Sometimes being self-employed sucks.

You spend every waking hour (and some sleeping ones, too) working on your precious business – it’s your baby, your lover, your ever so slightly co-dependent best friend.

You spend so much time and energy on it that your real baby, lover, and best friend complain that there is nothing left for them.

But you can’t help it – you are obsessed. You are determined to share what you got with the world.

And sometimes people love what you’ve got, love you, and shower you with roses and orders and blog comments and 83% organic dark chocolate.

And sometimes? Sometimes, not so much.

Sometimes it’s dead quiet out there and you feel a tad exposed. You troll Twitter and everyone’s tweets are so peppy, all about how great their businesses are doing, you start to feel a tad bad. The story line, “What was I thinking?” starts sucking you in. Read More

This is a guest post from my creativity and business coach, Charlie Gilkey. It’s one of the most relevant posts I’ve read in a very long time. You should read it. He gets a real bio at the end.

Things started out great. You had this creative thing that you loved to do. It was fun. And then you figured out that other people wanted your thing, too. YAY!! So you started selling your thing.

Then things went to shit.

In The E-Myth Revisited, Michael Gerber tries to address why things went to shit. (Naomi’s note: E-Myth is one of those books everybody tells you that you absolutely must read before you start a business or your wife will leave you and your dog will die.) He talks about Entrepreneurs, Managers, and Technicians; he discusses who should be doing what and when, all told using Sarah’s “All About Pies” as a case study. It’s a great read, but it leaves one not-too-small question unanswered: Read More

This is a guest post by one of the great loves of my life, Tim Brownson. He’ll get a proper byline at the end.

My guess is that if you are reading this fine blog you are in some way interested in either marketing, selling online or foul and abusive language. Or maybe you are heavily into foul and abusive language online about marketing and this place is your little corner of heaven.

On the other hand, you may have absolutely no interest in sales whatsoever and are contemplating heading off to YouTube to look for amusing videos of squirrels nibbling through power cables, dogs skateboarding and crop circles in the shape of the Virgin Mary’s underwear. Well before you do, humor me by answering the following questions:

Do you sell to other businesses?

Do you ever have to sell yourself over the phone? Read More

You’re hanging out here on the IttyBiz blog because there’s something you want to do, something different than what you’re doing. Maybe you just want to get the hell out of your day job, maybe you have a tiny spark of a dream of doing something you actually love, maybe you saw a need that you could fill better than anybody. Doesn’t matter why you care about having an ittybiz, but I bet you might also be here because something stops you.

When you want to do your thing, or even just spend some time figuring it out, does other stuff get in the way? Sometimes it’s “stuff” (picture big finger quotes) like a crammed schedule, tight finances or family responsibilities. Other times, it’s actual stuff, as in physical clutter. Read More

Editor’s note: This is a guest post from Hunter Nuttall, the “stop sucking and live a life of abundance” guy you may have read about in “The Last Lecture.”)

What a pleasure to be guest posting here at IttyBiz, where finally I can say “fuck” without needing the slightest hint of a reason.

I’ve always thought that recessions are bullshit, but this time I happened to lose my job during one, when my company eliminated every single one of their “safe and stable” jobs. Fuck.

After the shock wore off, I decided it was actually a welcome transition. I had been given the freedom to redefine my life. Lots of free time means lots of possibilities.

But without the structure of a job, I fell victim to one of the deadliest entrepreneurial traps: complete and utter lack of focus. While trying to find something that not only matches my talents, but that I find meaningful, and that other people will pay for, I considered many options, and split my attention between all the ones that seemed appealing. Read More