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These 21 Questions Are Guaranteed to Make You More Successful

Real success comes from defining what matters to you and going after it.

Get a roadmap for your own success!

Most of us live our whole lives chasing after a success that belongs to someone else.

We never ask ourselves the questions that’ll get us closer to a version of success that feels good. We make goals and achieve them and never feel content. 

Real success can’t be measured by external milestones; it can only be measured by the quality of our inner life. Do I feel good? Am I becoming stronger, more confident, and more at peace with every goal I hit? Or do I feel empty and unfulfilled? 

Last January, I spent three days on a self-styled retreat with one of my best friends.

We were both ready for some big internal changes. Our professional lives had undergone seismic shifts the year before, but our inner lives had yet to catch up.

Almost by accident, we ended up asking each other a series of questions that forced us to re-evaluate how we were living our lives on a micro day-to-day level.

12 months later, both of us have undergone personal transformations. On a recent walk, we were comparing how we feel now compared to last December. We both brought up feeling less stressed, happier, and more at peace. We joke that our DIY retreat felt like it lasted an entire year because we covered so much ground.

In the search for a picture-perfect life, we often forget who we are and stop doing the things that actually make us feel joyful on a daily basis. | Photo by Joanna Kosinska on Unsplash

These 21 challenging questions (yup, it’s not easy to answer all of them truthfully!) made the last 12 months the most internally and externally successful of my life.

You can answer them solo or do this as a shared experience with a friend. Either way, writing down all of your answers will give you a roadmap for your own personal success journey. Instead of jumping on the emotional roller coaster of New Years resolutions that are bound to fail, try this. 

1. What are your priorities?
This is what matters most to you. This comes first. Nothing else is more important. My priorities are health, friendships, and creative expression are priorities.

2. How are you currently living in alignment with your priorities?
If you say that health is a priority, are you actually putting yourself first? 

3. What are your top five values?
This is what drives your life. They are non-negotiable. They are a part of who you are. Living in alignment with these values will allow you to live a more fulfilling life.

4. How well have you been living in alignment with your values?
This isn’t about making yourself feel bad. It’s about being honest with yourself. Often our values get put to the side as we try to live up to other people’s expectations. But this is a backwards and entirely unfulfilling way to live. 

5. How do you want to feel this year?
Do you want to feel powerful, alive, electric, calm, serene, on fire? You get to decide how you want to feel.

6. What are your intentions for the year?
These aren’t goals. They don’t have to be specific and measurable in any external way.

My intention last year was this: 

To do enough, not too much. To be active and engaged, not so so busy. To rest. To heal. To put my heart first. 

7. What three thoughts can you let go of that don’t serve you anymore?
This is about limiting beliefs. Everyone has limiting beliefs that are no longer useful. Pick three.

8. What three thoughts can you replace those with?
It’s nearly impossible to just drop one way of thinking without replacing it with something else. What song will you play instead? Last year I replaced “It’s not enough,” with a question. Instead, I would ask, “Is it enough?” That minor switch made a big difference in how I felt on a day-to-day basis.

9. When life gets busy, what can you let go of, stop doing, or put on hold?
This is chaos planning. Most of us make life plans and lists of goals with no thought of the many things that can and will go wrong. Starting your year with the understanding that things will go sideways is deeply helpful. What can you put on the back burner when life gets crazy? 

Last year my list included googling, personal e-mail, extra shopping, making new plans, adding personal to-dos, and working on courses. When life got busy, I put all of those non-essential activities on hold.

10. What are your biggest dreams and desires?
These aren’t SMART goals. These are the delicious and outrageous dreams that we usually stop ourselves from acknowledging. As kids, we had tons of wild dreams. But as adults, we stop ourselves from having even one. What beautiful dreams live inside of you? List a few. Give them space to ferment. Want to know something weird? I actually achieved two of my dreams last year. Turns out, they weren’t so wild after all.

Do you have a wild dream? Something that seems unattainable? Write it down anyway! You might surprise yourself. Some incredible dreams are closer than we think. | Photo by Nicholas Sampson on Unsplash

11. What are your top three financial goals?
Pick a major goal and two small ones. They don’t have to be epic. You could automate your banking or read a book about investing. Whatever you do, make sure your financial goals are in alignment with your values. If you attach a powerful reason to your goals, you’ll be more likely to achieve them. 

12. What are your top three personal goals?
Often in career-driven stages of our lives, we don’t make goals for our relationships or mental health. Again, pick a big goal and two small ones. Last year I focused on my relationship with my parents and my partner. 

13. What are your top three business or career goals?
Sometimes in the business/career area, we go crazy with goals. We come up with a list of 10 goals, and all of them are meaty and tough to achieve. It helps to apply a minimalist framework to your business or career goals and focus on one primary goal and two smaller ones. This forces us to be brutally honest about what matters most. It also means that each month we can quickly assess where we are with our goals.

