Entrepreneurial Well-Being Is the Key to Growth—Jennifer Gray Explains Why

Photo Credit: Hope Kemp Photography.

Jennifer Gray is an entrepreneurial well-being expert whose own journey to find a fulfilling career inspires her work. From running a successful business in New York’s finance sector to becoming a multi state licensed mental health therapist and EMDR clinician, Jennifer offers a unique blend of business expertise and therapeutic insight. She specializes in supporting entrepreneurs, financial professionals, and architects in navigating the many challenges of executive strain and work-life balance. Jennifer’s actionable strategies foster self-discovery and sustainable change with transformative tools for personal and professional growth.

Can you tell our readers about your background?

I started my first business in high school, helping older adults who had lost their partners and were struggling to manage their household finances. Over a few years, that evolved into bookkeeping and business consulting for multimillion-dollar businesses on Long Island. I was skilled at the work, but after doing my own personal therapy, I realized I wanted something more. That led me to pursue graduate school, obtain a counseling degree, and start a private therapeutic practice. I began specializing in entrepreneurs almost immediately because I lived the experience, and I saw it intimately from the outside, working alongside my clients. I recognized their unique struggles—overwhelm, burnout, and the constant push to be productive at all costs. I wanted to create a space where they could finally slow down, gain clarity, and build a life that actually felt good instead of just looking successful on paper.

What inspired you to start your business?

Having been deeply involved in the business world, I understood the challenges entrepreneurs face, and I saw a real need for tailored mental health support in that space. Entrepreneurs, financial professionals, and architects manage an immense amount of responsibility, often with little to no real support. Traditional therapy approaches don’t always resonate with them because they’re highly action-driven and accustomed to solving problems on their own. Many of them feel like they should be able to “fix” themselves the way they fix problems in their businesses. But it doesn’t work that way. I built my practice to bridge that gap—offering therapy that is direct, deep, results-oriented, and designed specifically for those navigating the high-pressure demands of running a business. I help them get out of their own way, break patterns that no longer serve them, and actually start living the life they thought success would give them.

Where is your business based?

I work 100% virtually (telehealth) with clients in Arizona, Colorado, Florida, Oregon, Washington, and Wisconsin. This allows me to serve entrepreneurs across multiple states while they navigate their busy businesses. I also plan to expand into events, workshops, and retreats to complement my one-on-one work, giving clients immersive experiences that take them beyond just talking and into taking real action in their lives.

How did you start your business? What were the first steps you took?

After getting licensed, I immediately started my private practice. I didn’t wait for permission or spend years building slowly—I knew this was needed, and I was ready to deliver. With my background in business, I knew the importance of visibility, so I focused heavily on SEO, media contributions, and clearly defining my niche. I made sure that when entrepreneurs searched for therapy, they found me. I wasn’t trying to appeal to everyone—I was speaking directly to overwhelmed business owners who needed no-BS support. From day one, I positioned my practice as a space for entrepreneurs seeking long-lasting, actionable change.

What has been the most effective way of raising awareness for your business?

SEO, media features, and guest spots on podcasts and live TV have been invaluable. I made sure my website was optimized for exactly the kind of clients I wanted to attract. I also leaned into thought leadership—writing articles, appearing on TV segments, and speaking at events to ensure my name and expertise were out there. My messaging is straightforward, and I don’t divert from it just to fill my caseload. I also rely on word-of-mouth referrals from clients who have seen a real transformation in their lives and businesses. Entrepreneurs talk, and when they find something that works, they share it.

What have been your biggest challenges and how did you overcome them?

State licensing restrictions have been a challenge because every Board is different. Since I can only provide therapy in the states I’m licensed in, my ability to work with entrepreneurs nationwide is limited. But instead of letting that stop me, I’ve found ways to expand my reach. I contribute to media, write articles, and do public speaking to ensure my insights reach a wider audience—even if I can’t work with them directly. This way, I’m still offering value and helping entrepreneurs who might otherwise not have access to therapy that truly speaks to their needs.

How do you stay focused?

I maintain clear boundaries between work and personal time. Productivity isn’t about doing more—it’s about managing energy effectively. I work within structured hours and make sure to unplug when needed to avoid burnout. I am always tracking my energy levels and being honest with myself about what I can and cannot do (and what I want to do and don’t!). This is something I also teach my clients—business isn’t just about output; it’s about sustainability. Knowing when to stop is just as important as knowing when to push forward.

How do you differentiate your business from the competition?

