Creativity Tips: How to be a Successful Freelancer

In 2017, I will celebrate 15 years of working for the best boss ever -- ME. At this point, I would be a truly pathetic employee for anyone else. I like to work on my pace, on my timetable, and in my jammies.

As a matter of fact*, I'm writing this post in my jammies, and it's 9:38 a.m. at the moment.

Now, the flip side of that story is that at 9:38 last night, I was working on a hot deadline for a client that came in after "closing time" for most businesses. So, let's not think it's all lollipop kids and unicorns here.

But, I digress. Here's the point of this post: After 15 years on my own, I'm frequently asked for advice by people considering a career move into the freelance world. Here's what I tell them:

1. Treat yourself like a client. Think about the move strategically.
   What is your career goal? What is your monetary goal? Can you reach these goals as a solo practitioner? What is your financial situation? Can you afford slow times? 
2. Treat yourself like a friend. Again, think about it strategically -- but with heart. 
   Do you like being alone? Will you miss the water-cooler chats? Do you have the willpower and resolve needed to get up and go to work when no one will notice if you don't?
3. Talk before you act.
   Network. Talk with friends who are freelancers. Contact freelancers who aren't friends, and see if they have any advice to offer. (Some of us are friendlier than others, I've discovered.) Consider this a research paper: Get all the inputs possible, then shift through and decide what is of value to you. 
4. Work with professionals. 
   I didn't do this at the start, but -- looking back -- it seems like it would have been a good idea to talk to an attorney or banker or someone at the SBA who knows about small business and might have informed ideas re: the best way to set the business up. I benefited from the help of a friend who is my accountant, and it has all worked just fine. But "seat of the pants" isn't your recommended route. 
5. Line up your first freelance job, before you leave your current job.
   What? Did I hear you say you don't have a choice? That you've lost the old job and that's why you're thinking about freelance? Uh-oh. Sorry, my friend, but it's time to re-evaluate. The freelance life is not easy or simple. If you're choosing it as a last resort, I suggest you look for a "real job" a little longer. 
6. Put half of every paycheck away for taxes, business expenses, etc. 
   My friend Phil gave me this advice when I was going through Step #3. You will do a job for a client. They will send you a check. It will seem HUGE, to use the adjective of choice these days. What you need to remember is this: The client didn't take any taxes out of that check. The client didn't take any healthcare fees out of that check. The client isn't buying your office supplies. By putting half of every paycheck into your business savings account (or holding it sacred in the business checking account), you will be able to pay bills when they come due. 
7. Stick to a schedule, even though you don't have to. 
   This advice came from my friend Jamie, and it got me out of a rut. Go to work on time. My office is in my home, thus making it easier for the whole jammies and unicorns approach. However, it is totally separate from our living space and dedicated to work. I am in my office every morning, Monday through Friday, between 8 - 8:30 a.m. and am typically there until 5 p.m. Bonus: Clients know they can contact me during regular business hours. I'm not a "flaky" freelancer. 
8. Plan to spend more time than expected on billing and other really unfun aspects of work. 
   When I was creative director at Blades & Associates, I had the luxury of focusing on copy and design. The account pros took care of clients and monthly reports; the accountants took care of billing. Or someone did. I don't know -- it wasn't me. All I had to do was track my billable time. Now, it's all me. Oh, sure, I could hire that out. But when you're a freelancer, every dollar you spend is YOUR dollar, so you approach money differently. I choose to spend the time and do it myself. But I had no idea how much time would be involved. Consider yourself warned. 
9. Get comfortable with chaos.
   Two weeks ago, I had more work than I could accomplish in a day. I worked from early morning until my creative brain gave up. Today, I have two relatively quick jobs to do, and I'm putting them off because they're not due today ... and because I wanted to write this post and wrap a few holiday gifts. I also woke up this morning to an ASAP request from a client in Europe, who is seven hours ahead of me. So her ASAP really is ASAP, because her day is almost over when mine is starting. I never know what the day/week will hold. I'm OK with that, but the random nature of freelancing could make a normal person crazed. 
10. Keep networking. 
    Get out of the office, especially if your office is at home. You will think better, create better, feel better if you have regular contact with other human beings. 
11. Enjoy the benefits. 
    Sure, I have to pay my own health insurance. Yeah, I have to do my own billing. On the other hand, I can run a load of laundry while writing an annual report. And I can take time in the middle of the day to go see Mom if I want to -- because no one cares if I'm writing at 10 a.m. or 10 p.m., as long as I hit their deadline. 
12. Manage your reputation. 
    We're back to Step #1 and Step #2. And this may be the most important part of being a freelancer. You are all you have. Your reputation is everything. Be nice to people. Treat them fairly. Talent and quality obviously matter to clients. But success as a freelancer goes far beyond that. Be a good person. Be someone you would want to work with, if you had a choice -- because your clients have a lot of choices. Why should they work with you? Are you kind? Are you friendly? Are you responsive? Do you care about their success? 

I could keep going, but a dozen tips seems like a good number. Basically, my friends, freelance life is absolutely lovely when you surround yourself with a circle of creative friends and clients, watch your finances, continually keep business in the pipeline, embrace chaos and enjoy solitude. I do all of that, and have managed to make a lovely life -- and an excellent living -- as a writer. My job is a gift that I am grateful for every single day.

Questions? Post away or email me. I'm a Jewish momma. I'm happy to give advice.

*Advice: When you say, "As a matter of fact" or "Frankly" or any of those kind of phrases, you imply that everything else you're saying is not fact or frank. Best to avoid them.

Designed by Chandler, at Kalimizzou. See Step #4 above.
And check out his creative design process for the logo here!