The Experienced Entrepreneur

Being in business long enough, you've faced this question: "Do I stay the course… or am I self-sabotaging?"

In this week's solo episode of The Experienced Entrepreneur, we unravel one of the most complex challenges seasoned business owners face — knowing when something in your business still has staying power, and when your desire to quit is actually coming from fear, fatigue, or avoidance.

This is not a beginner conversation. This is a maturity conversation — one that honors both your intuition and your data.

For years, the online business world taught us that ease equals alignment, that discomfort signals misalignment, and that the moment something feels hard we should pivot. But the truth is far more nuanced for entrepreneurs who have been in business 5, 8, 10+ years.

In this episode, we explore:

Not all discomfort is misalignment — some of it is growth. Not all fear is a sign to stop — sometimes it's a sign you're on the edge of something important.

Most experienced entrepreneurs are either intuition-led or data-led — but neither alone is enough in your second decade of business.

We talk through the real interplay between gut instinct, metrics, and emotional maturity… and how blending these two creates the clearest decision-making you've ever had.

We break down the subtle forms self-sabotage can take — from calling fear "intuition" to reinventing instead of refining.

This is the wisdom piece no one teaches: how the work that is still yours will continue to pull you forward even when it's challenging.

You'll learn the signals of a wobble vs a warning — and how to see your business clearly again.

• You're an established entrepreneur craving clarity in your next chapter

• You've questioned whether you're meant to stay or pivot

• You've felt discomfort and weren't sure if it meant misalignment or growth

• You want to make decisions from wisdom, not fear or exhaustion

• You're ready to rebuild a steadier, more grounded relationship with your business

And if this episode illuminated something for you — if it helped you see where you've been wobbling, or where you've been tempted to burn down something that still has staying power — I would love for you to join me for the focus group for my brand new offer The Monday Meeting.

It's live. It's intimate. It's waitlist-only.

And it's designed specifically for long-term entrepreneurs who lived through the unpredictability of 2025 and are craving a steadier, clearer, more grounded way to run their business in 2026.

We'll talk honestly about what's been missing from your business, what's working, what's not, and what kind of support actually feels nourishing in this season of your journey. You'll also get a first look at how The Monday Meeting is being built for entrepreneurs who aren't newbies anymore — the ones who are ready for less chaos and more clarity.

Get on the waitlist at marissalawton.com/waitlist.

What if the real measure of a healthy business isn't how much you make—but how much you keep?

In this episode of The Experienced Entrepreneur, Marissa Lawton shares why she's shifting her focus to profit margin and what that means for seasoned business owners who are ready to step off the "scale at all costs" treadmill.

After more than a decade in business, Marissa has seen every iteration of the CEO era—the endless hiring, the tech subscriptions, the outsourcing, the pressure to look like you're growing faster than you actually are. But now, the most experienced entrepreneurs are craving something different: stability, discernment, and financial breathing room.

Inside this episode, you'll learn:

• What profit margin actually means and how to calculate it.

• Why mature entrepreneurs are prioritizing profit over growth.

• The difference between smart and wasteful investments (and how to know which is which).

• How to simplify your tech stack, trim recurring expenses, and build true financial resilience.

• Why keeping more money isn't about scarcity—it's about sovereignty.

If you've been feeling the weight of too many expenses, too many tools, and too little clarity, this conversation will help you get back to what matters: a business that's efficient, steady, and deeply sustainable.

Listen to Episode 10: Why I'm Focusing on Profit Margin Right Now

There's a difference between running a business and playing at one.

In this episode of The Experienced Entrepreneur, Marissa Lawton breaks down what it really means to work hard without burning out — and how to reclaim your energy through intentional effort.

You'll learn how to spot the difference between hustle (reactive, fear-based, endless) and a sprint (focused, strategic, time-bound). Marissa shares her framework for designing "seasons of sprint" that move your business forward without tipping you into exhaustion — including how to track what's working, when to rest, and how to tell if you're running your business or if it's running you.

If you've been feeling like slowing down means losing progress, this episode will help you reframe your relationship with effort, rebuild trust in your discipline, and remember that running a real business takes time, energy, and heart.

• The crucial difference between hustle and hard work

• Why running a business should take effort — and how to make that effort sustainable

• The five key elements of a healthy sprint: purpose, time frame, metrics, focus, and rest

• How to recognize when you're sprinting intentionally versus avoiding stillness

• Why rest isn't a reward, but a strategic part of your success rhythm

The online business space has changed — and so has the way people buy.

In this episode of The Experienced Entrepreneur, Marissa Lawton breaks down what's really happening behind today's slower sales cycles and why it's not a bad thing. You'll learn how buyer psychology has evolved, what the new customer journey looks like, and how to adapt your business strategy with more steadiness, connection, and confidence.

Marissa shares how the old "seven touchpoints before a sale" rule has ballooned to nearly eighty — and what that means for your marketing, your mindset, and your metrics. You'll explore how to meet buyers where they are, build genuine trust over time, and make sales that feel aligned instead of forced.

