Need Advice? Veteran Freelancers Share Their Tips to Success

By Tom Bentley, Contributor, on February 12, 2018

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Veteran freelancers have battle-weary perspectives on the demands, skills and glories of practicing their trades. After all, experience hones skills and approaches that newbies can only dream of.

Here are two veteran freelancers who know the pitfalls, procedures and pleasures of their crafts. Meet Rick Flowerday, an executive adviser in management consulting, and Becky Blanton, a ghostwriter.

How long have you done this kind of work, and who do you work with?

Rick: I began freelancing in 2001. Since then, I’ve moved in and out of positions as partner in several management consulting firms, and I’ve worked as a sub-contractor to other firms. In the management consulting industry, you’re a free agent once you attain a certain level of expertise. My clients are generally large financial institutions, especially retail banks and insurance companies. I’ve also served clients in telco, pharma, software, government, food and beverage.

I work on the cost side of the balance sheet, looking for ways to save money through operational improvement and processes that have to do with how companies buy and manage assets. Mostly, I’m stripping the fat out of the supply chain.

Becky: I’ve been a journalist for 23 years and a freelance writer for more than 30 years, but I’ve focused mostly on ghostwriting the past eight years. I’ve ghostwritten 40 books in that time — for Fortune 500 companies, NFL players, celebrities, talk show hosts, a member of the UK’s House of Lords, TED speakers, architects, financial analysts, columnists, motivational speakers, hypnotherapists and soccer moms writing memoirs for their kids.

How do you find your clients?

Rick: [I find my clients] through my network, almost always referral. I’ve never marketed at all. When I want to sell business, I take people to lunch — lots of lunches. That either leads to business directly, or to referrals.

Becky: In the beginning, I found clients on eLance. Once the books I wrote for those clients began to do well, those clients referred me to their friends who read and liked the books and wanted their own ghostwritten. I now have a couple of large publishers who hire me to write for their clients. Now, 30 percent of my work is word-of-mouth referral, 50 percent from publishing houses or other ghostwriters and the rest from LinkedIn.

What kind of client challenges do you face, and which strategies do you use to tackle these challenges?

Rick: As a change maker, I have to deal with people’s fear of change and of personal economic insecurity. My work is almost exclusively project-based and deliverable-driven, so I’m far faster and more driven to adhere to project timelines, since I don’t get paid until work actually gets done.

Since mine is a service industry that is very relationship-driven, managing this requires a deft touch. Usually I create a page in an update doc which shows slippage from schedule with sources and causes, and then only show this to my day-to-day client.

Becky: The number-one challenge I see with every client, no matter how rich, successful or accomplished they are, is overcoming their fear of publishing their first book. They all worry about what people will think of it.

I deal with it several ways: I give them an “expiration date.” It’s a deadline, but “expiration date” sounds more ominous for some reason. I break the tasks down into smaller steps, and charge more when they miss a deadline — or we go to a non-refundable retainer fee.

How has your work changed over time?

Rick: [I have] much more freedom about work style and less need for face time. I now only see my clients once every two to four weeks. Projects are now smaller in scope and KPMs are better defined, which increases selling expense as a percentage of revenue. But staying up-to-date is a challenge. I read a ton and think a lot about how to transfer techniques to seemingly novel problems.

Becky: I’ve systematized [my work] and streamlined it. [I’ve learned that] the three things every ghostwriter should have are:

  • Other writing friends you can consult with, vent to and laugh with, and a place to go for advice, support, encouragement and help.

  • A system for creating the book and a system for creating the way you market, invoice and collect payments.

  • Most importantly, a business plan: Not the traditional “business plan,” but a plan for how you run your writing business, how you get clients and keep them, how you make money and what you ultimately want to do with your life.

What are the biggest challenges of being a freelancer, overall?


  • Isolation: It has upsides and downsides. There’s really no substitute for face-to-face idea exchanges with smart colleagues. I miss that.

  • Constantly selling.

  • Business drought and monsoon: Having some staff both helps and creates complexity with that cycle.

  • Never being able to fully detach from clients while vacationing.


  • Time and attention management: No one will guard your time or attention better than you.

  • Setting and enforcing boundaries: Clients, vendors, editors and publishers will wring every minute, hour, weekend and holiday out of you.

  • Financial planning: Most writers ask, “How much should I charge?” and don’t ever do a break-even analysis to see what they need to charge.

If you could start over, what would you have done differently?

Rick: I’d focus on taking only projects that lead to original IP that’s scalable via processes and systems. Developing several of these would have led to the (possible) sale of one or more along the way and made real money.

Becky: I’d have gotten organized, written down my goals for myself and systematized my system. I’d have paid more attention to the business aspect, like invoicing, learning how to run my business and budgeting my time, money and clients. I needed to learn to say “no” to unreasonable demands on my time and resources.

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