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 and follow Tim on Twitter to stay on top of all the awesome podcasts he is involved with!

Good Cop & Bad Cop: Laying Down the Law and Keeping People Happy As an Independent Business Owner

Earlier this week I met up for coffee with a client of mine. The two of us originally met when his employeer was my client and after leaving that job he hired me to customize his personal blog and we formed our own client/designer relationship. I was excited when he emailed me last week with the news that he was starting a new business venture and wanted to discuss working with me on branding and marketing materials.

We filled each other in on all that we’ve been up to, talked about family and pets and work. He expressed his excitement over building his business (which is a partnership with another owner) and that while he is working non-stop, he is loving it! We talked about dealing with clients… the art of retaining clients vs selling to new ones. The balance of looking out for your clients and also not being a push over. He said, “I don’t know how you handle this without a business partner. I need a ‘good cop’ in the scenario — I’m only capable of being ‘bad cop.'”

This got me thinking — am I both Good Cop and Bad Cop? I guess as an Independent business owner, you kind of have to be! It’s delicate balance of being able to lay down the law and tell a client something they may not want to hear, holding your foot firm on policies and generally being able to deal with people on a purely “getting business done” level and the Good Cop side is the smile you close with, the empathetic comment you offer when a frustrating situation arises, the hand holding for those high maintenance clients. It’s tough to play both of these rolls, but not impossible.

I’ve been dealing with a frustrating project lately. A client wants a feature added to a project that was not part of the original scope — trouble is, they didn’t anticipate the added cost of this from the get go, so they are struggling with passing along that expense to THIER client. It’s a mess and while yesterday I had almost reached the point of saying “I don’t care WHAT you do, here’s the bill for the time I put in — and here is some referrals to other devs you could hire to finish the project!” Instead I slept on it, pulled myself together (the good and bad halves) and told them “I know you’re in a really frustrating situation since you did not anticipate this feature being part of the project so the added cost was not part of your original budget (that was the Good Cop, now time to switch gears… Bad Cop, I know you have a ‘but’, right?) — BUT I have offered up some really good solutions and you can either go with the less expensive one that is CLOSE to what they want, but not exactly… OR you can go with the more expensive option that’s going to give that JUST what they want.” While the previous email from the client had been a little huffy — her next response after this message said “Thank you so much for all the time you’ve put into this! I am going to talk this over with my client and follow up with you next week.”

Thank you Good Cop and Bad Cop for Liz and her clients sane! :)

Do you recognize this in yourself? Is there one side you feel you need to get more in touch with?