45 Questions You Must Answer Before 2017 Rolls In

9 min readDec 30, 2016

Let’s be honest 2017 won’t look very differently than 2016 unless we ask ourselves tough questions, and then face the potential ramifications of our answers. I’ve outlined some of the questions that would stop me in my tracks and encourage me to rethink core assumptions. Give them a try and let me know how I can help you as one human to another — not some coach trying to land a client. The string that connects these reflective questions is that they are meant to shake up your thinking. I’ve categorized them so that you can easily hone in on the section (s) that matter most to you.

Relationships

My hope in outlining these questions is for you to stop the preventable consequences of not nurturing your relationships — with others as well as yourself. Your community matters. It is affected by your behavior. Take the time to consider how you can enhance your community now so that it’s lifted in 2017.

What would you hate to see happen to your loved ones in the next 365 days? How do you intend to shield them from these possibilities?
What relationships do you value least today? If you had to shift your energy from increasing their value to strengthening your most valuable relationships, then what change in your behavior (s) would that require?
If your princess or prince charming does not arrive in 2017 or leaves you — how will you feel? What would you do? Would you be worse or better off?
What if you could foreshadow that your child will pick up one of your worse habits in the next year? How far would you go to break this habit in the next few months so that this does not happen?
Thinking about your legacy — what is your legacy as it stands right now? Are you living up to your expectations? What about your family’s?
Who was there in 2016 to help you through your biggest disappointments? How have you returned the favor? Who can count on you and do they know this?
How did you handle coping with hypocrites in 2016? In what ways were you hypocritical? How do you plan on working on that or accepting your ways?
What if you turned into one of your parents — who would you not want to turn into and why? How can you change your circumstances today so that you prevent this highly likely outcome?
If you could bestow one talent of yours to your children — what would it be? How would you want them to use it? How would you feel if they stored it away and never used it? What if they didn’t fully tap into its potential? Where are you with this talent — fully used up in its potential?
If you could meet anyone of your ancestors — whom would it be? What would you hope to learn from them? How can you capture and secure that same information so that your future generations will be in the know?

Financial Success

It should be easy to list our current assets — a great career, investment properties, academic degrees, etc. I think up until the 2008 financial crisis many of us took for granted that these assets would always carry their worth. The reality is that despite being well-guarded against extreme levels of poverty (I’m thinking about my career coaching clients in particular who earn upwards of $125K USD), we should proactively find ways to mitigate financial risks. These questions are about laying out some “what if” scenarios. They should help you think more creatively about diversifying your balance sheet in 2017.

If you could tell your boss to go walk off a short plank on January 3rd with zero regrets — what would you do next?
Who do you secretly admire at work or in your industry? Have you told them that they impress you? I encourage you to, with the greatest details possible, let them know they matter to you and why in 2017.
How would you treat your subordinates differently if they could directly influence whether or not you secure your next promotion?
If you could give Jimmy Fallon (or anyone who is popular) one great idea that would absolutely go viral then what would it be? What’s stopping you from giving it to him? Ignore whether you think it’d really go viral. It’s a great exercise in talking to folks who might have seemingly “hard-to-achieve” levels of success in their categories.
How about if I told you that the only way to achieve success is by having uncomfortable conversations every day for the next 90 days? Could you stomach these chats?
What if you had a rich aunt / uncle that you never knew existed and they passed thus leaving you with oodles of cash — what would you do with that money? What would you definitively not do with that money?
What if your employer fired you sometime during the first 30 days of January — would your financial house be in order? Could you make it on unemployment?
What if you had no bills to pay in 2017 — where would you invest your income? How would you invest your time? What one bill can you cut in 2017?
What was your greatest investment in 2016? Think about its short-term return. Are you happy with your results?
If you lost one of your greatest assets, then how would you make up for that loss?

Well-Being

If you are physically incapable of walking more than 500 feet or unable to manage anxieties or lack strategies that can help you live a healthier lifestyle today (or for the last five years consistently) then what makes you think that all of a sudden when the clock strikes midnight on January 1st that you will change your lifestyle into one that supports a healthier one? My goal is not to dissuade you from trying to change. My motivation comes from being someone who lived a grossly unhealthy lifestyle for many years until I focused on my mental well-being. I honestly think a change in health requires more work in your brain than in your pantry. I’ve outlined some questions meant to pick your brain however rather than buy that diet solution in January — start by dealing with your mental well-being first — spend the time and money there. Tune out the diet ads.

