10 Questions to Ask Yourself to Create Your Best Year Ever

In a year from now, you’ll wish you started today.

When I want to have the best year ever, I look at this quote. This is one of my favorite quotes because it keeps me focused on what I’m committing to when I procrastinate. Every time I say no to getting up and getting out there, I’m saying yes to missed opportunities; yes to broken promises to myself; yes to feeling overwhelmed later when I feel like I haven’t gotten anything done; yes to excuses – the list goes on.  When I say yes to those things, I’m also saying no to success; no to opportunity; no to connections; and no to myself.

In a year from now, you bet your ass I will wish I had started today.

Throughout my years coaching clients all over the world, the one constant among them is the dreaded new year’s resolution. It’s something we all seem to make and more often than not, all seem to bomb. What typically stands in the way of committing to it an following through is a lack of clarity. Sure, you may know what you want to be, do, or have in the new year, but are you also aware of the habits you need to create to make it happen? Do you know what you need to leave behind to move forward successfully?

In this episode, I’ll introduce you to 10 questions to help you “complete” this year, and prepare you for the new one. I’ll guide you through each step, and you’ll come out on the other side with a better idea of what you really can really do to have the best year ever.

Take a listen and let me know what you think in the comments below. [Subscribe Here]


When you think of New Year’s Resolutions, what comes to mind most often? Is it excitement? Is it a vision of you making the commitment on New Years Eve and then fast-forwarding to you accomplishing it? Or, unfortunately, is it the same sense of dread and disappointment you’re used to year after year?

Look, not all resolutions made on NYE are crap. Some turn out to be powerful moments of clarity and conviction that alter the direction and trajectory of your life. There’s the guy that decided once and for all, to get in shape. He goes on to lose 100 pounds, and improves nearly every aspect of his life.

Then there’s the girl that decides she’s had it with deadbeat guys. She vows to stop being nice and start being deliberate in her decisions. She stops saying yes to maybes and focuses more on finding the right man – a man she has a clear picture of in her heart (and her journal). Fast-forward to December of that year, and she’s wildly in love with a man that wouldn’t dream of spending the rest of his life without her… and has a ring to prove it.

Both of these situations happen(ed). A friend mine from college is the first example, and a former client of mine is the second. They are wonderful examples of resolutions gone right. Their success came because they had clarity in their commitment. They knew what they wanted, and they knew what needed to happen to get there. The following questions will help you get to your goal too.

So take minute, grab a pen, and write these down.

What do I want in the new year?

More than just a sentence, I invite you to write a full page about this question. Unpack your desire in as many words and images as you can muster. What do you really want in the new year? Tell me about it. No really, describe what it is. What will it get you? What will that be like? What’s your day going to look like once you be, do, or have this thing you want? Describe your life with it.

An example of a resolution we hear (and sometimes make ourselves) is, “I want to lose weight.” One of the biggest errors in making this happen is we resolve ourselves to “losing weight” but never get clear in our minds, a picture of ourselves at our goal weight. We see ourselves losing weight, but never weighing or looking our best. We create a resolution based on the journey and not the destination – in the case of weight loss, the destination is the most important focus point.

Get clear on your destination. Get so clear, you can feel it in your body when you think about being, doing, or having what you want in the next year. Clarity is king, my friend.

What do I NOT want?

Sometimes this question is more powerful than the first. The only two reasons people change are because the want is so rewarding or the do not want is so damaging. Think about it for a second. The last big goal you accomplished – did you fight through the inevitable challenges and achieve it because you wanted is badly, or was it because you couldn’t stand not having it any longer?

In many cases, the most appropriate example is a relationship. Whether it’s a relationship with a person or a work relationship (your job is a relationship after all), you know when it’s time to cut and run. “This will be the year I finally quit that stupid job.” When the pain of staying where you are is great enough, you’ll leave. There’s nothing wrong with letting that pain be the catalyst to your big change.

Get clear on what you do not want in the new year. What kind of frustrations do you want to avoid? What pain are you not willing to endure any longer? What is the opposite of what you want? Get clear on what you don’t want so should it show up, you recognize it and change course.

What do I want to leave behind?

This question is more about the beliefs, habits, sensations, and routines you’ve been carrying that no longer serve you – at least in the pursuit of your new year’s goal. Occasionally, this also involves people and/or certain relationships, but the juice lies in what beliefs, habits, routines, and emotions are stirred and strengthened in those relationships.

Year ago, I worked with a client that was trying to get himself into a position of power…for the first time in his life. We’ll call him Bob. Bob was in a relationship that was exhausting and keeping him small. He was raised to be selfless and provide – both admirable qualities – and he ended up taking it to the point of self sacrifice. He couldn’t ask for what he wanted. He couldn’t stick up for himself. He was passed up for promotions and just had to be a “team player” through it all. When we first began working together, he wanted help getting promoted at work, but it was so much more once we explored the beliefs and routines he carried.

His resolution, once equipped with clarity and conviction (found in questions 1 & 2), was to leave behind shame. He felt shame whenever he didn’t bend over backwards for others. He wanted to be a good husband, and when he stood up for himself or argued with his wife, he felt shameful and selfish for wanting something different than she did.

