Start, Stay, or Leave

1. Start with the End in Mind: Define Your Legacy

By creating a clear picture in your mind of your final destination, you will be better equipped to make decisions that ensure you reach that desired place.

Envision the final scene. Begin by imagining your life's closing argument – what do you want people to say about you at your funeral or memorial? This exercise helps clarify what you truly value and what you want to accomplish. It's about defining your legacy, not just your career path.

Accomplishment vs. Activity. There's a difference between what we "do" and what we "accomplish." Accomplishing something requires intent and purpose, a clear vision of the end. It's about making a difference, not just going through the motions. For example, choosing a college major based on what you want to accomplish in life, rather than just what you need to do to graduate.

Holistic approach. Consider all areas of your life – relational, vocational, educational, and personal – when defining your legacy. A well-lived life isn't just about professional success; it's about a balance of all these areas. It's about how you made others feel, not just what you achieved.

2. Look in the Mirror: Define Success Internally

Define success in terms of what you can control—your words, your mindset, your effort.

Internal vs. External Validation. Shift your focus from external measures of success (titles, achievements) to internal ones (character, purpose). The pyramid and ladder models of success are flawed because they rely on external validation. True success comes from within.

Control your actions. Focus on what you can control: your words, your mindset, your effort. Derive fulfillment from the active choices you make, not just the outcomes. For example, choosing to use respectful language in an argument, or deciding to be optimistic about a project.

Self-reflection is key. Regularly look in the mirror (metaphorically) and ask yourself: Are you making decisions for yourself or for others? Will this decision cause a rift in the relationships and things that bring you joy? Will this decision lead you closer to your desired closing argument?

3. What's the Worst That Could Happen?: Plan for Failure

A huge part of wisely deciding to start something new is preparation.

Worst-case scenario planning. Before starting something new, ask yourself: "What's the worst thing that could happen?" Then, create a plan to deal with that worst-case scenario. This approach helps you manage fear and move forward with confidence.

Risk vs. Reward. Don't assume risk is directly proportional to reward. Some risks are just plain stupid. Focus on identifying the worst possible outcome and creating a safety net to survive it. This allows you to pursue your goals without being paralyzed by fear.

Decision-making mantra. Develop a personal mantra to guide your decision-making process. Whether it's "What's the worst that can happen?" or "Do not go through life saying what you wished you had done," having a go-to phrase can help you make better choices.

4. Consult Your Dreams: Balance Logic and Aspiration

When weighing the risks and rewards, pros and cons, passions and obligations, we often discover that there is a dream, a hope, a goal, an aspiration pulling us in some direction despite what others might consider a more prudent course.

Dreams as a compass. When making decisions, don't ignore your dreams, goals, and aspirations. They can be powerful forces that guide you, even when logic suggests a different path. Let your dreams roam your mind as you explore where you want to go.

Logic and dreams as roommates. Logic should take the lead in decision-making, but dreams should be respected and considered. They help chart the longer course, even if they don't dictate short-term decisions. It's about finding a balance between practicality and passion.

Evolving dreams. Acknowledge that your dreams may evolve over time. What you wanted at 20 may not be what you want at 40. Be open to change and allow your dreams to grow and adapt with you. It's okay for your dreams to change, as long as you are still moving toward your desired closing argument.

5. Checks and Balances: Integrate Head, Heart, and Gut

While I am a big proponent of logic-centered decision making, I have learned to appreciate the value that our intuition and emotions play in our lives.

Three branches of decision-making. Like the three branches of government, your head (logic), heart (emotions), and gut (intuition) should work together to provide checks and balances. None should be minimized to the point of having no power.

Taming fear. Fear can be a valuable ally if you use it as a way of understanding the weight, consequences, and risks of a decision. But don't let fear drive the car. Turn it into a passenger by acknowledging it, assessing it, and creating a plan to mitigate it.

Emotions as punctuation. Let your emotions be the by-product of a good decision, not the driver. Use them to warn, amplify, confirm, delay, and ratify what your mind tells you. They can punctuate, not dictate, your decisions.

6. Staying to Build: Commit and Gain Experience

Staying, even when the job, class, or relationship isn’t exactly what you were expecting, enables you to prove to yourself that you are capable of commitment.

Commitment is key. Sometimes the results of a decision are different from what you expected. Instead of fleeing, commit to sticking with it for a period of time. This builds endurance and proves to yourself that you are capable of commitment.

The value of experience. Experience is something you can't rush. By staying, you gain valuable skills and knowledge that will benefit you in the long run. It also builds a reputation for reliability and loyalty.

