The end of the year is just 5 weeks away! Being the goal digger that I am, of course, I’m already planning for 2020. While I think it’s important to enjoy these final weeks of the year (and the decade!) by spending time with family and friends, I believe it’s also important to have some alone time to think about the year ahead.

In fact, I’m scheduling a Dreaming Day for myself in the coming weeks. On this day I am going to go somewhere quiet with my journal and favorite pen in hand and answer some important questions about my hopes, dreams, and plans for the future.

Here are 20 questions you should answer for yourself as you begin to prepare for 2020.

What’s your word for the year?

I asked this question on Instagram at the end of last year and that post received the most comments of almost anything I posted in 2018. People love answering this question and so do I. Picking a word for the year can really help you set your intention for the year and truly focus.

What do you want your life to look like by the end of the year?

Stop chasing dreams that are not your own. Get clear on your vision for your life. Take some time to write down what you want every area of your life — your career, your relationships, your health, the finances, and your spiritual life — to look like by the end of the year.

What are my specific, measurable, measurable, achievable, realistic, and timely goals for 2020?

After you have a vision for your life in 2020, create a list of goals to make that vision a reality.

What 2019 goals did you not achieve do you want to work on in 2020?

If these goals weren’t already covered in the list you made after working on your vision, add them to the mix. But be careful not to have too many goals for 2020. The fewer goals you have the more time and energy you’ll have to give to each one.

What has kept you from reaching your goals in the past?

Having too many goals is exactly what has held me back in the past. Maybe for you, it’s a lack of consistency or commitment. Or maybe you’re being hindered by fear. Do some soul searching and figure out what’s standing in your way.

What did you achieve in 2019 that made you feel proud?

So often we’re so busy planning for our next set of goals we don’t take the time celebrate what we’ve already accomplished. I’m certainly guilty of this. So I’m going to spend some time during my dreaming day giving myself a pat on the back for what I’ve already achieved.

What has helped you be successful in the past?

Focus. Focus, Focus. When I look back on my biggest successes in life the key to accomplishing my goals has been focus. Maybe for you it’s been accountability or staying in touch with your “why.” Figure out what’s helped you achieve your biggest goals in the past and how you can bring that into 2020.

What smaller steps do you need to take to achieve your goals for 2020?

Break down each of your goals into smaller steps so you don’t get overwhelmed. Consider adding a deadline to each of these tasks if you have a tendency to drag your feet.

What will be your focus for each quarter?

You can do it all, but not all at once. So decide which goals you’ll focus on each quarter of the year.

What healthy habits will you adopt in 2020?

If you’re not healthy and happy, working on your 2020 goals will be tough. So start developing habits now that will nourish your mind, body, and soul. Meditate, journal, exercise, and drink more water.

Related Reading: Five Healthy Habits for 2020

What bad habits do you need to break in 2020?

Just as healthy habits can propel us forward, bad habits can hold us back. Are you wasting too much time scrolling social media or watching too much TV? Consider what habits you need to get in check.

What fears will you conquer?

Perhaps there are goals you haven’t accomplished because you’ve been too afraid to take the steps necessary to do so. If so, it’s time to put your big girl panties on in 2020. It’s time to feel the fear and do it anyway.

What thing have you been putting off will you finally do in 2020?

Most likely, you’re procrastinating out of fear, not laziness. So just decide you’re going to do it scared and go after whatever “it” is. For me, it’s starting a podcast. For you, it may be going live on Facebook or Instagram or public speaking. If you’ve been putting off starting a blog, be sure to check out my new course, See Jane Blog. Use the code BLKFRI now through Black Friday to get 50% off!

Are there people you need to spend more time with in 2020?

You know the saying — teamwork makes the dream work. In 2020, surround yourself with people who will encourage and support you as you go after your goals. Make an effort to spend more time with friends and family, too.

Are there people you need to spend less time with in 2020?

Next year, make sure you’re spending time with people who lift you up, not pull you down. If there’s someone disparaging and discouraging you, it may be time to cut them loose.

What things will you do to have more fun in 2020?

People wiser than I often say, “Don’t get so busy making a living that you forget to make a life.” So in 2020 try to do something fun every day or at least every week, even if it’s something small.

What new experiences do you want to have next year?

Along with everyday fun, plan some adventures and new experiences, too. Maybe you’ll take a trip to a city or country you’ve never visited. Or maybe you’ll finally try axe throwing!

Who will help hold you accountable this year?

Do you have a friend or family member you can share your dreams with who will keep you on track? Perhaps you’ll share your goals with a community that you’re a part of, like the See Jane Write Network Facebook group. Or maybe you need more structured guidance from a coach. I am currently accepting new clients for 2020. Email me at if you’re interested.

What planner will you use in 2020 to hold yourself accountable?

I, of course, will be using my Day Designer. But remember the magic is in the planning, not the planner. That pretty, expensive planner you bought is pointless if you don’t use it! If you’ve had trouble in the past consistently using a planner, sign up for the See Jane Write 7-Day Planner Challenge.

How will you celebrate all of your 2020 successes?

Show yourself just how confident you are that you will slay your year by planning RIGHT NOW how you will celebrate when you accomplish each of your goals.

What other questions are you asking yourself as you prepare for 2020?

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