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I’ve been wrestling with a question of late. It’s got some layers to it, but the quick version is, “When is giving up on the dream the right thing to do?”

From 2000-2012, I was gainfully employed as an owner and publisher of weekly newspapers. At the end of 2012, I had to shutter the doors due to a change in state law where I operated my business.

The year before that, I finally, after a lifetime of desiring to do so, published my first novel. This blog, along with a few other websites, a few twitter handles, and a Facebook page, were also created to help promote that novel, its sequel, which came out earlier this year, and those that are to follow them.

The idea, at the time, was to keep publishing newspapers, support myself and my family through them while I continued to write and publish novels. As any self-published author knows, the mountain is almost always high, the climb steep, the road long. I wasn’t expecting an overnight success, though I think we all dream of such things. I had, believed, however, that I would go on publishing newspapers for as long as it took to get the books written and promoted.

I was wrong.

Back in 2009, just before the biggest year our newspapers ever had, I felt I should try to put them up for sale. At the time, I wasn’t entirely sure why. That was the first year we’d actually had an increase in revenue, and while it wouldn’t be the record, businesses are always more valuable when there’s the potential for greater growth. Without going into details, suffice it to say, I kept the newspapers.

I now know why I was supposed to sell them.

Fortunately, I followed other promptings. I paid off our house, two cars, put some money in the bank, and renovated our forty-year old office. With the first three, I wasn’t entirely sure why, again, but the fourth one seemed pretty necessary at the time, given the state of the building. Even it, however, turned out to be for the same reason. The newspapers were going out of business in a couple of years, and now that building is up for sale.

For the last nine months, I’ve been trying to develop some other revenue stream, either through another business venture, or through employment. Neither has produced anything. In between job searching and business developing, I’ve been trying to promote the books. I’m currently offering The Foolish and the Weak for free at thefoolishandtheweak.com. As of this writing, there are twelve chapters available, with more planned.

Thanks to the savings and the lowered expenses, along with a smattering of other income, we’ve made it this far without major changes in our lifestyle. However, this can’t go on indefinitely, so, as I opened this post, I’ve been questioning whether or not it’s time for me to put the dream back in its box and hope someday to bring it back out again.

With the newspapers, I had employees and freelancers who did the bulk of the work. I had time to write and promote them.

I’m told I could do the same thing with a full-time job. I know that’s not true. I tried it already. That’s a big reason why I waited so long to work on a novel, let alone try to promote it. My priorities were first having a family, and then not just supporting them, but spending meaningful time with them. It’s not all about quantity, but you don’t get to quality if you’re never or very seldom around.

Besides, the tools available now to make a career as an independent author successful didn’t exist twenty-odd years ago, so I was okay with putting the dream on hold.

To do so now, though, feels like giving up. If I can’t make it now, when there’s time and resources still available to do it, when will I be able to?

But I can’t just walk away from my duty as breadwinner, either. I know my wife would be willing to take on more to make money, but I just can’t ask her to do that.

So, I know there are many of you out there following a dream of some kind. Maybe you find yourself in similar circumstances as me. I know what I want to do, but I’d really be interested in hearing from anyone, even if you don’t have personal experience in answering the question, what you would do if you were in my shoes. When is it time to hang up the dream?

Feel free to leave comments, please, or reply to me on Twitter @AgeORestoration.