Life changes. You know that. I know that.
But why is it so sad when you leave a part of it behind and move on? I really didn’t think I would miss the old work life but I do. Do I miss it enough to go back?
I left my corporate accounting career to work for myself. I was ready to leave the long hours and burnout behind, and I looked forward to having more freedom. I didn’t expect to miss parts of my old work life.
The biggest surprise has been how much I valued structure. A blank calendar can feel less like freedom and more like drifting, so I’m learning to create routines and boundaries that help me stay focused.
I also miss the everyday connection of having coworkers nearby. I don’t miss the office drama or the problems I experienced in public accounting, but I do miss casual conversations and feeling part of a community. I’m hoping to find some of that connection among other creators. You hear about how being an entrepreneur is a lonely pathway, I see that now.
At work, feedback and milestones gave me a sense of how I was doing. As an entrepreneur, progress can be harder to measure, and it takes practice to keep going without regular validation. I still believe mistakes are a valuable way to learn, but some reassurance along the way would be welcome.
Then there’s the predictable paycheck. I miss knowing when money would arrive and being able to plan around it. Self-employment can be unpredictable, which makes budgeting and saving more challenging. That’s not a surprise though. The biggest risk is the money aspect afterall.
I miss having a clearer end to the workday, too. A traditional job didn’t always make it easy to switch off, but having a boss and set hours gave me more separation. Now, work can follow me into my evenings unless I deliberately set limits.
Missing these things doesn’t mean I want my old job back. It means I’m figuring out what I need: structure, community, feedback, financial stability, and time to rest. I can work toward building those into a life that still gives me the freedom to choose my own path.
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