Jessica Cumming spent more than 20 years building a successful tech career before she realized that her success wasn’t working for her. She had to redefine success for herself. Now she works as an executive life strategist, helping professionals in a similar situation reinvent themselves and their careers.
Tell us about yourself and your business
I’m Jessica Cumming, Executive Life Strategist, keynote speaker and host of the podcast We Are Women, Unapologetically. After nearly two decades leading global teams at Dell Technologies, I founded JC New Beginnings, a leadership development and coaching brand dedicated to supporting high-achieving professionals and organizations through major transitions with clarity, confidence and intention.
What makes this work one-of-a-kind is the blend of lived executive experience and strategic personal growth. I’ve built careers, built teams and rebuilt myself. Now I guide professionals and partner with organizations to navigate reinvention, leadership transitions and the decisions that shape what comes next.
Through coaching, keynote speaking, workshops and honest conversations on the podcast, I support individuals and organizations through transition, strengthen leadership and drive better decisions and stronger results. This isn’t about reinvention for the sake of reinvention. It’s about reconnecting to what actually matters—and having the tools to act on it.
Because when you get clear, you move differently and you lead with purpose.
Describe your company in three words
- Unapologetic
- Clarity-Driven
- Purposeful
What inspired you to start your business?
I had previously held roles I loved, was traveling the world, launching teams in eight countries across three continents, training people and doing work that made an impact. Years later, people still reach out to say thank you. That was the kind of work I knew I was meant to do.
Over time, I was placed in a role that didn’t reflect my strengths or my purpose. I was overwhelmed, burned out and applying for new roles only to hit a wall when hiring freezes took every opportunity off the table. Then came the layoff. Two weeks. No options.
It felt like everything collapsed. But the truth was, I wasn’t just looking for a new role. I was looking for myself.
And in that stillness, I remembered who I had been all along. At eight, I was training my mom’s employees. At sixteen, I told Zig Ziglar I wanted to travel the world and train people. That calling never left. I had just spent years trying to squeeze it into someone else’s structure.
JC New Beginnings was born from that clarity.
I didn’t build this business because I had to. I did it to return to the work I knew was my calling. Now I help others do the same: realign, reclaim and lead lives that actually fit them.
What was the first step to starting your business?
The first step was telling the truth to myself. I had spent nearly 20 years in a successful corporate career, but deep down, I knew I had outgrown the version of success I was living. Once I admitted that, I realized I couldn’t keep doing what I was doing just because I was good at it.
So I paused. I gave myself space to ask better questions: What do I really want? What impact do I want to make now? Who do I want to serve and how? That clarity became the foundation for JC New Beginnings.
From there, I invested in my own growth. Training, coaching certifications and surrounding myself with people who were already building what I envisioned. But none of that would have mattered if I hadn’t first acknowledged that it was time to build something that reflected who I’d become.
What’s a business myth you’d love to bust?
That you have to have it all figured out before you start.
I can’t tell you how many brilliant, accomplished professionals stay stuck because they think confidence has to come first. But confidence often comes from the act of doing. You don’t need a perfect plan, a polished pitch, or a 10-year roadmap to begin. You need honesty, courage and one solid step toward your goal.
Waiting until everything makes sense is fear dressed up as strategy. If I had waited until I felt “ready,” JC New Beginnings wouldn’t exist. Neither would my podcast, my coaching practice, or the impact I get to make today.
What’s one mistake you made early on in your business, and what did you learn from it?
One of the biggest mistakes I made early on was trying to hold it all together, perfectly. I was running a one-woman business, juggling every piece of it coaching, content, branding, admin and doing everything I could to make it look seamless on the outside.
Instead of giving myself grace, I put more pressure on myself. I thought the “professional” thing to do was to always look polished and in control, even when life was happening behind the scenes. Under that pressure, I worked reactively instead of creatively, performing instead of building from clarity.
High standards don’t have to mean high stress. You can be excellent without pretending you’re invincible. Now, I lead from intention instead of urgency. I protect my time. I’ve learned that showing up honestly, as a real human, not a curated highlight reel is part of what builds trust and impact.
How do you differentiate your company from similar offerings?
