I have a bad habit that drives me crazy sometimes.

It’s one of those things that, even though I know I’m doing it, I feel like I can’t stop myself.

The habit is overthinking things.

Take this blog for example… I started it because I wanted to document my journey as I leave “Egypt” (a broke self-employed guy) and enter the “Promised Land” (owning a business that generates profit without my presence).

I got really excited about this after reading Austin Kleon’s book, Show Your Work (my notes here). Austin wrote:

“Become a documentarian of what you do. Start a work journal: Write your thoughts down in a notebook, or speak them into an audio recorder. Keep a scrapbook. Take a lot of photographs of your work at different stages in your process. Shoot video of you working. This isn’t about making art, it’s about simply keeping track of what’s going on around you.”

When I read that I was like, “Boom, that’s it! That’s what I want to do!”

I got this vision of documenting my journey in a real, honest way over the span of 10 years so others could one day read it and hopefully learn a thing or two. Maybe it’ll only be my kids. I don’t know.

But I just felt compelled to do it. So I made a crazy, and yes probably rash, decision to publish a post every day for 10 years. Well, now here I am on Day #189 and I’m a mess!

You can just look back at some of my recent posts and see for yourself. I’m all over the place. I’m trying too hard to “inspire and educate” people, all the while wrestling with the frustration of having very few readers.

And then I think, “why should I have more readers? Would I even read my blog!?”

Then I spiral down from there. Until I’m on the verge of quitting. But I don’t actually “quit,” instead I call it “changing directions.”

For example, the other day I decided it’s “stupid” to post on here every day when I could be spending that time posting on my business blogs because that would help me make more money whereas this blog has no revenue generating feature to it at all!

So I decided I would NOT post on here every day anymore. I realized I could still honor my commitment of publishing daily for 10 years by posting on all these other blogs too. I never said I’d publish daily on this blog.

So I let myself off the hook…

…but something keeps drawing me back here. I still have published on here every day. I haven’t “broken the chain” and I’m nervous to. I don’t know if I want to. I’m getting cold feet.


Because when I remember the original vision I had of “documenting my journey” I get stirred up again to take this to the next level instead of “changing directions.”

So how do you decide when to quit/change directions and when to persevere?

I don’t know! I’m asking you! I’m not the expert here… I’m just trying to figure this stuff out too.

But here’s a question that helps me get perspective:

“Imagine it’s 10 years in the future and you’re looking back at what you’ve done in the last decade. What would have had to happen for you to be happy with your progress?”

(Easy question to answer, right!?)

Sometimes this question excites me, other times it makes me mad because there are so many options and I don’t know what the “right” one is!

So I start to plug in different scenarios (remember the issue I’m dealing with is “where” to publish).

1) Personal Blog: one scenario is that I continued to publish daily on my personal blog. 80% of my posts were simply “documenting” my journey as an entrepreneur. I eventually got into video and podcasting too. But the spirit of it never changed… it was always about honestly documenting my journey.

2) 3–4 Blogs: another scenario is that instead of publishing daily on my personal blog, I decided to only publish there when I had something worthwhile to say. The other days I would publish posts about copywriting, marketing and how financial advisors and insurance agents could be more successful. (Man, I’m already bored just reading that scenario!)

3) Copywriting Blog: for the last 10 years I went deep down the rabbit hole of copywriting and direct response marketing to the point where I have one of the most read blogs on these topics. (Again, I’m not too excited about this).

…There are a few other scenarios I could think of (like posting daily reflections from meditations on scripture, for example), but I’ll leave it at three.

When I read those 3 scenarios I can’t shake #1.

I don’t know why. But I feel like that’s what I need to do. Hopefully, I can be at peace with it and just do it!

But no promises… like I said I’m prone to overthinking things so I may still change my mind. But for now the daily personal blog lives on… one day at a time!