just have to be strategic,” she says. “People still want long-form content, but you have to meet them where they are and understand how to monetize in a way that makes sense for your audience.” 

At its core, The Confused Millennial is more than just a business for Ritlop—it’s a conversation. “I never wanted to be someone just talking at people,” she says. “I wanted to build something where people felt seen, where they could come and say, ‘Okay, I’m not alone in this.’” And for millions of readers, that’s exactly what she’s done. 

From Crisis to Clarity: The Unexpected Journey to Entrepreneurship 

For many, career success follows a predictable path—degrees, promotions, and a steady climb up the corporate ladder. Ritlop’s story takes a different route, one shaped by setbacks, self-discovery, and an unwavering refusal to settle for work that drained her. What looked like failure on the surface—getting fired twice in a single month—became the push she needed to carve out something entirely her own. 

“I had spent years doing everything I was ‘supposed’ to do,” she says. “I earned my master’s, got a respectable job, and tried to make it work. But every day, I felt like I was losing a piece of myself.” Counseling had always been her passion, but the reality of the profession—low pay, high burnout, and limited autonomy—left her questioning if she could sustain it long-term. 

Without a traditional job to fall back on, she turned inward, leaning on what she knew best: helping others make sense of their lives. She poured everything she had into writing a 200-page life skills curriculum, tackling the very issues she had witnessed firsthand in both her clients and peers. “People needed more than just therapy,” she explains. “They needed real, actionable guidance—how to manage money, how to build a career, how to take care of themselves in a way that wasn’t just survival.” 

That work didn’t go unnoticed. Treatment centers soon began reaching out, asking for her input on refining their programs. Consulting gigs followed, as did weekly group sessions where she worked directly with people trying to rebuild their lives. It was rewarding, but she knew she could reach more people if she took her insights online. “I wanted to help on a larger scale,” she says. “One-on-one work was incredible, but I kept thinking, ‘How do I make this information accessible to more people?’” 

At first, the answer seemed to be digital coaching. She set out to create an online business built around structured programs, but something about it felt off. “I was trying to force myself into this polished, professional version of what I thought an online coach should be,” she admits. “But that wasn’t me.” The breakthrough came when she stopped trying to present herself as an authority figure and instead embraced exactly where she was: figuring it out as she went. 

“I was sitting on the couch, completely overwhelmed, and I just said out loud, ‘I’m another confused millennial with no clue what I’m doing,’” she recalls. The phrase stuck. Within 48 hours, she bought the domain, built a basic website, and hit publish. 

What began as a personal outlet quickly turned into something much bigger. Readers flooded in, drawn to Ritlop’s honesty and willingness to share the ups and downs of her journey. The blog became a space where others could see their own struggles reflected—career uncertainty, financial stress, the pressure to have it all figured out. And as her audience grew, so did the opportunities. Brands started noticing. Consulting offers increased. What started as a moment of frustration became the foundation of a business that would impact millions. 

Building a Brand on Instinct and Authenticity 

Some entrepreneurs spend months refining their business plan before ever making a move. Ritlop took the opposite approach. The Confused Millennial wasn’t the result of a carefully structured rollout or a meticulously researched market gap—it was built on instinct, frustration, and an unwillingness to follow the rules of an industry that often felt performative. She had seen firsthand how traditional career paths and even the coaching world had turned into something transactional, prioritizing polished sales tactics over real solutions. So instead of mapping out every step in advance, she launched fast—within 48 hours, the blog was live. 

“It was messy. There was no perfect business plan, no fancy branding,” she says. “I just knew I had something valuable to share, and I wasn’t going to waste time overthinking it.” That quick decision-making wasn’t reckless; it was backed by a year of real-world experience. The life skills curriculum she had developed and the consulting work she had taken on had already laid the foundation for her content. What she had been teaching in-person simply transitioned online, allowing her to reach a wider audience without sacrificing depth. 

That fluid approach extended beyond the initial launch. Six months in, she moved the site from Squarespace to WordPress, fine-tuning the design to improve user experience and increase revenue potential. While many blogging experts insist on hyper-specific niches, Ritlop resisted the idea that success required strict categorization. “People kept saying, ‘Pick one topic—career, money, or wellness,’” she recalls. “But life isn’t that simple. Millennials aren’t just thinking about their jobs or their finances in isolation. Everything is connected.” That broader focus set her apart, proving that authenticity and relatability could be just as powerful as a narrowly defined brand. 