A lot of coaches and programs focus on surface-level strategy: updating your resume, building a personal brand, or checking boxes on a career pivot checklist. That’s fine…but that’s not what I do.
At JC New Beginnings, I go deeper. I help high-achieving professionals, especially women, get honest about the version of success they’ve outgrown, find clarity about what they want and need now and rebuild their life to fit their new definition of success.
I guide people through the real inner work of rewriting narratives, making powerful decisions and giving themselves permission to lead without apology. I bring mindset, manifestation and strategy together, so my clients don’t just pivot, they rise.
My work doesn’t try to fix my clients. It reconnects them to what they truly want.
What’s your proudest business milestone so far?
My proudest milestone was launching my podcast, We Are Women, Unapologetically.
Launching the podcast was the moment I stopped hiding behind strategy and started using my voice, publicly and boldly, to create space for women navigating transition, reinvention and the quiet unraveling we don’t always talk about. By hosting a podcast, I was claiming my message and sharing the truth behind success, burnout, clarity and identity shifts.
The messages I’ve received since from listeners who feel seen, understood and finally validated remind me that the impact is real. That podcast became a movement. That movement is still growing.
That was the moment I stopped waiting to be ready and started building from who I really am.
What excites you about your work?
What excites me most is watching someone go from uncertain and overwhelmed to clear, confident and fully in their power.
There’s nothing like the moment when a client finally says, “I know what I want and I’m ready to go after it.” That shift from living on autopilot to leading with intention lights me up every time.
I get to help high-achieving professionals reconnect with themselves, rewrite the rules and rebuild lives and careers that actually feel like theirs. And I do it through real conversation, deep strategy and unapologetic truth-telling. Whether it’s in a coaching session, on stage, or through the podcast, I’m helping people see themselves clearly again.
Who’s a female entrepreneur that inspires you?
Hands down, Oprah Winfrey, not just as a businesswoman, but as a force.
When I was a little girl, I used to say, “I want to be Oprah when I grow up.” Not because she was famous, but because she made people feel seen. Heard. Empowered. She led with wisdom, heart and an unapologetic presence. I saw myself in that kind of leadership long before I had the language for it.
One story that has stuck with me was when Oprah shared a conversation she had with Dr. Maya Angelou. Oprah said she believed her school for girls in South Africa would be her greatest legacy. Maya Angelou told her, “You don’t get to decide that. Your legacy isn’t one thing—it’s every life you touch.”
That shaped how I see my own work. Whether I’m coaching one-on-one, speaking on a stage, or hosting my podcast We Are Women, Unapologetically, my mission is the same: help high-achieving professionals reconnect with who they are and create a life that feels like theirs again.
Legacy is the sum of how you lead, live and show up over time. Oprah modeled that. Now, I live it.
What advice would you give to other female entrepreneurs?
Don’t confuse being busy with being intentional. Just because your calendar is full doesn’t mean your business is growing. Prioritize activities that actually move the needle.
Structure your business to protect your peace. Build systems and boundaries that support how you want to live, not just how you want to work. If your business runs you, it’s not sustainable.
You’re not for everyone—and that’s a good thing. Stop diluting your voice to be more “marketable.” Clarity and conviction attract the right clients faster than a watered-down pitch ever will.
Know your value and price accordingly. If you’re undercharging to feel safe or liked, you’re building resentment into your revenue model.
Own the role of CEO, even if you’re a team of one. Treat your time, decisions and energy like executive assets. Get support when you can, automate what you don’t need to touch and stop waiting for a bigger team to lead like the visionary you already are.
Anything else you want to share with our audience?
Finding clarity is hard work, especially for high-achieving women. We’ve been conditioned to believe that being busy means we’re succeeding. That the more we do, the more we matter.
Clarity doesn’t show up when your schedule is packed and you’re running on autopilot. It shows up when you stop. When you sit with yourself. No phone. No checklist. No distractions. Just you, in silence.
That kind of stillness can feel uncomfortable, even terrifying. But it’s necessary. Without it, you’ll keep building your life around what you know instead of what you want.
If you’re feeling off, misaligned, or restless, nothing is wrong with you. It just means you’re ready for something deeper. That’s where your real power begins.
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