From Stuck to Success: Rewriting My Future
I was in the career I thought I wanted, but over time, doubt crept in. I worked hard, chased success, yet deep down, I felt misaligned—like I was searching for something I couldn't quite name.
I remember listening to Carolina Liar’s “Show Me What I’m Looking For” song longing for an answer. I wanted to know what it would feel like to do work that came naturally - work that felt like me.
The truth is, I already knew. I had always been drawn to coaching and professional development, but fear held me back. I was tethered to the safety of corporate life—the paycheck, the title, and the team. Taking a risk to rewrite my future felt impossible.
Then life forced my hand. A personal crisis made the pressures of work feel insignificant. I had a major proposal due, but my heart needed to be elsewhere. That moment was my wake-up call. I realized I couldn’t keep pouring energy into something that no longer fulfilled me.
So, I quit. I started my own marketing consulting business, thinking it would be the answer. But the nagging feeling didn’t go away. I wanted to make a real difference—to help people transform their careers and lives.
I finally enrolled in coach training, and as I found my calling, the world shut down. COVID wiped out my consulting work—but also wiped away my excuses. With nothing to lose, I fully stepped into my new identity as a career coach and launched Position for Success Coaching & Consulting.
In speaking with women, I uncovered a common theme: they were coasting through their careers, feeling stuck in golden handcuffs, yet unsure how to break free. So, I created the What’s Next Program—a space where women take control, gain clarity, and rewrite their futures with intention.
Now, ten groups later, I hear the same transformation again and again: from rudderless and burned out to confident, motivated, and clear. Watching these women step into careers they love reminds me why I took the leap—and why it’s always worth rewriting your future.
What experiences have had the biggest influence on your career or business?
Looking back at my career, I see how every role—each challenge, success, and even uncertainty—was a steppingstone leading me to where I am today. At 55, I have the advantage of hindsight, recognizing how each experience played a pivotal role in shaping not just my expertise, but my perspective on the full career journey.
Now, I use that insight to help others connect the dots in their own paths and intentionally design careers that align with their strengths and aspirations, creating their ideal future chapter.
Of all my career experiences, the most transformative was my eight years as a marketing consultant specializing in strategic branding and innovation. This period provided the foundation for how I differentiate myself as a career coach today. It honed my ability to:
Apply innovative frameworks to career planning and professional growth.
Identify and deeply understand pain points, a skill I now use to help women break free from career stagnation.
Create engaging and effective training materials that simplify complex ideas into actionable steps.
Develop public speaking confidence, allowing me to present to large audiences and lead coaching groups with ease.
That consulting experience didn’t just teach me skills, it showed me the power of reinvention, strategic thinking, and purposeful growth. Now, I help my clients see their own careers through that same lens, guiding them to step into work that excites and fulfills them with clarity and confidence. It's never too late to rewrite your future!
Who or what inspired you to take the first step toward your goals?
Two people have had a profound influence on my journey, shaping my belief in myself and giving me the courage to pursue my dreams.
The first was my mom, Betty Cobb. She became a Director with Mary Kay Cosmetics when I was in first grade, and I watched her transform not just into a businesswoman, but into a leader who empowered other women to improve their lives. I saw her standing on stage in front of large crowds, not realizing until years later how terrified she was. I watched as she built a team, stepped outside her comfort zone, and inspired women to create better lives for themselves. She won awards, jewelry, and even a pink Cadillac but her true legacy was the confidence she instilled in others.
She was my biggest cheerleader, and when I shared stories of the women I was coaching, she’d say, “I’ve got goosebumps!” I once told her that coaching was my version of Mary Kay. She passed away in 2024, but I know she passed the torch to me to continue helping women see their true potential and build the lives they deserve.
The second person who changed my path is my husband, Joel. From the moment I met him at 23, he knew he wanted to be an entrepreneur, and he built a multi-million-dollar business from scratch. His belief in me has never wavered. When I hesitated to leave the “security” of corporate life, he saw something bigger for me. He pushed me to dream beyond what I thought was possible, to step into my natural talents, and to create a business that truly changes lives.
How do you empower and uplift others through your leadership?
Empowerment is at the core of everything I do. Through my coaching programs, I help women rewrite their futures by guiding them from uncertainty and burnout to clarity and confidence. My leadership is about seeing the potential in others before they see it in themselves and then giving them the tools, strategies, and mindset shifts to step into that potential.
I lead by creating a safe, supportive space where women can explore new possibilities without fear of judgment. I challenge them to think bigger, to advocate for their worth, and to take intentional action toward a career that fulfills them. My approach is both strategic and deeply personal, blending marketing insights, career coaching, and personal development to help women step into work that excites them.
Beyond coaching, I empower through thought leadership, storytelling, and community-building. Whether it’s sharing my own journey, hosting group coaching sessions, or offering actionable career insights, my goal is always the same: to help women break free from stagnation and step into careers that align with their strengths, passions, and values.
How has resilience played a role in your journey?
Creating a business and income from scratch is not for the faint of heart! I have remained determined to build my coaching business by remaining focused on the impact I am having and knowing that I am doing the work I was born to do. Now that I have experienced this, I cannot go back to doing work for a paycheck that is not important to me. I view this as a "long game" and that requires commitment and resilience.
