The Lifestyle Entrepreneur | The 10 Entrepreneur Type Series
What if your business was designed around your life, not the other way around?
The Instagram Post That Changed Everything
Cass Danson was a 33-year-old mom in Melbourne with a passion for creating colorful murals. Like most parents, she was juggling her creative interests with raising kids and running a household. She started sharing her vibrant artwork on Instagram—not because she had a business plan, but because she loved creating and wanted to connect with other people who appreciated colorful, joyful art.
What started as a creative outlet slowly began attracting attention. People weren’t just liking her posts. They were asking where they could buy her designs.
At first, Cass brushed it off. She was a mom who made art, not a business owner.
But the requests kept coming.
Finally, in 2023, Cass decided to test the waters. Instead of trying to build a traditional art business with galleries and high overhead, she took a different approach. She partnered with local printers to create wall decals featuring her designs—a way to bring her art into people’s homes without the complexity of shipping fragile original pieces.
The lifestyle entrepreneur approach worked exactly as she’d hoped.
Cass designed her business around her life as a mom, not the other way around. She could create designs when inspiration struck, work around her children’s schedules, and grow at a pace that felt sustainable. She wasn’t trying to build the next big art empire. She was trying to build a business that funded her creative life while still being present for her family.
The results spoke for themselves: In her first year, Cass made around $40,000 in profit. By year two, she was approaching $100,000 and expanding into apparel—all while maintaining the flexible, family-first lifestyle that motivated her to start in the first place.
If Cass’s story resonates with you—if you want to build a business around your life and passions rather than sacrificing everything for growth—you might be a Lifestyle Entrepreneur.
The Lifestyle Entrepreneur Difference: Freedom-First Business Design
Lifestyle Entrepreneurs don’t build businesses to maximize revenue. They build businesses to maximize freedom and life satisfaction.
While others chase rapid growth and external validation, Lifestyle Entrepreneurs design their businesses around specific lifestyle goals and personal values.
Here’s what makes them different:
They make decisions based on what matters to them. Not what business books say they “should” do. If spending afternoons with your kids matters more than hitting certain revenue targets, that guides every business decision.
They build systems that work without them. Their business can’t require constant attention, or it defeats the purpose. They need to be able to step away.
They protect their boundaries. They’re crystal clear about when, where, and how they work. And they stick to it.
They adapt as life changes. New baby? Health issue? Want to travel? Their business model can flex with them.
They serve fewer clients better. Quality over quantity. They’d rather do excellent work for 10 clients than mediocre work for 100.
But here’s the key difference: Lifestyle Entrepreneurs measure success by the life their business enables, not just the money it generates.
The Freedom Advantage (And The Trade-offs)
When Lifestyle-First Works
Cass’s approach created several advantages that traditional entrepreneurs often miss:
She built around what she already loved. Creating art didn’t drain her energy—it filled her up. Work felt fulfilling instead of exhausting.
She could be present for family. By partnering with local printers and focusing on digital designs, she worked around her kids’ schedules. She didn’t miss school pickups or bedtime stories.
She started with low overhead. Wall decals meant minimal inventory, no gallery rental, and the ability to test demand before investing heavily. Less financial risk means less stress.
She could grow without working more. Digital designs could be reproduced without her constant hands-on involvement. The business could scale while she slept.
She could work from anywhere. Laptop and internet connection? That’s all she needed. Home, coffee shop, vacation rental—didn’t matter.
The Lifestyle Trade-offs
But Cass also learned that lifestyle entrepreneurship comes with specific challenges:
Income grows gradually. Getting from $40K to approaching $100K took patience and consistent effort. Lifestyle businesses often grow more slowly than high-pressure startups.
You have to educate your market. She had to help customers understand the value of her designs and the quality of her wall decal products. That takes time.
You need serious self-discipline. Without a boss or office structure, she had to create her own systems for consistent work, marketing, and customer service.
Every growth decision gets complicated. When the opportunity came to expand into apparel, she had to ask: “Does this fit my family-first priorities? Or will it take over my life?”
You’ll compare yourself to others. Watching other entrepreneurs pursue rapid growth made her question whether her steady, lifestyle-focused approach was “enough.” Spoiler: it was. But the doubt still showed up.
Signs You Might Be a Lifestyle Entrepreneur
Does this describe what you want from your business?
✅ You want a business that adapts to your life, not a life that adapts to your business
✅ You value time freedom and flexibility more than maximizing revenue
✅ You’d rather have a smaller, sustainable business than a high-stress, high-growth venture
✅ You want to work from anywhere without needing much infrastructure
✅ You prioritize personal relationships, health, and hobbies alongside professional success
✅ You’re okay with variable income in exchange for lifestyle flexibility
✅ You want to step away from your business without it falling apart
How Cass Built Her Lifestyle Business (The Real Strategy)
Here’s what Cass learned: you have to start with your life priorities first, then find business models that support them. Not the other way around.
She Started With Her Life First
Cass didn’t think “What business should I start?” She thought “I love making colorful art and I need to be home with my kids. What business model fits that?”
The business came second. Her life came first.
She Tested Without Quitting Everything
Instead of leaving everything behind to pursue art full-time, she tested demand through Instagram. Started small with local printer partnerships. Kept her risk low while she figured things out.
This is crucial: You don’t have to burn the boats to build a lifestyle business. Test it first.
She Built Once, Sold Many Times
Wall decals were genius for her lifestyle goals. She could create a design once, and it could be produced and sold many times without her touching it.