14. What actions will you need to take to achieve those goals?
If you’ve ever dabbled with the Getting Things Done philosophy created by David Allen, then you know the first step in achieving a  goal is identifying the most essential action you need to take to get started. List out the next action step for each of your nine goals. Allen recommends stating the place and the tools you’ll need to take action. For example, “Brainstorm about guest posting ideas in my office with pen and paper,” is an ultra-clear next step. Whereas just, “Brainstorm about guest posting,” doesn’t provide as much guidance. It forces me to think instead of just getting down to the task.

15. Being honest with yourself, do you have time to work on all of your goals right now? I mean really…do you have the time?
There are 15 waking hours in a day. You also need to eat well, exercise, spend time with your friends and (chosen) family, have a shower, rest and relax. If your goals are not achievable based on the actual (not overestimated) time you have available, take another look. How can you tweak your goals to make them attainable? Maybe your small goals need to be even smaller. There’s no sense setting yourself up for failure. 

16. What are you committed to this year?
This isn’t a goal or an intention. This is a desire for yourself, for your life. Simplifying your life is a commitment. Putting your happiness first is a commitment. Being compassionately honest is a commitment. Fill in the blank: “I am committed to______.”

We make commitment to other people. So why don’t we make them to ourselves? | Photo by Ben Rosett on Unsplash

17. What is required to make this the best year yet?
This could be anything. It could be something external or something internal. This might sound super basic, but for this year, my answer is to stretch my body every day. Stretching makes me feel so insanely good and yet I don’t have a daily practice. Simple. Easy. Doable. 

By this point, you might have noticed that it’s possible to get repeat answers when you go through all these questions. That’s perfect! It just shows that those repeats are exceptionally important to you. 

18. What thoughts will you cultivate to help make this year more delicious?
What you think is your reality. If you only develop the external and not the internal, you’re leaving your experience of life up to chance.

19. What will you stop doing this year to make room for more goodness?
It’s just as important to stop doing the things that don’t move the needle and don’t make you feel good. Is it stressful, tedious, wasteful or unnecessary? Well, there’s no need to keep doing it.

20. What will you start doing to make this year more beautiful?
Maybe you’ll begin daily runs or meditation, or you’ll spend more time with friends. It doesn’t have to be something gargantuan to make a noticeable difference. It can be something tiny. Write as many or as few as you like.

21. What will you keep doing that you find truly valuable?
It’s just as important to recognize the things that we do that work and to keep on doing them. This is how we ensure that our good habits don’t slide. It’s also how we honor our good practices. 

Bonus Questions:

What is vital to feeling yourself? What do you need to feel like yourself? For example, I need plenty of alone time and long walks in nature. I also need time to read a good book just for fun. And I need an outlet for my creativity. Knowing what I need in order to feel like myself allows me to take self-care steps that actually nourish me. The knowledge also helps ensure that I don’t choose goals that’ll rob me of the things that make my life my own. 

If you go through these questions one-by-one and really answer them, it’ll be impossible not to make progress.

Being clear about where we are and where we want to be is the first step towards internal and external growth.

Unfortunately, most success literature is targeted towards the external.
Our society is focused on measurable goals, reaching physical targets, and increasing revenue and net worth with no thought to whether this will make anyone’s life better.

What does success mean to you?

Will earning six figures make you happier? Not if you’ve earned that money doing something you dislike. Not if you’ve been stressed and tired the entire time.

We all know that the journey is what matters. Yet, in our daily lives, we often forget that wisdom. We get out of bed, jump on the hamster wheel, and do everything we can to achieve our goals or the goals our companies have created for us.

2019 was the best year of my adult life.

It was brimming with challenges, yet it was incredibly fulfilling. It was a year full of surprises and productivity. I achieved some goals while abandoning others. But it wasn’t the productivity or the goals that made me feel successful; it was the personal transformation. It was the feeling of inner peace that came from knowing that I was living an honest life. I wasn’t chasing someone else’s dream or ignoring my own needs. I had a roadmap for success that was personal and clear. 

Personal transformation will make you feel more fulfilled than external achievements.

The external metrics for success that our society promotes are rarely a good fit for the individual.

They’re like hand-me-down clothes that might look great on someone else but aren’t tailor-made for us. They sag and bag in all the wrong places, and we walk around feeling like a not-quite version of ourselves. 

These questions (if answered honestly) will create a custom-made success strategy. You’ll be saying buh-bye to the cookie-cutter goals that make you feel like you’re stretching towards a life you don’t really care about. Instead, you’ll have a roadmap that’ll make you feel grounded and purposeful as you tackle the challenges that life tosses your way.

The greatest lesson I learned in 2019 was this: real success comes from defining what matters to you and going after it.

Do you have any questions that you ask yourself every single year? How do you evaluate your life or create a roadmap for your own personal success? Share your tips below so we can all learn together! 


—Colette Nichol is a writer, filmmaker, and entrepreneur based out of rainy Vancouver. Obsessed with personal development and marketing, you can usually find her attempting to read ten books at the same time. Through her website, StoryEnvelope.com, Colette helps creatives make more money doing what they love. Join the inbox party: get actionable tips on how to make more money doing what you love by signing up for inspiring emails on her website. 

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