What I Carried from Employee to Entrepreneur

Now I am building my company around the work.

That shift has made me realize how much of my career came with me into entrepreneurship. Customer service. Operations. Product Management. Leadership. Burnout. Even the slightly unhinged process of shouting presentation content in my home office until I could embody it.

I did not leave my career behind when I left corporate work. I changed the context in which I am using it.

I wrote about what I am discovering in What I Carried from Employee to Entrepreneur.

The business is new. The instincts behind it are not.

Now I am building my company around the work.

That shift has made me realize how much of my career came with me into entrepreneurship. Customer service. Operations. Product Management. Leadership. Burnout. Even the slightly unhinged process of shouting presentation content in my home office until I could embody it.

I did not leave my career behind when I left corporate work. I changed the context in which I am using it.

I wrote about what I am discovering in What I Carried from Employee to Entrepreneur.

The business is new. The instincts behind it are not.

What I Carried from Employee to Entrepreneur

For most of my adult life, work came with a structure someone else had built.

There was an organization around me, a role to step into, leaders to learn from, colleagues to work alongside, and customers to serve. Even when I was creating something new, leading a team, shaping a product, or helping an organization navigate change, I was still building within a structure that already existed.

Entrepreneurship is very different. There is no company surrounding the work. I am building the company around it. Honestly, that difference has required more of me than I could have anticipated. And that’s been part of the fun!

The years before the business

I didn’t spend my career preparing to become an entrepreneur. At least, I didn’t think I did. My first jobs were hourly customer service roles where I learned how to listen, solve problems, deliver news people could hear, and say no without leaving someone feeling dismissed. When I discovered the idea of customer delight, I was all in! I may have taken it a little too seriously … there were spreadsheets involved.

Technical support introduced me to HR technology. Leadership taught me how much trust matters. Consulting widened my understanding of organizations, cultures, systems, and change. Operations taught me to bring structure to complexity. Product Management strengthened my ability to recognize a problem, understand who was experiencing it, make choices, test ideas, and continue learning. Although the work kept changing, the throughline did not.

The work underneath the work

I always paid attention to the people experience. I noticed where people became confused, discouraged, energized, or overlooked. I wanted to reduce friction and create experiences that left people with more clarity and possibility.

What I loved most, though, was developing people. I loved recognizing a gift someone hadn’t yet learned to trust, helping someone work through a challenge that had begun to limit what they could see, and watching people grow into capabilities they once thought belonged to someone else. I loved helping people reconsider what work could offer them and what they could offer in return.

That last part really mattered. Growth at work doesn’t happen separately from the organization around it. I was especially interested in the place where a person’s goals and the organization’s needs could meet. How could someone use their strengths more fully? What did the team need from them? What opportunity could create value for the organization while helping that person grow?

Helping someone find that connection could change how they saw their career and how the organization experienced their contribution. Sometimes a colleague came to talk through a decision and discovered that the real dilemma was whether they trusted themselves to make it. Sometimes a leader came with a team challenge and found themselves considering the kind of leader they wanted to become.

I didn’t always call this coaching. Sometimes it looked like leadership, mentoring, a career conversation, or ten minutes together after a meeting had officially ended. Whatever we called it, it was consistently the work I loved most. Coaching was the thread long before I made it the job title.

The ending was not a clean beginning

I’d like to say I left corporate life with a fully formed vision for Eleven Eleven Coaching and complete confidence about what came next. That’s just not true.

During the later part of my Workday chapter, I experienced deep burnout. Looking back, I can see that no single explanation contains the whole story. The work was deeply meaningful and incredibly rewarding, and I also have a strong tendency to become a workaholic when I’m passionate about something and excited to move it forward.

Before burnout, during it, and while recovering from it, I loved my job, the work we were doing, and the people I was doing it with. That love made the work matter. It also made it easier for me to keep asking more of myself than I could sustainably give.

And burnout showed up in some strange ways. When someone came to my desk to pick up a conversation we’d had days earlier, I often needed a few words to help my brain find the thread again. At first, I asked them for five words. Then it was ten. Then twenty-five. Then fifty. At some point, I realized I had basically become a very expensive Magic 8-Ball.

I could help once I found the thread, and my team learned how to help me find it without making the moment heavier than it needed to be.  They met me with patience, humor, and incredible support. My leader also knew what I was experiencing and responded with care and understanding. She helped ensure that my priorities were clearly defined while I worked on getting well, and leaders above her were supportive too. I wasn’t left to manage burnout silently or entirely on my own.

During this time, preparing for customer conference presentations also became difficult in a way it never had before. My brain couldn’t hold information the way it used to, and none of my usual tricks worked. So I did what any reasonable, totally normal person would do: I locked myself in my home office and shouted about why I loved HR software, why I believed it helped people and organizations, and how Workday helps businesses realize real value and grow.

I mean, who does that? Who screams presentation content at the top of their lungs as if they’re trying to physically hammer it into their own skull?

Well, it worked. During one user group presentation, my slides went completely blank mid-talk, and I kept going without missing a beat. I hadn’t memorized the content. I had embodied it, one unhinged shouting session at a time.

Work that once came naturally was requiring much more effort. This was happening as AI rapidly reshaped the work and nearly every conversation around it, while I was still expecting myself to keep pace in the ways I always had. The irony wasn’t lost on me that I was leaning hard into AI tools just to keep my own thoughts straight while helping design AI for everyone else.

