Chicago Ultimate Writing Retreat™

Make big plans for bigger writing income

Chicago picIs it time to add “author” to your title?

Tired of seeing other writers make it while you’re still struggling?



Join me and a small group of aspiring copywriting rock stars June 19-22, 2013

Last year in June my son Solomon and I kayaked down the Chicago River you see above. We were awestruck as we gazed up at the third most impressive skyline in the world (after Hong Kong and New York.)

Chicago is head and shoulders above the competition. You will be, too, after coming to the Ultimate Writing Retreat™.

Tall order? Yes, and I’ll explain how I’ll deliver in a minute.

Steve Roller here, inviting you to Chicago, Illinois, June 19-22, 2013, for a writing retreat unlike anything you’ve ever experienced. The theme of the retreat is “Make Big Plans,” inspired by Daniel Hudson Burnham, principal architect of the city of Chicago.

Can a writing retreat really transform your writing, your business, and your life in three days?

If you’re with the right people in the right place, most definitely.

Why retreats spur your most productive, creative work

See, it’s easy to get caught up in our day-to-day work, isn’t it? Client projects, other jobs, and personal responsibilities get in the way of doing the big things that would really propel us forward. That ebook, special report, money-making website, or book gets pushed to the back burner.

I know, because I’ve been in the same boat. But whenever I carve out dedicated time to work on a personal writing project, it gets done.

It happened again at the beginning of May when I spent three days immersed in writing in Santa Fe. It was my most productive writing in a long time, and you’ll be the first to see the results (including my first book) when you join us in Chicago. I also give credit to the people I was with – it didn’t happen completely on my own.

You generate serious power when you focus on a single purpose with other sharp, like-minded people in an inspired location. My goal is for the same kind of writing magic to happen for you in Chicago June 19-22.Young businesswoman at a sidewalk cafe

“If you’re interested in developing a strong and prosperous copywriting business, I recommend that you ‘roll into success with Steve Roller’!”

– Melanie Garrett, copywriter at Prize Copy and author of Under His Helmet

Are you ready to take your copywriting to the next level and start getting more clients, bigger projects, and higher fees? Is it time to transform your big idea into an actual ebook or book that will set you apart from your peers? Is this going to be the year you finally say, “yes” when someone asks you if you’re a published writer?

If not now, when?

Whether you’re just starting out or an experienced pro, the Chicago Ultimate Writing Retreat™ will take your copywriting to the next level. You’ll also come away with a completely framed-out ebook, second website, or book idea, along with a detailed blueprint for finishing it within 60 days of the retreat.

Don’t have an idea yet for a big writing project? No problem. Our special guest speaker, Cyndi Fine, will conduct a one-on-one brainstorming session with you and each of the other writers prior to your arrival in Chicago. She normally charges $150 for this, but I’m including it as part of your retreat experience.

I call Cyndi a “creative instigator” because she has a gift for helping you discover your own unique talents, develop creative new ideas you wouldn’t think of on your own, and map out an action plan based on those ideas.

Cyndi has owned numerous successful businesses over the past 33 years, and is one of two people who pushed me to take action on this whole Copywriter Café adventure.

A one-of-a-kind retreat deserves a one-of-a-kind location

I’ve traveled the world over, and Chicago remains one of my favorite cities anywhere. I’ll not only be your master host for the Ultimate Writing Retreat™, I’ll be playing tour guide, too.Hotel Allegro

Your retreat experience will mix fun Chicago excursions with high-level instruction in both small group and individualized settings. You’ll get solid writing sessions, inspiration, and a plan of action to take home. We’ll be working hard and enjoying ourselves at the same time.Stardust Suite 1

We’ll kick things off with a meet-and-greet opening session over hors d’oeuvres and drinks (included in your retreat cost) on Wednesday night at the Hotel Allegro’s Stardust Suite. A luxury boutique hotel in the heart of Chicago’s Loop and theatre district, the Hotel Allegro is next door to the historic Cadillac Palace Theatre and only six blocks from world famous Michigan Avenue.

We’ll be at the Allegro Wednesday through Saturday, and I’ve even reserved a block of rooms at a special group rate so you can stay right on the premises.

