Hi, I’m Jenny Shih.
I work with experienced business owners whose businesses need to change, but figuring out how isn’t simple, obvious, or easy. What they’ve built may still be successful by all external measures, but it no longer works for the person running it.
Because your business matters. Your clients, reputation, history, and years of work matter. Your team—and the responsibility you feel for them—matters. Your income matters, too. So changing some or all of it feels big, scary, and loaded.
We look at all of it: you, the business, the strategy, the practical considerations, the income needs, the personal realities, and your life as it stands now. We figure out what’s no longer working, why it no longer fits, what you need for yourself and your life today, and which possibilities make the most sense for you and your business.
From there, we can create a map for strategically realigning your business to fit who you are, the life currently you’re living, and the business that will most support you going forward.
I don’t have formulas or blueprints, because there isn’t one right answer. My job isn’t to hand you a prepackaged plan or tell you what you should want. It’s to help you see the situation clearly enough that the next steps, even if they aren’t easy ones, become apparent. Then I stay alongside you as you make decisions, implement changes, and respond to what you learn along the way—making sure the business supports you and your life in the ways you need it to.
I call this work Strategic Business Realignment, and it’s the work I’ve been preparing for throughout my entire professional career.
How I Got Here
I started in the online industry in 2009, so to say I’ve seen a lot, tried a lot, and done a lot wouldn’t be an exaggeration.
Before I started in the online space, though, I spent a decade in corporate America, first working as an engineer then as a project manager running multi-million dollar projects spanning four continents and overseeing dozens, or sometimes hundreds, of team members.
While my peers worked nights and weekends, I experimented with time management, efficiency, and delegation so I could have a life outside my job.
I managed my staff, got my work done, and handled big projects in far fewer than 40 hours a week, leaving time for mid-day yoga, early-exit Fridays, and extended weekday lunch dates with girlfriends.
But after 10 years in the corporate world, I wanted to do work that felt more fulfilling. After a fair amount of soul searching, I decided to train with Martha Beck and Byron Katie so I could launch a life coaching business for people stuck in jobs they didn’t like.
With extreme optimism and equally extreme naivete, I quit my six-figure corporate job and started my life coaching business.
The Struggle Before Success
From the moment I quit, I felt tremendous pressure to make money. I was the household breadwinner, and I was constantly worried that my business wouldn’t make it and I’d have to crawl back to my corporate job. So I worked hard and tried (and failed at) a lot of things.
While I was doing this, I was asked by an experienced coach if I would be her virtual assistant. I needed the money and figured it was worth a shot.
I took quickly to the work, and slowly started getting referral after referral. Soon I was doing far more virtual assistant work than coaching … until I began coaching my VA clients on their businesses. Turns out, I loved this kind of coaching a heck of a lot more than life coaching.
It eventually became clear that straight-up life coaching wasn’t my thing. But coaching on the practical how-to’s and strategies for online business? I loved it.
In late 2010, I closed my life coaching practice and regrouped. In early 2011, I launched jennyshih.com, offering virtual assistant and project management services plus coaching to make ideas happen. I immediately knew I was on the right track, even though I still had a lot more to figure out.
I dove head first into learning about marketing, and within a year of launching my new business, it started to take off. I loved what I was doing, understood how to “make it work,” and the thought of going back to my job had faded completely.
By the end of my third year in business at jennyshih.com, I was bringing in multi-six-figures in revenue with very high profit margins. I loved my work. I loved working for myself. I loved the schedule. I loved my clients. I loved all of it, and it had been worth every bit of struggle to get there. I couldn’t have asked for more.
And then I got terribly ill.
The Roller Coaster Ride
As jennyshih.com was ramping up, my health began declining, and it wasn’t from over-working. I had averaged a 25-hour week pretty consistently.
But after a while, I realized that extreme fatigue, all-over body pain, and persistent brain fog were real problems and not imagined ones. After nine months of chasing doctors and diagnoses, I finally had an answer: I had Lyme disease.
Unfortunately, a diagnosis didn’t mean an instant cure, and it took me over a year of getting worse before I started to get better and several more years to recover.
I eventually got mostly-kind-of-better, and as my health grew stronger, so did my business, in revenue and size.
Over the course of several years, I grew a significant team of employees, contractors, and coaches. I had missed the leadership and management aspects of my corporate days, and I loved putting those skills into play in my business; it became my favorite part.
