I went to get a haircut at 9am on Monday. The rest of the world was scurrying off to "work" and here I was, standing outside the barbershop, waiting for the door to get unlocked alongside a couple of retirees.

The previous night had been eventful. My son came down with a biting cough that kept me up most of the night, checking on him every hour, bringing water, adjusting pillows, GPT-ing croup symptoms at 2am. We missed the bus as a result (the one that normally comes at 7:30am). His cough eased up by 8:30am, so I drove him to school and then swung by the barber shop.

At the shop, before the cape was even fastened around my neck, the barber started with a comment: "Not working today?"

I said, "Just taking care of some errands. I don't start until later today.".

She replied, "Oh, must be nice," and let out a big sigh. Turns out she has four kids. Her husband was watching the younger ones while the others were at school and she was working.

I noticed a slight tinge of guilt cross my mind. Here I was on a Monday morning getting a haircut while the rest of the world was busy working. I let the thought pass, walked out of the barber shop and into the grocery store next door. Filling my cart with some essentials and several impulse buys (fresh apple cider and apple crisp!), I headed to the only open checkout line.

The clerk promptly said "Hi" and followed it up with, "Not working today?" in a motherly tone. The lady appeared to be in her late 60s with reading glasses slung low on her nose.

"Just running some errands!" I said, keeping my voice light.

Again, the irony of these comments (which I've come to expect by now) made me laugh as I walked out to my car. There was zero malevolence in them. In fact, both women were kind and curious about my day. How nice!

What struck me was that tinge of guilt I felt at not being hard at work on a Monday morning. The guilt that appeared, unbidden, when a stranger made an innocent observation about my schedule.

Here's what made it ironic: I had been working. I'd been up half the night doing the most important work there is (caring for a sick child). I'd started my day at 6:00am answering a few client emails while I fed the dogs and got breakfast ready for my kids. I had a couple coaching sessions scheduled for later that day and a bunch of planning for the week ahead to take care of. I got my son to school at a reasonable time.

My work wasn't absent. It was just invisible to someone looking at me standing in a grocery store at 9:30am on a Monday.

But the guilt didn't care about any of that.

The Grip of the Old Script

I wrote last week about how it recently hit me that I've been coaching for 11 years, and away from my previous role as a tech leader for nearly 12 years. That's over a decade of working differently. You'd think the guilt would have faded by now. Old mental habits die hard sometimes.

Until my mid-30s, my world revolved around the predictable daily routine: school and sports turned into college classes and study sessions and club meetups, which turned into busy internships and an even busier post-college career. The rhythm was relentless and consistent. In the office from 8am to 6pm, sometimes later and often earlier. Meetings stacked like Tetris blocks. Lunch eaten at my desk. Planning bathroom breaks like F1 pit stops, squeezed between a deluge of meetings.

Then I stepped off that path. I wandered the wilderness for the better part of a year with no schedule before re-entering civilized life as a coach.

But here's what nobody tells you about choosing a different path: the old script doesn't just disappear. It lives in your nervous system. It lurks in dark corners of mental thought patterns. It shows up in the checkout line at the grocery store. It whispers when you see everyone else's cars leaving the neighborhood at 8:15am. It makes you feel like you need to justify taking a walk at 2pm on a Wednesday, even though no one is asking.

For years, I equated long hours and a predictable work schedule with impact and effectiveness. If I wasn't visibly busy during business hours, was I really working? If I couldn't point to a full calendar and back-to-back meetings, did my work really matter?

Breaking free from that mindset has been harder than I expected. Because it's not just my mindset, it's woven into the fabric of how society thinks about work. It's in every "must be nice" comment. Every surprised look when someone learns you're not chained to a desk on a random Tuesday afternoon. Every well-meaning question about what you do all day.

The Loneliness of Working Differently

The life of a coach, particularly a solopreneur, is not cookie-cutter.

Most of us have general availability during business hours, but our days vary based on the number of clients we serve, their time zones, vacation schedules and review cycles. It's also, generally, not the case that coaches sit in back-to-back Zooms for 8 hours a day. I've had periods like that, but when I'm working with a "full" practice of clients, I have a few sessions a day ranging form quick 15-minute check ins to 90-minute (or even multi-day) immersive sessions. These are punctuated by breaks in which admin, follow-ups, preparation for future sessions; and of course, LIFE - all happens.

There are also natural rhythms to the flow of work. Sometimes I work a lot, especially at the beginning of the year and early fall when clients return home from summer vacations. Other times I work less, or not at all, like during winter break or mid-Summer.

