18 Insightful Questions to Help You Steer Your Year

insightful-questions-for-new-yearIf you’re not paying attention, you could end up in a much different place in life than you actually want to be. That’s why reflective practices are so important to make sure you’re participating in the direction of your life.

There’s no better time than the beginning of a year to reflect on what’s going well for you — and what might need to change. For those of you interested in self-improvement, checking in with yourself at least once each year is a must if you want to make positive changes in your life. And what better time to assess how things are going, reset your intentions, and find focus than the New Year?

How do you determine exactly what’s going well, what to change, and what to focus on to create more success and fulfillment in your life? Start by asking yourself these important questions.

  1. What’s one thing that’s going really well in my life right now?
    Focusing on the one thing — that has no hesitations or shadows — can uncover a lot of magic. What elements and flavors are present in this one thing that you can cultivate in other areas of your life? Paying close attention to the best things in your life — no matter how big or small — will help you bring more of those feelings into other areas of your life, too.
  1. How do I spend my time?
    If your main goal is to write a book, but you spend two hours each day cleaning your house and only two hours a week actually writing, your time spent is not in alignment with your mission. Your time is precious; take a conscious look at how you pass your time to make sure you’re spending it wisely. Try keeping a time log to discover how much time you’re actually spending on different tasks.
  1. Do I have trouble falling asleep?
    What’s keeping you up at night? Is your mind racing about a particular problem or issue that keeps you up? Assess your bedtime thoughts to see what is nearest to you. Are you eating, working, or spending time with your screen too close to bedtime? Assess your bedtime routine to ensure it provides enough space for winding down before bed.
  1. Which relationships are most valuable to me?
    Take a look at the important players in your life and notice how much quality time you’re spending with them. Are you putting enough effort into the people and relationships that bring you the most value and joy?
  1. Are there any relationships that are not offering me value or joy?
    Are you spending time and energy on people and relationships that don’t offer reliability, trust, joy, or value? If you let go of those relationships, or place less energy on them, you’ll have more quality time for the people who appear in your response to question #4 — those relationships that are most valuable.
  1. Do I feel tired or fatigued most days?
    Getting enough sleep is one of the best things you can do for your health, and one of the most overlooked priorities. People sacrifice sleep for TV, work, and fun all the time, and in return, end up tired and stressed. Take a look at your sleep habits to make sure you’re getting your Zzzz’s.
  1. What is one emotion or mood that shows up in most of my days that I don’t appreciate about myself?
    Do you find yourself frustrated, sad, angry, lazy, greedy, jealous, guilty, shameful, impatient, or bored too often? What are some things you can do, people you can spend time with, or activities you can begin that will counter that constant mood or emotion?
  1. What is one mood or emotion that I would like to experience more in my life?
    Joyous, ambitious, hopeful, content, proud, courageous, enthusiastic, relaxed, peaceful, accepting …. Are you craving any of these positive emotions? If so, outline some things you can do to cultivate them in your life. Hint: Think of the things in your life that DO offer those emotions.
  1. If money, time, responsibilities, or location were not an issue, how would I spend a day off?
    Where would you be, who would you be with, and what would you do? Outline your ideal day in chronological order, starting with when you wake up. Notice the things you identify in this perfect day — how can you bring more of the essence of those activities into your everyday life?
  1. What is one bad habit I would like to break this year?
    We all have bad habits, whether they are detrimental to your health, your relationships, your career, or your mindset. What is one of your bad habits that you would like to declare a thing of the past?
  1. Where do I see myself in 5 years?
    Who do you want to be 5 years from now? Envision yourself in all capacities … where do you work? Where do you live? What do you look like? Dress like? Who are you with? What is your mood? Visualize your future ideal life.
  1. What’s the biggest mistake I made this year?
    Identify the mishap, your role in it, what you learned about yourself through making this mistake, and what you would do differently if you were in the situation again. Was it also your biggest lesson of the year? (If not, what was?)
  1. Is there anything in my life I are currently saying YES to, that I should be saying NO to?
    Are you a people pleaser? Do you often find yourself overbooked or overwhelmed because you too often say YES when you should say NO to requests? Follow this advice to evaluate your habits around your promises and commitments to see if they are working in your favor. 
  1. What is the one thing I fear most in life?
    Is there a fear or worry — reasonable or not — that is not only present in your life, but also seeping into multiple areas of your life? Is it getting in the way of your relationships, career, or happiness in some way? In what ways can you face the fear to overcome it?
  1. What does success look like to me? Describe it personally and professionally.
    Do you have a clear vision of what personal, professional, financial, and relationship success looks like to you? How do you measure it? Describe success in each of the key areas of your life, with as much detail as possible.
  1. What obstacle(s) is in my way of achieving success?
    Is anything getting in the way of your success? What might you be able to do to troubleshoot or remove this roadblock?
  1. What motivates me more than anything else in the world?
    What drives you? What do you dive deep for? Take a look at the times when you feel most inspired and driven. What are some recent memories you have that hold those emotions? What were you doing and who were you with? How can you infuse more of those enthusiastic feelings into your day-to-day life?
  1. Who inspires me most in life? Why?
    Notice the person or people who you admire most. What about them is inspiring? What are they doing that you are not doing? In what ways can you learn from them and use them as role models?

Spend some time reflecting on these questions anytime you sense a need for change, whether or not it’s the New Year.

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Melissa Eisler

Melissa Eisler, MA, PCC, is an ICF certified executive coach. She partners with leaders to develop their systems thinking, resilience, strategic communication skills, and executive presence in order to reach individual, team, and organizational goals. She blends more than 15 years of experience in leadership positions in the corporate world, with her master’s degree in organizational leadership and extensive background in mindfulness to help her clients master their leadership skills and steer their teams through challenges and change. Learn more about Melissa here.


  1. Lisa on January 17, 2017 at 5:28 pm

    Hi Melissa. Another good post. I just did a blog for the New Year that focused on #13. Hope you check it out. Here’s to a great 2017! Lisa

    • Melissa Eisler on January 18, 2017 at 10:19 am

      Thanks, Lisa! Wishing you a wonderful 2017 as well. 🙂

  2. Roe Corbin on January 18, 2017 at 5:53 am

    Excellent list of questions to reflect on. Thank you for sharing.

    • Melissa Eisler on January 18, 2017 at 10:19 am

      Thanks Roe! Happy to hear you found the list helpful.

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Melissa is the founder and executive coach at Wide Lens Leadership and a Partner at Evolution. As an ICF Certified Executive Coach with a Master's degree in organizational leadership, Melissa has coached hundreds of leaders ranging from C-suite to entrepreneur, from Fortune 500 companies to startups, and across diverse industries. Her work focuses on helping high-performing senior leaders and their teams magnify impact by building trust, collaboration, accountability, and healthy communication skills.