I have to say that I probably ask myself this question every single day these days.  As most of you know, I’m currently writing full-time.

Now, that needs to be distinguished from paying my bills with my writing.  And we may need to amend the definition of full-time just a tad.  But I’m writing and working on self-publishing related tasks probably thirty hours a week or more and not working on anything else.

And while I’ve made some progress–I’m very happy with the latest novel and I’ve broken $1,000 with my sales of my shorter works–I’m not necessarily happy with where I am right now.

So the question I ask repeatedly is: Do I just need more time?  Will working at this another six months mean I finally break through?  Is it a matter of getting more product out there?

Or is it a matter of being smart about getting that product in front of others?  Do I already have enough out and just need to advertise and promote it better?

Or…am I just not good enough?  Am I someone who can easily write a boring 100-page work report on risk and controls, but can’t tell a good story to save my life?

(I like to think that the handful of reviews I do have so far that are in the 3-star+ range are telling me that I have some ability to tell a story.  But…I’m a paranoid writer.  And my income isn’t increasing exponentially month-to-month like I’d hoped it would.)

And then there’s the other question.  Is the game changing so fast and in such a way that I can’t break in?  I had a very successful (for me) story in December.  I published a follow-up to that story in January and for the first few days the sales pattern was the exact same as the first story.  And then…it stopped dead.

It didn’t trickle off.  Sales stopped cold.

Same thing happened with the third story in that series.  Day one sales were even better than the first and second stories.  And then…nothing.  Dropped off a cliff.

Is it that people read that first story and didn’t like it enough to ever read anything else by me?  Or am I somehow on the bad side of the Amazon algos?  And, if so, how the hell do I get on the right side of them?

I’m lucky.  I can afford to be arrogantly stupid for a bit.  I’m single, so no family to support.  If I really need to I can use my retirement savings to get myself through a couple years.  (At the end of which I won’t have any traditional retirement savings but could have a couple hundred works published.)

I also have degrees and work experience that should be able to get me a job that puts a roof over my head in the space of six months at most.

And while I hate to ask favors, I’ve built a solid track record with a number of people and if I needed to do so I could go begging for help and likely receive it.

So I’m taking a huge risk on myself, but I also know there’s a big safety net under me.  It shrinks by the day, but it’s there.

Mine is a calculated risk.

But that doesn’t mean I’m not being stupid.  It doesn’t mean that I’m not letting hubris blind me to the fact that this is not going to work.

So, which is it I ask?  Do I just need to keep faith in myself until I succeed?  Or do I need to stop and recognize that I have shortcomings that will prevent me from ever succeeding?

(Now, keep in mind, I’m choosing to do a lot of things the hard way.  I have a fairly limited set of agents I’d be willing to work with if I went that route.  I also have a limited set of publishers I’d be willing to work with.  And I’ve focused my self-publishing efforts on short fiction which it’s pretty much agreed does not do as well as novels.  I also do most of my own covers which people say not to do.  And only about five people know my pen names, so I haven’t even leveraged the friends and family boost that most authors start with.

So some of the struggles I’m facing could just be my own choices and nothing to do with my writing ability.  But those choices are as much a part of whether I’ll succeed at this or not.  I have to ask the question taking it all into account.)

At the end of the day, it’s an interesting situation because I’m one of those personalities that doesn’t give up easily.  I occasionally lose interest in something, but I’d be hard-pressed to give you an example of when I’ve quit trying for something I really wanted.  In poker terms, I’m the jerk at the table that’ll call someone just to see what they have even when it’s likely I have the losing hand.

So far that approach to life has paid off in the end.

But maybe it won’t this time…

All I know is that if I quit now, I’ve definitely lost.  And I hate to lose.