Whether you're a coach, service provider, or creative entrepreneur, this conversation will help you reframe what success looks like in a maturing market — and remind you that your experience is your greatest asset.

In this episode, you'll learn:

• What a sales cycle actually is (and how to track yours)

• Why buyers are taking longer to make decisions in 2025

• How to shorten your sales cycle without pushing harder

• How to build a business that supports longer buyer timelines

• Why slower doesn't mean broken — it means sustainable

Listen now to Episode 8: How to Sell in Today's Market and learn Why Sales Cycles Are Getting Longer (and What That Means for You) like how to sell smarter, lead softer, and build a business that lasts.

What if the next level of success isn't about scaling up — but settling in?

In this solo episode, Marissa Lawton explores the idea of right-sizing your business — designing a company that supports your life instead of swallowing it whole.

For years, online entrepreneurs have been told that growth is the only direction that matters. More offers, more revenue, more everything. But what happens when "more" starts costing you your peace, your energy, or your joy?

Marissa invites you to rethink the "bigger is better" mentality and consider a softer, more sustainable approach — what she calls a cottage business. It's not about shrinking your dreams. It's about building something that fits.

In this episode, you'll learn:

• How to identify your "enough number" — the revenue that covers your bills, taxes, savings, and experiences

• Why growth doesn't always mean expansion (and what it can look like instead)

• How to recognize when your business has outgrown your capacity — and what to do about it

• The difference between scaling for ego and scaling for sustainability

• Why your business should fund a well-lived life — not just your lifestyle

If you've been feeling stretched thin or secretly craving simplicity, this conversation will feel like an exhale.

Because building a business that's right-sized for you isn't playing small — it's playing smart.

Listen now to Episode 7: Are You Craving a Cottage Business?

What if "ordinary" isn't a limitation — but the new definition of success?

In this conversation, Marissa Lawton and longtime entrepreneur Jessica Freeman — founder of Jess Creatives and The Ordinary Business — explore what it really means to build a business that's sustainable, satisfying, and still fully your own.

Together, they unpack how the online business world has evolved over the last decade — from the hustle-heavy, seven-figure dreams of the 2010s to a quieter, more grounded version of success that prioritizes freedom, fulfillment, and a well-lived life.

Jessica shares how her Ordinary Business philosophy was born from both experience and exhaustion — a realization that you don't have to scale endlessly or chase viral moments to be proud of your work. Ordinary doesn't mean small. It means sustainable. It means building a business that pays your bills, supports your family, and leaves you enough energy to actually enjoy your life.

Inside this episode, Marissa and Jessica talk about:

• The rise of the Ordinary Business movement — and why it resonates with experienced entrepreneurs

• How to detach your worth from revenue milestones and comparison culture

• The "trust recession" in today's online space and what it means for your marketing

• Why steady growth often outperforms constant scaling

• The mindset shift that turns "good enough" into exactly right

If you've been feeling weary of the "more, more, more" mentality or craving a simpler rhythm in your business, this episode will remind you: you're not behind — you're evolving.

🎧 Listen to Episode 6: The Ordinary Business Revolution with Jessica Freeman

Because in this new era of entrepreneurship, success isn't about doing everything — it's about doing what matters, with intention.

Connect with Jessica Freeman:

• Website: jesscreatives.com

• The Ordinary Business: theordinarybusiness.com

• Instagram: @jesscreatives

Your brand isn't something you create — it's something you uncover.

In this episode of The Experienced Entrepreneur, Marissa Lawton is joined by designer and brand strategist Shaina Longstreet, founder of Dawn and Delight Creative, for a deeply grounded conversation about what it really means to build a business that feels like you.

After nearly two decades in creative work, Shaina has developed a powerful philosophy she calls identity-led branding — an approach that starts with who you are at your core, not with trends, templates, or what everyone else is doing online.

Together, Marissa and Shaina explore:

• Why your unique identity is your greatest differentiator in business.

• The difference between "building a brand" and becoming one.

• How to operate in your zone of genius (and stop trying to do it all yourself).

• The reality of choosing your hard in entrepreneurship — and why the right kind of challenge still feels fulfilling.

• Why visual branding is only one piece of the puzzle — and how your values, voice, and visuals must align for long-term growth.

• How an identity-led foundation keeps your brand relevant, adaptable, and authentic through every pivot or rebrand.

Shaina shares her four-part Dawn Approach — a process that blends strategy, visuals, and meaning — and explains how identity-led branding naturally evolves as you do.

This conversation is for the business owner who's tired of "pretty but empty" marketing and ready to root their work in something deeper: purpose, consistency, and truth.

