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20 Questions to Help You Reach Your 2020 Goals

Scheduling time for reflection will never be a waste of time

By Megy Karydes

When making New Year’s resolutions, some people choose to set an intention or goal and some choose a particular word to help them stay focused. Others, like Chicagoans Tracy Marks-Seglin, founder of Strategic Words Communications, and her urban planner husband Dave, think about what they want less (and more) of in the coming year and write those things down.

New Year's
Credit: Adobe Stock

Regardless of how you approach the start of a new year, you’ll likely reflect on the past year and how you can make the coming one better. Since we’re entering a new decade, this type of reflection can take a bigger meaning in 2020.

So, here are 20 questions that can help you reach your goals in 2020 and beyond:

1. How do I define success? This may differ each year, so think about your definition for 2020.

“A lot of the time, we set goals to please other people: a spouse, family member or colleague.”

2. What am I most proud of in the last year — or the last 10 years? Start 2020 by celebrating your wins, says Amy Throw, president and chief encouragement officer with Amy Throw Group, a Saint Charles, Ill.-based coaching firm for women.

3. What did I enjoy doing the most in 2019? And what didn’t you enjoy? Don’t waste those learnings. “If you jump into 2020 without taking a moment to reflect, you can't leverage 2019's lessons and insights,” says Cathryn Lavery, productivity expert and founder of BestSelf Co., a personal development firm in Austin, Texas.

4. Whom do I want to become? “This is a deeper question that once answered, allows you to set up a lifestyle, and consistently improve to get closer and closer to your goal,” says Jody Michael, executive coach and founder of Jody Michael Associates, a coaching and consulting firm in Chicago.

5. What are my nagging regrets or unresolved issues from this year or earlier? Michael Hyatt, author of Your Best Year Ever and former chairman and CEO of Thomas Nelson Publishers, encourages people to write these down. Then, he says, consider what you can do in the coming year to address them.

6. What do I want more of in my life? Tracy Marks-Seglin and her husband, who are 54 and 58 respectively, write the answers on strips of paper on New Year’s Eve. Then, they hang the strips in a triple-ziplocked bag (to protect them from the elements) from a backyard tree and open them the following New Year’s Eve to see how many came to fruition. “At that point, we’re either really happy or mildly disappointed,” Tracy laughs.

7. What do I want less of in my life? Marks-Seglin and her husband repeat the above exercise of writing these things down on strips of paper. But rather than hang these from a tree, they burn them in the fireplace. “Burning the things we don’t want is so visceral and feels so freeing,” she admits.

8. What do I want to focus on? That’s a question suggested by Rebecca Kiki Weingarten, a professional and personal development coach at New York City-based TradeCraft Coaching and Consulting.

9. What can I stop procrastinating? Create a list of the “I SHOULDS” that you keep delaying and ask yourself what’s holding you back, says Throw.

10. What goals do I want for my own life, not for others? “A lot of the time, we set goals to please other people: a spouse, family member or colleague,” says Hyatt.

11. What support systems do I have in place to help me reach my goals? And, conversely, figure out the roadblocks to plan for; note these so you can think through strategies to deal with setbacks and slumps, says Weingarten.

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12. What is one new thinking pattern I can discipline myself to use in 2020? Throw says that knowing this will require developing new habits.

13. What is one good habit that I have? Look for ways to better profit from it.

14. What is one habit I want to change? After you come up with this, determine how you can fix it.

15. What is one behavior or activity I will say NO to in 2020? Coming up with the answer will make it easier for you to say YES to an activity that will get you closer to your big bold audacious goal, Throw notes.

16. How can I parlay what I love doing into other opportunities? Marks-Seglin takes a hard look to identify what makes her happy personally and professionally. Then she works backward to think of ways she can incorporate these into other parts her life.

17. How can I be 1% better today than I was yesterday? For Jennifer Wisniewski, a certified life coach in Chicago, New Year’s resolutions seem to be more about the goal than the process. “If your concentration is only on the outcome, you will probably give up before that goal is reached,” she says. Use the “1% better” marker to focus on the present rather than looking at the future for your happiness, she advises.

18. When am I most relaxed to properly give myself the time I need to go through this process? Schedule the time, so it’ll happen.

19. What is the one big, bold audacious goal that gets me most excited? Throw says: Think how can you employ your natural skills, experience and successful behaviors to work toward this goal.

20. What can I do right now or in the next day, week or month, to help reach my one big goal in 2020? The hardest part for some people is getting started. “It can take longer than you thought it would to make real changes happen,” Weingarten says.

These 20 questions might be too many — or too few — for you. But you can use them as a starting point to help identify what makes you happy and what you need to put into place to help reach your 2020 goals. Good luck!

Megy Karydes is a freelance writer whose work has appeared in Politico, Forbes, Fortune, USA Today and elsewhere. She is also an adjunct professor at Johns Hopkins University, where she teaches graduate-level communications courses. Read More
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