How to Stop Second-Guessing Your Choices

Making choices between potentially good options can be one of the biggest challenges in life. Getting stuck in indecision leads to lost opportunities, leadership failure, damaged relationships, and tremendous anxiety.

Few things bring as much relief as getting decisions made. With practice, you can improve your ability to make quality choices. Here are 17 tools to start using today.

17 Decision-Making Tools

Tool #1: List Out All The Facts

I find this tool crucial to sorting through the confusion. Things are fuzzy in your head and much clearer on paper. List all the details, and the right direction might become clear.

Tool #2: Own Your Emotions

Acknowledge how you truly feel about this situation. See your fears as useful signals—they point directly to where growth is possible. Use these questions to gain clarity.
1. Am I acting to protect myself, or to genuinely help others?
2. Am I choosing short-term comfort, or what will be helpful in the long run?
3. Am I acting from fear, or from real concern?

Tool #3: Analyze Your "Not so Great" Decisions

Identify a few life choices you regret. Examine why you made them. Were they driven by fear, people-pleasing, or self-sabotage? Did shame convince you to walk away from opportunities? Did you override your intuition? Every one of these decisions holds insight if you’re willing to learn from it.

Tool #4: Set a Deadline

If there isn't already a deadline, set one right away. Deadlines channel your creative problem-solving abilities. They force productivity, which eliminates indecision.

Tool #5: Error on the Side of Courage

Good decisions come from avoiding the easy. Take a risk. This might mean saying "no" or saying "yes". Sometimes quitting is the most courageous decision. What's the most daring decision in your current situation?

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Tool #6: Talk to Emotionally Mature Friends and Family

Get the opinions of your emotionally mature friends and family. People with enough distance from the issue to give good counsel. Sometimes, family is too close to the issue and to you to be objective. Sometimes they are the best people to ask because they know you so well. 

Tool #7: How Would You Advise a Close Friend

I've witnessed many people make major decisions right after a loss (e.g., Retirement, divorce, death of a loved one, etc.). We don't make our best choices during major life transitions, while depressed, or while grieving. True friends dare to tell us the truth at these times. Be a good friend to yourself. If a close friend came to you for advice on this issue, what would you tell them? 

"Once you make a decision, the universe conspires to make it happen." - Ralph Waldo Emerson

Tool #8: Create & Use Filters

Uncovering and clarifying your core values, life purpose, mission, and vision for your future is an incredibly valuable investment in yourself. They serve as filters for making decisions. Say "no" to decisions that don't align.

Tool #9: Worst Possible Outcome

Write down the disaster scenario for making a specific choice. "If I take this new job/position, I could be miserable and leave within a year." Then describe how you think you'll successfully handle this realistically worst possible outcome. This can give you confidence in your choice, or help you identify that it's a very bad one. 

"Decision is risk rooted in the courage to be free." - Paul Tillich

Tool #10: Deal with Your Past 

Unresolved past trauma keeps people stuck. Living immobilized, often subconsciously, believing that will keep them from getting hurt again. Many only make reactive decisions or continually let others decide. Gaining awareness of how your past impacts you today can clarify the right path.

Tool #11: Listen to Experts

Accountants and attorneys have saved me from costly mistakes. Utilize trusted experts for direction. Many experts have laid out steps to follow. Buy their books, listen to their podcasts, and read their blogs. Here's a list of my favorite books, many with expert advice.

Tool #12: 5 Minutes, 5 days, 5 months  & 5 Years

Imagine you made a specific decision. Write down how you think you'll feel about this choice in 5 minutes, 5 days, 5 months, and then years later. I discovered this great tool in an excellent book called Decisive: How to Make Better Choices in Life and Work by Chip & Dan Heath.

If this was helpful, SUBSCRIBE TODAY and get instant access to my free video and worksheet: Shatterproof Yourself — 7 Small Steps to a Giant Leap in Your Confidence.

Tool #13: Trust Yourself

Intuition is the most crucial decision-making tool of all. This unexplainable thing inside that's much wiser than the voice in your head. Your intuition won't lead you astray, but anxiety will. Slow down, get space, and follow your instincts. 

"Intuition is more powerful than intellect" - Steve Jobs

Tool #14: Detach

Do something to detach from thinking about the decision. Go on a walk, listen to your favorite music, or engage in a favorite hobby. Prayer and meditation are ways of "letting go" of the outcome. Detaching gets you in touch with your intuition.

"In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing" - Theodore Roosevelt

Tool #15: Fight Perfectionism

Is wanting to make a perfect decision holding you back? Perfectionists won't decide unless they can do it perfectly. Fight this tendency! On a scale of 1 to 10, be satisfied with a 7. Permit yourself to make the best choice possible, fail, and learn.

Tool #16: Listen to Procrastination

Don’t see procrastination as a flaw. See it as information. It may be telling you that you’re not the right person to execute this decision—or that the decision needs more input. Sometimes procrastination is simply a signal to slow down, involve your team, and ask for help.

Tool #17: See Failure as growth

Reflect on how you've grown from decisions that didn't end up with the results you hoped for. The only bad failure is one you didn't learn from. Failure means you tried, learned, and you're growing. This mindset toward failure takes away the pressure.

"My greatest concern is not whether you have failed, but whether you are content with your failure." - Abraham Lincoln

Every decision has consequences. Mistakes are part of growth—unless you keep repeating them. When a risk doesn’t pan out, don’t beat yourself up. Be gracious. Step back, use these tools, and make better choices going forward.

Your move. What decision are you wrestling with? You have 17 tools—use them, decide, and grow.

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