Transitioning Life: The Tombstone Test

What’s written on your tombstone? Think about it. What does your epitaph say? Is that what you want it to say? More about that in a minute.

Over years of doing this, I've learned not everyone has the courage to dream of a life fulfilled. Even fewer have the determination to make it happen. If you find yourself wondering how you can live that better life, you are not alone and I'm here to tell you that you can. I’ve had a lot of conversations with people about how to “transition life.” What it takes to leap off the precipice of fear and learn how to land, hopefully, in a place that is more rewarding, fulfilling and meaningful.

First, let me establish my street cred in this area: I’ve died (yes, you read that right, see my TEDx on Life 2.0 for more), started three companies, almost gone bankrupt from the risk, left multiple jobs without a safety net, moved across the country several times, had significant personal strife, and coached dozens of people about how to change their lives. In short, I know something about the art of changing your life. I have struggled mightily at times and have found my way through it—and in between, I have lived a life worth living. My story is not without pitfalls and plot twists; it has plenty of perils and provocations. But it also has positivity, perspicacity and passion. You can too. Whatever your circumstances. But it takes determination, courage, strategy and pain to get to there, and I want to share what I’ve learned through that—and what I most commonly hear from others looking to leap.

7 Keys to Changing Your Life

Despite the many types of transitions I hear people looking to make (job, love, life, etc), the key elements to making meaningful life change are usually similar:

  1. The Tombstone Test. For people who are searching for “the meaning of their life," consider the Tombstone Test: what would it say on your tombstone if you were to die today? What would you WANT it to say? If you can figure out what you want your tombstone to say, you have just found your meaning—or at least an important step in the right direction. Consider whether that epitaph matches how you currently spend your time. If not, how can you change that?
  2. Twenty Seconds. That's what's required: twenty seconds of insane courage. You need to find the courage to ask for what it is you really want….and it will seem insane at the time. Let your heart speak for twenty seconds and say what you mean, need or want. It is the start. The jump. And it is where most people choke or fall short. Just know that this is what’s required. Just twenty seconds--for the rest of your life.
  3. Unhappily You. People will accept unhappy circumstances for their entire lives because they are afraid of change and the unknown—this is true—and science. Think about that. People will spend their lives in a generally disappointed, disenfranchised and occasionally miserable condition because they are more afraid of the unknown than unhappiness. Many people think a state of dismay is ok—and should be expected. That is what you’re fighting against as you transition, and why many others will not understand your choices. That’s ok. This is about THE REST OF YOUR LIFE. Have the courage of your convictions and remember that other people's opinion about you is none of your business.
  4. Warning: Anger Ahead. In a similar vein, people will be angry at you for changing your life. There are a multitude of reasons for this including fear of change, pain, self-interest, and many times an unwillingness to acknowledge that they wished they had the same courage. Misery loves company. Just let the haters hate and keep moving. One foot in front of the other. Be strategic and deliberate. Slow and steady. And shed the energy vampires.
  5. Handle Anxiety and Worry. The future creates anxiety and the past is embedded with worry that will paralyze your decision-making. Don’t pre-suppose HOW the future will unfold and don’t allow the past to shackle you, but instead, consider what it is you want and what it might feel like to have it. Don’t trust to hope, but be intentional about taking steps to move towards that future and remember that you deserve happiness, fulfillment and a life worth living.
  6. Don't Be Fooled! It's not easy. Don’t shy away from the pain you will feel. Part of living life—in truly living—is knowing that even the hard things deserve their day. Leaving a job, breaking up or putting yourself at risk is uncomfortable, but no great adventures happen without sacrifice. And feeling pain is not a bad thing—it is the very definition of being human. Just don’t mistake pain and guilt. Guilt is not productive, but pain is. Give yourself time every day to feel the pain of your situation so you can acknowledge it and move on. I did this by watching the sunrise and sunset over 300 times in a year so I could spend the time I needed to feel my days. That allowed me to move on more quickly.
  7. Celebrate Your Life and Share. As you begin to move down this bold new path, remember to share your experience--good and bad--with others. Be candid. This is not easy and each journey is unique, but it is incumbent upon us to share our journey with others. That is part of the cosmic code. Don't ask me why, I've just learned it is. Share what you learned with others and celebrate your wins with others along the way! It makes it more fun and meaningful.

In the end, I've learned there is nothing easy about making a big, scary life transition, but it's also not as bad as you think. The truth is it takes persistence and determination to change your life and most people will continue to move down life's offered path with very few deviations, but if you are a Map Maker, willing to plunge off into the unknown, I hope these tips will help you along your journey!

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