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Chasing Freedom

If you think about it, it's a fascinating dichotomy how entrepreneurs throw their blood sweat, tears, and pretty much everything else into building their dream company - all while chasing the ultimate goal of freedom. Lets do a little reality check here: you work an insane numbers of hours, take on inhuman levels of stress, and bet your ASSets, all to be free to do the things you want to do - if you can ever find the time. Sounds pretty crazy when you really look at it, but I'm right there with you chasing my version of freedom.

Contrary to popular belief, this "chasing freedom" thing really isn't about escaping your company to travel the world, live in a cabin by a lake, pursue your hobbies, or be with family. It's about the freedom to chase your dreams and reach your full potential. It's about the freedom to truly test the limits of your abilities - and to do it on your own terms. Yes, this chasing freedom thing is as profound as it is life changing.

Here are some no-compromise thoughts on chasing freedom:

  • Define your end game: Think of it as your BHAG (Big Hairy Audacious Goal) - your vision on steroids. What do you want your company to be worth when you sell it? What do you want your career and professional achievements to look like? What do you want to be remembered for? How do you want to change the world and the lives of others? Freedom is about all of these things and more. Freedom is choosing your path and what you want to do with your life.

  • Understand the trade offs: Freedom has a price. Building an extraordinary company will require sacrifice. It always does. I remember the times I had to leave my son's little league games to catch a plane somewhere. I remember going weeks without a break, and there are times I still do. I loved my 30-foot sailboat, but I had to sell it when Strategies really took off. It was time to drive my company, not my sailboat. Freedom doesn't mean having everything you want.

  • The clock is ticking: Actually, the clock is ticking faster than you realize. Before you know it the kids are grown and your business is all grown up too. This September 13th, Strategies will be twenty years old, but it seems like only yesterday that I first started my company. Achieving your end game means achieving many milestones. That means getting things done today, not tomorrow. Procrastination is the killer of otherwise extraordinary end games.

  • Make course corrections: There is no direct pathway to freedom. Sooner or later, you will encounter roadblocks and setbacks. You will find that tactics and strategies that worked wonderfully yesterday are no longer effective today. Part of chasing freedom is knowing when to make course corrections. Sometimes small course corrections are enough, but there are times when major course changes must be made. All major course changes require leadership, courage, and tenacity. Fear of change and staying on a bad course means surrendering your freedom to fight for what you want most.

  • Recharge: Leaders need to recharge their batteries in order to perform their best. It's fine to take on extended periods of intense work if you balance it out with time to recharge. Taking an extra-long weekend off can do wonders. Put some vacation time on your calendar. Take a few afternoons off to do something fun, or to do nothing at all. Respect your body and your mind. If you keep saying, "I have no time," than you will never have time to recharge.

  • Be relentlessly curious: Part of the joy of freedom is the ability to be relentlessly curious - to explore new opportunities and ventures. Companies must evolve and adapt to survive long term. That means the company you started out to build may look very different from the one that will exist near your end game. As a leader, you must evolve with your company and always view yourself as a work in progress. Being curious and getting to explore different ways of doing things is one of the many gifts of freedom. Don't squander it.


Chasing your version of freedom is what leadership and growing a company is all about. It's what no-compromise leaders do.

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