Jake Poinier: Freelance Writer and Author of ‘The Smooth-Sailing Freelancer’

Jake Poinier

Jake Poinier has experienced immense flexibility in his role as a freelance writer and editor for the past 16 years. The publishing guru works on projects ranging from penning web copy to ghostwriting books, and he’s self-published three of his own titles: The Science, Art and Voodoo of Freelance Pricing and Getting Paid, Help! My Freelancers Are Driving Me Crazy!, and the recently released The Smooth-Sailing Freelancer: How to Find, Sell, and Retain More Freelance Business.

The 48-year-old Phoenix resident shares his knowledge of the freelancing world on his website, www.DoctorFreelance.com, where he is available to answer questions and creates blog posts focused on freelancing. He shared his tips for existing and aspiring freelancers, and you can hear him name his five favorite reasons for loving living in the Valley in a video.

What brought you to Arizona?

I was born in Boston and grew up in Massachusetts. After graduating college, I was working at a golf magazine called Golf Digest magazine in Connecticut. Two years later, I quit my job and attempted to ride my bike cross-country and was run over in Montana by a pickup truck, which cut that short. Even so, the first 1,100 miles introduced me to the beauty of the West’s mountains and desert.

After going back to Massachusetts after the accident, a guy who had left Golf Digest to become the editor at a magazine here in Arizona, called Golf Illustrated, called me. It was a classically awful New England night, 33 degrees and raining, and he said, “Hey, do you want to come to Arizona to be my managing editor?” I said, “What time is my flight?” I flew out and haven’t looked back since.

What’s your educational background?

I went to Yale and got my English degree and have my MA in organizational management from University of Phoenix.

What’s your earliest memory of wanting to write?

My granddad had this incredible library and worked for McGraw-Hill Books. He was like an oil gusher for books, so I was always an avid reader. I had a few high school teachers who really encouraged me and saw more talent in me than I saw. In college, I had some professors who were encouraging, as well, and helped me stylistically and pushed me to work harder at specific things.

What has your career evolution been like?

I started as an intern at Golf Digest, which turned into working full time for them. When I moved out here, Golf Illustrated was a fantastic job. Unfortunately, the business model wasn’t too good, so I read the writing on the wall and left and worked for Best Western corporate headquarters for about 18 months in public relations, which was a great education.

Next, I was an editor for McMurry Publishing and eventually moved over to the publishing and sales side, which was a great education on how the business and sales side of magazines works. Also, seeing sales guys in action was so educational. This goes beyond freelancing, but no matter what, you need to understand how good salespeople do what they do. It’s important to know how people work and what makes people motivated or de-motivated.

I went into business for myself in 1999. I got to the point where I was no longer a good fit for the company, and I saw a lot of freelancers, the people I was hiring as an editor, who were making a good living. I thought to myself, “They seem like really happy, well-adjusted people who are making a good living, and they’re independent. I think I could maybe go with this.” My family saved money for about nine months before I decided to take the leap.

I knew I could go back to a corporate job, but that wasn’t really appealing to me. My dad was an entrepreneur, so I always saw that as an option. Yes, it causes crazy instability in some ways. You might have to work really hard for certain periods of time, but I also can structure my world the way I want to. I am really productive from 5:30 in the morning until 1 o’clock in the afternoon, and after that, I’ll do menial tasks. I know that about myself, and that doesn’t go really well in an office environment.

I made the leap and have now been in freelance for 16 years. As a freelancer, you go through great periods, and you go through really rough periods. The key for me was surviving going through the really rough period, in about the post-dot-com economic downturn in 2001. Many of the budgets of people I had been working with had dried up. I started doing cold calling, which is something everyone should have to do at one point or another. It’s a challenge, and I admire the people who are really good at it. It was sufficient enough to get a bunch of clients from a bunch of cold calls, and I haven’t done it since.

If I had to restart, and all my clients went away tomorrow, I know what I would need to do to get restarted. You really need to be a go-getter and find the clients and industries you like. There are a lot of bad jobs out there, and the sooner you figure out what you don’t like, that’s helpful, too.

Besides saving money, what else do you recommend for people who want to leave the corporate world and become a full-time freelancer?

Talking to people who have done it successfully is important. Part of the reason I created the DoctorFreelance.com website was to be available to people. There are so many things I got taught by people along the way, I feel like it’s my way to pay it forward and help other people who want to make the leap.

There are a bunch of different ways you can do it. You can take on freelance stuff on the side while you’re working, and that’s helpful, because you’ve sort of got one foot in each camp. I couldn’t really do that, because my corporate job was so intense. I had to take the route of, “OK, I’m jumping out of the airplane and hope my parachute works.”

