When Your Business Stops Feeling Like Yours: How to Find Your Way Back to Alignment With Jennifer Hill

What happens when the business you built to create freedom starts taking away your freedom? In this episode of The Story Engine Podcast, I sit down with Esther Wildenberg to unpack one of the biggest challenges I’ve experienced as an entrepreneur: losing alignment while chasing growth. Esther shares her definition of alignment—not as a way to make life easy, but as a way to get back to a place where your energy, purpose, relationships, leadership, and business are working together. We talk about the warning signs of “founder’s fatigue,” why entrepreneurs often blame employees, clients, or circumstances for problems that are actually reflections of what’s happening internally, and why slowing down can sometimes be the fastest way to solve a problem.

Esther also gets incredibly personal about the period during COVID when her company needed to pivot, her wife was on bed rest, their son was born ten weeks early and spent six weeks in the NICU, and Esther found herself questioning her identity and direction. Her story helped me recognize just how powerful it can be to step outside the trenches instead of trying to solve everything from inside the problem. We dive into Esther’s unconventional three-day process of taking entrepreneurs completely out of their normal environment—including taking away their phones—to create the space for clarity, perspective, and realignment. We also explore the future of work in an AI-driven world and why Esther believes our ability to deeply connect with other human beings may be the most important skill we can develop.

Highlights

(02:49) – What alignment actually means and why it can make business growth feel effortless
Esther explains alignment as the point where your purpose, passion, identity, heart, and environment are working together—and why that creates the conditions for the right people and opportunities to find you.

(03:58) – Why alignment requires something most entrepreneurs hate: slowing down
We explore why silence, solitude, reflection, and time away from the daily hustle are essential for recognizing whether your business, relationships, and decisions are actually moving in the right direction.

(06:49) – The biggest challenge that comes with building a team
Esther explains why employees will never care about your business exactly the way you do, and how entrepreneurs can let go of that expectation while still building teams that genuinely connect with the company’s mission.

(08:50) – The interview questions Esther uses to uncover whether someone is truly aligned
Esther shares her unusual approach to hiring, including why she asks whether a candidate’s previous employers would hire them again—and why an honest “no” can sometimes be a better answer than a polished “yes.”

(09:23) – The warning signs of “founder’s fatigue”
If you constantly complain about your employees, clients, finances, or marketing, Esther says it may be time to stop looking outward and ask what those problems are reflecting back to you.

(12:17) – The hidden cost of the endless hustle and grind
We unpack the “I don’t have enough time” mindset and how constantly prioritizing money and productivity can quietly damage your health, relationships, and overall quality of life.

(12:55) – Why entrepreneurs may need to think in 90-day cycles now
Esther explains why the speed of technological and cultural change means entrepreneurs need to develop their ability to pivot rather than relying solely on traditional three- or five-year plans.

(14:48) – Esther’s radical three-day reset: leave your business and give her your phone
Esther reveals the process she uses to help entrepreneurs get out of their own way—including removing them from their normal environment and taking their phones away for three full days.

(17:34) – Why changing the people around you can change the problems you’re able to solve
Esther explains the power of stepping into a room with different people, including other successful entrepreneurs, and getting perspectives from people who understand the challenges you're facing.

(19:33) – How one hour of solitude can completely change your productivity
Esther shares how starting her day with the beach, her dog, meditation, silence, and solitude changes her energy and creates more productivity and “inbound energy” throughout the rest of her day.

(20:36) – Esther’s personal experience with founder’s fatigue during COVID
Esther opens up about navigating a company pivot while her wife was on bed rest, her son was born ten weeks early, and their family spent six weeks in the NICU—all while being isolated from the people and environments that normally grounded her.

(22:55) – The moment Esther realized she needed to get her life back
After months of feeling lost, Esther began reading, hired a coach, and redirected her company toward community, connection, and helping people thrive rather than simply chasing sales and revenue.

(24:31) – The question that changed how Esther saw her own impact
A simple question at the end of a podcast made Esther realize she had been underestimating the impact of her work—and helped her understand that touching even one person deeply can be enough.

(26:00) – What happens when you stop preparing and start trusting yourself
Esther explains why she stopped over-preparing for podcasts and stages and began trusting what naturally comes through her in the moment.

(31:52) – The story of founder’s fatigue, told through my own experience
I share my own journey through COVID, the pressure of leading a team, becoming a father, and realizing that I couldn’t change the world around me—but I could change my response to it.

(32:15) – Why vulnerability makes stories more powerful
Esther explains why she intentionally shares the raw and vulnerable parts of her life and how personal stories can become tools that help other people move through their own challenges faster.

(34:12) – The skill Esther believes will matter most in an AI-driven future
As AI and technology transform the world of work, Esther argues that our ability to communicate, connect deeply, and build genuine human relationships may become more valuable—not less.

(35:21) – Why community may be one of the best investments you can make in your future
Esther closes with a powerful reminder: technology may change almost everything around us, but our human experience, relationships, and ability to connect remain uniquely ours.