Hi, I’m Jenny Shih.
I’m a seasoned business owner and strategic problem-solver. I offer strategic advising and coaching for experienced business owners who want help working through a complicated problem, decision, or change.
You started your business, worked hard, and built something real. You’ve worked through countless difficult situations, made big decisions, and navigated complicated changes. You’re smart, resourceful, and capable of figuring things out.
But now you’re facing a problem, decision, or change that isn’t so straightforward. You might be confused or stuck, or you might want another perspective as you think it through the situation.
You’re way past generic formulas or business blueprints, and you’re not looking for someone to tell you how to run your business. (Okay, some days you are.)
What you want is a second brain to work through the problem with you. Someone who can understand the complexity of your situation, ask intelligent questions, challenge your assumptions, contribute ideas, and help you think through the options and tradeoffs to figure out what might actually work.
You’re not looking for someone to come in and take over the problem. You want someone to work with you and help you solve it.
When we work together, I don’t come with a predetermined solution or simply hold space while you figure it out yourself. We work on the problem together, sorting through the complexity without losing sight of the bigger picture or rushing toward a particular solution.
We consider the whole situation, including the practical realities and limitations you’re dealing with. We want to understand what’s really going on, what makes the situation complicated, and how the different parts affect each other.
Then we work through possible solutions in detail. The goal is to find a workable way forward given the circumstances and the very practical realities you’re dealing with.
This work is hard to describe because it doesn’t fit into a clear box. But it’s the heart of the work I’ve been doing for my whole career: looking underneath what’s obvious to get to the real issue, sorting through the real limitations of a situation, then finding a way forward that actually works for the person and the business.
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 knew I wasn’t going back to teaching beginner business owners, doing what I’d previously done in large groups but in a one-on-one way. I loved that work, but that chapter felt complete.
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 things like how I wanted to contribute, what I had the capacity to hold, what my day-to-day work life would entail, my values, 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 wrote and rewrote offers. I had conversations, considered different possibilities, questioned assumptions, and kept trying to understand what wasn’t quite right about the ideas I was coming up with.
Eventually, I began to see that what I most wanted to offer wasn’t advice on any one aspect of a business.
Instead, I wanted to use my love of complicated problem-solving and strength at getting underneath a seemingly impossible issue to find a way forward. I love the moment when someone realizes that what they thought was the problem isn’t actually the problem, or when they discover a way forward they couldn’t see before.
This was the work I wanted to do.
Looking back, the process of figuring out my own next business direction is a good example of why this kind of work matters. I didn’t just need a new offer or a new business model. I had to consider the whole situation, including my experience, my capacity, my values, my personal circumstances, what I wanted from my work, and what I needed my business to provide. All of those things mattered to the decisions I was making.
That’s why I now offer strategic advising and coaching for experienced business owners who want help working through a complicated problem, decision, or change.
We look at the whole situation together. I ask questions, challenge assumptions, bring new perspectives, and help them untangle the different pieces so they can understand what’s really going on and make decisions about what to do next.
Their business—and all that it has provided them—matters. They, as the person running it, matter, too. And it’s all accounted for when we look for the way forward, together.
You can learn more about my strategic advising and coaching here.
You can read my latest articles here.
To creating success on your terms (especially when those terms change),
