I get vulnerable and real about the messy side of entrepreneurship — the parts we don’t see on Instagram. From debt and negative months to burnout and the emotional rollercoaster of running a creative business, I’m sharing my behind-the-scenes truth and why I believe these struggles need to be normalized.

This isn’t about chasing shiny revenue numbers. It’s about redefining success, letting go of shame, and realizing you’re not broken if business feels hard sometimes. This episode is for every creative entrepreneur who’s ever thought: “Am I the only one going through this?”

• Why I almost didn’t record this episode (and why it matters)

• Whether success is only about money (spoiler: it’s not)

• Debt and why it’s not the big bad monster it’s made out to be

• Permission to have a negative month in business

• The emotional toll entrepreneurship takes on your mental health

• Why artists and creatives often feel undeserving of success

• The importance of normalizing struggle in our industry

• Asking the real question: Can I be excited about it all?

⛺️ Camp Clarity kicks off September 18 — This is my 3-month live group program for creatives ready to get clients, build clarity, and make cash in their business—with no blueprints required. Apply here!

🛝 Recess for Creatives is the community playground where you’ll find connection, collaboration, and support. Two live calls a month + a whole network of creatives who get it. Join the playground!

☎️ Follow me on Instagram @dianadaviscreative for more behind-the-scenes and daily business real-talk.

✅ Success isn’t only about revenue
✅ Debt doesn’t define your worth or your business
✅ You’re allowed to have a negative month
✅ Artists are allowed to be successful
✅ Entrepreneurship takes an emotional toll — and that’s normal
✅ Struggle doesn’t mean you’re failing — it means you’re human
✅ Sometimes the messiest moments bring the clearest answers

00:00 – Embracing Vulnerability and Authenticity
07:39 – Redefining Success Beyond Financial Metrics
10:34 – Navigating Debt and Business Challenges
13:41 – The Emotional Toll of Entrepreneurship
16:58 – Normalizing Business Struggles and Failures
19:46 – The Artist’s Dilemma: Success vs. Authenticity

Some episodes feel like a warm, soul-honest hug—and this one with Jera is exactly that.

Jera is a social media strategist, content creator, and real-deal creative who’s walked the wild path from fitness influencer to brand-builder and business owner. In this convo, we talk about what it really means to build a personal brand while staying true to yourself—especially in a space that can reward performative over personal. She opens up about separating your self from your business, how social trends shape our creativity, and the importance of setting boundaries in a career that lives on your phone.

We also go deep on her transition into this next season—becoming a mother, shifting her pace, and dreaming up a future that includes more art, more slowness, and more joy. There’s plenty in here about growth, grit, and the identity shifts that come with doing the thing differently.

Whether you’re craving a biz pivot, feel disconnected from your audience, or you’re just ready to make your online presence feel more like you, this one’s a must-listen.

✅ Vulnerability in business isn’t weakness—it’s your superpower.
✅ It’s okay to outgrow the version of yourself your audience first met.
✅ Authenticity > algorithms. Every. Single. Time.
✅ Boundaries are sacred—especially when your business is also your face.
✅ You get to change your mind and start fresh.
✅ Not all growth is visible—and not all success is measured in likes.
✅ Art, presence, and play are valid forms of productivity.
✅ The journey is allowed to evolve as you do.

Ways to Plug In

⛺️ Camp Clarity kicks off September 18th — we strip away the noise, get you clear on your story, your offers, your marketing, and your money — so you can finally run a thriving business that feels as creative and fun as the work you do. Apply here.

🛝 Recess is the creative community you've been looking for. Try it for 3 months for $55/month. You can sit with us.

☎️ Follow me on Instagram @dianadaviscreative for more behind-the-scenes

In this episode.

I get personal and raw as I share the behind-the-scenes of navigating a recent breakup—and how it’s rippled through my life, mental health, and business. This isn’t just about relationships. It’s about the messy, beautiful recalibration that happens when you let go of something (or someone) that isn’t aligned—and finally make space for something better. This is for anyone who’s felt like their personal life is bleeding into their work and wondered if that’s... actually a gift.

We talk about:

• What grief and business have in common

• The emotional toll of breakups (and why they hit so hard when you’re a biz owner)

• Why giving yourself grace is a strategy

• The power of recalibrating your desires after heartbreak

• Letting go of connections so new ones can find you

• Setting boundaries with yourself (not just other people)

• Avoidance patterns and the sneaky ways they block growth

• How life’s messiest moments can lead to the clearest business decisions

Ways to plug in

🧭 Camp Clarity kicks off again this September — This is the signature program for creatives ready to get clients, build clarity, and make cash in their business—with no blueprints required.

🛝 The Recess 30-Day Social Media Challenge is happening now inside The Playground — Come play, get visible, and sell your work without it feeling like a chore.

🎤 Our free masterclass, WORTH, is live on July 25th — We’re talking about what’s really blocking your creative biz income (and how to shift from crickets to cashflow this week).

🧘‍♀️ Our first-ever IRL Recess event is happening in LA on August 17th in collab with One Down Dog — FLOW & CONNECT. You in?

☎️ Follow me on Instagram @dianadaviscreative for more behind-the-scenes

Key Episode Takeaways
✅ Give yourself grace when life hits hard
✅ Your personal growth will shape your business (whether you like it or not)
✅ Boundaries with yourself are powerful healing tools
✅ Grieving is not weakness—it’s recalibration
✅ Avoidance holds you back more than failure ever could
✅ Letting go creates space for aligned opportunities
✅ Your desires are worth honoring
✅ You don’t have to compartmentalize to be successful

Episode Chapters
00:00 – Navigating Breakups and Personal Growth
07:47 – The Interconnection of Life and Business
16:08 – Lessons from Relationships and Grief
24:05 – Recalibration and Moving Forward