The more connections you can make to other types of creatives, from photographers to graphic designers, the better. Ultimately, so much of the work I do is coming from those types of entities, or from partnerships with those entities. If all I knew were other writers, I wouldn’t have such a strong network.

What tips do you have for cold calling potential clients?

Leave your ego at the door. Don’t worry about “no.” Find an approach that works for you. Don’t get frustrated. I would say maybe one out of 10 calls went the way I wanted it to. Wait for the ones that are good.

One client I still have, I got from a cold call, and they had happened to lose one of their freelance writers, so my timing was good. There are going to be days when nothing bites no matter what you throw out there. Other days, you’ll get three really great responses. Focus on the positive.

If you’re getting to the point where you’re starting to bore yourself, shut it down for the day, and do something else. If you’re boring yourself, you’re probably boring the people you’re calling.

What are the biggest benefits and challenges to being a freelancer?

The biggest benefit is freedom — not just the freedom to set hours, but to choose whom I want to work with or no longer want to work with. It’s the freedom to try different things, like having my website or writing my books.

For freelancers who want to get out of writing and into editing or out of editing and into writing, you can take those avenues. I like having something different every day, because I never get bored. Yesterday, I was writing a video script. The day before that, I was ghostwriting somebody’s book. The day before that, I was working on copy for somebody’s website. I have the freedom to do all of those things and to choose what types of work I want to go after.

A common challenge is pay: either not getting paid or not getting paid enough. A lot of people like to write or edit, which is why they freelance. I like those things, but I don’t love them. The business aspect is what I love. 

You can’t solve the low pay thing after the fact. You have to solve those issues up front. You need to go after audiences that are lucrative as far as pay. Usually indicators of slow payment will come up in your first meeting. If they talk about how things are tight with budget, you’ve been warned.

Another common challenge is feast or famine. That’s a matter of balancing things out. You have to enjoy and embrace the feasts, and to prevent famine, you have to market while you’re busy, or else, you’ll always be cycling. Or, if things are really slow, cold call or send letters of introduction to tell potential clients how you think you can help them.

What has been your most memorable interview?

I’ve interviewed so many interesting people across the country, it’s hard to choose. Here in the Valley, I really enjoyed interviewing Shane Doan from the Phoenix Coyotes. He toured me around the house, and it was cool having him show his paraphernalia. He’s super-humble, but seeing some pieces of history in his house was really cool.

What inspired The Smooth-Sailing Freelancer: How to Find, Sell, and Retain More Freelance Business?

What inspired the book is that I gave a presentation to a conference last fall called Communication Central in Rochester, New York. I was the keynote speaker, and I wanted to do something unique. I thought of a sailing analogy to relate to the freelance business, as I’ve always enjoyed sailing throughout my life. People responded to the presentation well, and instead of handing out papers, I decided to announce I’d be giving out a copy of my e-book related to the presentation, which incentivized me to put together the book.

A few weeks ago at this year’s Communication Central, I did a presentation on how to get more referrals for your business — and I’m going to turn that into a book within the next few months. I’d like to put on a similar conference for freelancers here in the Southwest at some point.

Right now I’m actually helping some people self-publish, as well, which is new to me and exciting.

What are your goals?

Sailing around the Caribbean is a big one.

On the business side, on the DoctorFreelance.com website, I’ve got a couple new offerings. I’ve started doing webinars and the first one, on freelance marketing, went really well. My goal is to monetize those.

Consulting is something I’ve done loosely before, but I want to formalize that into the business side. People can always ask me questions on the blog, which is fun for me, but sometimes people don’t have a complex question that can can’t be answered in a 500-word blog post.

Finally, publishing other people’s books is a goal of mine. In fact, I just published Juggling on a High Wire: The Art of Work-Life Balance When You’re Self-Employed, by Laura Poole. It’s packed with tips for people who are freelancers or work at home, or who are considering it.

Why would you encourage people to visit DoctorFreelance.com?

There are around 160 blog posts on all sorts of different topics related to freelancing. If you have a question you want to ask, ask it, and I’m more than happy to answer. I want it to be an interactive thing.

I’ve had the blog since late 2009. I’m always surprised and always like it when people ask me questions I’ve never heard or considered, so I can think about how I’d approach them. If I can inspire someone to take a more business-like approach to freelance, I find they’ll have more fun with freelancing, too.

Why would you encourage someone to hire you?

I will get done what you need done and do it well. I’m a quick learner and a team player. I like to be the freelancer clients want to hire again. I want to be the guy who can help with not just the immediate thing, but everything down the road.

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