That’s the key to lifestyle business: find ways to make money that don’t require trading your time hour-for-hour.
She Grew at a Sustainable Pace
Rather than pursuing rapid expansion that would’ve consumed her life, she grew steadily from $40K to approaching $100K while maintaining her family-first priorities.
The systems that got you to $40K won’t get you to $100K. But you can rebuild those systems at a pace that doesn’t wreck your life.
She Expanded Strategically
When she moved into apparel, it was a natural extension that fit her existing design process and lifestyle goals. Not a desperate grab for more revenue.
This wasn’t just about starting a business. It was about designing a business around her ideal life.
The Discipline You’ll Need (Nobody Talks About This)
Here’s the thing nobody tells you about lifestyle entrepreneurship: The biggest challenge isn’t building the business. It’s maintaining the discipline to stick to your lifestyle priorities as the business grows.
When opportunities show up that would require working evenings or weekends—away from her kids—Cass has to constantly remind herself why she chose this path.
A gallery wants to feature her work, but they need her there for evening openings? No.
A big client wants custom work, but they need weekend availability? No.
A partnership opportunity could double her revenue, but it would mean regular travel? No.
Lifestyle entrepreneurship isn’t about working less. It’s about working more intentionally within boundaries that support your ideal life.
Cass learned to say no to opportunities that didn’t align with her lifestyle goals, even when they were financially attractive. Even when other people thought she was crazy to turn them down.
This discipline is what separates successful lifestyle entrepreneurs from those who drift back into traditional business models and wonder why they’re miserable again.
Let’s Be Honest About What This Really Takes
If you’re reading this thinking “This sounds perfect,” here’s what you need to understand:
Lifestyle entrepreneurship isn’t easier than traditional entrepreneurship. It’s different.
It requires serious self-discipline. You need careful financial planning. You need the confidence to turn down opportunities that don’t fit your lifestyle parameters.
You need to be comfortable with variable income. You need to accept potentially slower business growth in exchange for lifestyle flexibility.
And here’s the guilt nobody warns you about: You’ll watch other entrepreneurs hustling 80-hour weeks and wonder if you’re lazy. You’ll see people hitting big revenue numbers and question if you’re thinking too small.
You’re not lazy. You’re not thinking too small. You’re playing a different game.
The question isn’t whether you want more freedom. Everyone wants that.
The real question is: Are you willing to design your business systematically around that freedom and stick to those principles even when it’s hard?
What You Actually Need to Succeed
Cass’s journey from “mom who makes art” to successful lifestyle entrepreneur required developing specific skills:
Boundary management – Setting and maintaining clear limits on when, where, and how you work. Then actually enforcing them.
Value-based decisions – Choosing opportunities based on lifestyle alignment, not just money. This is harder than it sounds.
Systems that work without you – Building processes that run without your constant involvement. Your business can’t need you every hour.
Client education – Helping clients understand and respect your working style. Some won’t get it. That’s okay—they’re not your people.
Financial planning – Managing variable income and planning for your lifestyle goals. You need a cushion when some months are lean.
Self-discipline – Maintaining productivity without external accountability. No boss, no office, no one watching. Just you.
Confidence – The self-assurance to charge good prices for quality work delivered on your terms. You’re worth it.
Cass learned that successful lifestyle entrepreneurs don’t just stumble into freedom. They systematically build businesses designed to create and protect that freedom.
Your First Steps (If This Is Your Path)
Want to start building a lifestyle business? Here’s what you can do today:
- Define your non-negotiables. What aspects of your life are you absolutely not willing to sacrifice? Be specific. “Time with family” is vague. “Home by 3pm every day to pick up kids from school” is specific.
- Audit your current skills. What do you already know how to do that people would pay for? Start there.
- Look for “create once, sell many” models. Digital products, designs, templates, courses—things that don’t require your time for every sale.
- Test before you leap. Don’t quit everything. Test your idea on the side. See if people actually want what you’re offering.
- Build a cushion. You’ll need 3-6 months of expenses saved before going full-time. Variable income is stressful without a buffer.
Discover Your Freedom-First Path
If you recognize yourself in Cass’s story, you’re likely someone who values lifestyle flexibility. But here’s the real question:
Are you suited for the unique challenges and opportunities of lifestyle entrepreneurship?
Our entrepreneurial assessment analyzes your natural approach to structure and boundaries, your relationship with variable income, and what it’ll take to build a business that truly serves your lifestyle goals.
In just 10 minutes, you’ll discover:
✅ Your exact entrepreneurial type and how it relates to lifestyle business building
✅ Your top 3 natural strengths as a freedom-focused entrepreneur
✅ Your top 2 challenges and what to expect on your lifestyle entrepreneurship journey
✅ Your strategic advantage in building businesses around your life
✅ Hidden opportunities specific to your type (often $30K-50K+ annually)
✅ Your competitive weak spots and how to protect against them
✅ A relevant framework to guide your lifestyle-first entrepreneurial decisions
Take the Assessment Now – Discover Your Exact Entrepreneurial Type →
https://www.assess.seanmatkinson.com/sean-dzysmiaq
Remember This
You don’t have to choose between business success and personal fulfillment. With the right approach, you can build a business that funds your dream life instead of consuming it.
But it won’t happen by accident. It requires intentional design, clear boundaries, and the discipline to protect what matters most to you.
Ready to discover whether lifestyle entrepreneurship is right for you, or if you’re better suited for another approach? Your assessment results are waiting.