Rather than pouring money into ads or chasing viral trends, she built The Confused Millennial through organic growth. SEO, social media engagement, and direct connections with her audience fueled its expansion. “I never wanted to be in a position where my business depended on paid traffic,” she explains. “So I focused on content that had lasting value—things people would search for years down the line.” That strategy worked. Instead of short-lived spikes, her readership grew steadily, turning casual visitors into a loyal community. 

Her day-to-day operations reflect that same philosophy. She spends an hour optimizing Pinterest, another diving into SEO analytics, and additional time engaging with readers on social media. But while strategy plays a role, relationships remain at the core of her business. Collaborating with brands, partnering with other bloggers, and staying in direct contact with her audience through newsletters and comments have all contributed to long-term success. 

More than anything, Ritlop sees The Confused Millennial as a conversation rather than a platform. Readers don’t just skim articles—they respond, they ask questions, they share their own experiences. That connection has translated into real-world impact. “Meeting readers in person, hearing how something I wrote helped them make a big decision or feel less alone—that’s what keeps me going,” she says. For her, it has never been about chasing numbers. It has always been about building something that feels real. 

Scaling Up: Shifting from Hustle to Sustainability 

For years, Ritlop built The Confused Millennial through a mix of consulting, sponsored content, and hands-on client work—active income streams that required her direct involvement. But after becoming a mother, she saw a critical flaw in that model. “If I wasn’t working, I wasn’t earning,” she says. “That wasn’t sustainable long-term, especially with a baby in the picture.” The realization forced her to rethink her approach, prioritizing revenue streams that could grow without demanding constant output. 

The first major shift came with ad placements on her website—something she had avoided early on. “I was hesitant at first because I didn’t want to compromise user experience,” she explains. “But I realized I was leaving money on the table for content that was already performing well.” The move turned her existing blog posts into an ongoing source of income, generating revenue from readers who were already engaging with her content. 

Affiliate marketing became another key piece of the puzzle. Rather than relying solely on one-off brand deals, she structured partnerships so that product recommendations continued earning long after a post went live. “I wanted to make sure my past work kept working for me,” she says. “Affiliate income allows that to happen, especially when you focus on products that truly align with your audience.” 

But the biggest evolution in her strategy came with video content. YouTube, in particular, became a major focus—not just as a creative outlet, but as a long-term investment. “Blogging is great, but video has a different level of connection,” she says. “It’s personal. People see your face, hear your voice—it builds trust in a way that written content alone can’t.” The shift wasn’t just about engagement; it was also about monetization. With ad revenue, sponsorship opportunities, and the potential for evergreen content, video offered new income streams that complemented her existing business. 

Scaling The Confused Millennial wasn’t just about automation—it was also about mindset. Early on, pricing had been one of her biggest challenges. “Like a lot of entrepreneurs, I undercharged at first,” she admits. “It’s tough when you’re just starting out because you don’t always know what your work is worth.” Her approach to solving that was straightforward: raising her rates gradually with each new project. “I kept increasing until I got pushback. That’s how I figured out where the market valued me,” she explains. Learning to confidently articulate her value and stand firm in negotiations turned consulting and brand partnerships into some of the most profitable aspects of her business. 

With passive revenue streams in place and video content gaining traction, Ritlop continues refining a business model that supports both financial growth and personal freedom. “I don’t want to be tied to my laptop 24/7,” she says. “The whole point was to create something that works for my life—not the other way around.” 

Breaking the Rules and Finding Success 

Conventional wisdom says entrepreneurs should specialize, narrowing their focus to carve out a defined niche. Ritlop did the exact opposite. Instead of confining herself to a single topic, she built The Confused Millennial around the reality that millennials don’t experience life in silos. Career struggles intertwine with financial challenges. Personal growth intersects with relationships and mental health. By embracing that complexity rather than forcing herself into a rigid category, she proved that versatility could be just as powerful as specialization. 

“I never wanted to box myself in,” she says. “People kept telling me to pick one thing—career advice, personal finance, wellness—but life doesn’t work like that. Millennials aren’t just one-dimensional. We’re figuring it all out at the same time.” That philosophy not only resonated with readers but also positioned her as an authority in multiple spaces. Her ability to speak authentically across industries led to consulting opportunities with major brands like Coca-Cola and Century 21, as well as features in top publications such as Forbes and Fast Company. 

