No Commute, No Boundaries: The Work-Life Balance I Didn't Plan For

After 28 years of leaving my house each morning and driving to school, I thought I understood what it meant to work hard. I was wrong—or at least, I was incomplete in my understanding.

Here’s what I’ve discovered: there’s something almost sacred about the physical act of leaving your workspace and coming home. For nearly three decades, I had an office persona and a home persona. I’d walk through my front door, and while I occasionally opened my laptop after dinner to finish something urgent, there was a clear delineation. Work happened there. Home happened here.

Now my office is down the hall.

And I’m realizing this might be one of the most challenging aspects of entrepreneurship that nobody adequately warned me about.

The Slow Creep of Always-On

The transition happened in stages. At first, working from home felt wonderfully strange and foreign. I’d sit at my desk thinking, “What am I even doing today?” There was an adjustment period where the freedom felt almost uncomfortable. Then I crossed into what I thought was the sweet spot—I loved working at home, loved the flexibility, loved being able to structure my day however I wanted.

But somewhere along the way, I crossed another threshold. The one where “I can work whenever I want” became “I’m working all the time.”

I’m still doing family things. I’m still engaging with the people I love. But if I’m honest with myself—and that’s what this Substack is about—I’ve noticed I’m always working. A quick email between dinner and dessert. A strategy session with myself while everyone else is watching TV. Refining a proposal on Saturday morning. Checking in on client communications on Sunday afternoon.

It’s getting to an unhealthy place, and I’m aware enough to recognize it, even if I haven’t figured out how to fix it yet.

The Guard Rails I Wish I’d Built Earlier

When you work at a school, the structure is built in. The bell schedule, the faculty meetings, the academic calendar—they all create natural boundaries. Even the most dedicated educators eventually go home (even if home includes a bag full of papers to grade).

But when you’re building a business that serves schools? When every email could be the next client, every hour you’re not working feels like a missed opportunity, and every moment of rest whispers that you should be doing more? The boundaries dissolve.

I’m sharing this not because I have the solution figured out, but because I wish someone had told me to think about this on day one. Here’s what I’m learning I should have done from the start:

Create physical boundaries. Even if your office is at home, treat it like it’s somewhere else. Define when you’re “at work” and when you’re “at home”—even if they’re just rooms apart.

Set actual working hours. I know, I know—one of the perks of entrepreneurship is flexibility. But unlimited flexibility can become unlimited work.

Build in rituals. When you don’t have a commute to create transition space, you need to manufacture it. A walk around the block. A dedicated “end of workday” routine. Something that signals to your brain: work is done.

The Uncomfortable Honesty

I don’t have a tidy conclusion here. I’m not going to wrap this up with “here’s how I solved it” because I haven’t. What I can offer is the awareness that this is real, and if you’re considering leaving your school position to start a business, this is something you need to think about now, not later.

The irony isn’t lost on me: I spent 28 years helping students and colleagues find balance, structure their time, and set healthy boundaries. Now I’m struggling to do the same for myself.

Maybe that’s the most important lesson of all. Knowing what you should do and actually doing it are two very different things—especially when you’re building something from scratch and every hour feels precious.

So if you’re already on this entrepreneurial path: How are you managing this? What guardrails have you put in place?

And if you’re contemplating making the leap: Think about this now. Because the freedom of working from home is real, but so is the danger of never actually leaving work.

I’m still figuring this out. I’ll let you know when I get it right.