Thursday and Friday will be jam-packed with more informative sessions in the Press Room, including:

  • 7 steps to crafting a high-profile image
  • How to cultivate and keep solid clients
  • What you need to know about the True Business Success Pyramid
  • 5 offbeat steps to becoming an in-demand, well-paid copywriter
  • A writing lesson from an unlikely source: What a funeral director taught me about “deeper” writing
  • How to write and publish your book in 40 daysPress Room 1
  • The art of selling and positioning for creative types: A guide to getting paid what you’re worth

… and much more, including feedback and individual critiques each day.

The full Chicago experience will boost your writing

I want you to get the most out of our three days together, so be prepared to start early and end late. I also believe in finding writing inspiration in unusual places, however, and since we’re in Chicago, I have group activities planned to see:

  • A show at Second City, the world’s premier comedy club/theatre and school of improvisation. This is where John Belushi, Bill Murray, Tina Fey, Steve Carrell, and many other famous funny people got their start.
  • The Art Institute of Chicago, featuring the largest Monet collection in the world and amazing exhibits of Chagall, Dali, and others.
  • An architectural riverboat tour. American novelist and journalist Theodore Dreiser called Chicago “the Florence of the Midwest” – every major architect has a signature building here, and Chicago has more moveable bridges than any city in the world.
  • The Magnificent Mile – a stretch of Michigan Avenue that rivals the Champs-Élysées in Paris.
  • The Willis Tower (formerly the Sears Tower), North America’s tallest building. A perfect scene to set the stage for your big writing plans, you can see four states on a clear day from the 103rd floor Skydeck.

Chicago skylineOh, and one more thing if you decide to extend your stay past the noon Saturday ending time (I highly recommend spending the entire weekend in Chicago if you can.)

The Cubs aren’t my team, but how can you come to Chicago and not see the fabled ivy-covered walls of Wrigley Field? Join me at one of America’s most storied baseball venues for a classic experience, whether you’re a baseball fan or not. We’ll talk once you’re registered for the Ultimate Writing Retreat™.

Finally, Saturday morning we’ll gather for one final powerhouse meeting back in the Stardust Suite.

Stardust Suite 2I’m saving the best for last and will send you off with:

  • How to leverage your book into bigger things
  • Wining and dining your way to success
  • Designing your ultimate lifestyle of adventure and intrigue

Plus, you’ll get these three bonuses …

Bonus #1: Two follow-up phone calls with me. These two 30-minute sessions will combine training, accountability, and action steps, designed to help you complete the project you launched in Chicago within 60 days. Value: $150

Bonus #2: Your copy of the Ultimate Writing Retreat™ Guide to Bigger Writing Income, including updates for life. Value: $100 (or thousands, depending on what you do with it)

Bonus #3: Exclusive perks as an Ultimate Writing Retreat™ Member. As American Express used to say, “Membership has its privileges.” Yours will include discounts on future retreats, priority access to me for copy critiques, and more important, a chance to hang out with some of the coolest people you will ever meet. Value: You can’t really put a number on this one.

Are you starting to see that this is not your typical writing or copywriting conference?

“I landed a multi-million dollar company as a client a few months after I began to study copywriting. Fortunately for me, I met Steve Roller a few days later! Thanks to Steve’s generosity and expert guidance, my new client was happy, and I gained the hope and confidence that I could become a successful copywriter. Steve is an excellent teacher.”

– Tanya MarCia, Web Copywriter at

The destination alone is worth making the trek to Chicago, but my main purpose in gathering here is to help you become a better writer, a more prolific writer, and a published writer.

And it probably goes without saying – helping you make more money is always part of the picture.

“Okay, I’m in. What’s the cost?”

I think you’ll be pleasantly surprised.

Most big conferences run anywhere from $1,500 to $5,000 for three days, and they’re well worth it in my opinion.

With the Chicago Ultimate Writing Retreat™ you get …

  • Three intense days of writing and copywriting workshops, professional critiques during the retreat, a one-on-one brainstorming session with our guest expert, and follow-through with me after the event.
  • Three bonuses worth hundreds of dollars alone.
  • An intimate environment with a small group of committed writers who are motivated to make big things happen.

This is going to be special, and I’m pulling out all the stops.

I’ve secured top-notch meeting space in a beautiful boutique hotel in the heart of the city. I’m including food and drinks on Wednesday night, coffee and snacks throughout the retreat, a couple breakfasts, as well as the Second City show and a couple other excursions I mentioned above.

If you’re staying with us at the Hotel Allegro (see details below about the reasonable group rate they gave me), you’ll also enjoy their free hosted nightly wine hour from 5-6 PM.