But for Ritlop, success isn’t just about revenue or recognition—it’s about freedom. Leaving behind the traditional 9-to-5 allowed her to build a career that aligned with her strengths, personality, and lifestyle. “Routine never worked for me,” she says. “I love new challenges, new projects, and new creative outlets. Content creation gives me that.” Every day looks different, blending writing, video production, consulting, and audience engagement in a way that keeps her work fresh and fulfilling. 

For those who struggle to stay engaged in a single career path or feel constantly drawn to new ideas, she believes digital entrepreneurship offers an opportunity to embrace that adaptability rather than suppress it. “So many people feel like they have to pick one thing and stick with it forever,” she says. “But there’s another way. You can build a business that grows with you.” 

Through The Confused Millennial, Ritlop has done just that—creating not only a thriving business but also a lifestyle that supports both financial success and personal fulfillment. And for those willing to reject the standard roadmap, she has shown that success isn’t about following someone else’s formula. It’s about having the vision—and the courage—to create your own. 

Success Factors: Why Did The Confused Millennial Succeed? 

• Authenticity and Relatability: Ritlop built The Confused Millennial on honesty and transparency, openly sharing her struggles with career uncertainty, financial stress, and personal growth. Readers connected with her real, unfiltered approach, which fostered trust and a loyal community. 

• Broad Yet Cohesive Content Strategy: Rather than limiting herself to a single niche, Ritlop embraced the interconnected nature of millennial life. Covering career, finance, wellness, and personal development, she created a space that resonated with readers who were navigating multiple aspects of adulthood simultaneously. 

• Business Savvy and Strategic Monetization: She diversified revenue streams from the start, incorporating consulting, sponsored content, affiliate marketing, and eventually, ad placements and video monetization. This ensured financial stability and long-term scalability without relying on a single source of income. 

• Organic Growth Over Paid Advertising: Instead of pouring money into paid traffic, she focused on long-term strategies like SEO, Pinterest, and social media engagement. This approach built sustainable, consistent traffic rather than short-lived spikes from ads. 

• Adaptability and Willingness to Pivot: From shifting her site from Squarespace to WordPress to expanding into video content, Ritlop continuously evolved her strategy to meet changing audience preferences and business needs. She also recognized when her time-for-money model needed to shift toward passive income, making strategic adjustments to ensure sustainability. 

• Confidence in Pricing and Value: Ritlop overcame the common entrepreneurial challenge of underpricing by gradually increasing her rates and testing market response. This mindset shift allowed her to command higher fees for consulting and brand partnerships, significantly boosting revenue. 

• A Strong Focus on Community and Relationship: More than just creating content, she prioritized engagement—responding to readers, collaborating with brands and fellow entrepreneurs, and fostering direct relationships through newsletters and social media. This connection-driven approach helped build a dedicated following. 

• Freedom-Driven Entrepreneurship: Success for Ritlop wasn’t just about financial gain—it was about designing a career that fit her lifestyle. By structuring her business in a way that allowed flexibility and creativity, she built something that worked for her, not the other way around. 

Key Lessons to Learn 

1. Authenticity Builds Trust and Longevity: Ritlop didn’t try to present a perfectly polished version of success. She shared her real struggles—career uncertainty, financial challenges, and the emotional ups and downs of entrepreneurship. That honesty resonated with her audience, proving that people connect more with authenticity than with an idealized version of success. 

2. You Don’t Need a Perfect Plan to Start: Many entrepreneurs get stuck in the planning phase, waiting until everything is “just right.” Ritlop launched The Confused Millennial within 48 hours, without overanalyzing every detail. Her story highlights that action often matters more than perfection—adjustments and refinements can come later. 

3. Versatility Can Be a Strength: While conventional wisdom says to specialize in a niche, Ritlop’s success shows that a broader approach can work if executed well. By covering interconnected topics—career, finance, personal growth, and wellness—she addressed the real-life challenges her audience faced, proving that flexibility can be just as powerful as hyper-focused expertise. 

