Jessica Maxson shared their story and experiences with us recently and you can find our conversation below.
Hi Jessica, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What are you being called to do now, that you may have been afraid of before?
For years, I had one foot in the corporate world and one foot in my entrepreneurial dreams. Since launching Simplified by Jess in 2017, I always kept a corporate job as my “safety net” – terrified of fully committing to my business. But twelve months ago, I finally took the leap and went all-in on Simplified. No more salary crutch, no more playing it safe.
That transition forced me to ask the hard question: What’s my highest and best use as a one-person operation? How do I scale my impact without burning out?
The answer became crystal clear: digital products. I realized I was spending all my time doing one-on-one work, but my real calling is creating resources that can help thousands of entrepreneurs simultaneously. Now I’m focused on building tools that solve the exact problems I see every day – whether that’s helping someone launch their first startup, hack their productivity, organize their operations with comprehensive SOPs, or harness the power of AI to transform their business.
What I was afraid of before was letting go of that guaranteed paycheck. What I’m called to do now is leverage everything I’ve learned from years of simplifying businesses and package it into resources that entrepreneurs can access anytime, anywhere. It’s scary to bet everything on your vision, but it’s also incredibly freeing to finally align your work with your true purpose.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Jessica de la Torre Maxson, the Founder and Principal of Simplified by Jess, I help entrepreneurs optimize their businesses by treating mental clarity as their most valuable operational system. Because the clearest thinking creates the most efficient businesses.
After 7+ years of supporting dozens of startups and small businesses, I noticed a pattern: most entrepreneurs were drowning in complexity. They’d get so caught up in elaborate systems, endless tools, and overcomplicated processes that they’d lose sight of what actually moves the needle. That’s where Simplified by Jess comes in.
My approach is built on four core principles: harmony, collaboration, quality, and efficiency. These aren’t just business buzzwords – they’re the mental health principles that transformed my own entrepreneurial journey and now drive measurable results for my clients. When your business operates in harmony with your values, collaborates without people-pleasing, prioritizes quality over perfection, and runs efficiently without burnout, everything changes. Instead of adding more layers to your business, I strip away everything that doesn’t serve your goals. Think of me as the Marie Kondo of business organization and operations – if it doesn’t spark growth, it’s got to go.
What makes Simplified unique is that I don’t just consult and disappear. I’m one of the few business consultants who explicitly connects mental health with operational efficiency – because I’ve learned that your mindset is your most important business system.
I’ve created an entire ecosystem of digital resources that entrepreneurs can access long after our work together ends. From comprehensive SOP templates that streamline operations, to AI prompt collections that supercharge productivity, to startup guides that eliminate launch chaos – everything is designed around one core belief: your business should be simple enough to scale.
The real magic happens when entrepreneurs stop trying to do everything and start focusing on their zone of genius. My job is to handle the operational complexity so they can get back to what they do best – growing their business and serving their customers.
Right now, I’m laser-focused on scaling this impact through digital products that put powerful business tools directly into entrepreneurs’ hands, whenever they need them.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What breaks the bonds between people—and what restores them?
The answer to both is the same: communication. More specifically, radical honesty.
I’ve seen relationships crumble when people dance around the truth, avoid difficult conversations, or say what they think the other person wants to hear. Conversely, I’ve watched the strongest bonds form between people who can have those uncomfortable conversations with respect and genuine care.
In my business, this philosophy is everything. I’m incredibly grateful to work with clients who value honest feedback as much as I do. They don’t just want me to nod along with their ideas – they want me to challenge them respectfully when I see a better path forward. And I expect the same from them. Some of my most successful client relationships started with someone telling me, “Jess, I think you’re completely wrong about this approach.”
As an entrepreneur, you absolutely must surround yourself with people who will push you to grow, even when it’s uncomfortable. That’s why I built a Harmony Clause directly into my Simplified Client Agreement. Before we start any project, we establish clear expectations around communication – how we’ll handle disagreements, give feedback, and navigate challenges together.
It might sound overly formal, but setting these ground rules upfront has saved countless relationships. When everyone knows it’s safe to be honest, when respect is built into the foundation, that’s when the real magic happens. Both personally and professionally, the people who stick around are the ones who can handle the truth – and dish it out when necessary.
Radical honesty isn’t always easy, but it’s always worth it.
What fear has held you back the most in your life?
The fear of failure has been my Achilles heel for as long as I can remember, and honestly, it still rears its head more often than I’d like to admit. But I’m learning to push through it one day at a time.