This flexibility is one of the things I love about this path. It's one of the greatest benefits of being a solopreneur. I can take my son to school when he misses the bus. I can get a haircut at 9am instead of squeezing it into a Saturday when the shop is packed. I can go for a run when my brain needs a reset, not just when the clock says it's lunch time.

But here's the challenge: I'm not surrounded by a society that understands this. The barber doesn't have this flexibility (she's counting on every appointment, every hour). The grocery clerk is working a shift that started before dawn. My neighbors leave for offices at the same time every morning.

I don't have colleagues in the next cubicle who are also stepping away for a mid-morning haircut. I don't have a team that shares my rhythm. I don't get to be part of the collective sigh when someone says, "Thank God it's Friday," because my Fridays don't always feel different from my Tuesdays.

This is the hidden cost of freedom: you can feel very alone in it.

When you work differently, you're constantly bumping up against other people's assumptions. And because most people you encounter in daily life don't have this flexibility, there's no reinforcement for your choices. No normalization. No casual validation.

Instead, there are these small moments ("Not working today?") that land like tiny questions about whether you're doing it right.

The Courage to Keep Going

After I loaded my groceries into the car, I sat there for a moment before starting the engine. I thought about that guilt. About why it still appears after all these years.

And I realized: the guilt isn't really about the haircut or the grocery run. It's about choosing to live differently in a world that's not set up to understand or support that choice.

It takes courage to build a life and a work style that doesn't fit the standard mold. Not the loud, dramatic kind of courage (the quiet, persistent kind). The kind that says, "I'm going to structure my days around what actually works for me, even when I'm the only one in the checkout line at 9:30am on a Monday."

The kind that refuses to manufacture busy-ness just to look legitimate.

The kind that trusts that impact and effectiveness aren't measured in hours logged or faces shown in an office.

I also think about the work I do. The tech leader who finally found clarity on a decision that had been paralyzing her for months. The founder who learned to have difficult conversations with his co-founder. The Product Manager who stopped burning out her team because she learned to recognize her own patterns. This work doesn't happen because I sit at a desk from 9 to 5. It happens because I'm rested enough to be fully present with a clear mind. Because I've given my brain space to make connections. Because I've structured my life in a way that allows me to bring my best self to each conversation.

There's a deeper truth here about the insidious nature of forcing yourself to work 9-5 (or 8-6, or 7-7 or 996!) when you don't have to. It creates resentment for the work you do. It limits the creative flow of ideas, because insights often arrive when you least expect them (in the shower, on a walk, while getting a haircut). It turns work into a performance of work, rather than the thing itself.

I've had some of my best coaching insights while making breakfast. I've solved client challenges while running. I've crafted the perfect exercise for a stuck leader while driving my kid to his Thursday swim lesson. None of this would have happened if I'd forced myself to stay chained to a desk just to prove I was working.

What I'd Say Now

If I could go back to Monday morning, here's what I wish I'd said (not to the barber or the grocery clerk, but to myself):

You're not cheating the system. You're not being lazy.

You're fully embracing the life presented to you. You're working in a way that is aligned to your commitments and your humanity. You're proving that there's more than one way to be effective and in service to the world. 

The truth is, I'm still learning to hold my ground. To not explain myself when I don't need to. To let the "must be nice" comments roll off without triggering that old guilt. To remember that the people making those comments aren't judging me (they're speaking from their own experience, their own constraints, their own version of normal, their own thinking). And maybe, just maybe, some of them are wondering if there's another way.

The Work Continues

I drove home from the grocery store that morning, put away the food, and sat down at my desk. My first client session was at 11am. We worked on how he could best showcase his talents in a leadership interview happening later that day. We unpacked a few powerful stories he could tell, and the qualities he had that would really be in service of the company he was meeting. He had a powerful insight during our session. The kind that tend to surface more often when I am present and fully engaged.

I could only do that work because I'd taken care of myself first. Because I'd gotten the haircut. Because I'd grocery shopped without rushing. Because I'd built a life that gives me the space to show up fully. The guilt still appears sometimes, but the voice is soft and fades fast. I'm better at recognizing it for what it is: an old story, one I don't have to believe.

I'm writing this for anyone else who's chosen a different path and still feels that tinge of guilt. Who wonders if they're doing it wrong. Who feels alone in their choice.

You're not wrong. You're not lazy either. You're just brave enough to work the way that works for you. And that, as it turns out, is the hardest and most important work of all.