I recently returned from a three-day trip to Chicago to attend the inaugural Creative Freelancer Conference, an event put on by HOW magazine (for which I have been a long-time contributor, and to which I fully attribute my one-thing-leads-to-another brand of career success) and Marketing Mentor. HOW is renowned for its excellent HOW Design Conference, with great content and big-name speakers in the design world every year. I was excited about being part of getting the CFC off the ground.

Over three-ish days (short programs on Wednesday and Friday and a full day on Thursday – no doubt meant to address the internal struggles that all of us freelancers felt with taking three days away from ridiculous piles of work) we addressed the big stuff. This being the first conference, we jumped right in to the stuff that really bothers us. How do we charge? How do we manage our time? How do we make sure we get paid? It shouldn’t have been a surprise to any of us that our fellow creatives struggle with exactly the same things. I’d say 25% to 30% of the people there were copywriters — the rest were designers, natural due to the HOW connection — but whether talking to writers or designers or Web developers or illustrators, I discovered that many of us were there for the same reasons. We all grapple with the insecurities that being isolated can bring; the head-scratcher about how to take the time to market oneself when inundated with client deadlines; the universal battle with learning how to say “No!”.

I took two major things away from the conference. First: I’m not doing so badly after all. I have a contract and a process for doing estimates in place; I’m doing pretty well with client communications; I am slowly but surely learning how to better manage my time so I don’t take on too much work.

But second: I have a lot left to learn. I have major problems with overpromising. I still, in my gut, think like a full-time employee who believes all my clients are looking over my shoulder, expecting me to jump when they call. I feel scared a lot. I worry about the future even when I’m underwater in the present.

But the conference was a great way to get away from all of that for a few days, clear my mind, be around a lot of amazing people with great ideas floating in their heads, and gain some perspective. Here are a few key takeaways that I brought back to my office from the week — and that I’m working on putting into practice as we speak:

• Say “I am,” and then be it: Too often, creatives fall into the trap of not being assertive when it comes to saying what services they provide. They say things like: “I’m just a writer,” or worse, try to be everything to everyone without clearly defining what they do well. Decide what you are, and then say, “I am this.” People will believe you. Do what you need to do to back it up, and be this with all your heart.
• Lions don’t apologize. The lead-in title of this bullet is taken from a line in a fun storybook I read to my daughter — but it’s appropriate. Many times creatives share their costs with clients or prospects and then either apologize for them or immediately retract by offering flexibility in pricing. I am guilty of this, especially with my small business clients who are on budgets. The outcome of course is that we feel resentful or tend to back-burner the project if it’s not paying enough. Be strong upfront. You cost what you cost. I like the analogy that your lawyer or doctor wouldn’t blink when stating the price of a consultation. And would expect the money upfront. Creatives need to do the same thing. Our services are equally valuable.
• Creativity doesn’t happen at your desk. OK, this isn’t always true. But the point is that learning what your sources of inspiration are, and making a date to go and find them, is invaluable with creative freelancing. Suggestions included everything from visiting stationery stores to going to museums and galleries. We don’t have the benefit of a team surrounding us to constantly share things they’ve read, leave articles on our chairs, drop by with gossip and ideas, or bounce things off of when we’re stuck. We need to find these things ourselves. I was living this at the conference. I arrived in Chicago with a half-dozen or so creative blocks. Within two days, I had a new elevator pitch, a new business card design, and a revised design for the home page of my Web site, which I’ve been working on redesigning and have been stuck on for weeks. This was all just from talking to people, trading business cards, seeing samples of what other people were doing, and talking about my business with others. My account got unlocked, if you will. Things started flowing again.
• The best time to market yourself is when you’re already busy. I liked this advice from well-known logo designer Jeff Fisher. His advice is to carve out time for yourself, and make it non-negotiable, even when you’re swamped with deadlines. Because it’s better to take time now than to have three or four really quiet months in the near future. This is the toughest one for me, but I love that I feel like I have permission to do it now. The “reading and blogging” recurring event that appears on my calendar twice a week will from here on in be the real thing, not just another calendar notification to be ignored.
• You’re in control. This is seriously the toughest one to reconcile. I’ve been a full-time employee for nearly 12 years, with internships and plenty of part-time minimum-wage jobs before that. If there’s one thing I’ve gotten from that, it’s the ingrained workers’ guilt — that I’m not working hard enough, not performing well, that I’ll “get in trouble” for taking a lunch break — and that creeps into my daily work now too. If a client calls while I’m at Peets writing, for example, I immediately apologize for the noise and worry that my client will disapprove of the lack of professionalism. The truth is that I’m the “Night Writer” for a reason. I work where and when I can, and sometimes my best work happens on my sofa, or at the wi-fi café at Whole Foods! Jeff Fisher’s advice: “Don’t let clients tell you how to work.”
• Refuel before you’re on E. We didn’t talk about this an awful lot at the conference, but there was an undercurrent of it that I picked up on simply because it’s a major theme for me right now. We all have our limits. We all have our ways of refueling. I have learned that if I wait until I’m running on fumes, I do not perform my best. Clients don’t get my best work out of me. I’m unhappy with the result. I need to find ways to refuel every day. Blogging, reading, playing choo-choo trains with my daughter, snuggling with my dog, doing yoga, going to the gym — they all have to be part of my schedule. They are essential parts of my work. Without them, my work will be nothing.