Listen now to learn: → How to recognize your business's core identity → Why authenticity is the strongest growth strategy → How your brand can evolve with you — without losing its soul

Resources Mentioned:

• Free workbook: Discover Your Deepest Why

• Connect with Shaina on Instagram → @dawnanddelight

• Learn more at dawnanddelight.com

Connect with Marissa:

• marissalawton.com

• Follow The Experienced Entrepreneur for weekly, heartfelt conversations about business sustainability, brand clarity, and staying steady as you evolve.

The true purpose of business isn't growth for growth's sake — it's alignment, sustainability, and impact that lasts.

In this powerful first guest episode of The Experienced Entrepreneur, Marissa Lawton sits down with Quinn Tempest, entrepreneur, strategist, and founder of Create Your Purpose®, for a conversation that cuts through the noise of hustle culture and redefines what it means to build a business that truly serves your life.

Quinn has been a business owner for more than 13 years, evolving from freelance design to strategic consulting and community leadership for women entrepreneurs. But her path wasn't linear. After a severe burnout early in her career, she rebuilt her business from the inside out — redefining success as something deeply personal, intentional, and sustainable.

Together, Marissa and Quinn unpack what it means to mature as an entrepreneur — to trade the frantic chase for grounded purpose, and the "frazzled nimbleness" of constant reaction for what Quinn calls purposeful nimbleness.

Inside this conversation, you'll hear:

• The difference between a freelancer mindset and an entrepreneur mindset, and how that shift changes everything.

• How to make decisions from alignment instead of anxiety and lead yourself consciously through growth.

• Why your business is an ecosystem that requires regular updates — an entrepreneurial operating system, as Quinn calls it — to stay healthy and responsive.

• What it means to listen to your business through metrics, not vibes, so you can make informed and intuitive decisions.

• How to navigate the messy middle and come out more grounded, resilient, and purpose-driven on the other side.

Quinn and Marissa also explore how the online business world itself is maturing — moving beyond quick wins and trendy tactics toward depth, honesty, and sustainable leadership.

This episode is equal parts practical and soulful — an invitation to slow down, tune in, and reconnect with what your business is really here to do.

If you've ever felt the quiet pull to re-evaluate why you started your business, or if you're ready to build with intention instead of urgency, this one's for you.

✨ Listen now to hear: → How Quinn rebuilt her business around purpose after burnout → Why your "operating system" as an entrepreneur must evolve → How to stay steady and intentional through the messy middle

Favorite Quote: "Entrepreneurship is a mirror — it reflects everything you bring to it. The goal isn't perfection, it's awareness." — Quinn Tempest

Connect with Quinn:

• Free Priority Planner for business owners → quinntempest.com/priority

• Follow on Instagram → @quinn.tempest

Connect with Marissa:

• marissalawton.com

• Follow The Experienced Entrepreneur for cozy, candid conversations about sustainable business, metrics that matter, and staying steady in entrepreneurship's shifting seasons.

After more than a decade online, I don't want to run my business the way I used to. No endless funnels. No chasing perfection. No over-editing every piece of content. No building big teams just to manage the growth.

In this episode, I'm pulling back the curtain on what I'm doing differently in this chapter of business — and why it might resonate with you, too. I talk about:

• Why I'm keeping things simple (no team hires, no complex funnels).

• Why these podcast episodes are intentionally raw and unedited.

• Why I'm leaning on high-touch connections, personal conversations, and old-school relationship marketing.

• Why collaborations and community are my growth strategy this season.

If you've been craving a simpler, steadier, more connected way of doing business, this episode will affirm what you've been feeling in your gut. Sometimes the best strategy isn't scaling faster — it's reconnecting.

I also share how this approach ties into the values of The Experienced Entrepreneur and my upcoming offer, The Monday Meeting. It's all about steadiness over scramble, relationships over transactions, wisdom over hacks, and integration over burnout.

If you're nodding along, you're in the right place.

Listen now for an inside look at how I'm doing things differently this season — and how you can, too.

Every business owner eventually comes to a crossroads: Do I keep going the way I have been, or do I do it differently?

This very first episode sets the stage for what you can expect from The Experienced Entrepreneur. Every Monday: raw, real conversations about the long game of entrepreneurship. Not the Instagram highlight reels, not hustle culture advice that burns you out, but the steady rhythm of showing up year after year and letting your wisdom lead the way.

If you've ever felt unseen in the online business world — like the conversations happening out there don't reflect where you actually are anymore — this podcast is for you. The Experienced Entrepreneur is about creating space for those of us who have been around the block, who know the highs and lows, and who are ready to embrace a different way of running our businesses.

In this episode, I share why I stepped away for a while, what made me come back, and the triple meaning of the word experienced:

• Established in business (this isn't for beginners).

• Lived experience as a true life asset.

• Enriched and resourced — letting business fund a full, vibrant life.

So if you've been searching for a place that affirms the value of your wisdom, normalizes the messy in-between seasons, and encourages you to keep building a business that feels steady and sustainable, you're home.

Subscribe now so you never miss an episode, and join me every Monday for cozy conversations that feel like pulling up a chair at the kitchen table with a friend who gets it.