I combine my firsthand business experience with my expertise as a therapist, offering a highly specialized approach that entrepreneurs relate to. I integrate EMDR with action-based therapy to help clients not only understand their challenges but actually implement lasting changes. I am not the head-bobbing therapist who just repeats, “Tell me more about that.” That doesn’t serve anyone. My clients value that I’m direct, real, and not afraid to challenge them when necessary. They don’t have time for surface-level talk—they need deep transformation, and that’s exactly what I provide

What has been your most effective marketing strategy to grow your business?

Strong SEO—making sure I’m easily found when entrepreneurs search for therapy.

Media and thought leadership—contributing to TV, podcasts, and articles with no-fluff honesty. When entrepreneurs interact with my media, they quickly realize that I get it on a different level than the average therapist or business coach.

Client referrals—when clients experience real results, they send others my way. Entrepreneurs trust other entrepreneurs, and word-of-mouth referrals are one of the strongest marketing tools I have.

What's your best piece of advice for aspiring and new entrepreneurs?

Let me get very real with you… Stop trying to do everything yourself. Seriously. It’s a one-way ticket to burnout, and no, working harder isn’t going to magically fix everything. The reality is, you don’t have to prove you can “handle it all” before you deserve help. Whether it’s therapy, mentorship, outsourcing, or hiring, the sooner you start letting go of the things that drain you, the sooner you’ll actually see progress. Success isn’t about grinding 24/7—it’s about learning to work smarter and understanding that efficiency beats effort every time. The people who build sustainable, fulfilling businesses are the ones who invest in support early, not the ones who stubbornly white-knuckle their way through every obstacle alone. Get strategic, ask for help, and focus on the things that actually move the needle forward instead of just keeping you busy. That’s how you grow—not by muscling through it solo, but by making smart, intentional moves that set you up for long-term success.

What's your favorite app, blog, and book? Why?

I don’t rely on just one. I consume a wide variety of content—business books, psychology research, industry blogs, and even podcasts. Growth doesn’t come from a single source; it comes from combining insights from different places. A book might give me a new perspective on business strategy, a research article might sharpen my clinical work, and a podcast might introduce a new way of thinking about entrepreneurship. The key is staying curious and adaptable, always seeking knowledge that adds value to my work and my clients' lives.

What's your favorite business tool or resource? Why?

My team is one of my best resources. No business owner should be doing everything alone, and I practice what I preach. Having a solid team in place that I trust and respect allows me to focus on what I do best—helping clients—while knowing that certain aspects of my business (which I can’t stand doing on my own) are being handled by experts. Delegation is a game changer, and it’s something I encourage my clients to embrace as well.

Who is your business role model? Why?

Rather than looking to one person, I take insights from a range of professionals—therapists, researchers, therapists-turned-coaches, professional organizations, mental health experts, and business leaders. Every field has something valuable to offer, and learning from diverse perspectives helps me stay sharp. I don’t believe in following a single blueprint for success because my work is unique, and I need insights from multiple sources to keep refining it.

How do you balance work and life?

I don’t view work and life as competing forces but as elements that should complement each other. I set intentional boundaries and make sure that my business serves my life, not the other way around. I prioritize activities that recharge me and say no to anything that doesn’t align with my values. My clients often struggle with feeling like they should always be “on”—I show them how to step back without feeling like they’re failing. I don’t just speak the truth about entrepreneurship well-being, I truly live it.

What’s your favorite way to decompress?

Spending time outdoors, reading (fiction and non-fiction), connecting with loved ones and pets, quiet time for introspection, journaling and writing, enjoying dancing and music, and having personal time without any work distractions. I also prioritize my own therapy because even professionals need support. I encourage my clients to build self-care routines that truly work for them—not just the trendy ideas, but what actually helps them recharge on a deep level. Being intentional about rest is just as important as being intentional about work.

What do you have planned for the next six months?

Launching a non-diagnostic toolkit to help people determine whether they need therapy or coaching (instead of spending too much time, energy, and money on something they don’t need).

Exploring the possibility of writing a book on therapy vs. coaching to expand on the non-diagnostic toolkit.

Expanding my media presence with more podcasts, articles, and other speaking engagements.

Continuing to educate the public on mental health through a monthly segment on my local news.

Continuing to expand my reach through licensure.

How can our readers connect with you?

Entrepreneurs and professionals looking for real, actionable mental health support can find me at https://www.jennifergraycounseling.com/. Here you can find my personal bio, my career transformation story, and my media contributions – all available to help you get to know me a little better.