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10 Questions You Need To Ask Yourself Before 2020

Reflecting on a mountaintop

As we discussed in a previous post, reflecting on your work can drastically improve your career performance. Research conducted at Harvard Business School found that “taking time to reflect on our work improves job performance in the long run” and that “learning from direct experience can be more effective if coupled with reflection”.

Now that we know how powerful reflection can be, what can we do as 2019 comes to a close and 2020 begins?

Reflecting on what you’ve learned this past year can help you more clearly see what you need to focus on in the coming year. 

To help you out, here are 10 questions you need to ask yourself before 2020. If you’re a mentee, share your answers with your mentor and get moving on your goals for 2020. Likewise, if you’re a mentor, share it with your mentee and help steer them in the right direction for the year to come.


1. What are three accomplishments from 2019 you’re most proud of?

Taking note of your proudest moments of the past year can help you better understand how you derive a sense of fulfilment and purpose. How did your accomplishments help move you along the path to where you want to be?

2. Which of your strengths has been best serving you?

We are all born with certain strengths. Identifying what they are and how they serve you can better help you harness them in the future. What are some strengths you have that you like about yourself? How have they helped you move forward?

3. Which of your weaknesses have been holding you back?

Much like strengths, we all have natural weaknesses as well. Being mindful of our blind spots can help us better prepare for them. Which of yours have been hindering you? How can you pivot to either improve them or make them work for, not against you?

4. What were your key relationships this year?

Most often, moving forward is a team effort—it takes a lot more time and effort to try and get there by yourself. Who do you have to thank for your forward progress this year? Who helped you get over a setback or gave you the kind words or advice you needed to persevere?

5. How has your career trajectory evolved in the past year? Where do you see it going in the year to come?

To get to where you ultimately want to be in your career, you first need to identify where you need to be at various stages. This can be accomplished by seeing how your peers are progressing, or learning where someone you admire was at when they were as far into their career as you are now.

6. What were the biggest obstacles or challenges you faced?

Obstacles will always pop up in our paths, but how we overcome them can truly speak to our fortitude and dedication. What were the biggest challenges you faced in 2019 and what did you learn from them—both about your career and yourself?

7. What is the state of your financial well-being?

While money isn’t everything, ensuring your needs are met and being able to live a life you enjoy is. That’s why it’s important to keep tabs on your financial well-being, and if your career is getting you where you need—and want—to be.

8. What are your top three values? How are these serving your work life?

Identifying our values is important, as it can give us insight into what we’re ultimately working for. What would you say are your top three values in life? How are these informing your career?

9. Are you doing work you care about?

Feeling like the work we do matters can give our work—and by extension our lives—meaning and purpose. If you truly care about the work you do, you’ll enjoy an overall sense of well-being that will spill into other areas of your life.

10. What in 2019 are you most grateful for?

Looking back, when did you feel an overwhelming sense of gratitude in 2019? This can be derived from a person, a specific experience, or acknowledgement of something you accomplished.

Have you set your 2020 goals with your mentoring partner? If not, connect with them today to set up a time in the coming weeks that works best for both of you. Being able to not only reflect, but discuss your 2019 reflections and 2020 goals with someone you trust can truly bring what you want into perspective!


If you’re interested in learning more about how Mentorloop has helped over 20,000 users find meaningful relationships which have helped shape their careers, speak to a mentoring specialist today.

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Emily Ryan

Em is our Marketing Manager at Mentorloop. That's a lot of 'm's! | She is passionate about crafting messages, crafternoons and craft beer.

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