When you work for yourself there will be times when you’re working by yourself. While building Jump Ship we’ve heard from people who have gone into business for themselves say that’s one of the hardest challenges. On one hand, owning a business means that you don’t rely on others to make decisions, but it also means that you, alone, must determine priorities and direction for the company. It’s not difficult to do but from our experience, it can lead to many rabbit holes of working in circles while wearing the blinders of a single perspective and self-doubt.

Large companies hire a board of directors to help guide leadership decisions. And while that accepted practice is generally useful, it’s not very plausible for a company of one. But, what if it wasn’t?

Years ago, about a year into forming Second Wave Dive, Ryan was struggling a bit with making decisions alone. While we had plenty of conversations about business decisions he was working through, I wasn't always able to meet with Ryan when he needed different perspectives relative to his own in real time. During one of these conversations, I had an idea to help inspire a different perspective for Ryan when I couldn’t be there.

Enter the Imaginary Board of Directors

In the 1990s, you might recall seeing people wearing yellow rubber wristbands stamped with the acronym, WWJD. The wristbands were created to give young people a way to guide their decision making by asking the rhetorical question, "What would Jesus do?" While I never participanted in that subculture the idea is simple and sound. Give people a way to check their judgement in the absense of having someone around to guide their decision making.

So, I thought, why not take this idea and apply it in a different way so that when I'm not around, Ryan can ask some hypothetical questions that gives him a path forward. Intead of relying on a single persona, let's make it a handful of people from all walks of life who inspire through their struggles, achievements, and outcomes. And, what if the group included places and things with qualities and attributes that you admire? With those prompts, Ryan got to work and assembled an Imaginary Board of Directors that included artists, leaders, coaches, zines, characters, and a Walkman.

As you can see in the photo, his Imaginary Board is rock stars like David Bowie and Freddie Mercury alongside Wierd Al Yankovich. The group includes Dori Tunstall, former dean of faculty at OCAD and design anthropologist from the University of Texas, his burlesque instructor, Coco Lectric, Pew Scholar and MacArthur Fellow Donella Meadows, and a good, life-long friend Jeff. In addition, these very real people are just the opposite. Prince Vultan (whose line, “Second wave, dive!” was the inspiration for the company), the Atari game Pitfall, book covers for Nudge and On Strategy sit next to a pair of Chucks and a Sony Walkman from the late 80s (there to remind him of his freedom to go in his own direction). 

After about thirty minutes, Ryan has a board of directors that he can channel at any time to guide his decision-making. Strong symbols to help keep him out of the rabbit holes and moving in the right direction. Especially when having to work alone.

How to Staff Your Own Imaginary Board of Directors

Because of the grounding effect this exercise had on Ryan, we included it in our new Restart workshop. It’s one of the first activities to help get participants in the right mindset to think and dream about the future. 

We begin the activity with this introduction: “Your Imaginary Board of Directors is a fantasy board of business, creative,or inspirational people who will assist you in overcoming your business challenges. Moving forward, when you have a challenge, consult the members of your board and imagine how they would solve it.”

This is followed by a simple prompt: “Think of 3-5 movers and shakers, living or dead, whom you admire most.” Who’s work, art, or activism inspires you? Who had to push through adversity to achieve greatness or maybe just get the job done? Who’s the story that will give you energy during the tough times? Remember, these are folks that you’ll someday ask yourself, What Would [Director’s Name] Do?

Adding fictional characters and objects aren’t necessary, but they do make this exercise fun and the results can be interesting. Look for a few things that have traits you’d like to see in your own business. These can also be things, likely from our past, that shape who we are today and remind us of who want want to be tomorrow.

Hold imaginary board meetings

Your imaginary board is there when no one else is around to help you think through a question, idea, or situation. Ryan turns to his board when he's writing and finds himself editing the same text over and over again. Dori Tunstall reminds him that he gets to define what words mean for him. While Weird Al reminds him that there are no “B” cuts when working on a project—"Once I decide," says Al, "it’s exactly what I set out to do." You can gain a lot of helpful perspective by asking your board questions.

The best way to do this is to use interrogative words or the Five Ws: Who, What, When, Where, Why, and How?

Let’s use Ryan’s board of directors to ask all kinds of example questions:

  • Who would Bowie collaborate with on this project?
  • What would this look like as a zine?
  • When would Queen say no to this gig?
  • Where would Dori Tunstall go for more information?
  • Why might Donella Meadows say no to this project?
  • How could this service create a sense of freedom for customers?

Keep in mind these are just examples but you should get a sense of how you can take what’s in front of you and with the right interrogative question, gain a different perspective or insight that you might not otherwise have. This is certainly true when, as business owners, we find ourselves working in circles.

You still need to connect with real people

Use your board often, but remember that this method should be used when you can’t get out of a rut and no one is available to listen and help you think through the challenge you’re facing. It’s important for all of us going into business—those who are years into running their business—to connect with people on a regular basis. or you’ll run into burnout. Lastly, keep in mind that while you selected the members of your Imaginary Board to help guide you, they come from some part of your existing perspectives. Seek out people, real people, to help broaden your views.