The breakthrough came through therapy over the last ten years. I had this massive realization that perfection ISN’T REAL. It’s not real. For my entire life, I’d been measuring myself against this impossible standard that literally doesn’t exist. No wonder I felt like I was constantly falling short. And here’s what shocked me: when I finally let go of perfectionism, my business actually performed better. My decision-making became clearer, my creativity flourished, and I could finally focus on revenue-generating activities instead of endlessly tweaking things that were already good enough.
What is real is doing the best you can every single day. And here’s the kicker – that “best” looks completely different each day, sometimes each hour. Some days I wake up with 100% energy, eyes on the prize, ready to conquer the world. Other days? I’m operating at maybe 35%, drained by the constant news cycle or just the weight of life in general.
Learning to listen to my body and mind when they’re telling me to step away from the screen has been revolutionary. I’m constantly reframing my mindset from “achieving perfection” to “achieving my own best for today.”
This shift has actually made me a better entrepreneur and consultant. When I stopped trying to be perfect, I started being more honest with my clients about realistic timelines and expectations. I give myself permission to iterate, to test, to fail fast and learn faster. And I help my clients do the same.
The fear of failure hasn’t disappeared, but now I know that “failure” is just data. It’s information that helps me refine my approach and serve my clients better. That’s infinitely more valuable than any impossible standard of perfection.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What’s a belief or project you’re committed to, no matter how long it takes?
Mental health awareness and removing the stigma around it. This isn’t just a cause I support – it’s woven into the very fabric of who I am and how I run my business.
I’m a huge supporter of Project Semicolon, and if you look closely at my Simplified by Jess logo, you’ll notice it incorporates that semicolon symbol. It’s not an accident. A semicolon represents a pause, not an end – just like mental health struggles don’t define your entire story. They’re part of your journey, but they’re not your destination.
I also champion organizations like NAMI (National Alliance on Mental Illness) for their incredible work in education, support, and advocacy. These resources are game-changers for people who need them.
Here’s what I’ve learned: the clearer you are on the state of your mental health, the more clearly you can run your life and your business. This isn’t just feel-good advice – it’s strategic. When entrepreneurs ignore their mental health, I see them make the same costly mistakes: analysis paralysis, perfectionist bottlenecks, people-pleasing that dilutes their brand, and burnout that kills momentum. The entrepreneurs who treat mental health as a business skill? They make faster decisions, delegate more effectively, and scale more sustainably.
But when I prioritized my mental health – through therapy, through honest conversations, through giving myself permission to not be “on” 100% of the time – everything else started falling into place. My business became more efficient, my relationships became more authentic, and my impact became more meaningful.
That’s why mental health advocacy will always be part of my mission. Because entrepreneurs especially need to hear this: taking care of your mental health isn’t selfish or weak – it’s strategic. It’s the foundation that everything else is built on.
No matter how long it takes, I’ll keep having these conversations and breaking down these barriers.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Could you give everything your best, even if no one ever praised you for it?
This is probably the toughest question you could ask me, because it hits right at the heart of a personal contradiction I’m still working through.
Intellectually, I know the wisdom from Don Miguel Ruiz’s “The Four Agreements” – specifically, don’t take anything personally, good or bad. The praise isn’t about you, and neither is the criticism. In theory, I should be able to pour my heart into my work regardless of external validation.
But here’s the honest truth: my love language is words of affirmation. A heartfelt conversation with a client about how our work together transformed their business? A handwritten thank-you card? Those moments absolutely fuel my soul and motivate me to keep going.
So could I give everything my best without any praise? I’d like to think so, and I’m actively working toward that level of inner confidence. But I’d be lying if I said external validation doesn’t matter to me.
What I’ve learned is to find balance. I’ve built systems to remind myself of my “why” on the days when praise is scarce. I keep a folder of client testimonials not for marketing, but for those moments when I need to remember the impact of my work. I’ve also learned to give myself the affirmation I need – celebrating small wins, acknowledging my growth, recognizing my effort even when the results aren’t immediately visible.
The goal isn’t to become immune to praise or criticism – it’s to become less dependent on them for my sense of worth. I’m getting better at doing excellent work because it aligns with my values, not just because someone might notice.
It’s a work in progress, and I’m okay with that.
Contact Info:
- Website: https://simplifiedbyjess.com/
- Instagram: https://www.instagram.com/simplifiedbyjess/
- Linkedin: https://www.linkedin.com/company/simplified-by-jess/
- Facebook: https://www.facebook.com/simplifiedbyjess
- Soundcloud: https://soundcloud.com/simply-the-jess-voice-over
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