By declaring that he was going to leave behind shame, guilt, heaviness, resentment, and timidness, he took a stand and planted his flag. He told his wife where he was and what he was no longer going to accept. You know what happened? She loved it. She had been conditioned to treat him a certain way, even if she didn’t want to – it just kind of happened. They started working together and a year later, he took a promotion at another company, started getting paid what he’s worth, and his marriage is stronger than ever.

What do I want to take with me?

Now that you’re clear about what you want to leave behind, let’s explore the opposite side. What has worked for you in the last few years? What 5 habits, beliefs, routines, actions make you feel strong, powerful, resourceful, etc.? In the above example, Bob left behind shame and needing to be everything to everyone, and took with him the best parts of who he is: kindness, resilience, big-picture-thinking, resourcefulness, drive, and passion – to name a few.

Get clear on what you want to take with you as part of your arsenal of achievement. You can even take it a step further and think about your relationships as well. Bob wanted to take his best friend Chris with him. Chris is his springboard, his confidant, and his bullshit meter. He was grateful for that level of honesty and encouragement. Who do you have in your life that you want to take with you into the new year? Here’s an episode from 2 years ago that talks about one of the greatest things you can take with you into the new year –> Radical Forgiveness

What am I relieved about?

For this question, imagine yourself a few months in the future. Unless you’re quitting a job and moving far away, in which case you can be literally relieved to never see someone/something again starting tomorrow, relief won’t be realized for a few months. So imagine it’s now March and you’re sticking to your new commitments. You’ve made some changes and are holding onto that clarity.

What are you relieved about? What are you relieved to have left behind? What are relieved to be experiencing now?

What am I excited about/for?

As you look to the future, you must be excited about something, right? This goes back to the hard truth I discussed earlier: you only move if the pain of staying is too great, or if the pleasure of moving is great enough. So what pleasure are you excited to experience? One way to really bring this point home and lock it in, is to imagine being, doing, or having achieved your goal – what is that like? What’s exciting about it?

To use the weight loss example again, imagine the excitement you’ll feel wearing clothes that fit well. See yourself looking down at the smaller numbers on the scale every morning. Imagine the positive attention you’ll receive from others because you look so much leaner and sexier. What’s exciting about that? What excites you most about achieving your new year’s resolution?

What do I anticipate?

When you look to the future, you want to be excited and eager, but you also want to be prepared. Simply staying passionate but ill-prepared means you’ll fail, but may not notice until it’s exhausted you beyond measure. Think of someone that loves camping, but never packs correctly. He’s out there every weekend because he loves camping and nature, but he wakes up in a cold, wet tent. He’s freezing because he didn’t pack the right gear. He goes hungry some days because he didn’t prepare to hunt.

He’s a passionate camper, but he’s not a very good one, right? He may love it, but truth be told… he sucks at it. And so it is with your goal – what do you anticipate in three areas?

  • What do you anticipate before you get started?
  • What do you anticipate along the way?
  • What do you anticipate when you’ve achieved it?

These answers don’t have to be negative either. I anticipate, after you’ve reached your goal, an incredible amount of confidence coursing through your body. I anticipate we’ll need a bigger table at the restaurant for all the people you’ll have at your celebration dinner. I anticipate you’re going to get pretty good at getting things done and setting even bigger goals.

What’s most important for me in the new year?

This is the “moment of truth” question. And there’s a reason why it’s this far down the list and not at the top. If you ask yourself this question first, you’ll answer it differently – it will be less specific, less authentic, and less helpful to you. Now that you’ve explored what you want, what you don’t, what you want to take with you and what to leave behind, and the beliefs, emotions, and anticipation you have in front of you, you can answer this question.

What, above all else, is most important for you in the new year? Is it self-realization? Is it providing more for yourself or your family? Is it breaking through a barrier? Is it stepping up to the plate.

Look, it’s never about getting a better job or a better girlfriend. It’s deeper than that. We both know that. This question is for you to explore the personal stuff beneath the surface of your goal. What will that new job get you? What will getting that damn credit card paid off bring you? What will finally telling that woman at the office that you’ve been in love with her since the day you two met do for you? Go for it, my friend. And know why it’s important to do so.

What will I do if I get stuck?

Now that you’re clear on the landscape ahead, what will you do if you get stuck? Where will you turn when things get difficult? Who do you have in your corner? What resources do you have available to you?

This is your opportunity to get your resources, people, places, and backup identified so when the going gets tough, you don’t cut and run. Know who to call when everything feels like it’s falling apart. You don’t need to have an answer for everything, you just need resources to call upon for brainstorming, support, and balance.

Am I ready to let go and move forward?

While this question may seem silly, it’s a big deal. Many guys will say they’re ready to let go of old habits and commit to their new resolution and path, only to immediately fall back into old patterns the following week. If you’re not truly ready to let go of your old shit, don’t make a new year’s resolution that asks you to. Setting yourself up for failure because you read one article or inspirational quote on the internet and are biting off more than you can chew is a stupid (and frequent) thing to do.

Look, you’ve got it in you to make incredible things happen in your life, but you can only do so if you’re truly ready to let go of what is holding you back and tackle what will elevate you, even if it’s scary. You can have the best year ever in 2018, I know it. Just spend some time cultivating clarity, and commit to letting go and moving forward.

I believe in you. Happy New Year!

What do YOU want in 2018?
What is something you’re proud to leave behind? Any stories you want to share?
Leave a comment below so we can connect!


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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.