When letting go is the hardest... and best thing for your business
I want to start this final blog with a story I don’t talk about often.
In 2021, I parted ways with my business partner and closed a version of my business I loved. She and I had spent four years building a business that supported women making the leap from corporate into entrepreneurship and female founders as they were building and growing their businesses.
The decision to go our separate ways happened gradually and then all at once. There were signs that the end was coming. She preferred to work with women in corporate, and I was (and continue to be) very focused on helping founders and business owners.
As we kept pressing forward and trying to serve, our marketing efforts felt at odds as we were attempting to speak to two different audiences. What we each needed and valued in each other and the business started to diverge, and it became clear quickly that continuing to fight for this business no longer made sense.
That decision and the aftermath was one of the most challenging times in my life as a business owner. Knowing something is the right decision and actually moving forward with it, especially when you’re talking about closing a business you poured your heart and soul into is beyond hard.
Through that process, and even now, I love what she and I created… and releasing it was also the best thing for both of us.
Release is hands down one of the hardest and heaviest Crossroads we can navigate as business owners. Our identity is often deeply tied to being a business owner or the creator of the business you built.
Today, we’re going to dive into the two ways business owners find themselves at Release, how to release it when it’s time with compassion for yourself and others, and why it’s okay to let it go when the time is right.
If you have yet to take the Business Crossroads Quiz, you can do that here.
When Your Business Feels Complete
Most business owners find themselves navigating the Release crossroads in one of two ways. First, and perhaps the best case, is when they feel complete. The business they built was intended to serve a purpose or do a particular job for them or others, and it’s done that.
I say best case scenario because even though it may feel like a hard decision, it’s often accompanied by a deep sense of satisfaction and the desire to move toward the next thing you’re being called into.
When I was running When Cookie Met Cupcake almost 17 years ago, I hit a period where I felt like the business, even though it was profitable, had run its course. I built it just before I left my corporate job at Boeing, and it served as a bridge between what I was leaving and what would ultimately become Jessica Sato Consulting.
When you’re navigating a Release moment like this, perhaps the biggest shift is around your identity as the creator of fill in the blank with your business. People know that version of you, and often a big part of our self-worth is deeply entwined with it. You’re also letting go of some of what drove your daily purpose and social standing.
So, how do you know when you’re bumping against this particular angle?
For me, it was this sense of restlessness. I felt like I was being called into work I truly loved to do and was really good at. I wanted to apply my brain in a different way, and I felt hamstrung by what I had created. I knew my original intention behind When Cookie Met Cupcake was to fill the gap between leaving Boeing and whatever came next, and finally, what came next - Jessica Sato Consulting - was clear.
Other times, the sentiment you’re navigating is low grade guilt. You know you’ve built something successful, and you feel guilty for wanting to release a business that is actually working and profitable. You know you’re in this space when you keep thinking, “People would kill for this setup, so why am I unhappy?”
If you feel like you’re getting close to completion in your own business or feel that low grade guilt about moving on, here are a few questions to help you think through that:
Am I staying out of loyalty to who I used to be, or because this business still serves who I am now or what I feel called to do in the world?
If I could duplicate this exact level of success in a new way tomorrow, would I jump ship immediately?
Has the core problem I set out to solve been answered, or am I just repeating the solution out of habit?
What parts of this business can I safely release or delegate so I can step into my next chapter?
This business is no longer working for me.
The second and harder to navigate scenario for Release is when your business no longer fits your life stage, your financial needs, or your values.
In cases like this, Release often feels deeply painful. For many business owners, this crossroads is often tied to profound burnout. When you’re in the grind of trying to force a business to work with your life, or you’re trying to fix a business that just doesn’t want to be fixed, it’s absolutely exhausting.
One of my colleagues built a truly successful business, but as a mom to young kids, she was running ragged trying to keep all the wheels on the bus. In her case, it wasn’t a question of operational inefficiencies or even the business model; it was tied to what she needed and wanted in her own life, and the business could not do that for her anymore.
