Toward the end of 2025, I started filling my calendar with vacation for the following year. I booked so much time off that I would have run out of vacation days halfway through 2026.
That wasn't poor planning. It was intentional.
I'd spent months thinking about leaving corporate America after roughly two decades. I had built a successful business on the side, and I wanted to give it my full attention. But knowing I wanted to leave and actually resigning were two different things. My vacation calendar was a way of forcing myself to make a decision I kept postponing.
I sometimes describe the feeling as standing at the edge of a cliff. You want to jump into the water below, but even when you believe you'll be fine, taking that step is frightening.
Over the holidays, I finally gave myself time to think about what I wanted. At the end of January 2026, I left my corporate job. I didn't wait for my vacation plan to make the decision for me.
Nine months later, I consider it one of the best decisions of my career. But the adjustment has been more complicated, and more interesting, than I expected.
I Wanted to Own My Time and My Work
I had a long career in finance, product management, and project management. I was used to full calendars and days spent moving from one meeting to another. At the same time, I was building Lucky Domains, my own business. That meant working evenings and weekends to keep both going.
It wasn't that I suddenly disliked working. I was already putting in plenty of hours. I wanted to decide which work deserved those hours and when I would do it.
I also wanted to build something that belonged to me. When you work for a company, the company benefits from the value you create. That's how employment works. When you own a business, you also take on its expenses and risks, but you have more direct ownership of what you're building and more opportunity to participate in its success.
I didn't leave on impulse. I'd set a financial test: the business needed to show that its rolling three-month net income could exceed my take-home pay from employment. That helped me make a practical decision instead of relying entirely on enthusiasm.
Even so, the numbers didn't eliminate the emotional difficulty of leaving a stable career. That's why I ended up with that unusual vacation calendar.
Freedom Requires Building a New Routine
When I first started working for myself full-time, I worked an enormous number of hours. Then I took a lot of vacation, during which I sometimes worked only a few hours a week. Going between those extremes made it hard to know what a normal workweek should look like.
I'm still figuring that out. The difference is that I get to make the decision.
One of the biggest changes is the number of meetings. In corporate project management, meetings could fill most of my day. Now I might have a couple of calls, or none. I can decide whether a meeting is important or whether an email will do the job.
I've also found that working for yourself doesn't automatically create boundaries between work and personal life. At first, I worked from home. With my work always a few steps away, it felt natural to keep going, even when the workday should have been over.
A couple of months after leaving, I rented an office. If I could change one practical thing about the transition, I'd have rented that space on day one. I don't think everyone needs an office, and I still appreciate being able to work from home. But having a physical place to go, and a place to leave, helps me separate business from the rest of my life.
The Part of Corporate Life I Didn't Expect to Miss
There's another adjustment I hadn't anticipated: I'm a social person, and corporate work had given me regular interaction with people throughout the day.
I wanted fewer unnecessary meetings. I didn't realize how much I'd miss the conversations that came with them.
Working independently can be isolating if you don't make an effort to connect with people. I've developed closer relationships with business partners, clients, and consultants. I also joined my local Rotary Club to volunteer and become more involved in my community.
Those relationships aren't a replacement for a corporate office. They're something I'm choosing to build into this stage of my life. And because I'm working fewer weekends, I can enjoy more time with friends and family without feeling like I should be catching up on work.
Would I Do it Again?
Absolutely. I'm happy I made the move, even though I'm still in a transition period.
My instinctive advice to someone who has wanted to start a business for years is simple: try it. You won't know whether the life suits you until you experience it. But that encouragement comes with an important qualification. I had a working business and a financial benchmark before I resigned. I wouldn't tell someone to ignore their obligations or leave without a plan.
Prepare carefully, understand what you can afford, and think about the routine and relationships you'll need after you leave. Then recognize that preparation can only take you so far. At some point, you still have to make a decision.
I spent a lot of my corporate career managing schedules, deadlines, and projects. It's a little funny that I needed to overload my own vacation schedule before I could finally make this change.
I'm still deciding what my ideal workweek looks like. For the first time in a long time, though, that's a decision I get to make for myself.
