Vision 2020: 12 Questions to Look Back & Plan Ahead

by | Dec 5, 2019 | 0 comments

UPDATE: There’s a brand new set of questions for Dec 2020/Jan 2021! Get them here: Before you kick 2020 to the curb ask these 12 Questions

Now back to original post for Dec 2019: a version of this article is also now published at the Globe and Mail

Wow. Another year soon to be behind us. Swoosh!! Where did it go? If you have been following me, you know it’s time for my annual “12 Questions” — guided reflection prompts to help you complete your year and plan ahead.

This year is a little different (well a lot actually!) — We are on the cusp of a whole new decade. 2020 has a nice ring to it doesn’t it?

As we complete a decade and get set for another, this year brings an even more salient opportunity to learn from the past and lean in with intention towards the future.

We live in an increasingly high-pressured, and frenetically paced world of work and life. Reflection is not a luxury (although it feels like it is) — it’s a necessity for resilience, efficacy, and overall well-being.

If you are a leader, aspiring leader, and/or simply anywhere in the continuum of your career (and life) and just want to live and be your best, then this is for you: reflection with intention can help you be more impactful, mindful, and intentional in your work and life.

A Few Tips for This Year’s Reflection: 

Before we get to the questions, here are few tips on how to make it work for you.

  • Cast your reflection as wide or narrow as you like. You might want to consider the year behind; or perhaps cast a wider glance at the whole decade. Or do both if you are ambitious!
  • Take your time and do a question or two at a time. And no need to do all of this in order. Start with the questions that speak to you first. That said, I do encourage you to include at least some questions for the year (or decade) past as this might inform thoughts for your future.
  • Write vs. Just ‘Think’. Whether you like to write out these reflections electronically or on paper, the act of writing gives you a deeper experience vs. just thinking in a fleeting way. You can also review what you wrote later on as a helpful touchpoint.
  • Solo or with others in your life? Some people have shared with me that they like to do the questions with their partners or other family members, and/or friends. This is a wonderful opportunity to connect and to share ideas and plans for the future.  Think about who  you might share this experience with. And no need to do ALL the questions together. Maybe pick a few. This could be a wonderful conversation during the quiet days of holiday time.
  • Take these questions with you throughout the year. Each question can be asked at any point and for any timeframe. They need not be reserved only for the end or beginning of the year.
  • Be generous with yourself. T’is the season after all and who wants to be a grinch when reflecting your past and future.  Dig in to find those nuggets and positive moments. I promise – if you do, pay-offs await with a greater sense of meaning and an aspiring vision for your professional and personal well-being.

Okay, ready? Here we go!

12 Questions for your “Vision 2020”

Look Back…

1) What went well?
A staple in our annual question bank, this one can (and should) be asked all year-round. It might seem counter-intuitive if you’ve been having a tough time of late but when frustrations and challenges are top of mind it’s even more important to intentionally notice the good.  Our brains are built with a default to hold on to what is wrong and didn’t go well. Bringing focus on the good balances your perspective and provides more meaning to your year and life.

2) What do you need to acknowledge yourself for?
How often do we default to our own inner critics chastising us that we didn’t do enough or ‘coulda shoulda’ done better? Or we wait for others to praise our accomplishments?  Ditch that self-limiting narrative and, instead, celebrate your wins – large and small. Not comfortable acknowledging yourself? Do it anyways. An emotionally intelligent leader knows how and when to meaningfully acknowledge others — and themselves — to boost resiliency, motivation, and growth. If you are stingy with yourself, you may not be as generous with others. Practice, starting now!

3) What growth opportunities made you different and better this year?
Did you learn new skills? Develop a new leadership competency, or a healthy new habit? Grow from a tough challenge? Sometimes we grow by intention and other times by simply dealing with what life throws at us. Recognize your growth from all opportunities including the silver linings in the tougher moments. You can leverage this awareness and growth in the year ahead!

4) What needs to change or go?
Celebrating the good doesn’t mean we ignore what’s bad or no longer working. Recognize what is no longer working, needed, or must evolve?  What do you need to confront and let go of? Where do you need to be proactive to make change?

5) What was your impact on others?
Whether it be through your leadership roles, volunteer life, or simply by showing up with others — you made a difference. Hopefully for the better. Reflect on who you’ve had an impact on and what that meant to them and to you.

6) Give the year (or decade) behind a theme:
Celebrate and complete your year by giving it a theme. Complete this phrase: This was the year (or decade) of ________________”

Look/ Plan Ahead….

7) What do you want and are willing to invest effort in?
What do you really, truly, want for the year (or decade) ahead? Reflect through the lenses of your highest priorities, values and aspirations. What somehow keeps getting pushed to the side? Separate wishful thinking from genuine, meaningful aspirations. Then focus on what you can and will do in the year(s) ahead to bring this to the fore.

8) Where will you focus your attention?
There’s a war on attention these days. We multi-task, are distracted with enormous loads, say yes automatically, and get lost in time-consuming digital, social media mazes.  More than ever, we need to harness the competency of focused attention by setting ‘attention intentions’. Need to put more focus on your people vs. just tasks? More on your goals and higher priorities? More on what’s good and well in your work and life?  Pick at least one or two things to pay less attention to in the year ahead and one to two that you will focus more attention on.

9) Where will you intentionally stretch yourself?
To grow we must stretch — our minds, capacities (responsibly), and beyond our comfort zone. What will stretch mean for you this year? New habits, skills, responsible risk-taking? Rewards await: More confidence, experience, and expanded horizons just ahead!

10) How will you do more “We”?
While independence can be a virtue there’s a saying that ‘we go farther together’.  Today’s paradigm of work calls for more collaboration and greater connection to inspire success, engagement, and better results. Reflect on who you need to connect with more often and more meaningfully. Consider both your internal work network (teams, colleagues, other) as well as outside of work (volunteer, broader network, family, and other communities).

11) How will you give back generously? It’s said that those who give more get more in return. Where and with whom will you be more generous with? Your team? Your community? Family? In networking – pay more attention for how you can help others and you’ll likely be rewarded back.  Make generosity a priority!

12) What’s your word or phrase for your “Vision 2020”? What word or phrase captures your intentions for the year (and/or decade!) ahead? Complete this phrase: This will be the year of _______________.

UPDATE BONUS (in January 2020): Guess what? There’s a 13th Question — and a VIDEO!! Check it out here:

The 13th Question (Article and Video) for 2020 

Here’s to a wonderful, intentional, and reflective year-end and year ahead.

Want more like this? Are you a leader (aspiring, emerging, experienced) — or perhaps simply see yourself a leader in your own life (awesome!) and want to be your best in the continuum of your career and life? Join my community and get first priority invites, articles, and all kinds of goodness. Join a zoom hub gatherings on interesting topics; take in a webinar; You won’t be bombarded with excess emails (I don’t have time to do that!!). But you will be first in the know to hear of special invitations, get cool stuff (like these 12 Qs) and much more.  

Eileen Chadnick (@Chadnick) is a certified coach (and workshop facilitator) specializing in career, executive and leadership development and a communications pro (20+ years of experience). Principal of Big Cheese Coaching and Chadnick Communications in Toronto, Eileen draws from the disciplines of positivity, neuroscience, emotional intelligence – and Conversational Intelligence®(C‐IQ®) in her work as a coach, consultant, trusted advisor, and facilitator. In addition to authoring the book, Ease: Manage Overwhelm in Times of Crazy Busy, Eileen is also a contributing leadership and careers columnist with the Globe and Mail



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