Likewise, in the situation I was navigating with my former business partner, she and I had built something we loved, but as time went on, it became clear we wanted, valued, and needed different things from each other and the business. That tension also meant the business wasn’t running at its best. What we wanted to offer, how we wanted to serve clients, the business model we were using… all of it started to feel like a strain because we were trying to force two different approaches into one uniform answer. It just was not working.
In a number of the cases I’m seeing right now, the market has fundamentally shifted, and work that once commanded a premium can now be performed at a fraction of the price. For example, a colleague of mine was running a boutique SEO and content marketing company. For years, her small team of solo contractors commanded premium monthly retainers from clients who valued deep-dive, human-written thought leadership. But with the explosion of generative AI and subsequent shifts in search algorithms, clients began relying on DIY internal AI tools to do what she used to do for a fraction of the cost. She tried finding a space in the market to meet clients where they were, but she would have had to turn her high-touch, strategy-first boutique into a low-margin content factory, a model that completely violated her values of quality and depth.
Whether you’re making the decision because your life requires something else of you, the current business climate has evolved and what you built is no longer needed, or your values are at odds with your business, making the decision to walk away feels terrifying and like a massive loss.
If any of the above feels like what you’re navigating, here are few questions to help you think through this version of the Release crossroads:
Is the market telling me to reinvent this business model, or is my gut telling me to release it entirely?
If an investor offered to buy out all my liabilities and assets today, would I feel relieved or devastated?
Am I funding a broken business model with my personal health, relationships, and mental sanity?
If I stripped away the pressure to keep up appearances for my clients or peers, what is the actual financial and emotional toll of this business?
Let me acknowledge the emotions here. It’s okay and normal to go through the full spectrum of emotions when you’re in this space. You can feel sad, mad, exhausted, guilt, shame, happiness, and relief. They’re all legit, and that’s because the same drive and heart that made you capable of building this business in the first place is exactly what makes it hard to release. To me, it's tied to having built something that actually mattered to you, and saying goodbye hurts.
What to do when you know it’s time
I encourage every business owner I work with who is in this crossroads to look at three different areas:
Identity and Emotional Readiness:
Which door are you actually standing at? Mission complete or this no longer works for me and my life? As you have seen, that distinction matters a lot.
Honestly ask yourself, what would you grieve if your business closed tomorrow, and what would you feel relieved to let go of?
Financial and Operational Readiness:
What does walking away well actually look like?
Walking away well isn't about throwing in the towel and running away. You have the power to create a transition for everyone involved that prioritizes your integrity over appearances. It means securing your personal assets from business liabilities, honoring your team and clients with a clean off-ramp, and closing the legal doors intentionally before financial panic forces your hand.
Exit Path Clarity:
How do you want to exit this business? Do you want to sell it? Sell your assets only? Find a successor? Or simply close the doors?
What has to be true before you can leave on your own terms?
Thrive in Your Life
In the S.T.R.A.T.E.G.Y. method, one of the critical elements of evaluating your business is asking if this business still supports the actual life you want vs. the life you were building toward when you started it.
This requires a level of honesty from you that feels deeply vulnerable. It’s one of the hardest buckets to see clearly on your own, because you're not evaluating a neutral thing; you're evaluating something your identity is intricately tied to.
An outside perspective helps separate two questions founders get all twisted up:
Do I love what I built?
Is it still serving me?
Those aren't the same question, and conflating them is what keeps people in businesses long after they know, deep in their gut, that it’s time to Release.
Wrapping Up
We have covered a lot of ground over the last 5 weeks. Whether you’re navigating a clunky business that simply needs Refining, feel like you’re in need of a full-scale Reinvention, are navigating a growth edge that calls for real Expansion, or are standing at the edge of knowing it’s time to Release your business, I hope you have seen how knowing which crossroads you're at isn't the finish line, it's what makes your next move the right one instead of a guess.
If this series has spoken to you and you know you could benefit from support, the Founder’s Strategy Intensive is a custom-to-you experience that allows us to deep dive on what’s happening in your business, identify a path forward, and for you to get the support you need to build the life and business you want. You can learn more here.
