In Honor of Halloween: The Dark Side of Working for Yourself ( it’s spoooooooky! )

I wrote this for my newsletter subscribers this week. It got such a great response and really seemed to resonate with people, so I wanted to share it here, too.

Yes, this is a bit of an ominous title, but lately I’ve been thinking a lot about the hard parts of running this little design studio. I still count it as one of the great joys of my life, so don’t worry – this isn’t all doom and gloom. This is more of a realistic account of the ups and downs of boss-dom. It’s easy to read posts, tweets and blogs about how working for yourself is great, grand, never a bad day, I rock this business 24-7. That’s true sometimes. But I am going to be real with you. The past couple of weeks have been challenging. Looking deeper I realize there are aspects of this business I’m just going to have to suck it up and deal with – warts and all. So, if you are thinking about working for yourself (do it), read on for some real talk.

Being the one in charge of EVERYTHING from the smallest task to delivering a final, kick ass design makes you feel like everything is a big deal. Every email, every dollar, every new inquiry. And it is, to an extent. Last week I was waking up every night thinking about emails, projects, money, new clients, promotion, redesigning my site, rewriting my site, billing that client, did I bill that other client…and the list goes on. If you like deep, comfortable sleep – running a business might not be for you. I found myself longing for the sweet, albeit numb sleep I used to have knowing I was going to my steady 9-5 the next day. Still – I prefer this.

Vacations seem like a dream to me right now. Ok, so a lot of people have figured this out and I hope one day I will. Many people work for themselves for the freedom to take a vacation whenever they want. Technically, I can get on a plane now if I want, but I won’t. In fact my husband I have an opportunity to travel next month and I am still trying to talk myself out of it because in my anxious first time business owner brain, the 5 days I would be gone would cause my business to crumble. See the pattern here? Yes, it is that I am crazy.

You don’t know how it’s all going to turn out. Period.

Every day is a new lesson. You might learn it the hard way, you might pass with flying colors. There is always a learning curve and sometimes it will seem that everyone else has aced this test, but you. They will think this about you, too.

You won’t have a “boss-boss”. You’ll have a bunch of bosses, also called clients. This is not a negative, it’s actually a major upside. I would much rather talk to my client bosses about their ideas and vision, than have them filtered down to me from the top. However, there are a lot of people to please and a lot of needs to be met. You will sometimes feel pulled in 100 directions. If you can handle that, you’re golden. If you aren’t a people person, this might be challenging.

When I read other people’s accounts of business-running, I am always refreshed to read about the not so tweetable parts. I have been asking so many of my fellow designers for advice lately, I thought I might try to share a bit, as well. Hopefully this is helpful to someone out there thinking of or already running their creative business. It’s hard work, but it’s the best work. Getting support and doing one thing at a time will help your mind, body and work. So don’t beat yourself up for not knowing it all!

So, on this gorgeous Fall day I am going to try to focus where I am now compared to a year ago. And then 2 years ago. Would I trade one of these hard days for one of those easier ones?


I’d love to hear from you about challenges you are facing with your brand or business. What you are afraid of might just be a little less spooky than you think.

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I’m currently booking clients for early 2015. If you want to chat about how you can rebrand and refresh your business drop me a line.

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