Let’s talk about how much I suck at business lately….

A couple weeks ago, I saw a tweet come through my Twitter timeline from my buddy Tim Smith, a designer and podcaster saying, “2014 was my worst year in freelance. My business revenue declined by ~10k.” I immediately related, but hesitated to reply.

Who wants to talk about their failures? Business being slow is actually pretty embarrassing to me and the idea of broadcasting it out to the world sounded terrifying. I sat at my keyboard for a few minutes looking at Tim’s tweet — my hands poised over the keys. I wanted to reach out!

It was extremely brave of Tim to be so honest! I saw someone I admire standing out on a limb and I knew he didn’t need to be out there alone, so I typed out the words, “the last 2 years have been crap for me! Trying to turn things around this year!” and hit return. Of course Tim, came back with a compassionate and encouraging response. It was a good feeling to connect and reach out to someone about something I haven’t shared with many people.


Then he proposed something that I did not expect “want to talk about it next week on The East Wing?”


The tiny step of sending a single tweet out that would only be seen by those who follow both me and Tim on Twitter had my knees shaking, how could I possibly handle talking about my business failures live on a podcast and then having the recording of that live forever online?! There is just NO WAY!

Then Aaron Irizarry had to speak up, “But it can also be liberating, and encouraging to others who might be feeling the same way” Great, he hit right at my heart with that one. If Tim’s initial confession about his struggles hit me so hard and made me feel a little less alone, how could I turn down the opportunity to reach out to other freelancers and small-business owners in the same way? I took a deep breath… and then agreed to do it.


On Tuesday Tim and I recorded The East Wing Episode #7: If I Don’t Produce, I Don’t Eat together. It was both fun and terrifying, like karaoke… but with less whisky. Tim lead the discussion through talking about the things we’ve done right in business and then where we have fell short. We fielded a few listener questions and more than a couple times Tim said “you don’t have to answer this question, but…” I pushed myself to be honest and was inspired throughout the show to continue doing so because of Tim’s frankness. I took away from it, that being open and honest about my struggle is always the way to go. There are people out there who will be able to relate to you and who will have compassion, not judgement.


If you want to hear our full discussion, head over to goodstuff.fm/theeastwing and follow Tim on Twitter to stay on top of all the awesome podcasts he is involved with!

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