My entrepreneurial story

👋🏼 Hi, friend! I'm Jen (she/her). I'm currently based in Honolulu, Hawai‘i–born and raised–but am well traveled and lived for brief stints in Colorado and California back in my twenties (a.k.a. the 90s). As somewhat of an accidental entrepreneur, I am both proud of and grateful for the life I've been able to build for myself over the past decade.

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The launching point

My leap into entrepreneurship began in early 2012 when I left my faculty position with University of Hawai‘i (Hawai‘i Sea Grant) and launched a boutique consultancy that has pivoted a few times over the past twelve years–serving clients ranging from charitable foundations and government agencies, to community-serving nonprofits and small businesses.

At that time, being a business owner was never something I intentionally prepared for or even entertained as a possibility for myself.

On paper, everything looked phenomenal. The reality, however, was that I was burned out from working 60 to 80 hour work weeks (largely of my own doing). After nearly four years in my position, there was also a bit of disillusionment beginning to set-in due to the fact that despite bearing the responsibility of securing grants to cover all program costs including my salary, I would often get pulled into other projects outside of my interests and work plan.

So I approached my director to share that I'd decided to leave and wanted to work to develop a transition plan to sustain the grant-funded programs I'd built and led, rather than simply giving two weeks notice.

That decision–to openly plan for my departure, created the opportunity I never saw coming.

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An unexpected crossroads

But first, I began applying for my long-standing dream job: to lead a nonprofit. After advancing quickly through several recruitments, I found myself turning down the dream job offer and withdrawing from the final round of interviews for two other positions. Wait… whaaat? Walking away from the dream job–what happened?

When we hold the same goal or aspiration for an extended period, we often forget to check-in with ourselves to be sure it's still what we want or need when we finally reach that goal, or even allow ourselves to consider other pathways.

While interviewing for my dream job, folks whom I'd partnered or collaborated with through my work at Sea Grant began reaching out: “Hey, can we contract you to help us?” They knew (and valued) my skills and strengths and saw opportunities for me to support their work in a different way.

Faced with the option of continuing to do the same work I loved, on my terms and as my own boss–was a revelation. It suddenly became the new dream–the clear and best option I'd never even allowed myself to consider.

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Taking the leap

On February 6, 2012, I filed the articles of organization for my LLC which was officially approved the next day. Having leapt into self-employment without a mentor, savings, or support system in place, the next couple of years were a dizzying blur of doing-all-the-things as a solo practitioner and fledging business owner.

From branding and business development, to invoicing and fulfilling client deliverables, preparing proposals, acquiring insurance, doing the bookkeeping and more–it was both thrilling and terrifying.

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The breakthrough

It took me nearly seven years to break the six-figure mark. And honestly, it shouldn't have taken that long. There are many now-obvious factors, but the most important shift in crossing that threshold came from doing LESS. Yep. A lot less.

My business started consistently earning six figures when I worked fewer hours, enjoyed my weekends, indulged in afternoon naps and long walks, took extended work-free vacations, and made time for a budding relationship.

At that time, I began strategically scaling back my client portfolio to increase schedule flexibility and shift to a more singular focus on communications support for cause-driven changemakers. Previously, I'd taken on everything in my skill set, from interim executive leadership roles to board governance trainings, strategic planning, advisory services, project management, and even serving as a lecturer teaching a course in civic engagement and volunteerism for honors students at the University of Hawai‘i.

With this new found focus, the business was beginning to scale and on track for its highest multiple six-figure year, and I was beginning to allow myself to set my sights even higher. Then, my world was upended.

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Becoming a caregiver

During the first few months of 2021–peak Covid–everything changed. I got married in January, we bought a condo in February, and my husband was diagnosed with Amyotrophic Lateral Sclerosis (ALS; a.k.a. Lou Gehrig's disease) in May. ALS is a cruel disease for which there is yet no cure and the inspiration for the ice-bucket challenge.

People living with ALS lose their ability to move, eat, speak, and breathe over a period of months or years. Disease progression is unpredictable and extremely heterogenous; there's no way of knowing the speed or sequence of decline. Every few months, he continues to lose more function and mobility and rely more and more on me.

I've always been one of those people who manages to “do all the things” with grace, but caregiving has proven to be a humbling and life-altering fork in the road. Disrupted plans and upended schedules are now my norm; a huge adjustment for a type-A planner and do-er. For the first time in my life, I frequently felt overdrawn on precious social capital and routinely found myself disappointing people and projects I cared about.

The downshifting process I'd started needed to accelerate.

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A risky move

By the end of 2021, the idea of “retiring client services” had a magical ring to it. Even with the downscaling progress made to date, I was tired. I didn't want to stop working–nor was that financially feasible, but I'd lost the drive to chase contracts and invoices, and manage consulting clients and project teams.

But how? I wasn't sure, but continued transitioning retainer consulting clients to trusted colleagues and dabbling with different business models–including a membership (Comms For Causes).

A year later, on December 18, 2022, I made another leap and announced that I was retiring my consulting services (which I completed in June 2023) and pausing the membership without any certainty of what would replace it.

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The new dream

In January, I read We Should All Be Millionaires by Rachel Rodgers and everything shifted. EVERYTHING. Every time a marketing message landed in my inbox from her company, Hello Seven, I treated it like my homework.

A few weeks later, a message appeared on a Sunday morning announcing the Hello Seven Coach certification program. The curriculum weaves together business, money, and mindset coaching with the express purpose of serving historically excluded entrepreneurs who are underestimated and underserved—women, BIPOC, LGBTQIA+, and people with disabilities—how to grow a business from 0 to 7 figures.

I applied immediately, and was accepted into the inaugural cohort of Hello Seven certified coaches. April marked the beginning of my coaching journey.

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Permission to prosper

It's taken a horrible and heartbreaking diagnosis for me to fully embrace and pursue my dreams. Dreams and aspirations bigger than I ever allowed myself to entertain. So yes, part of the goal is to be better equipped financially to support my partner's care and our life together.

But what's lit a fire under me is allowing myself to expand that goal to include the ability pay it forward through philanthropic influence and supporting other aspiring business owners and purpose-driven entrepreneurs to dream, do, and achieve bigger things, too.

The launch of this new website marks the first step of openly embodying that new vision. To capture the powerful sense of permission that I've gifted myself in this next season of life. Permission to prosper, unapologetically. And I want that for you, too.

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