Quitting a job feels like rebellion. No more pointless meetings. No more answering to a boss who makes you question their basic competency. No more pretending to care about whatever new initiative they’ve cooked up to boost morale.
And freelancing? That’s freedom. That’s waking up when you want, working on projects you love, and never again dealing with that one guy who emails “Gentle Reminder” like it’s a hostage situation.
Except… no. That’s not how this works.
Working for yourself isn’t just not having a boss. It’s being the boss. And not in the cool, CEO-with-a-corner-office way. In the Who’s going to send the invoice? Who’s chasing the client? Who’s making sure the work actually gets done? kind of way.
No one hands you deadlines. No one tells you what to prioritize. No one deposits a paycheck every month just because you showed up.
And motivation? That thing people assume will just magically appear when they work for themselves? Turns out, it’s a terrible employee. Some days, it doesn’t even show up to work.
Hating authority doesn’t mean you have the discipline to be your own. Wanting freedom doesn’t mean you can handle the uncertainty that comes with it. And thinking, I’ll just figure it out is a fantastic way to end up broke, overwhelmed, and wondering if you should’ve just stayed put.
That doesn’t mean freelancing is a mistake. When you get it right, it’s exhilarating. But getting it right means accepting that success isn’t just doing the work—it’s running the whole operation.
So if freelancing feels worse than your old job, it’s not because you failed. It’s because you thought you were escaping. But real freedom? That only comes when you learn how to run the show.
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