My six-week sabbatical gave me the opportunity to sleep, rest, and remove pressure wherever I could. I returned with more energy, but I also began to understand that recovery and returning weren’t the same thing. With coaching, leadership support, clearer priorities, and new practices that made room for rest and renewal, I began learning how to work differently. I was on the mend.

Recognizing what had been there all along

During a trip to Panama, I noticed a small stack of books left on a table at a beach resort we visited, the kind travelers leave behind for whoever comes next. Most had the glossy, forgettable covers of beach reads. One didn’t. It was a small, old, red hardbound book, missing its jacket entirely and worn like a book that had traveled well and been read hundreds of times. Out of a dozen options, it was the one I picked up.  Looking at it now, I'd say it's the one that picked me.

I read The Seven Spiritual Laws of Success cover-to-cover with sand between my toes. Then I read it again the next day. And the day after that. I'm a little embarrassed to say the book left the resort, and Panama with me.  It's an easy read on the surface, but each time I opened it, I found something new to sit with. I kept returning to it until something settled.

My husband had been telling me for years that I was the best life coach he's ever known. My own coach told me she believed I would be an amazing one. I had heard them both. This time, with a heavily dog-eared book in hand, I could finally hear myself.

Coaching wasn’t an idea that appeared from nowhere. It was a name for work I had been doing in different forms throughout my life. What became clear wasn’t only that coaching was something I could do. I wanted to make developing people the center of my work, rather than the work I kept finding ways to do alongside everything else.

I wasn’t leaving Workday because I had stopped loving my corporate career. I was choosing to devote my next one to the part of it I had loved most.

When the familiar introduction disappears

Leaving a long career changes more than a calendar. For years, I could introduce myself through my work. My title and company gave people an immediate frame of reference. Then the familiar introduction was gone. There was freedom in that. There was also a quieter identity question beneath it: Who am I when I’m no longer connected to the title, the meetings, the goals, or the steady rhythm of being needed inside an organization?

I’ve come to believe a title can describe the work we do, but it can’t contain who we are. Knowing that intellectually and living it are different things, though. I had to spend real time sorting out what had been tied to my title and the roles I held, and what had always belonged to me.

The curiosity was mine. The ability to hear what was said and notice what remained unspoken was mine. The desire to help people recognize their gifts was mine. So was the belief that serious work can still include laughter, even when that laughter is me, alone, yelling about HR software into a home office wall.

Building something of my own

Creating Eleven Eleven Coaching has asked me to use familiar capabilities in unfamiliar ways. The work includes coaching, but it also includes defining offers, making financial decisions, building a website, choosing systems, shaping a brand, writing content, and deciding what the business will and will not become.

The business-building can be complicated. The reason I’m doing it is not. I want to spend this next chapter helping people recognize their gifts, work through challenges, see opportunities differently, and grow in ways that serve both their lives and the organizations around them.

Inside an organization, those responsibilities are distributed across teams. As an entrepreneur, they all come back to me. Even when other people contribute their expertise, I remain responsible for the choices. That’s what fully owning a business is beginning to mean: not doing everything alone, but being accountable for what I create and how people experience it. I’m learning that ownership can feel freeing, demanding, vulnerable, and deeply meaningful, sometimes within the same day and sometimes within the same hour.

Entrepreneurship has also made visible how much my career prepared me for this, even the shouting-in-my-office part, honestly. Customer service shapes how I want someone to feel when they first encounter Eleven Eleven Coaching. Operations helps me think past the idea to how the experience will actually work. Product Management reminds me that something can be thoughtfully built and still keep evolving. The skills came with me. What changed is the context in which I’m using them.

A different way of measuring progress

Employment gave me familiar markers of movement: a promotion, a successful launch, recognition from someone whose opinion mattered to me.

Entrepreneurship has offered fewer external signals, and I feel the absence of them more than I expected to. Right now, progress mostly looks like moving through the steps toward an October launch date without overthinking every decision along the way. I’m not always succeeding at that. I’m on my third website revision, which is either diligence or avoidance, and some days I honestly can’t tell which. There’s no team high-five waiting on the other side of getting it right, so some days the quiet nags at me. It can feel like proof I’m behind, even when I know better.

Other days, progress is a decision. It’s finally finding language for something I’ve been trying to say for weeks. It’s admitting an idea isn’t ready yet, no matter how much I wanted it to be. I’m learning to measure progress not only by what is finished, but also by what is becoming clearer. No one else is defining the milestones now. I’m deciding what growth means and what enough looks like, one website revision at a time, apparently.

What came with me

I’m not writing this from the other side of entrepreneurship. I’m writing it while building: mid-mess, mid-figuring-it-out. I’m learning when to rely on what I know and when to become a beginner again.

Most of all, I’m learning that becoming an entrepreneur doesn’t require me to reject the employee I once was, brain fog, shouting sessions, and all. That part of my life gave me experiences, capabilities, and perspective that now shape what I’m creating.

There was a version of me who once needed fifty words just to find the thread of a conversation. I think about her sometimes when a decision feels tangled or the launch date feels close. I don’t need fifty words anymore. I just need to keep choosing, one thread at a time, which ones are worth holding onto and which ones I can finally let go of.

The red-covered book came with me, too. But I think it has finished what it came to do. It’s time to place it on another table, the way someone once left it for whoever came next, and trust that it will find someone else trying to make their way toward something they cannot fully name yet, but deeply need.

The business is new, but the instincts behind it are not. The work at its center isn’t new either. It came with me. Now I get to build around it.