Big Questions to Ask Yourself For the New Decade

The New Year is a time for renewal. We have the chance for personal reflection, ends and beginnings, death and rebirth, new intentions and directions.

Late December is one of the quietest periods of the year, when work slows down, when we can savor the moment, spend time with family, when we have the opportunity to travel to distant lands or meditate in tranquility.

I look forward to this time every year, because it gives me the chance to read more, to focus on non-work activities, and consciously deliberate on my year ahead. My birthday is on Dec. 30, which makes it especially important for me.

I am naturally very introspective and spend at least some time every day in deep thought. However, my ability to find daily clarity is somewhat limited in the context of the frenzy of daily life. I need more time and space to connect with myself.

I’m turning 29 this year, and we’re entering a new decade. 2020 will be personally, communally, nationally, globally, perhaps cosmically transformative.

More than ever, success in the upcoming decade will be defined by our ability to make sense of it. Reality is a far, far more complicated place than it was twenty years ago, fueled by the sheer amount of information that we have access to. We need to redefine what it even means to be human.

For many people, overwhelm leads to extreme fear, confusion, and ideological fervor. But if we take the time to process the dynamics of life, to create coherence, we can see through the clouds and recognize that the sun is most certainly still shining through.

At the end of the day, we are responsible for our own sanity.

The end of the decade is a great time to zoom out and ask the big questions. This isn’t just about wins and losses in the past year; it is about examining the shifting conscious and unconscious tectonic plates of the past decade, and our entire lives. It is about remembering that, as Victorian Poet William Ernest Henley encouraged in his poem Invictus, we are still the Masters of Our Fates, the Captains of our Souls.

And so, in the spirit of the time, I prepared a list of questions that I am asking myself for the New Decade. There are no right or wrong answers, but there are better and worse answers. The best thing you can do is be completely honest with yourself, in order to get as clear as possible on living an extraordinary life in 2020 and in the flow of years past it.

We are entering a period of intensity and acceleration, presenting an opportunity for us to rise to the times; unleash our greatness; let it loose like never before.

I prepared a number of questions, so it might take some time for you to fully work through this. I also deliberately wrote in them in an uncategorized manner, in order to facilitate out of the box thinking and give you the chance to connect the dots. I hope these questions are helpful for you in gaining perspective, depth, and clarity.

The Questions


How am I radically different today compared to who I was in 2010? How am I the exact same as who I was in 2010?

What were the earthshaking decisions over the past decade that played an outsized role in making who I am today? What were the inflection points that changed everything?

Which people, events, or things have revolutionized the way that I looked at the world?

Which people have been the core anchors of my life over the past decade? Who have I relied on in my darkest hours?

What has been my deepest suffering and what have I done to heal it? What have I done to avoid or run away from it?

What is my shadow, AKA my dark side? How much have I been willing to look at it?

What were my peak experiences of the past ten years that lead to transcendent joy, peace, or mystery? What did they feel like and what did they say about me? How did I integrate them?

What were the most vivid dreams that I have ever experienced?

What have been my sources of deep wisdom and intelligence?

Where have I already achieved intense excellence? Why did that happen? What is naturally easy for me that is really hard for most other people?

If my life over the past ten years was a movie, why was it worth watching? What was the deeper story?

Have I found a tribe that I feel deeply aligned with? If no, what concrete things am I really seeking, and why haven’t I found them yet?

Have I genuinely empathized with people who are of an opposite different political or religious perspective? If not, why not?

What has life obviously been saying to me and asking of me (and maybe I’m ignoring)? What does the world desperately need from me?

Where have I really pushed myself? What are the scariest risks I took that REALLY paid off?

Where have I felt deeply, deeply stuck and blocked in life? Why is that? Have I asked whether there is a much better way of looking at the situation?

What are the moments and coincidences in my life that seem far beyond the realm of chance? How have I made sense of them?

What are the most important memories of the past decade and how will I carry them with me?

How will I commemorate or celebrate the past ten years?


What excites me and bothers me most about the direction that society is headed?

How will I take responsibility for systemic problems in society and the broader collective? Where am I best positioned to take on very important challenges?

Who are the commentators or thinkers in the public sphere that are best equipped to understand the direction society is headed, and how can I learn from them?

What is one thing that would change my life forever if it happened? Who would I need to meet?

What has changed in society makes my dreams possible in a way that wasn’t ten years ago?

What will keep me grounded, mentally and physically in the years ahead?

Who are the most genuine, effective, and brilliant people in my life and how can I spend more time with them?

Who do I know that is likely to experience a meteoric rise in success over the next ten years?

Am I willing to experiment with new lifestyles that bring me dramatically closer to people?

Am I willing to embark on a bold adventure if life invites me on a journey?

What can I do to rapidly and radically expand my consciousness?

Who will I be in ten years? Who will I NOT be in ten years?

What activities would be a total and complete waste of time?

What am I going to do to heal my traumas? How far am I willing to go to really deal with problems?

What problems or weaknesses do I still anticipate having ten years from now? Is that a problem?

How am I going to do a better job exploring and being my true self? I.e. Ethnicity, ancestral roots, spiritual inclinations, authentic personality, deepest talents, niche passions, artistic expression, inner voice.

What do I believe now that will likely be wrong in ten years? What are things that the vast majority of people believe that will be proven wrong?

If I knew for a fact that I had only achieved 3% of my potential, what do I need to do to unlock it?

How will my family life change over the next decade? Will I “settle down” or transform no matter what the context?

If I knew for a fact that there was a God, or a Spirit, or some sort of omnipotent transcendental Other beyond time and space, how would that change how I live my life over the next ten years? What if I knew there wasn’t one?

How am I going to fully activate in the years ahead? How am I committing to live the most dynamic, intentional, profound, and aligned years of my entire life?

Co-founder, Streetlight.