What happens when you comment on Humans of New York

Well it seems the best way to get started is to offer to help others.

I’ve intended to add a marketing blog to my website for months, but never got around to it. Then I read a story yesterday on Humans of New York about a young man with a writing degree who didn’t know how to make a career with it. I immediately commented on the story and suggested he get into copywriting and content marketing as a way to use his writing skills to generate an income.

And then I offered to help him if he needed advice. On Humans of New York (HONY), one of the biggest, most popular pages on Facebook.

Since I didn’t want to disappoint the people who had reached out to me help, I knew it was more efficient to create a blog post and direct people to it instead of responding to each person individually. I did NOT intend my offer to help to be a sneaky way to get people to visit my website — that kind of shit really bothers me — so I apologize if anyone thinks that.

It’s obvious that a lot of people are struggling to create a writing career, and since I’ve had one for 20 years now (both as a marketing/communications employee and as a freelance writer), here’s what’s worked for me.

I started out as a freelance journalist for my town’s local newspaper in 1995 and I got that gig on the strength of me being a short story writer. You can read my background story here. I’m currently working full time as a content writer for an Internet Service Provider where I write web content, press releases, video scripts, ad copy, technical sell sheets etc. It’s a great company, but I’m leaving my role later this month to do a bunch of other things, and I’ll be freelance writing again. So this is perfect timing because I’ll be going through the same thing as you as I work to build my client base.

Luckily, there are so many resources available for writers now, from books to websites and business coaches.

Books in my library (some are dated, but helped me get started back in the day):

To learn how to market to small businesses:

Duct Tape Marketing by John Jantsch

To learn basic marketing:

Marketing for Dummies by Alexander Hiam, MBA

To learn how to run a freelance writing business:

Writing Freelance by Christine Adamec

Start & Run a Copywriting Business by Steve Slaunwhite

Bob Bly’s Guide to Freelance Writing Success by Robert W. Bly

The Wealthy Freelancer by Steve Slaunwhite, Pete Savage and Ed Gandia

The Well-Fed Writer by Peter Bowerman

To learn how to write copy (writing to sell):

Ogilvy on Advertising by David Olgilvy

Writing Copy for Dummies by Jonathan Kranz

The Copywriter’s Handbook by Robert Bly

The Ultimate Sales Letter by Dan S. Kennedy

To learn content marketing (sharing information to build relationships with customers):

Epic Content Marketing by Joe Pulizzi

Content Inc. by Joe Pulizzi

Everybody Writes by Ann Handley

To learn about self-employment:

Free Agent Nation by Daniel H. Pink

The $100 Startup by Chris Guillebeau

Useful websites

About content marketing:




About copywriting:




About how to run a freelance writing business:



My advice for anyone who wants to get their freelance writing business ramped up quickly: you can’t beat cold-calling and direct mail as effective ways to get clients.

Research the companies you’d like to work with and find out the name of their marketing manager or marketing director. Then call them to see if they ever use freelancers and offer to send them some samples. Calling is scary, but it helps you avoid any anti-spam laws in your country that you might have problems with if you sent a cold email instead. Or you can write a sales letter that showcases your skills and mail it to them — and then follow up with a call in a week or two if they haven’t called you.

I also recommend you have an active LinkedIn profile and join appropriate groups there. Post relevant articles on your page and share information with other writers. I have a ton of connections from around the world that I will never meet in person, but we have a great online relationship and really help each other with suggestions and moral support.

You can also learn marketing, copywriting, and content marketing with LinkedIn Learning. I get free access though my public library, so check that out if you are looking for free training or you can sign up for a paid membership. There are also a ton of affordable courses on Udemy.

Also check out groups on Facebook. For example, I belong to the Cult of Copy Job Board and there are a lot of very cool writing gigs posted there.

Oh, and partner with graphic designers too. I’ve gotten a lot of writing projects that way.

If you’re totally new to writing and don’t have any samples, find an existing ad, web page, email etc. and re-write it. Improve it. Take what you’ve learned and use the before and after as an example of what you can do for the client.

HONY friends, I hope this helps you a bit. While I’m not a freelance writing coach, I am a life design coach (one of the things I will be concentrating on when I leave my day job this month). I help people create the type of life they love. You can like my page on Facebook if you want to stay in touch or you can follow this blog for updates.