A Habit of ‘Win to the X’ for Writers, Professionals, Small Business Owners…All of Us

Photo by peterkai at 123rf.com.

Up your win-win mindset to an exponential level

Not either or…and! Not you over me or me over you…us! We all know what win-win is — securing positive outcomes for both parties rather than one side winning at the other side’s expense. It’s naturally a great attitude for success in relationships and business, and it’s an important habit for those of us like writers, freelancers, solopreneurs, and small business owners who need to stretch every marketing task and interaction into as much win-potential as possible. The good news is that once you get going it’s very easy to boost win-win to “win to the x” (can’t do superscripts here), that is, get some exponential winning underway.


Bookseller Javier Ramirez and author Keir Graff run Publishing Cocktails, a bastion of winning for everyone involved. Publishing Cocktails, which will presumably resume after the pandemic, is a regular drinks night in Chicago for authors, editors, booksellers, publishers, publicists, marketers, librarians, and devoted readers. Getting this particular crew together is fundamentally based in symbiotic admiration and opportunity, but J&K keep going. Every event takes place at a different locally-owned bar (boosting another favorite cause of theirs — supporting the local economy) and sometimes they tie their event with cash mobs: Before we drink together and engage in some key schmoozing, we spend money together . . . at a local bookstore. Afire with winning.

One of my go-to’s of uber-winning is hiring a trusty Uber driver I once met to deliver large book orders. The minute it becomes cheaper to pay him to deliver books than to send them by FedEx, I give him a call. He makes more than his typical hourly rate (win) and for me it feels great paying an individual directly rather than dripping another deposit into FedEx’s corporate coffers (win). Then, not only do I save money on shipping (win), I save time by not having to specially prepare the books for FedEx — reinforcing box seams with extra tape, filling out online forms, and printing labels (win). Finally, my customer gets their books sooner (win) and with a greatly reduced chance of damage (win). One time, I received an order at 3 p.m. on Thursday, I texted Max about his availability (he was available), and by noon on Friday, my customer 100 miles away had safely received ten cases of books. I saved $10 on shipping and an hour of time, pleasantly surprised my customer, and gave a guy with a newborn some extra money and an easier day’s worth of work.

Here’s a starter idea for anyone promoting a book — adapt as necessary for your product, service, or creative output situation— to get the hang of instigating a chain of wins. Before your next book signing, visit the store and take a photo of yourself holding up your book (if there’s a splashy display for your event in the background, all the better). Introduce yourself to the staff and ask if you can send them the photo for event promotion on their website, on their social media sites, in their newsletter (spell it out for them). Use the photo yourself on your own social media sites to promote yourself, your book, and the upcoming event. Send the photo to a local paper and a local blog to see if they’ll also cover the event. At the event itself, take another photo and repeat.


You may have heard of Triple Bottom Line companies? They measure their results by how well they measure up not just on profit, but in terms of people (their employees, customers, and vendors), and the planet (sustainability, low-impact). They are on this exponential winning track, and their three Ps provide a framework for running through types of extra winning.


  • Am I making money? Enough?

  • Am I saving money? Getting a better deal? Getting real value for this expense?

  • Are the other partners in this transaction also making money or getting a good value for what they’re spending?


  • Are those who work with me better off for it? Have I added value? Expanded their network or opportunities? Improved their mood, their products, their profitability?

  • Have we improved our relationship with this transaction, joint project, team effort? Increased trust, understanding, and mutual appreciation?

  • Are there others who can be included in this win? What do they need?


  • Have we minimized or offset our environmental impact?

  • Have we considered possible externalities of our decision, undertaking? How do we address that cost?

  • How can we improve our surroundings and community as we do this?


For you:

  • Attunement. However you do it. Start absorbing the idea that there are rippling powers of winning in most of your writing, professional, small business, living-life activities and interactions.

  • Use the next couple of marketing activities on your list, whether social media tasks, events, media pitches, or other, to practice supercharging win-win. How can you add more value for yourself and others in the way you carry out your marketing?

  • Over time, create checklists for the building blocks of your business to capture and systematize winning approaches, always leaving room to add new inspirations as they arise.