From Boring to Biggie: How to Live a More Interesting Life

Originally published on the Never Stop Dreaming BIGGIE podcast

Are you stuck in the same routine day after day, wondering why your life feels predictable and uninspiring? You’re not alone. In episode 20 of Never Stop Dreaming BIGGIE, host Angel Holmes tackles one of the biggest challenges facing ambitious women today: how to break out of boring patterns and create a life that’s truly worth living.

The Problem with Playing It Safe

Many successful women entrepreneurs fall into what Angel calls the “comfort zone trap.” You wake up, follow the same routine, take the same routes, sit in the same spots, and interact with the same people. While routines can be beneficial for productivity, doing the exact same things repeatedly without variation leads to stagnation.

“I think we get caught up in our lives doing the same thing over and over,” Angel explains. “And I think routines are really important. I’m a big routine person. I’m a time blocker and I do a lot of the same things. However, I mix them up.”

Why Community Building Is Essential for Personal Growth

One of the most powerful insights from this episode centers on the critical importance of community for ambitious women. Research consistently shows that isolation is one of the biggest factors holding back female entrepreneurs, yet many women try to build their dreams in silos.

“We were made to be together in community with other people,” Angel emphasizes. “Find your community. Find your place with other people like you that can really light you up, that can really help you with all of these things. Help you get more interesting. Help you get more diverse. Help you get more well-rounded.”

The benefits of intentional community building include:

• Mentorship opportunities from women who’ve walked similar paths
• Accountability partners who keep you moving toward your goals
• Fresh perspectives that challenge your thinking
• Professional networking that opens new doors
• Emotional support during challenging times

Social Skills Development for Modern Women

In our increasingly digital world, developing strong social skills has become more important than ever for personal and professional success. Angel shares practical strategies for becoming more socially engaging and interesting to be around.

“The best way to be interesting, guys, is to be around other people, first of all, and to not talk a lot, to ask a lot of questions, but also just to do a lot of different things,” she advises.

Key social skills to develop include:

• Active listening instead of waiting for your turn to speak
• Asking thoughtful questions that show genuine interest in others
• Being present in conversations rather than thinking about what’s next
• Showing up consistently even when you don’t feel like it
• Following through on commitments and invitations

Breaking Out of Your Comfort Zone: Practical Strategies

Angel provides concrete, actionable steps for diversifying your experiences and breaking out of predictable patterns:

Small Daily Changes

• Take different routes to familiar destinations
• Sit in different spots at your regular locations (coffee shops, yoga studios, coworking spaces)
• Try new classes or workshops in your existing interests
• Engage with different people in your network

Strategic Social Engagement

• Say yes to invitations that align with your values and goals
• Attend events where you can support people you care about
• Join communities of like-minded ambitious women
• Respond promptly to invitations, even when declining

Travel and New Experiences

• Plan trips that expose you to different cultures and perspectives
• Attend conferences or workshops outside your immediate field
• Volunteer for causes that matter to you
• Take classes in completely new subjects

The Power of Saying No to Energy Drains

Personal development isn’t just about adding new experiences – it’s equally important to eliminate activities and commitments that drain your energy without providing value. Angel encourages women to audit their commitments regularly.

“What is not bringing you joy? What is not aligned with your vision and your goals and your career aspirations?” she asks. “You need to start saying yes to the right things, start saying no to the wrong things.”

Consider these questions when evaluating your commitments:

• Does this activity energize or drain me?
• Does this align with my current goals and values?
• Am I attending out of obligation or genuine interest?
• Could this time be better spent on priorities that matter more?

Overcoming the “I Don’t Want to Go” Feeling

One of the most relatable moments in the episode comes when Angel discusses the universal experience of dreading events we’ve committed to attending. She references comedian Jim Gaffigan’s observation about hating having obligations on the calendar – something most people can identify with.

The key insight: pushing through this resistance often leads to the most meaningful connections and opportunities.

“I have found when I am in that state where I’m like, I don’t wanna go out. I don’t wanna do anything. I don’t wanna be there. And I push through and I go, cause I’ve made that commitment. I’m going. I am so glad I went because I always will meet at least one person,” Angel shares.

Building Your Support Network

Angel emphasizes that finding your community is non-negotiable for living a fulfilling life. Whether you join an existing group like The Brighter Side Society or Like Minded Charleston, or create your own network, the important thing is connecting with people who understand your ambitions and challenges.

“I tell people if you can’t, if you don’t want to join my community, find a community, find a place with other people like you,” she explains. “Find your place. Find your community wherever you are that’s your people that can really light you up.”

Spotlight: Becky Connelly’s Entrepreneurial Journey

This episode also features Becky Connelly, founder of Non-Disclosure Apparel, as the Biggie Member of the Week. Becky’s story perfectly illustrates the principles Angel discusses about breaking out of comfort zones and building something meaningful.

After years of frustration with bralette options that were either completely unlined or uncomfortably padded, Becky decided to create her own solution. Despite having no fashion industry connections, she started making phone calls one at a time.

“I had to end up quitting my job and it took me about six months of sitting on my hands, paralyzed, not really knowing the first step,” Becky admits. “I just started making one phone call at a time… every single call and every email kind of led to the next one.”

Six years later, her Elli Bralette is helping women worldwide, demonstrating how personal problems can become profitable solutions when you’re willing to step outside your comfort zone.

The Ripple Effects of Living More Fully

When you commit to breaking out of boring patterns and building genuine community, the effects compound over time. You become someone with interesting stories to tell, valuable connections to share, and fresh perspectives to offer. This enhanced version of yourself naturally attracts more opportunities, relationships, and experiences.

“You want to be fully you and interesting. You got to keep that brain going,” Angel concludes. “That’s what we do when we’re Biggie. That’s what we do, people.”

Taking Action: Your Next Steps

Ready to transform from boring to Biggie? Start with these concrete action steps:

1. Audit your routine: Identify three small changes you can make this week
2. Research communities: Find one group of ambitious women to connect with
3. Practice social skills: Set a goal to ask three genuine questions in every conversation
4. Plan something new: Schedule one activity outside your normal routine
5. Evaluate commitments: List current obligations and assess which align with your goals

Remember, living a more interesting life isn’t about constant adventure or dramatic changes. It’s about intentionally diversifying your experiences, building meaningful connections, and staying curious about the world around you.

The path from boring to Biggie starts with a single step outside your comfort zone. What will yours be?

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Listen to the full episode “From Boring to Biggie: How to Live a More Interesting Life” on the Never Stop Dreaming BIGGIE podcast, available on all major podcast platforms. Connect with Angel Holmes on Instagram @angelpholmes and learn more about The Brighter Side Society at sipindipity.com.