10 Questions About Your Past That Lead to Your Future


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Is reflection on the past Your key to career Happiness?

The short answer is “H-E- double hockey sticks to the NO”.

(mostly because I love hockey and a little because reflection is not the magic bullet alone!)

But what’s the longer more nuanced answer?

To be clear; reflecting on the past alone is not going to get you where you want to go in your career or your life. It will take intentional action to move toward work that fits you, your values, and your strengths (and even your income expectations). 

But what’s also true is that for the action to be intentional you must know exactly what you want. 

How do you do that? Let’s start by watching the video and completing todays exercise below! 

You can use your past as a platform for the future no matter what your past is like… Yes this is true, all those things that are rolled up in your past; successes, baggage, events, close calls, experiences, jobs, etc.

All of these can either help you move forward OR help you put up barriers for yourself to not move anywhere. It’s your decision!

Today we are going to choose to take steps forward, but before you going laying down on the psychologist’s couch, let’s establish that what we want to accomplish

I want you to have a productive inventory of the past that will help you evaluate your future.

The Questions (… This is the Hard Work)

Below you will find 10 questions to help you evaluate what from your past you want to carry into your future. We’ve developed a handy worksheet version of these questions to assist you! Click to download it here.

Write down your answers to the questions… then dig even deeper by asking “why?”

1. What do I love enough to do for free?

2. What do I do that causes time to feel differently? What causes me to lose track of time?

3. If I had to teach something, what would I teach?

4. What do people typically ask me for help in?

5. What makes me feel great about myself?

6. What do I enjoy regardless of the opinions of others?

7. What are my favorite things to do in the past? What about now?

8. What has hurt in the past that you don’t want others to go through.

9. What were some challenges, difficulties and hardships you’ve overcome or are in the process of overcoming? How did you do it?

10. What causes do you strongly believe in? Connect with?

Bonus Question!

If you were to stop living TODAY, what would you regret not having done already? What would you want people to say at your funeral that maybe they wouldn’t or couldn’t right now?

Next steps
  • Answer the questions above OR Download our handy worksheet version of these questions.
  • Keep the answers to these questions someplace safe (evernote, in your filing cabinet, a google doc, etc)
  • BONUS: Check out these podcast episodes with other people just like you that have already figured out their ideal careers