Part 1: The Power of the Past

Everyone makes mistakes, and we all fail at some point. It’s tempting to try to forget these failures, pushing them to the backs of our minds. But the mistakes we make lead us to better choices, and ultimately help us discover our True North. That’s why the past is the first thing I’m going to examine in this six-part series to help you determine what it is you’re looking for at this stage in your life – and the steps you need to take to get there.

While you don’t want to be a prisoner to the mistakes of your past, you do want to carefully examine your experiences for takeaways you can apply to your present and future. With that in mind, consider the following questions:

1. What is your biggest regret? If you could go back and have a ‘redo,’ what would you change?

Be careful with this question. It’s easy to get caught up in the many ways your life would have changed if you had made a different choice. The point of asking yourself this isn’t to follow the domino effect of doing something different, and any rosy fantasy of the future you missed out on is just that – a fantasy. Instead of focusing on ‘what could have been,’ think about why you made the decision that you made. Did you make the best choice at the time? Hindsight is always 20/20, after all, but you may have had to make do with the information at hand at that moment. On the other hand, maybe you made a legitimately bad decision. If so, why? Did you ask for advice from others? Did you get advice, but ignore it? Learn something from the mistake you made and move on.

2. What did you like to do when you were 10 years old? When was the last time you did that activity?

Soccer practice, arts and crafts, the school play…what did you love when you were young? For many people, the complications and time constraints of the day-to-day get in the way, and you gradually give up those things. But if you loved it then, you may find that bringing one of these activities back into your life will reinvigorate you. Your workplace probably isn’t putting on a play, but acting is a lot like public speaking. Join Toastmasters or seek out opportunities to talk in front of a crowd. You’ll get that same rush you used to get from acting – and improve your leadership and communication skills.

3. If yourself from 10 years ago met you today, would he/she be impressed with where you’ve gotten? Why or why not?

Imagine it. You from ten years ago bumps into you today, and you get to talking. What would a ten-year-younger you think of the life you lead? Would she be shocked to learn that you’re still working at the same company – and you haven’t gotten a raise the entire time? Would she be impressed by your time management skills, or horrified because you eat take-out almost every night? And the most important question: Would she have a point? How would you respond to your younger self’s criticisms and compliments? Priorities are dynamic; perhaps the goals you used to have are less important to you now. What do you think (or hope) you’d say if you met yourself in ten years?

4. When was the last time you embarrassed yourself?

The only way to grow as a leader and as a person is to step outside your comfort zone, and that means you’re going to feel embarrassed at some point. Again, you don’t need to throw yourself so far out of your comfort zone that you’re burning with shame. Take small steps. If you normally wouldn’t speak up during a meeting, make a comment or ask a question. If you have the opportunity to meet with a client or go out to lunch with a peer, do it. These baby steps will expand your comfort zone.

5. When was the last time you told a lie? Why? What would have happened if you told the truth?

Whether it’s a little white lie or a major whopper, this answer will reveal something about yourself and your motivations. Perhaps it was a “kind lie” and you wanted to spare someone’s feelings. But if you had told the truth in a kind way instead, what’s the worst that would have happened? Maybe you told your boss you started a project when you hadn’t. It may not hurt anyone (and you did start it right after you told the lie) but it does demonstrate that you need to work on your time management skills. You can’t lead authentically if you’re telling lies or half-truths. Understand the motivation behind any deception, and consider what the consequences would have been had you been honest. People will appreciate the honesty and reciprocate by being clear and open in their communication with you.

For more thought-provoking questions, read my blog on 30 Questions to Help You Discover Your True North. In my next blog, I’ll be looking at questions you can ask yourself to define where you are in the present moment.