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This is where I talk about my work, my discoveries, my creative process, and the ins and outs of marketing in the arts.

Lessons from the HOW Design Conference

June 30, 2011

Filed under:

freelance life, wisdom
HOW Design Live Keynote Event

When you are on the right path, great things serendipitously will drop into your lap. I like to think of it as having the many threads of your life in alignment, attracting like-minded people and resources toward you. Just such a thing happened when, not even a year into quitting a crummy retail job to become a freelance illustrator/designer, the HOW Design Live conference came to Chicago.

I only attended the first day and half, which was the Creative Freelancers Conference (though now I wish I’d had the money and foresight to attend the entire conference). Still, in that short amount of time I learned a lot. Like, really, a whole lot. Here, I’m going to display the six major pearls of wisdom I picked up in my time there (many of which augmented ideas I was already learning). These concepts are not just good for freelancers—they can be applied to most small businesses. I can tell already that they would be great for anyone in Chicago developing a young theatre company.

1: Structure Your Business Around Your Strengths

Build Your Biz As A Reflection Of You

It may seem obvious, but Steve Gordon (who is an amazing speaker, btw) pointed out how many people who left a big company to be their own bosses nonetheless adhere to the old business customs, such as a 9-5 work day. Perhaps you work best from 10pm to 3am. Perhaps you get a burst of ideas in the morning, then need the afternoon off and come back to finish up other business in the evening. Align your hours with your own creative clock.

Or perhaps you love creating logos for new businesses, but keep doing big business brochures and trade show exhibits because of the money. Von Glitschka dropped the idea on us that you should fill your portfolio with the work you want to get—even if you have to create that work on your own for imaginary clients. Don’t put work that you didn’t enjoy in there. Advertise yourself doing the things you love to do, that you are most passionate about, and steer your business in that direction.

Find your strengths, and put them front and center in your business.

2: Get Your House In Order

Don't Let Entropy Win

Be disciplined and organized, otherwise you waste half your energy on the mess. I am certainly guilty of this one. It’s an exercise in entropy watching my workspace deteriorate over several weeks, watching piles of papers multiply and stacks of stuff infest what was once beautiful empty space. Make the effort to tidy up at the end of each day. Create dedicated places to put incoming work, incoming checks, outgoing invoices, etc. Let this idea move into your cash flow as well. Presenters Joseph D’Agnese and Denise Kiernan, authors of The Money Book, gave concrete examples of how to do this, such as creating separate bank accounts of different needs (income tax, business overhead, retirement savings, etc).

Once your immediate surroundings are in good order, look to the future. Strategic planner Luke Mysse schooled us on developing business goals and making them inspirational. Rather than losing 50 pounds, decide to hike a mountain range. Or, in my case, rather than looking to just increase and stabilize my income, I want to get a larger apartment so I can have a dedicated office of my own, paid for by the business. Write these goals down (I have a dry erase board) so you are always reminded of them, and develop strategies to achieve them. It’s work, but it will pay off

Get Visible

Don't Be Shy

Nobody will hire you if they don’t know who you are. Allen Murabayashi encouraged us to think big and increase our footprint, moving from just a portfolio website into areas where we hope to find new clients, places like Facebook, Twitter, Flickr, etc., and to optimize our SEO so internet searches will actually find you. SEO is a deep topic: learn it.

Even more than that, I would advocate getting off the internet and into the real world. Identify your target clients and put yourself in front of them. Attend conferences that they attend, put up a booth at your neighborhood festival, introduce yourself to everyone. Don’t be shy.

4: Set Your Fees Accordingly

Know What To Charge

I’ll admit, this was a big problem for me since I came from the hellish world of retail, where your worth is set by your hourly wage. How much you charge a client, though, is not how much you make. You must factor in the cost of business—computer equipment and maintenance, office space, design materials, and don’t forget insurance, savings, and taxes! Subtract all that from what you charge, and that’s how much you personally make. Once you’ve found that base price, increase it.

That’s not to say you can’t dip below it for a project you really want to work on (that will perhaps pay you in another way, like exposure or a portfolio piece). Perhaps you negotiate a lower fee for a charity or non-profit group. That’s fine, as long as you’ve charge more elsewhere and it balances out in the long run. Don’t short yourself, or you won’t last long.

5: Don’t Go It Alone

Find A Circle of Colleagues

Freelancing can be a lonely profession. Develop colleagues who do what you do, who encounter the same challenges. Make them your friends. Since I came to this line of work through the theatre, I know lots of actors and directors; I know very few designers. I did meet a lot of local freelancers at the conference though. So seek out like-minded folks and get yourself a circle of design buddies.

Both Von Glitschka and Luke Mysee also advocated developing a board of advisers—people you know and trust who can give you advice on your business, people who have created businesses themselves. Take them out to dinner every couple months and use them as a sounding board for what you’re doing right and where you’re drifting off course. Just like designers often need a second pair of eyes to critique their work, get critiques on your business.

6: Take The Time

Take The Time

All this seems like a lot of work that doesn’t involve a lick of design or illustration, and it is! Running a business takes time and effort. None of it will magically just happen if you don’t plan for it. Everyone at the conference advocated taking one day a week and designating it for your business, a day when you don’t work on client work. Take this day to balance your books, work on your marketing, get your office in order, develop plans for your business. And remember, this day isn’t a day off, it’s a day of work. When you are figuring out your fees, include the cost of this day as overhead cost, because that’s exactly what it is.


I’m guilty in many ways of not having these ideas in place in my business. Having developed my business around non-profits, I tend to make less hourly and therefore have to fill all my hours of the day with work to bring in the money. But with these concepts, I now have the tools to move forward and steer my business in a sustainable and profitable direction. I hope they can do the same for you.

My most immediate goal is to set aside enough money to attend the HOW Design Live Conference next summer in Boston, and this time attend the entire event. Will I see you there?


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