About Jennifer
The straight line was never really the point.
My career makes much more sense looking backward than it ever did while I was living it.
I’ve spent more than two decades leading organizations, building businesses, solving complicated problems, and making decisions without the benefit of knowing exactly how they would turn out.
Some choices worked the way I expected. Some sent me in an entirely different direction. A few were expensive lessons. All of them taught me something.
The Career Story
I learned business by running one. Then I learned it all over again by building one.
I spent the first chapter of my career inside professional services, including more than 18 years helping lead two law firms. I learned how organizations actually work: people, money, clients, culture, operations, competing priorities, difficult conversations, and the thousand decisions nobody sees from the outside.
Then I left.
I left the security of a six-figure executive career to build Entry Envy, an e-commerce subscription company, from the ground up. I raised capital, built a team, developed products and systems, won a $50,000 pitch competition, made plenty of expensive mistakes, navigated the realities of cash flow and growth, and eventually sold the business.
Entrepreneurship taught me things no MBA or executive role ever could. Not because everything worked, but because plenty of it didn’t.
The Turns
Leaving a successful career. Betting on an idea. Raising money. Cutting expenses when the business demanded it. Letting go of what wasn’t working. Selling something I had spent years building. Returning to executive leadership with an entirely different understanding of business than I had when I left.
We tend to tell career stories afterward as though every move led neatly to the next one. Mine didn’t.
And not all of the turns have been professional. I’ve gotten married, become a mom, gotten divorced, raised two daughters, rebuilt parts of my life, and learned that the hardest decisions rarely stay neatly contained in one category.
What I’ve learned is that changing direction isn’t necessarily evidence that the previous decision was wrong. Sometimes new information changes the answer. Sometimes you’ve changed. Sometimes the circumstances have. And sometimes courage looks less like continuing and more like choosing differently.
Data. Faith. & Guts.
Eventually, I realized I had a way of making decisions.
I didn’t create Data. Faith. & Guts. in a conference room. I recognized it by looking backward at how I had made the hardest decisions of my life and career.
I want the facts. I want the numbers. I want to understand what is actually true rather than what I hope is true.
But data has never made a consequential decision for me. There is always something that can’t be put into a spreadsheet: values, timing, conviction, purpose, instinct, faith.
And eventually, thinking has to become doing.
Data tells me what I know. Faith makes room for what I can’t know. Guts turns the decision into action.
Today, I bring all of it with me.
Today I serve as Executive Director of Woods Aitken, a law firm with offices in Nebraska and Colorado. I also work privately with people navigating consequential decisions and early-stage business questions, and I speak about decision-making, careers, resilience, leadership, and the very human experience of figuring out what comes next.
These may look like different kinds of work. To me, they’re connected by the same thing:
Helping people create enough clarity to make the next right decision.
A LITTLE MORE CONTEXT
20+ years in executive and organizational leadership
Executive MBA
Founder & former CEO, Entry Envy
Raised outside capital and built a national e-commerce business
$50,000 pitch competition winner
Built and sold Entry Envy
Executive Director, Woods Aitken
Mom to two strong daughters