Ep. 15 - The Guilt of Changing How You Work (And Why It’s Worth It Anyway)
Nobody warns you that changing how you work comes with a side order of guilt.
Not the big dramatic guilt. Oh noooo, the nagging, slightly embarrassing kind. The kind that shows up as: “Am I being difficult?” and “Are people going to think I’ve got above myself?” and “What if they’re upset that things are different now?”
If you’ve felt any of that then welcome! You’re in excellent company.
Where the guilt actually comes from
To be honest, it’s rarely about the business. The guilt of changing how you work usually has roots that go way back before you ever started a company.
Most of us (especially those of us who built businesses by being helpful, flexible, and endlessly accommodating) learned somewhere along the way that being easy to work with was how you earned your place. That your value was tied to your availability. That saying no, or putting any kind of structure around how you operated, made you difficult rather than professional.
So when you start changing things to protect your time, your energy, your capacity, well it can feel surprisingly personal. Like you’re betraying some unspoken agreement or you’re getting ideas above your station.
You’re not, honest. But the feeling is real, and it deserves more than a dismissive “just ignore it.”
The specific flavours solo business owners tend to feel
It’s rarely one big guilt. It tends to come in varieties:
Client guilt: “They chose to work with me based on how I operated before. Changing the rules feels unfair.”
Imposter guilt: “Who do I think I am, deciding I need boundaries? Other people manage fine without all this!”
People-pleasing guilt: “Someone’s going to be mildly inconvenienced by this change and I can feel it already and I hate it.” (This one I feel personally, just so you know you’re in good company)
Each of these is understandable and none of them are reliable signals that you’re doing something wrong.
Guilt is not the same as evidence
This is worth saying clearly: guilt tells you that you care. It does not tell you that you’ve made the wrong call.
You can feel guilty about something that is genuinely the right thing to do. Most good change comes with a bit of discomfort, because it disrupts the familiar and familiar feels safe, even when it’s not working.
If you’re changing how you work because the old way was unsustainable, because your health requires it, because your business needs it … well, that is not something to feel guilty about. That is grown-up, responsible, long-overdue leadership.
What the guilt is actually protecting
When I dig into this with clients, there’s usually something underneath the guilt that’s worth naming. Often it’s not really about the clients at all. It’s about comfort and specifically, the comfort of being needed in the old way.
When you’re the glue, the fixer, the person who bends their schedule and absorbs the chaos, people rely on you. And being relied on feels gooood. Changing that feels like a loss, even when the loss is of something that was costing you too much.
Naming that doesn’t make the guilt go away. But it does make it easier to act despite it.
Changing how you work is not a betrayal
The people around you - your clients, your collaborators - deserve a version of you who isn’t constantly running on fumes. They deserve a business that’s built to last, with a way of working that actually holds up, and a business owner who hasn’t burned out trying to hold everything together.
Redesigning how you work, protecting your capacity, getting some proper structure in place, is an investment in being able to keep showing up. Consistently. Sustainably. Over the long term.
If you’re in the middle of this and the guilt is making it harder to move forward, let’s talk it through. A discovery call is a good place to start.
