Twelve Questions that Will Help You Know Yourself Better

Oleg Zaezdny
First Step
Published in
7 min readAug 6, 2020

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My quest to find myself started ten years ago — back then I had a seemingly great job, but I felt something was wrong. I tried changing companies, jobs, roles — and yet I felt like I was living someone else’s life, not knowing how to find mine.

It took me almost ten years to get to know myself better, to become honest with myself to admit what I really like and who I really am, and to become brave enough to start doing first steps towards it.

I would like to share some of the ideas I have - here are twelve questions that will help you to get to know yourself better, and hopefully give you ideas regarding what you really want to do in life.

While answering them, try to be as open and unbiased as possible:

  • Answer what comes first to your mind — try to be free from the controlling part of yourself, and choose what you would really like to be or do, not what you can or should be doing. Imagine that anything is possible, and stick to it for the next 15 minutes
  • Forget about all the limitations that you might have (real or imagined), any beliefs about your skills or abilities
  • You don’t have to take into account your current career path — especially if you’re not happy with it. Just imagine that you’re about to finish high school and any path can be chosen.

And one more thing — it’s better to write the answers down, even if you’re not planning to share them with anyone — this brings more mindfulness and will help you when you will be reviewing your answers.

Ready? Let’s go.

Section 1 — What would be fun to study?

Imagine there’s a university in your city or town that offers any kind of classes or activities — for free, without any obligations — and you can attend them if you want to, you can also quit anytime.

  1. What kind of classes or activities would you attend — just because it’s fun? Yes, just fun. Which of the following areas sound exciting?
  • Classes related to creativity (for example, creative writing, design, theater and acting, music etc)
  • Science and engineering classes (for example, software engineering, robotics, artificial intelligence, microbiology, chemistry, astronomy etc)
  • Classes where you can learn how to create things with your hands (for example, hand-made, DIY, cooking, embroidery, knitting etc)
  • Classes when you can train your body or otherwise express yourself through the body and movements (for example, sports of any kind, dancing, yoga)
  • Entrepreneurship and leadership classes (for example, entrepreneurship, management, business administration, leading a team)
  • Classes about communicating and interacting with people (for example, how to conduct negotiations, how to persuade people, networking skills, public speaking)
  • Activities aiming at helping others (for example, teaching, organizing a summer school for teenagers, volunteering at a hospital, helping at an animal shelter etc).

2. Imagine you could pick three to five specific classes or activities — they don’t necessarily have to be the ones mentioned above — can be anything you want, as far as your imagination can go. Which ones would you want to attend or try doing?

Section 2 — Energy, enthusiasm, and joy

When we do something we really like, we feel energetic, enthusiastic, and excited. Doing those things lights us up and brings genuine joy. This section is all about this. We’re not talking about jobs here, we’re just talking about what brings you joy.

3. What are the things that you do regularly, the things that bring you genuine joy, the things that are maybe so common to you so that you don’t even realise how much you enjoy them? What do you do when you have free time and you are free to do whatever you want?

4. Which activities give you energy and make you feel alive? What are those things that whenever you have an opportunity to do them, you always excitedly say “Sure! Let’s go for it”?

5. If your salary depended on the amount of joy you feel doing a certain thing or participating in an activity — which activities would make you a millionaire?

6. Read your answers to the previous three questions. Pick the activities that feel the most joyful to you, that make you feel most excited and enthusiastic, and for each of them write what exactly lights you up and why.

Section 3 — Simplifying choices & removing limitations

Often it’s hard to understand what we really want because on one hand there are so many options, and on the other hand, we automatically discard the options that look unrealistic or not practical. Let’s try to simplify the choices and remove the limitations now.

7. Imagine you live in the second half of the 19th century. If you could choose any job available in those times, which one would you pick and why?

8. Now let’s travel to the future. Imagine interplanetary travel is a thing, and you’ve just landed on a far-off planet. People on that planet have no idea who you are, what you’d been doing on Earth, and have no expectations regarding yourself. Furthermore, there is one special thing about this planet: whatever you choose to do there, you will be really good at it — there’s no way you can fail. What would you be doing there?

9. Finally, let’s go back to Earth, our time. If right now you were offered a sabbatical — a year during which you could do whatever you wanted, and you would be still receiving sufficient income — what would you be doing during that year?

Section 4 — Purpose

The next three questions are both very easy and very hard. Easy — because most likely you know the answers, and they will come to you immediately. Difficult — because you’ll need honesty to hear yourself and bravery to let them come out. But once you know the answers, your future choices can become simple and clear.

Take three deep breaths, and let’s go.

10. If you were to deliver a TED talk, what would be the topic? If you were to write a non-fiction book, what would it be about?

11. What is that unique thing that only you can give to the world? And what does the world need that only you can give?

12. Imagine yourself when you’re 90. You’ve lived a happy and fulfilled life. You’ve been doing what you loved — and thanks to it the world has become a better place. You realise you would never feel this way about your life if back then, many years ago, you didn’t start doing… what exactly?

Making sense of it all

It’s time to review your answers and reflect on them.

Section 1 helped you identify the areas of your interest. Are you more into creativity or tech fields? Do you want to improve your people skills, or maybe you’d like to express yourself through your body? These do not define your potential work choice, just take a note and try to see how your preferred areas can be fit into your future life choices. Also pay attention to the actual classes you’d like to take — these are just starting points, but why don’t you give them a try? You’re not losing anything: in the worst case you’ll just know yourself better, but in the best case you might tap into something special.

Section 2 helped you see which things bring you energy and joy. Pay attention to the last question in the section and your answers — try to see what exactly gives you energy and why. How can you be doing more of this in your daily life? What kind of job or career would involve these things?

Section 3 hopefully gave you some clarity regarding the broad areas of your work (19th century question) and your aspirations if there were no limitations. Take a closer look into these. Maybe your aspirations aren’t so unrealistic? Are there any people who are successful at those? Probably there are. Why can’t you be one of them? If you think something is not realistic, most likely it will indeed stay not realistic for you. But if you ask different questions — how would I feel if it works out? Will it be fun? What if? How can I make it happen? Are there any other options how I can start doing that — even if just as a game, just to try? — then you invite the possibilities into your life.

And then Section 4 should have given you the ideas regarding the things that would make you fulfilled, the things that are unique to you, and the things that you can contribute to the world. These are the most important questions, especially the last one. It doesn’t necessarily mean that the answer you gave to it is the ultimate one — that answer can change as time goes by, and your purpose may change too. If you begin walking this path now, it may lead you to something totally different, and probably even more exciting! But for now, you have a direction to start.

If you have any feedback regarding these questions, or there are any questions you’d like to ask me, please let me know, I’ll appreciate any feedback.

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Writing about mindfulness and any other things that feel important to me