When I was a junior in high school, I was pretty sure I wasn’t ready for college. While other kids were preparing for the SATs, I was practicing my nun-chuck skills in our back yard while dreaming of becoming a professional archer who was also an astronaut.
“You’ve always had lots of sides to you, Chris,” my mom told me. “And while that may not be great for school, it will help you in life.”
She was right (sort of).
Dr. Jekyll and Mr. Hyde
If you’re like me (and most entrepreneurs I know) you have multiple personalities. I think they fall into two broad categories: Dr. Jekyll—the technical, buttoned-down, applied side of running a business—and Mr. Hyde—the chaotic, visionary, and creative side.
They don’t always get along well together, but every good entrepreneur needs them both. And if you don’t have both skill sets, you need to work on developing them everyday. Even if you can later give some of these responsibilities to others, you still need to know them well enough to manage the folks who are helping you grow your business.
Here are my five rules for managing entrepreneurial personality disorder:
1. Give Mr. Hyde some space. Create time to be creative. If you are an entrepreneur who hopes to change the world or develop something revolutionary you need to add a significant amount of creative thinking and problem solving to your schedule. This goes beyond just finding time to work on the business rather than in your business. You need to tap into a shaman-like level of inspiration and problem-seeing. Where this comes from is as varied and personal as the entrepreneur. One technique I use comes from the playbook of both Salvador Dali and Thomas Edison: the short power nap. I find all sorts of ideas for business problems in the fluid nether world between sleep and wakefulness. Daydreaming works too.
2. Put a time limit on Dr. Jekyll's analysis sessions. Dr. Jekyll wants to investigate and know that something is sound before moving forward. Remember that as much analysis as you do, you’ll never know if something is going to work unless you try it. Do the best research and data collecting as you can but don’t let it stop you from moving forward with real life testing and experience gathering.
3. Find a place where Dr. Jekyll and Mr. Hyde can test their ideas together. This is a tough one. It gets to the core of the entrepreneur’s risk tolerance. How do you balance Dr. Jekyll’s need for certainty with Mr. Hyde’s desire to take big risks? Finding a safe way to test your ideas is key. Can you find a customer who is willing to try something new with you so that your tests can turn quickly into real business? Can you test portions of your ideas so that all your eggs won’t be in one basket?
This obviously applies differently to different kinds of businesses (high R&D businesses will have different needs than less capital intensive businesses) but the concept is the same: Find a way to safely figure out if your creative ideas jive with the business analysis and economics. And always consider how the structure of your tests can create revenue to potentially fund the next step of testing or development. The best way to know if a business idea, or even if a portion of it, is sound is if someone will use it and ultimately pay you for it.
4. Explain your personality disorder to those around you so they know who you are when you are different. I find that this rule is often overlooked but it is important when building a business culture. Many of your employees are going to want stable leadership. The nature of a growth-oriented CEO or founder is to create a level of applied chaos to stimulate that growth. This is in conflict with creating a stable culture. Thus you need to let people know that you have multiple sides and will let them come out to serve different functions. When setting Mr. Hyde loose on others, let them know why you are doing it and what the bigger picture looks like. Make sure that key managers provide stability so your applied chaos doesn’t get in the way of business.
5. Master self-criticism. Dr. Jekyll and Mr. Hyde are in a constant tug of war as you hone in on ideas that work and discard those that don't. Self-criticism acts as an important referee that is constantly checking in between the two personalities to make sure that neither one gets too far out of control. This referee is important, especially when people you respect are telling you that you are doing great. Be skeptical of the things that you are sure are right, and know in advance that all of your ideas are not genius.