Wine hourHere’s the thing. Even if you got the same material in an online or written program (which would have been a lot simpler and less of an investment for me), you can’t possibly create the same experience as a live event in an upscale, inspired location like the Hotel Allegro in the amazing city of Chicago.

I’ve seen many online-only webinars that cost more than the Ultimate Writing Retreat™, and I’ve attended many three-day  events that were over $2,000.

This is only $787 .

Only five spots remain, and I’m anticipating these will fill up fast, so don’t wait.

Retreat Options

This obviously isn’t a big conference. You’ll get to know your fellow retreat members well (and knowing the writers who have registered so far, I can tell you that you’ll really enjoy them, too.) I’m anticipating a sense of camaraderie that will extend beyond the three days in Chicago together.

In fact, my intent is for this small group, intimate setting to be a launching pad for big things to come for all of us. I’ll be working on a “Big Idea” project myself (my next book) during the breaks and after hours.

My background and why I’m doing this now (for only three payments of $240!)

Yes, all this for only three payments of $240. Get one small idea, a spark of inspiration, or a finished writing project and it easily pays for itself. Hotel, travel to Chicago, and some meals not included.

So, why am I leading this retreat and what makes me an “expert”? Well, I don’t call myself an expert or a “guru.” I reserve those terms for a small, select group of writers and marketers.

I’m doing this because I have a passion for helping other writers, and a firm belief that our best writing happens in focused, intense, inspiring places.

I also happen to love traveling, and have big plans to host the Ultimate Writing Retreat™ in a bunch of other cool places the next few years (and you’ll get first dibs and a nice discount on any of those.)

While I’m not quite an A-level copywriter, I’m on my way. I’ve been a copywriter since 2004, full-time freelancing since March 30, 2009. I’ve written 115 articles for American Writers & Artists, Inc (AWAI), been published at, and had feature stories written about me in The Barefoot Writer and at

I’ve had a handful of regular monthly clients for the past three years, worked on a copywriting project with Dan Kennedy, and currently have a successful promotion in the mail and online that I wrote for master copywriter Mark Everett Johnson. I’ve carved out a very solid income as a copywriter while traveling seven to ten weeks every year.

“Steve Roller came through for me with solid research, sound insights and valuable input for a major copywriting project of mine, involving direct-response advertising encompassing every medium: print, direct mail, internet, and broadcast.”

– Dan S. Kennedy, Consultant/Copywriter, Best-Selling Author, No BS Series,

In addition, I also have a knack for teaching, training, and coaching. Over the past couple years I’ve worked one-on-one with a number of beginning and intermediate copywriters, helping people get to the next level. (Check out Café Buzz to see what other writers have said about me.)

“Steve is my go-to guru!”

– Gail Coleman, freelance B2B copywriter

Besides the Ultimate Writing Retreat™, I’ve also conducted eight two-day workshops already this year called The Copywriter’s Workshop. Attendees in Portland, Seattle, Boston, Hartford, St. Louis, Kansas City, Denver, and Las Vegas gave me high marks on both the content and how it was delivered.

Ready to register? Again, there are only five spots left, so go here and take care of it. Then come back and check out the itinerary and information about Chicago below.

Retreat Options

Chicago Ultimate Writing Retreat™ Itinerary

I’ll send you a full detailed itinerary before the Retreat. This is a rough outline:

Wednesday, June 19

We’ll have a “Meet and Greet” with food and drink starting at 6 PM in the Starburst Suite at the Hotel Allegro. Come earlier if you want to hang out and talk shop – I’ll be coming in early Wednesday afternoon.

Evening kick-off session (I told you this wasn’t a typical conference – we’ll be writing and doing things at odd hours.)

One-on-one brainstorming session with our guest expert, the “creative instigator.” This could set the tone for your whole retreat experience.

Thursday, June 20 and Friday, June 21

For early risers, meet me in the funky Hotel Allegro lobby for a really early writing session or a run down Michigan Avenue. Then …

Breakfast, followed by an intense morning of workshops. We’ll duck out at least once for a quick jolt of inspiration. Since we’re in Chicago, we have to take advantage of what’s out the front door.

Afternoon writing lessons and exercises. Time for individual writing and copy critiques.

Visits to Second City show, architectural boat tour, Water Tower Place, and the Art Institute will be interspersed into our days and evenings.

