Playing it Safe

So many people walk through life playing it safe — they have dreams and desires far beyond their current cubicle, yet rarely ever take risks.

It’s been nearly two years since I played it safe. I would take calculated risks within the safe environment of cubicle land, but the most I had to fear was being reprimanded by a boss or coworker. I continuously quenched the fire burning within me, but I was losing a piece of my soul.

Everything changed when I finally took a leap of faith and risked it all.

I’ve invested countless relational hours into friends with dreams. And there’s a common denominator among the ones that take great leaps of faith versus the ones that don’t. The ones that don’t take leaps of faith talk a lot about what they are going to do tomorrow, and rarely bring up what they should be doing today.

Gary Vaynerchuck calls it hustle. And I agree.

Break it Down

If you want to find success you don’t need good intentions, you need a plan. And plans require goals and steps followed up with action.

Here are 6 steps I try to keep in mind:

  1. Know what your passions are and make sure they are your own.
  2. Ask others to affirm or reject your vision of yourself.
  3. Take an inventory of things you enjoy that relate to your passions.
  4. Spend time creating a vision for what you desire your life to look like.
  5. Ask yourself if someone offered you an extra 10% raise to stay in your current job another year, would you take it.
  6. Evaluate your answers and determine if now is the time to take a risk.

Remember, there is no good time to take a risk. Conflict, stress, money issues, bad relationships, slow drivers, etc. will all still exist.

Risk Everything

Many of my friends have gone through all the steps above and are still working in their cubicles. I did this for years too because the final piece of the equation is the hardest — risk.

Risk has to cost something. It might cost you a location. A relationship. Pride. A deflated ego. Embarrasment.

In my case, the risk I took would have cost me everything. I left a full-time job to embark on my own. My wife stayed at home with our three children so everything rested on my shoulders. And the burden was heavy. I had only $200/month of guaranteed income. Barely enough to cover our cell phone bill. But it wouldn’t have been a risk if I had projects and clients lined up for my new company.

Looking back it’s a no-brainer. But taking the first step was the hardest thing I’ve ever done. And as a result, I understand why it’s the hardest thing many others never do.

Don’t Be Afraid

If you made it this far, I’m writing this for you. My journey is just one speck in a sea of opportunities seized. And my advice is simply don’t be afraid. People have gone before you to help and guide you.

But no matter how much you plan and prepare, everything changes the second you risk everything. And that’s when you need the encouragement. The community. The faith of all those who have gone before.

It’s the best thing you’ve never done, and the best thing you’ll ever do.

The world needs you.


Designer. Innovator. Entrepreneur. Dreamer. Thinker. Believer. Father. Husbander.

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