Playing the Long Game is a Winning Strategy

I’m learning how to play the long game—a mindset that allows me to make numerous investments now (of time, money, freebies, labor) with the hope that a pay-off I truly want is on the horizon.

At the risk of seeming like a cold-hearted b*tch, a lot of calculation goes into deciding what to say “yes” to now—not out of love and altruism (not exclusively), but as a stepping stone to more; something better, brighter, shinier; a thing I really want to be part of.

Let’s face it: The art world in general, and certainly the writing/publishing world, is often about who you know, who can help you, and who owes you a favor. Such transactions cannot occur in a vacuum; you have to help make something happen in order for something (or someone) to ping back to you.

This sounds cynically reductionist, I know, but it’s also—in part—how the creative world works.

If you’re making art to share with the world, you have to understand what sharing really looks like and how it operates. In the writing world, getting published is just the beginning. There’s your author brand-building to consider; getting in front of readers; meeting other authors, tastemakers, and event organizers who can boost your visibility; and so forth.

To be clear, I’m not simply talking about marketing. The long game is far broader than marketing and takes, well, longer to reach a goal post than, say, posting on Instagram three times a week.

I’m thinking especially of all the effort I’ve put into, say, volunteering for literary organizations as a means of gaining exposure to their membership and building trusted relationships that I can turn to later. Or spending out-of-pocket to travel to a conference, and speak for free, in exchange for making contacts that could land me an even better position at their next conference.

There’s no guaranteed pay-off from doing these things—but there’s certainly the possibility of one, especially compared to doing nothing.

Building goodwill—an intangible commodity—takes planning and effort!

Fortunately, playing the long game isn’t purely transactional. It’s also a solid investment in your skills and your future. Two prime examples of that, which have worked out well for me:

LONG-GAME STRATEGY:

• Teach a bunch of workshops online for a low-end vendor (not well known; attracts writers who aren’t that serious about writing; pays very poorly).

• Pitch better workshop sponsors, drawing upon the earlier experience and good reviews.

• Develop a growing batch of courses that can be taught online and in-person—and grab every reasonable opportunity to teach one or the other.

• Ratchet up again—building on experience to land great gigs at high-end writers conferences that offer good visibility and reputation-building opportunities.

PAYOFF: Land a teaching gig alongside one of the biggest names in the business (go ahead and guess).

ELAPSED TIME FROM GOAL TO PAYOFF: About five years.

LONG-GAME STRATEGY:

• Use my teaching and workshop leadership experiences to hone my skills as a public speaker.

• Stress-test my ability to hold an audience’s attention through hours-long master classes and deep-dive workshops. (Extending my “proof of concept.”)

• Get more comfortable making short video presentations and speaking spontaneously (and cogently) on podcasts. (The long game here involves loads of time and pitching in and of itself.)

• Pitch a couple of high-profile speaking events—and when I’m rejected, use that failure to track what success looks like; identify the likeliest opportunity; attend pitch-orientation meetings to learn more.

PAYOFF: Land an extremely competitive speaking slot with a well-known organization (can’t yet divulge).

ELAPSED TIME FROM GOAL TO PAYOFF: About two years (much longer if you factor in all the run-up skill-building through podcasts, etc.).

Playing the long game can mean doing stuff that feels tedious, but if you’ve chosen well, those seeds will grow into fragrant flowers that bring you joy.

Playing the long game also represents a great investment in your future self, through building and honing skills, raising your confidence, and acquiring a range of experiences that make you a well-rounded creative person.

Playing the long game builds resilience, too, and teaches you to think strategically about what you need now—and what you expect you’ll need in the future.

Be patient. Pick and choose your opportunities—with an eye to their potential. And never stop setting goals to go after, even if attaining them seems years away.

My new novel TENT CITY, is getting some amazing reviews —and now you can download the companion BOOK CLUB KIT, a rich resource for discussing the book!

“Amy L. Bernstein’s powerful novel reflects modern times with a twist, offering powerful insights into groups that used to work together and now find themselves seemingly at odds, but connected in unusual ways.

“The food for thought generated by this social and psychological examination will prove especially compelling for readers seeking literary reflections of present and future dilemmas surrounding haves and have-nots, simmering frustrations on all sides, and the raise of poverty that both births Tent City and portends its ultimate collapse, as well.

--D. Donovan, Senior Reviewer, Midwest Book Review