How do you stay motivated when things don’t go as planned?
I work on my mindset every day. I practice self-coaching using my own coaching techniques on myself! I believe in the power of positive thinking, which for me comes from what I listen to, what I read, and who I surround myself with.
Also, I had a colleague and friend who really believed in the work I am doing pass away far too young and after her death, when I was facing a lull in my business, I had this feeling of her saying to me "KEEP GOING." And so, I do.
What daily or weekly habits help you stay focused and energized?
I start my weekday mornings with what I call "coffee and contemplation", where I write in my journal and listen to something inspirational. This practice sets me up for a good day.
I also have learned that the more I pour into my clients, the more I need an afternoon nap! One of the benefits of working from home is that I can do that. I usually listen to sleep meditation and take a 30-minute power nap a few days a week.
Many women struggle with confidently selling themselves. How can female entrepreneurs master the art of self-promotion without feeling ‘salesy’?
For many women, self-promotion feels uncomfortable because we’ve been conditioned to be humble, to wait for recognition, and to let our work “speak for itself.” But the truth is, if you don’t tell people what you do and why it matters, how will they know how to work with you?
Mastering self-promotion starts with believing in the value of what you offer—because confidence isn’t about being the loudest voice in the room, it’s about being the clearest.
Here’s how to shift your mindset:
Reframe Selling as Sharing – If you had a life-changing book, you’d naturally want to tell your friends about it, right? Self-promotion works the same way. If your work can genuinely help someone, it’s your responsibility to share it.
Detach from Outcome, Focus on Connection – Self-promotion doesn’t mean convincing people to buy—it means helping the right people see if you’re a good fit for them. Approach it with curiosity and confidence, rather than pressure and persuasion.
Celebrate Your Expertise – Think of self-promotion as an invitation: “Here’s what I do, here’s why it matters, and if it resonates, let’s connect.” Your ideal clients WANT to hear from someone who can help them.
Lead with Impact – Instead of worrying about "selling," focus on educating, inspiring, and providing value. The more people see your expertise in action, the more naturally they’ll want to work with you.
When you shift from “self-promotion” to “helping people understand how I can serve them,” everything changes. The world needs more women owning their brilliance so don’t shrink yourself. Speak your value, stand in your power, and let the right people find you.
You’ve trained executives at major corporations. What’s a ‘corporate secret’ that solopreneurs can steal when crafting their own business pitches?
One of the most valuable lessons I learned from my time in Brand Management at companies like PepsiCo is this: successful businesses don’t market to everyone—they get laser-focused on their bullseye customer.
At big brands, we don’t just define a target market demographically; we go deeper into their psychographics, understanding their beliefs, motivations, and decision-making habits. This level of insight allows companies to craft messages that resonate deeply and drive action.
For example, when I was the Senior Brand Manager for Life Cereal, we identified our ideal customer as Gatekeeper Moms, who were mothers who prioritized balanced nutrition for their children and made purchasing decisions based on values, not just taste or price. This was a completely different mindset from Permissive Moms, who were more likely to buy indulgent cereals like Cap’n Crunch (another brand in our portfolio).
Similarly, when I worked on Kibbles ‘n Bits, our ideal customer viewed their pet as a “Dog as Child”—a beloved family member. This was a stark contrast to Dog Chow buyers, who saw their pet as a “Dog as Dog” and made practical, no-frills feeding choices.
Solopreneurs can steal this strategy by going beyond broad demographics and truly understanding the psychology of their ideal client. When you deeply know who you’re serving, what they care about, what keeps them up at night, and what language they naturally use—you can craft business pitches, messaging, and offers that feel tailor-made for them. That’s how you create marketing that speaks directly to your audience and drives real connection.
How do you spend most of your time?
I have always been an ambitious woman and feel best when I'm being productive. In a dual-entrepreneur household, my husband and I both spend a lot of time growing our businesses and supporting each other. Thank goodness I love what I do and care so deeply about the impact I am privileged to have on women, so it feels more like my mission than my work.
As you reflect on your journey, what are you most proud of and why?
I am proud of myself for finding the courage to make a bet on myself and leave my corporate job to pursue a more fulfilling career path for myself. At the age of 49, I invested in a coach training program at iPEC (the Institute of Professional Excellence in Coaching) to explore my long-time career dream. In the past 5 years, I've developed a deep knowing and confidence in my expertise, proven that I have skills that allow me to earn my own income rather than relying on a company, and felt the joy of knowing I am doing the work I was born to do!
Tell us a little about your family and what you do for fun?
I live in Chicago with my husband of 25 years, 2 daughters, and our dog Stanley. Some of the things I like to do for fun are walking along Lake Michigan listening to an inspiring podcast, creating fun mother-daughter experiences, traveling to cool places like Puerto Rico, and good conversation over wine with girlfriends.
Photo Credit: Meka Hemmons of SpiderMeka Portraits & Monika Demel of Demel Portraits
To connect with Jennifer, visit:
https://www.linkedin.com/in/jenniferspainhour-coaching/
https://www.facebook.com/jennifer.spainhour.3