What if your doctor told you that the medications that you’ve been taking are placebos then how would you aim to address your illnesses?
What if I told you that you could run faster or jump higher or outdo a top personal competitor in any sport in the next 365 days — would you do what it takes to make this happen? What do you think it would take?
What’s going to stop you from buying those sweets, treats, or anything bad for you? If it didn’t stop you in 2016 then what’s going to stop you in 2017?
How do you want to start out your next 365 days? In great detail, map out your aspirational morning routine — think about the most imperfect Tuesday morning.
If you had a standing daily appointment with yourself let’s say from 9 to 10 pm then how would you use that time to improve the quality of your life?
If you were diagnosed with a mental illness, then who would you trust to tell and help you? What vulnerabilities exist in you that you should shield in order to protect your mental well-being? Who would suffer most if you ignored your mental health?
What if you knew that you were going to die of heart disease by the age of 60? How would you change your habits today if you could prolong your life by an extra ten years?
What have you done when others have disappointed you in 2016? What pacifier did you turn to — drugs, alcohol, food, sex, etc.? How did it pacify your disappointment? How did you feel once its effects wore off? Plan on using the same “tools” in 2017?
If you lost one of your senses in 2017 — which one would you miss most? How would you cope with the inability to do X (ex.: smell, touch, etc.)? How would you use this sense in the last remaining hours of 2016?

Limitations

We all have ideas about what is possible as well as impossible given the truths, lies, and things we’ve been told. I want you to question these ideas. How else can we shift our thinking if at our core we are following a set of firm assumptions? It’s also important to play a little mental gymnastics by thinking about what it would it like if these truths didn’t exist? This section is meant to stretch your thinking. Have fun with it.

What if I told you that the rules (not law-breaking sort of rules) we’ve been following have simply been made up to organize us as a society or to retain someone’s profit margins but they have no bearing on how you should behave? Think more like rules on superficial deadlines, company policies, removing those tags off of pillows, etc. Which rule would you bend and why?
What decisions worked out in 2016? In what ways are you better off? What decisions should you face in 2017? Which do you plan on putting on the back burner — yet again?
What if I told you that your greatest weakness as defined by anyone else — a former boss, a parent, a mentor — didn’t exist. You never failed in that arena. What opportunities did you miss as a result of this belief? Now, thinking ahead, what opportunities would open up if you had no weaknesses — at least not those ones.
If everything you assumed about your personal success was flipped upside down, then how would you approach your most ambitious goals in 2017? For example, if you didn’t need a degree to land that gig or if you didn’t need to invest so much money to fund a prototype then would you move forward in 2017?
What stopped you in 2016 from feeling happier than you wish you had been? What’s going to stop you in 2017? How can you catch yourself and stop yourself from feeling less than optimally happy in 2017?
What opportunity did you miss out on in 2016? What skill was missing? How do you plan on preparing yourself now so that you don’t miss a similar opportunity in 2017?
If you knew your friends wouldn’t judge your decisions in 2017 then how would you prioritize the biggest decisions you’d like to make? How would you decide them?

Advantages

I want you to move forward in 2017. It requires that you think about what you learned in 2016 (and even before then). The goal is that you outline your learnings and use them to proactively better prepare yourself for what lies ahead.

When was the last time you had to be brave — really brave? How did that turn out? How did you ready yourself to step up to the plate? What if you had to do it again in 2017 — what shortcuts would you take to get ready faster?
What was so special about 2016? What if 2017 was even more special? What would it take to make it so?
If you could replay your favorite song over and over and out of that jam session come up with your best New Year resolutions — who would you be playing? Would you dance? What would be your first resolution?
What pissed you off most about the 2016 presidential campaign? What did you learn from that experience?
What in 2016 did not go in your favor? What was the REAL impact of that disappointment? What strategies will you try to address disappointments in 2017?
If you could have great clarity on one aspect of your life — career, relationships, faith, etc. Which realm would you choose and what would you hope to learn?
If you could have saved yourself from one moment of embarrassment in 2016, which one would it have been? Seeing how it happened and now you have to contend with its ramifications — how can you shift your thinking and move forward beyond that moment?
If you could go back to one defining moment in 2016 and change your reaction — what event would it be? How would you have changed your reaction? In what ways could you imagine being better off today as you enter 2017?
What disappointments are you bringing with you into 2017? What do you intend to do about them? How can you let them go?

Take these questions for a spin. Was there any section that stirred up the most emotions? Chances are you should prioritize working on that one section soon. Spend some time on the last day of 2016 if you can rethinking how you want 2017 to play out. Now, I’m sure you have some questions of your own.

What questions popped up for you — what should we be asking ourselves now so that 2017 is a better year? Just consider that we all have one thing in common — we all want 2017 to outperform 2016.

Share your thoughts in the comments section below.

Originally published on www.CareerOutcomesMatter.com.