4. Monetization Should Be Strategic and Diverse: Relying on one income stream can make a business fragile. Ritlop strategically monetized her platform through multiple channels, including consulting, sponsored content, affiliate marketing, ad revenue, and video content. This diversification ensured financial stability and long-term scalability. 

5. Adaptability is Essential for Growth: From shifting her website platform to expanding into video content, Ritlop constantly evolved her strategy. She recognized when her time-for-money model wasn’t sustainable and transitioned toward passive income streams. Her ability to pivot without hesitation highlights the importance of staying flexible in business. 

6. Confidence in Pricing Changes Everything: Like many entrepreneurs, Ritlop initially struggled with pricing her services. Instead of undervaluing her work, she systematically increased her rates until she understood what the market was willing to pay. Her experience reinforces the importance of knowing your worth and charging accordingly. 

7. Organic Growth is More Sustainable Than Paid Traffic: Rather than relying on expensive ads, Ritlop focused on SEO, Pinterest, and direct audience engagement to build consistent, long-term traffic. Her success proves that a strong organic growth strategy can create a steady flow of visitors and customers without ongoing ad spend. 

8. Entrepreneurship Should Align with Your Life, Not Take Over It: For Ritlop, success wasn’t just about revenue—it was about freedom. She built a business that allowed her to work on her own terms, balancing financial success with personal fulfillment. Her story is a reminder that entrepreneurship should enhance your life, not consume it. 

9. Success Doesn’t Require Following a Traditional Formula: Ritlop’s entire journey—from getting fired twice in a month to building a six-figure business—proves that success isn’t limited to those who follow a standard path. By trusting her instincts, challenging conventional advice, and creating a model that worked for her, she built a thriving brand on her own terms. 

Opportunity Matrix 

Founder Background 

Rachel Ritlop holds a master’s degree in counseling and previously worked as a mental health and substance abuse counselor. After being fired twice in one month, she shifted her focus to entrepreneurship, using her experience to help others navigate career and life challenges. 

Problem Identification 

Many millennials felt lost in their careers, finances, and personal growth but lacked relatable, actionable guidance. Existing resources often felt too rigid, overly polished, or disconnected from real-life struggles. 

Market Opportunity 

A growing audience of millennials (and later, new parents) actively seeking advice on career changes, financial literacy, entrepreneurship, and personal development. Increased demand for authentic, experience-driven content. 

Competitive Landscape 

Competed with traditional career coaching, self-help blogs, financial advisors, and personal development influencers. Differentiated through authenticity, broad content approach, and a relatable, conversational style. 

Market Research 

Ritlop leveraged firsthand experience from counseling clients, her own career struggles, and conversations within her network. Audience engagement and direct reader feedback helped refine content and business strategies. 

Business Model 

Initially relied on consulting, sponsored content, and partnerships. Later expanded into affiliate marketing, ad revenue, and YouTube monetization to create passive income streams. 

Initial Capital 

Self-funded with minimal startup costs. Built and launched the website within 48 hours without significant financial investment. 

Product/Service Development 

Started as a blog focused on career and life advice. Evolved into a multi-platform business incorporating consulting, brand partnerships, affiliate marketing, and video content. 

Marketing Strategy 

Focused on organic growth through SEO, Pinterest, and social media engagement. Built strong audience relationships through direct interaction, collaborations, and email newsletters. 

Milestones 

• Launched blog within 48 hours. 

• Grew into a multi-six-figure business within three years. 

• Attracted over two million readers. 

• Secured brand collaborations with Fortune 500 companies like Coca-Cola and Century 21. 

• Featured in major publications, including Forbes and Fast Company. 

Scalability 

Shifted from time-for-money services (consulting) to passive income streams (affiliate marketing, ad revenue, video content). Expanded into YouTube to increase reach and long-term monetization potential. 

Potential Risks and Challenges 

• Dependence on digital platforms and algorithm changes. 

• Need to continuously create engaging content to maintain audience interest. 

• Balancing personal brand growth with personal life and motherhood. 

• Market saturation in the online content space. 

Key Performance Indicators (KPIs) 

• Website traffic and engagement metrics (page views, time on site, bounce rate). 

• Social media growth and interaction. 

• Affiliate and ad revenue performance. 

• Brand partnership deals and consulting income. 

• Video content views and monetization growth. 

• Email list growth and subscriber engagement.