15 Questions to Make 2020 Your Best Year Ever

by Kristin Hedstrom


The last week of the year is one of my favorites. It might be chilly and dark, but I love reflecting on and savoring the year that just wrapped up and getting all excited about what’s to come in the next year. You too?

Have you ever gotten so excited about the next year that you set lofty resolutions, only to let them drift away as the months passed?

Have you gotten to April or September or December and wondered what those resolutions even were?

We often make resolutions that sound great but don’t take time to plan out how they’re going to fit into our lives, what achieving them will look like, and why we care about them.

Resolutions are like vague wishes. Like, this year, I’m going to lose weight, or be happier, or meditate more. That’s all great, but they’re not specific. Goals, on the other hand, are clear. If you’re looking to change your life, goals are where it’s at.

It just so happens I’m a big believer in goal setting. It was a huge part of how I got to the Olympic Games in rowing. The beauty of goal setting? It can be applied to everything, whether it’s establishing a workout routine, losing weight, improving your relationship, or finally making that career change.

It’s a simple process that will get you exactly where you want to go.

Since you’re 40% more likely to reach goals that you write down (yup, it’s true…how insane is that?!), I’ve created an Annual Goal Planning Worksheet that walks you through each step of the process.

Download your Annual Goal Planning Worksheet here

Print it out, grab your favorite pen and cozy up with a cup of tea. It’s time to step into your awesome.



Do you ever have years that go by in a flash? It can seem like a moment in time, but we forget how much can actually happen in 365 days. Before you start crafting goals for next year, I want you to reflect on this past year for just a moment. My New Year’s Eve tradition with Hans is to go through the year month-by-month and recap all the things that happened in our lives. It’s fun to think back on the memories we made, places we went, and things we were able to accomplish. And more importantly, it sets the stage for what we each want the next year to look like.

So what happened for you this year? What was your year like? Here are six questions to get you thinking:

  1. What were the three moments that defined this year for you?
  2. What was the accomplishment you’re most proud of?
  3. What as the most fun moment of the past year for you?
  4. What were you most grateful for in the past year?
  5. What was the most important lesson you learned this year?
  6. What were the trips you took this year?

Fill ’em into your Annual Goal Worksheet.



You’re on a roll! Now think about your big picture for next year. Think in general terms, not specifics just yet.

What’s important to you in the coming year? Have you been feeling overrun and want more meditation and chill time in your life? Have you had a big dream in the back of your head that you want to start moving towards? Is now the time to build a healthy lifestyle? What does that mean for you?

Once you’ve got some general ideas, let’s start categorizing. I want you to think of a couple important things you want to move towards in each of these categories:

  • Health/Wellness – this could mean hydration, healthy eating, how much you want to weigh, sleep quality, or limiting screen time before bed.
  • Fitness – this could mean weekly strengthening and cardio workouts, completing a race, like a 5k, yoga, or joining a team
  • Family – this could mean spending time together, helping your kids with their dreams, limiting screen time, vacations, or gathering around the dinner table a certain number of times per week.
  • Career – this could mean managing your email more efficiently, starting a side business, hiring an assistant, or taking a continuing education course.
  • Finances – this could mean allocating funds to areas you feel are most important, learning more about investments, protecting your investments, or long term planning
  • Mental / Emotional – this could mean meditation, journaling, dancing, talking to a counselor, or spending time with your spouse
  • Fun – this could mean taking a wild adventure, planting a vegetable garden, going on regular bike rides, or beautifying your home

If there’s another category that’s important to you, add it in too.


Finalize Your Goals

Now that you’ve got some ideas for each category, it’s time to nail down the specifics.

For each category, think realistically about your year. Define ONE specific goal for yourself. I know all the ideas in your brainstorm might sound super exciting, but I want you to narrow it down to what’s most important to you. Be specific with it. What exactly do you want to achieve in this area? What clearly defines success with this goal?

By the end of this, you should have seven goals that you’d be thrilled to have achieved by the end of the year – and you’re fairly certain you can get.

The last few questions are probably the most important.

Of the seven goals, what’s the most important one, and why?

Now think ahead to what this might look like for your year. What actions can you start taking TODAY to get yourself closer?

Now that you’ve thought through all these goals, it’s time to think through the nuts and bolts of achieving them. One of the best things you can do is to calendar out specific actions that will help you get there and decide on your progress checkpoints.

Click here to grab your Annual Goal Worksheet

Then, stay connected to your goals throughout the year. Share your goals with friends and family who will help keep you accountable. Post the sheet on your dresser or fridge, where you can see them every day.

Now’s the time to own your awesome. Go out there and get it.