People start their own businesses for a variety of reasons. But if you ask a dozen entrepreneurs why they struck out on their own, chances are around ten of you will mention one word:


People often talk about the freedom that comes from being your own boss—you get to set your own schedule, write your own to-do lists, set your own salary, approve your own time off, you name it.


For many, it conjures up a life of leisure—frequent vacations, late mornings, and dinner in a new restaurant every night. And while that might be true for some, that is far from the majority.

When my wife and I quit our teaching jobs to work for ourselves, we expected that our life was about to get much easier. And part of that was true—we didn’t have to wake up as early, we got to spend more time together, and our actual work was far less stressful than wrangling a hundred-odd teenagers throughout the day.

But it also paid a lot less. We had the freedom to take time off if we wanted, but we couldn’t afford to fly out to renew our vows in Hawaii. Some days, we could barely afford to make the two-hour drive to Chicago.

And it wasn’t just because of the cost of the trip. It’s because we’d lose out on money we could be making if we stayed home instead.


There’s no such thing as paid time off for a business owner: if you don’t work, you don’t get paid. While the day might come when you can afford to jet off to the Bahamas whenever you want to, it will take years for that day to come–if it comes at all.

The unfortunate truth is that many entrepreneurs are broke. 50% of businesses in their first five years. Among the businesses that survive, many entrepreneurs only make enough to keep the business open. They have to turn to other revenue streams in order to earn a living.


And currently, that’s our story. My wife spends most of her time managing our shop, but she doesn’t pay herself a salary. Our house bills all come from my freelance work.

If we want to take some time away, we either have to close the shop or pay someone to run the shop while we’re gone. Either way, it costs us. And while I might be able to work a little from vacation, I still work far less than when I’m at home. Strictly speaking, though, I do have the freedom to work more on either side of the vacation to make up for the loss of income.


At this moment, four years after quitting our jobs and three years after launching our current business, we have just finally gotten to a point where we don’t feel like we’re constantly struggling to make ends meet. The shop is paying for itself, and I’m making enough that we can afford to pay off debt, save up for retirement, and maybe even take vacations.

But it took a long time and a lot of hard work—and a few months of working third shift at a factory—in order to get to the same financial position we were in when we were teaching.


But if you were to ask me if our freedom was worth all the years of being broke, I wouldn’t hesitate to tell you, “absolutely.”

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