The Business Struggles of Gen X and Millennials...... #128
- Adrian Dionisio - business737 owner
- Feb 23
- 5 min read
Running a business isn’t easy. More than most it's Gen X & Millennial entrepreneurs who are struggling.
Gen X and Millennials are some of the most highly skilled, hardworking, and adaptable generations in history. They’ve lived through enormous technological shifts, economic downturns, and the rise of the digital economy.
However too many find themselves struggling to build a successful and sustainable businesses. But why?
The struggles of Gen X & Millennials
Shifting economies, technological disruption, and outdated career expectations have created a business landscape that is vastly different from what previous generations experienced.
Gen X (born between 1965-1980) and Millennials (born between 1981-1996) are caught between two very different economic and business worlds.
Boomers built wealth through traditional business models—long-term employment, pensions, brick-and-mortar businesses, and steady economic growth. They had a clear path to financial stability.
Gen Z, on the other hand, is fully digital-first, growing up with social media, influencer marketing, and online entrepreneurship as natural career paths.
Gen X and Millennials were promised a world that no longer exists. They were raised to believe that working hard, getting a degree, and climbing the corporate ladder would lead to financial success.
Instead, they were hit with economic instability, disappearing job security, and a rapidly changing business environment. Many turned to entrepreneurship as a way to take back control—but soon found themselves facing new struggles.
Unlike previous generations who built businesses in a relatively stable environment, Gen X and Millennial entrepreneurs have had to constantly adapt to new technologies, marketing trends, and customer behaviors.
Businesses used to rely on traditional advertising and word-of-mouth. Today, without a strong business strategy in digital marketing, social media, and automation, it’s easy to get left behind.
Attention spans are shorter than ever. Marketing today isn’t just about having a great product or service—it’s about consistently standing out online in a crowded, noisy marketplace.
For many Gen X and Millennial founders, keeping up with the speed of change is exhausting. They feel like they are always behind—learning new platforms, keeping up with algorithms, and struggling to maintain visibility in an oversaturated digital world.
The good news? These struggles aren’t impossible to overcome. With the right business strategy, you can take control, attract the right clients, increase revenue, and build a thriving, profitable business—without wasting time, energy, or money.
Common Business Struggles
1. Trading Time for Money
Many solopreneurs—especially coaches, consultants, and service-based entrepreneurs— fall into the trap of selling their time instead of their expertise. This leads to burnout, income plateaus, and the constant hustle to land the next client.
It’s an exhausting cycle. If you’re billing hourly or taking on one-off projects, you’re stuck in a model where your income is capped by your time. The problem is that you can’t scale time—but you can scale business growth by shifting your business model.
Case Study: A Gen X marketing consultant I worked with was charging by the hour. She worked long hours but struggled to scale her revenue. We restructured her services into value-based packages, allowing her to earn more while working fewer hours. Within six months, she doubled her revenue without taking on more clients.
Solution:
Shift from hourly rates to value-based pricing.
Develop signature offers that package your expertise.
Create scalable income streams like digital products, courses, or memberships.
2. Marketing Overwhelm and Inconsistency
Many Gen X and Millennial solopreneurs didn’t grow up in the social media era, making online marketing feel overwhelming. Others spread themselves too thin—posting sporadically on multiple platforms without a clear business strategy.
Marketing doesn’t have to be complicated. The key is focus. Instead of trying to be everywhere, hone in on one or two platforms where your ideal clients are active and develop a consistent content strategy.
Case Study: A Millennial life coach I worked with was posting on Instagram, LinkedIn, and X but wasn’t getting engagement or clients. We narrowed her focus to LinkedIn, optimized her profile, and created a simple content plan. Within three months, she was booking discovery calls weekly.
Solution:
Choose one or two marketing channels that align with your business.
Create valuable content that educates and attracts potential clients.
Focus on engagement and relationship-building instead of just broadcasting content.
3. Unclear Offer and Messaging
If potential clients don’t immediately understand how you can help them, they won’t buy. Your messaging needs to be clear, compelling, and results-driven.
A common mistake is offering too many services, making it confusing for clients to see the real value.
Instead, your offer should be focused and speak directly to a specific founder or entrepreneur’s pain points.
Case Study: A Gen X career coach I worked with had great experience but struggled to attract clients. Her website listed multiple services, making it unclear who she helped. We refined her messaging to focus on helping mid-career professionals transition to leadership roles. This simple shift resulted in a 3x increase in inquiries.
Solution:
Define your ideal client and their key challenges.
Craft an offer that provides a clear, measurable transformation.
Use simple, direct messaging that speaks to their needs.
4. Pricing Too Low
Many solopreneurs undercharge, often due to imposter syndrome or fear of losing clients. But low pricing not only limits income—it also attracts clients who don’t fully value the service.
If you’re constantly overworked and underpaid, it’s time to rethink your pricing. Pricing should be based on the value and outcomes you deliver, not just the time spent.
Both Gen X and Millennials are purpose-driven. They want more than just financial success—they want meaningful work, freedom, and impact.
The challenge is balancing impact with income—ensuring that the business is both profitable and fulfilling.
Case Study: A Millennial copywriter I coached was charging $50 per blog post. She was overworked and underpaid. We repositioned her as a high-value content strategist and raised her prices to $150 per post. She lost a few low-budget clients but gained premium ones who valued her expertise.
Solution:
Price based on results, not hours.
Position yourself as a premium expert in your field.
Test new pricing with higher-value clients and adjust accordingly.
5. Wearing Too Many Hats
As a solopreneur, you likely handle everything—marketing, sales, client work, admin, finance—which leads to burnout and inefficiency. But business growth requires working smarter, not harder.
Case Study: A Gen X consultant I worked with was spending 10+ hours per week on administrative tasks. We automated client onboarding and outsourced bookkeeping, saving her 30+ hours a month. This freed up time to focus on revenue-generating activities.
Solution:
Automate repetitive tasks.
Outsource admin and bookkeeping to free up time.
Prioritize high-impact activities that directly lead to revenue.
6. Information Overload and the “Always-On” Culture
The rise of social media and online business tools has made starting a business easier—but also more overwhelming. Gen X and Millennial entrepreneurs are bombarded with conflicting business advice, online courses, and marketing tactics that promise success but often lead to confusion.
Shiny Object Syndrome: Many solopreneurs jump from one strategy to another, never fully committing to a plan long enough to see results.
Comparison Trap: Social media makes it easy to compare yourself to others, leading to imposter syndrome and self-doubt.
Burnout Culture: Unlike Boomers who could “clock out” after work, today’s entrepreneurs feel pressured to be always online, always selling, and always creating content.
Many Gen X and Millennial business owners find themselves exhausted, overwhelmed, and unsure of what actually works.
How to Overcome These Challenges and Thrive
Create Scalable Offers: Move beyond hourly billing by offering packages, courses, or memberships.
Simplify Your Marketing: Focus on one or two platforms where your ideal clients are active.
Clarify Your Messaging: Make it crystal clear who you help and how you solve their problems.
Raise Your Prices: Charge based on the value you provide, not just your time.
Streamline Your Operations: Automate and outsource non-essential tasks.
Final Thoughts—Take Control of Your Business Growth
Gen X and Millennial founders, entrepreneurs, and solopreneurs have the skills, experience, and resilience to build highly successful businesses. But success doesn’t happen by chance—it requires business strategy, clarity, and the right systems.
If you’re tired of struggling with inconsistent marketing, unclear messaging, under pricing, or working too many hours without seeing real business growth, it’s time to take action.
Let’s make your business work for you—not the other way around!
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