Way Out #12: She Left Corporate Innovation to Build a Human-Centered Business with Ari DeGrote
We spend so much of our corporate lives curating our ideas to fit neatly inside pre-approved boxes. But what happens when you have too many ideas that don't fit the corporate mold?
For Ari DeGrote, a Kansas City-based change management leader, recovering perfectionist, and mother of two, the answer was to build her own company. Today, Ari is the founder of Upward & Inward, a coaching and consulting practice where she helps impact-driven leaders discover how to support and optimize people, profit, and purpose.
But getting to this point required her to untangle herself from a nearly decade-long career, radically redesign her "life systems," and realize that the risk of staying stagnant was far greater than the risk of taking a leap.
The Setup: A Career Built on Human Connection
Ari’s early life planted the seeds for her eventual leap. Growing up in a small Ohio town in the 1980s, she describes herself as a "free-range" kid who spent her days exploring outside on her bike. Because her brother and sister were 12 and 15 years older than her, she had the unique experience of being both a sibling and an "only child" once they left for college. This dynamic gave her a front-row seat to watch her older siblings make adult choices as "stair steps" ahead of her.
Her parents fostered an environment of curiosity, exploration, and resilience. Raised by a technical writer father and a lively science teacher mother, her childhood summers were far from ordinary. Her family would always take home the classroom animals that other students didn't get permission to take, meaning she grew up spending her summers with tarantulas and other creepy crawlies.
While her parents didn't force her into specific career expectations, they instilled two major core values: a responsibility to add value by trying your best to "leave things better than you found them," and a strict expectation of grittiness. If she committed to something, she had to see it through and wasn't allowed to bow out just because it felt "icky.”
Socially, Ari was highly adaptable and involved in everything. Because her small town didn't require massive tryouts, she was able to run track, play soccer, cheerlead, and participate in show choir and musicals. As a result, she became a social "floater" who moved between completely different friend groups without ever morphing who she was. She learned to identify the common threads and differences among diverse groups of people, a skill she credits with helping her build communities in her adult life and career.
She took that curiosity into her corporate career, starting in human resources and change management in the manufacturing sector during the 2008 financial crisis. Eventually, she found her way into the startup ecosystem, landing a role at the Sprint Accelerator (which later became the T-Mobile Accelerator). For nine and a half years, Ari led leadership growth programs for tech founders, creating a safe space for them to discuss the isolating, anxiety-inducing reality of building a company.
"I am really proud of my time there," Ari reflects. "I wouldn't have stayed as long had it not changed with me."
The Expiration Date
Despite loving her team, the T-Mobile merger brought a shift in the accelerator's focus toward rapid technical prototyping. Ari, however, wanted to go deeper into human-centered systems, culture, and leadership development. She soon realized she was facing a split in the road.
It wasn't just that the company was changing; Ari was changing, too.
"I definitely was feeling like I was a little stagnant in my own growth. Like I had reached my expiration date."
But she didn't leap immediately. In fact, her realization collided with a chaotic triple whammy: returning to work from maternity leave as a new mother, the onset of the COVID-19 lockdowns, and the massive corporate merger, all unfolding within a mere two-and-a-half-month window. She describes this period as a vital "oxygen mask moment." She had to temporarily put her side-hustle dreams on hold just to navigate the overwhelming transition and care for her family.
When the dust finally settled, she started looking at other corporate roles, but quickly realized nothing else out there would give her the depth and autonomy she craved. Ultimately, her departure wasn't about escaping a toxic job. As she puts it, she was "more running towards something than away from something.”
She had spent years coaching venture-backed founders through their intense isolation and anxiety, and she had to honestly ask herself if she was willing to take on that same terrifying entrepreneurial risk. She decided that the risk of ignoring her passion and staying past her expiration date would be a far bigger hit to her heart than the risk of striking out on her own.
The Strategic Exit: Prototyping a New Life
Ari didn’t rage-quit or leap without a parachute. She took a highly strategic, iterative approach to her exit.
In 2018, she officially formed her LLC and got her coaching certification, running her business as a nights-and-weekends side gig. During the chaos of the COVID-19 pandemic, becoming a new mom, and the merger, she let her business go dormant. It wasn’t long, however, before she began intentionally reaching out to her network, holding three to five virtual "coffee connects" a week. She used these conversations to test her ideas and speak her future into existence.
She slowly built out a year-long program designed for teams facing complacency or high-growth transitions. By the time she finally gave her notice, she wasn't jumping into the unknown—she already had her first two long-term clients signed.
The Reward: Designing a Life System
Today, Ari's life is defined by autonomy and intentional design. She no longer has to ask permission to sneak out in the middle of the day to walk her son home from kindergarten or squeeze in a workout.
She has also completely restructured how she works. She tackles marketing on Mondays, focuses on client deliverables Tuesday through Thursday, and leaves Fridays entirely open for creative writing, thinking forward, and big ideas.
Crucially, this open space has allowed her to explore practices she never could have touched in the corporate world—specifically, "emotional alchemy" and somatic practices. Ari realized that in the business world, we are conditioned to live strictly "from the ears up." We are praised for being highly cerebral and rational, completely ignoring the fact that we are emotional beings.
Now, she intentionally practices embodiment, allowing herself to "somatically kind of feel your feels and get it out and then move on.” She leans into the belief that our bodies are "telling us things way before our brain is trying to make sense of it or assign a story to it."
Tuning into her body and honoring her emotions feels like a profound luxury. As she points out with a laugh, "that's not something I would be doing in a fishbowl conference room at work."
For Ari, the ultimate goal isn't just about professional success; it's about redefining success as happiness, health, and deep connection. It's about taking the constraints off, getting back in touch with her own intuition, and finally getting to own every single decision.
Ari's Advice for Wayfinders
If you are looking to make a massive change in your life or career, here is Ari's advice on how to navigate the transition:
Don't Take Yourself So Seriously:
"This is not going to make or break you... dial it down, and let's look at this as: what is the next thing you'd like to experiment with?" Give yourself permission to just be curious and dip a toe in without committing to a permanent path.Treat Everything as Data:
In our productivity-obsessed world, trying things that don't work out can feel like a waste of time. But Ari stresses that "it's all data." You have to try things to weed out what you don't want, paying close attention to how you feel when you're actually doing the work.Learn to Love the "Never-Ending" Iteration:
"Anybody who says they have it figured out is lying," she notes. You will never find a perfect, static endpoint. Instead, you have to get comfortable with iterating. Build a life system, take in feedback, tweak it, and try again. Learn to love the fact that it is a continuous process.Build a "Life Raft" Community:
You cannot make massive life changes in a vacuum. Ari credits her sanity to finding "pods" of other women entrepreneurs. Having a group of people who know exactly what you are going through serves as a vital tether to remind you that your isolation is just an illusion.
Follow Ari’s Journey
If you want to connect with Ari, here is how you can find her:
Website: upwardandinward.com
LinkedIn: Ari DeGrote
This post is part of the 101 Ways Out series: stories of people who found the courage to exit the status quo and build a life of purpose, freedom, and joy.