I hosted live events, ran big launches, offered masterminds, curated digital products, and more.
In early 2020, my son was born. As planned, I took a 5 month maternity leave—except for exactly two meetings—and my team ran everything else.
I returned to work in the fall of 2020 with a 20 hour/week schedule, and everything was going along just as I had hoped … Until, inexplicably, it wasn’t. Less than a year after returning to work, I became literally unable to do my job.
I was overcome by a deep exhaustion that wasn’t remedied with 2-hour daily naps and 10+ hours in bed each night. My brain was so foggy that I couldn’t think critically, make strategic plans, or learn new things. It was confusing, exhausting, and overwhelming. I had no idea what was happening or why.
The most logical guess was burnout from being an older, new mom in a pandemic without any support, managing a sizable business, and dealing with lingering pre-pregnancy health issues. (I later learned that was very wrong.)
But even though I didn’t know what was happening or why, one thing was clear: I had to stop working—completely.
I made the most gut-wrenching business decision I’ve made to-date: I laid off my entire team, paused client work, and stepped back from what I built. I needed to figure out what was going on. That took three years.
Having a diagnosis was far from having a cure, but it did mean I knew what to treat and how to treat it (or at least what to try). Slowly (oh so painfully slowly), things began to turn around.
After making decent progress overall, I tried to return to work in late 2024. I wrote fresh blog content and sent emails to my list. I coached clients here and there. I offered a free class.
But I didn’t have the stamina to keep going. So I stopped everything (again) and returned my attention to my health.
On the heels of a global pandemic, I wasn’t just a new mom with no outside support dealing with a massive health crisis. Nearly every aspect of my life also came up for review. In rapid succession, I needed to reevaluate my identity, responsibilities, health, work, finances, family, and more.
As much as part of me wanted to, I didn’t run and hide. I faced it all, bit by bit.
By the second half of 2026, I was ready to return to work for real. I could feel the difference. The clarity I had about what I wanted to do had finally arrived.
A lot of my life remained in flux—and still is. But my work? That found its ground, and I was so grateful it did.
Finding My New Business Direction
It’s always been important to me to have a business that supports both me as a person and the life I am living. That’s been central to how I operate in business since I started in 2009 and still stands today.
So it wasn’t long into my medical leave that I realized I couldn’t return to the business I ran before I pressed pause in 2021. Not because it was wrong or I didn’t enjoy it; I did. I couldn’t go back to the way things had been because that business didn’t support who I had become.
This version of me needs a simpler, more sustainable, and even more flexible business. And that’s what I love about working for myself; I can create success on my terms, always.
That meant self-employment had to be my path, but I couldn’t simply recreate a smaller version of the business I’d had before. I needed to figure out what kind of business could support my life and current capacity while also using everything I’ve learned and done over the years.
I always loved one-on-one work, so that seemed like the right place to begin. But exactly what kind of work would I do?
I wasn’t going to teach beginner business owners again, doing what I’d previously done in large groups but in a one-on-one way. I love what I was able to do all those years, but that version of me has retired.
I have a lot of experience to offer experienced business owners, including leadership and team management, business and financial management, and strategic planning. I loved those aspects of running my business. I did some coaching and advising around them before and during my leave, and I enjoyed it a lot. And still, I could feel that wasn’t fully it.
Those ideas drew on my experience, but they didn’t account for the whole picture including how I wanted to contribute, what I had the capacity to hold, what my day-to-day work life would entail, what values I hold close in life and business, and what I needed my business to make possible in my life.
I started reflecting on the patterns of what energized me. I remembered what people had said to me about my work over the years. I considered the kinds of problems I most wanted to help solve and the ways I was and wasn’t willing to work anymore.
I started playing with language, hunting for specifics, and getting more curious. I wrote and rewrote many offers. For months, I played with ideas and reconsidered the problem, the people, the work, and how it would fit for me and who I am now.
Through working, writing, waiting, reconsidering, rewriting, conversations, and deep reflection, I finally figured out what the next version of my business needed to be to fit the person I am now, the life I’m living today, and where I see myself heading in the future.
This is why it makes sense that I work one-on-one with experienced business owners whose businesses need to change, but figuring out how isn’t simple, obvious, or easy. Their business—and all that it has provided them—matters. And they, as the person running it, matter, too.
You can learn more about Strategic Business Realignment here.
You can read my latest articles here.
To creating success on your terms (especially when those terms change),