Look at the film, not the snapshot. Focus on your long-term aspirations, not just short-term gains. Consider the big picture and make decisions that align with your overall goals. Don't be swayed by titles or perceived advancements.

7. The Power of Priorities: Align Actions with Values

When we have clear and unshakable priorities, we can put every other part of a decision—those aspirations pulling us, the pros and cons, the risks and consequences—into perspective.

Priorities as a compass. Priorities help keep you grounded and focused. When you have clear priorities, you can put every other part of a decision into perspective. They help you stay put even when something new and shiny is calling your name.

Dreams vs. Priorities. Sometimes your dreams can conflict with your priorities. When this happens, proceed with caution. Make sure you're not sacrificing too much well-being in one area to achieve something in another.

Compatibility tests. Consider how your decisions will affect all areas of your life: relational, professional, educational, personal, spiritual, physical, and emotional. What are you willing to sacrifice, and what are you not willing to compromise?

8. The Attainability of Dreams: Assess Means, Motive, and Opportunity

When you consult your dreams, it is imperative that you be honest and aware of their achievability, because this is what will inform how big of a role they play in your life.

Means, motive, and opportunity. Use these three factors to assess the attainability of your dreams. Do you have the talents and abilities (means)? What drives you (motive)? Are the opportunities available (opportunity)?

Lunch-hour dreams. It's okay for some dreams to remain just that – dreams. They can be a source of joy and inspiration, even if they're not fully attainable. But don't let them distract you from your day job.

Align ability and desire. When your abilities and desires align, that's when you're on the right path. Focus on developing your strengths and pursuing opportunities that match your passions. It's about finding the intersection of what you're good at and what you love.

9. Find Your Nathan: Seek Honest Counsel

If you want to make the very best decisions in life, you must know yourself, weaknesses and all. And you should have a Nathan in your life: someone who has the nerve to speak to you before you make significant decisions and the courage to counsel and correct you after you make poor ones.

The value of a Nathan. Find people in your life who will tell you what you need to hear, not just what you want to hear. These are people who have your best interests in mind, know you well, and are honest and courageous.

Humbling advice. Be open to receiving advice, even if it's not what you want to hear. Sometimes, the people closest to you can see things you can't see yourself. Be willing to listen and learn from their perspectives.

The opposite of Nathan. Be aware of people who are enablers, sycophants, or those who want to bring you down. Surround yourself with people who will challenge you and help you grow, not just validate your every decision.

10. Shelf Life: Know When to Leave

Sometimes even a job you love and derive satisfaction from comes at too steep a cumulative cost for you or those you care the most about.

Recognize the toll. Some jobs, relationships, or situations have a shelf life. Even if you love something and are good at it, it may come at too high a cost. Be honest with yourself about the impact it's having on your well-being.

Retire dreams. Sometimes, you need to retire a dream for your own betterment. It doesn't mean you failed; it means you're evolving. Let go of old dreams that are holding you back and focus on new goals that bring hope into your life.

Honorable exits. When it's time to leave, find an honorable way to do so. Don't burn bridges or make rash decisions. Focus on making a graceful exit that allows you to move forward with peace and dignity.

11. Assessing Your Environment: Choose Wisely

When you are considering leaving something, it is important to assess the environment you’re in and decide if it is an environment that will lead to your growth or draw you off course.

Environments shape us. Your surroundings play a crucial role in shaping your behavior and well-being. Assess your current environment and decide if it's one that will lead to your growth or draw you off course.

The lay of the land. Be aware of the political and social dynamics of your environment. Are you in a place where you can thrive, or are you constantly fighting against the current? Sometimes, the best decision is to leave an environment that doesn't serve you.

Life outside work. Consider the non-work aspects of your environment. Are you surrounded by people who support you and lift you up, or are you constantly battling negativity and criticism? Choose environments that align with your values and promote your well-being.

12. Selectively Selfish: Prioritize Your Well-Being

Making decisions based on outside forces that may not have your best interests in mind will leave you lost and lonely.

The value of "selfishness." It's okay to be "selectively selfish" and prioritize your own well-being. Don't let the expectations of others dictate your decisions. Ultimately, you are the one who has to live with the consequences.

Trust yourself. Learn to trust your own judgment and intuition. Seek counsel from others, but ultimately, the decision is yours. Don't let the opinions of strangers or acquaintances sway you from your path.

Own your decisions. Take responsibility for your choices, both good and bad. Don't let regret beat you down. Instead, learn from your mistakes and use them to guide you as you move forward.

Last updated: January 19, 2025