Dinner will be as a group at least one night.

Evening workshop time.

Saturday, June 22

Catered breakfast

Writing, reviews, two more sessions.

Wrap-up and send-off.

Finish by noon, with some of us sticking around longer to hang out and watch the Cubs at Wrigley Field, head to Navy Pier, shop along the Magnificent Mile, or rent kayaks from Urban Kayak and do some more river exploring.

The ideal Chicago hotel for the Ultimate Writing Retreat™

I’ve secured a block of rooms at the Hotel Allegro, a very nice boutique hotel where we’ll be doing the retreat (see for details.) Many hours and days went into finding and reserving the right spot.

Keep in mind, this is the second major city in the U.S., it’s high season, and we’re in a great downtown location. Their normal rates for these dates range from $249 to $399 a night. I have a block of rooms reserved at $219 a night for either a double double or a king premier.Double roomThese won’t show as available on their website, so you’ll have to call to get your room. Tell them you’re with the “Ultimate Writing Retreat™” and they’ll give you the special discounted group rate. The double rooms sleep two, of course, so if you know someone else who’s attending the retreat you can save money and share a room.And get this – every room comes with a yoga mat. Seriously.Yoga hotel

Go to for more information, and call them at 312-236-0123 to book your room.

Travel and Transportation Information

If you’re flying in, O’Hare is the best choice and least expensive (airport code ORD). There are always good deals at the travel sites like Priceline, Kayak, Travelocity, etc. Southwest often has cheap flights into Midway airport (MDW), but it’s a little further out than O’Hare.

On May 13 I found flights on Priceline from DC, Atlanta, Fort Lauderdale, and Albuquerque to Chicago, all for $265 or less.

From the airport, CTA trains run frequently to downtown and are only a few bucks (see for schedules), or you can easily grab a shuttle or cab.

My personal preference is to skip flying all together and take the Amtrak train right to Union Station. From there it’s a quick eight-block cab to the Hotel Allegro. Check out

Feeling really adventurous and want to see the country? Take a bus. A long trip from Atlanta to Chicago, for example, is only $89 each way on VanGalder is one that I use often to go to Chicago. On any of these, you want to get to Union Station in Chicago, the main hub.

However you arrive in Chicago, I know the city well and can help you with travel details. I’d advise against driving, since parking downtown is pretty expensive.

Local weather and what to wear

Chicago’s weather is absolutely perfect in June. Normal averages are low of 64° and high of 82° that week. Bring a light jacket or sweater for evenings and in case the hotel is cool. We’ll be casual for the meetings, no need to dress up. Some Chicago restaurants describe their dress code as “business casual,” so keep that in mind. I try to avoid looking like a tourist wherever I go, so I stay away from shorts, white socks, and tennis shoes (unless I’m playing tennis.)

What to Bring

A laptop or iPad if you have one (free WiFi at Hotel Allegro), a current project if you have one (or just an idea or two if you don’t have something you’re working on now), and an open mind and willing spirit! This is going to be fun, inspiring, and productive.

Questions? Email me at or call me directly at 608-848-COPY (608-848-2679).

I look forward to being your host, retreat leader, and tour guide at the Chicago Ultimate Writing Retreat™! Thanks for registering.

– Steve

P.S. I guarantee this will be the best, most productive three days of writing you’ve ever had, or your money back.

The Chicago Ultimate Writing Retreat™ will infuse you with new ideas to get you thinking bigger, and techniques and tips to not only make you a stronger and faster copywriter, but a better writer, period.

Come with an open mind and either a current writing project or an idea – an ebook, a rewrite of your website, a special report, a non-fiction book, a money-making website.

Return home from Chicago with a framed-out project, possibly a lot of it done, and the tools to finish it quickly after the Retreat.

Take advantage of the easy three-pay plan and Early Bird discount from now through June 4. Again, only five spots remain and I’m guessing they’ll go fast.


Retreat Options

Your satisfaction is guaranteed. If by the second day at noon (Thursday) you don’t feel like the Ultimate Writing Retreat™ is the right fit for you, I’ll refund your money (minus a $75 processing fee) and you can enjoy the rest of your weekend in Chicago.
Cancellations prior to the retreat will receive credit for another retreat if it’s within 30 days of the event, half credit and half refund if it’s 30-60 days out, and a full refund if it’s more than 60 days out.Thank you for registering for the Ultimate Writing Retreat™.