I’m at a bit of an inflection point in my career. For the last year and change I’ve focused on myself, my family, and just recharging. This is after both my wife and I went on some wild and fortunately successful startup journeys in NYC. We were both burnt out and needed to re-energize.
More recently, and certainly in the new year, I’ve had that itch for change and growth and the next big thing. Whenever I find myself in one of these valleys, I always turn to a personal collection of questions I’ve curated over the years that get the wheels turning. Some you may be familiar with, others I’ve only just discovered, but they always provide some clarity on where to go next.
These are my top 16 questions to ask yourself when you find yourself at a crossroads and need to look within to find the answer.
1. What is the world telling you to do? What is coming your way?
Oftentimes, you just need to take a step back and notice what is already happening in your life. The world has a funny way of telling you what to do or where to go next if you just pay attention. Instead, you get focused on something completely different and fail to see what is right in front of you. And it’s usually something you brushed off without truly considering what it was and what it could mean. Notice what’s already coming your way.
2. What about you is immutable?
This is one of my newest additions, but also one of my favorites. It’s asking more about what is something that is inherently you – not in a negative or self-deprecating way, but in a positive one that brings you joy. What do you love? What is essential to your being? Appreciating this you-ness can help you evaluate what opportunities feed that versus starve it.
3. What will you regret not doing when you look back on your life?
Also known as the Regret Minimization Framework via Jeff Bezos, this is a simple litmus test when you are deciding between options. When you’re old and look back on life, are you going to regret passing on this opportunity? If the answer is yes, then you may need to pursue it.
4. What and who is worth suffering for? What do you value?
Sometimes it’s less about what you want to do and more about who or what you care about. What would you suffer for? To provide a life for your children? To end poverty? To educate the world? To feel loved? If you have that inner purpose, the means may not matter as much as the ends do.
5. What did you enjoy as a child? What did you want to do?
A classic question, but also one that tells you more about yourself than you realize. Revisiting your childhood and paying attention to what you did then can provide you breadcrumbs towards where you should be going. The reality is, in your youth, you were simply attracted to things you enjoyed, that drew your interest. It is those very things that are worth pursuing now amidst all the noise.
6. What do you know you should be doing, but aren’t?
I stumbled upon this one as I was re-listening to The War of Art, one of my favorite books about the Resistance. More often than not, there’s a thing in your life that you know makes sense and that you know you should pursue. Despite that realization, you still avoid it. It could be for any number of reasons, fear, self-esteem, the unknown, and so on. But when you ask this question, it shows you both what you are avoiding, and the very thing that you need to chase.
7. What are your strengths and weaknesses?
Think about your life so far and pinpoint what your strengths are and what your weaknesses are. A good exercise can be asking peers their perspective as well. Once you have your list, there are different approaches, but what makes the most sense to me is to prioritize your strengths. By doing so, you push yourself closer to mastery and something that will truly set you apart. At the same time, spending a little time on weaknesses can go a long way and give you a breadth of skills that only complement your strengths.
8. What gets you into flow? What do you enjoy doing?
I remember when I first read Mihaly Csikszentmihalyi’s book on Flow and was instantly hooked. Who wouldn’t want to be in that state all the time? If you take some time and notice what gets you into flow you learn a few things. Most importantly, it shows you where you’re willing and able to spend time towards mastery and building something meaningful. At the same time, if you trace back your journey, you realize that it wasn’t always this way – flow takes time to achieve in every domain. If there are things you enjoy doing, but don’t reach flow in yet, it’s a matter of putting in the time.
9. What would you do if social media didn’t exist?
Unfortunately, you live at the peak of social media and external validation. Posting alternate realities on the amazingness of your life when 99% of the time it is not that. And don’t get me started on taking pictures of food. But it’s something that is part of life now and there is always that part of you that considers what others think of this next thing you’re considering. What would you do if that was not at play? If no one was looking or cared or gave notice? The reality is almost no one does, so act like it and see where it leads.
10. What is challenging? What will force you to grow?
At times, what you’re truly seeking is the next challenge, the next hurdle to overcome. The next chance of true growth. I feel like careers have natural peaks and valleys and when you’re in a valley, you’re comfortable. There’s nothing wrong with comfort, but after a while you feel stagnant and start seeking change – a new mountain to climb. What is that for you? It will be uncomfortable, but that’s exactly why you should pursue it.
11. What is urgent? What needs action now?
Another great question I’ve found useful is understanding what is time-sensitive? What needs to be acted on today, otherwise you miss out on the opportunity. Top of mind is of course all things in the AI world at the moment, but there are many different waves of innovation and opportunity to consider. This provides another unique way to look at things and think about what is next.
12. What is useful to the world? Today and tomorrow?
What does the world need? What problems are waiting to be solved? Despite all the innovation in the world, there are so many things broken that need people to be focused on. Think of things that frustrate you or that you wish worked differently. They’ll give you a hint on what may be worth pursuing.
13. What do you want to master?
There’s always something that you want to chase or achieve or see yourself doing. Even if it’s a romantic idea in your head that you haven’t truly pursued, there’s something to the thought of wanting it in the first place. These wants are telling you something. You would do well to experiment with them to see if they are a worthy outlet for your time.
14. What is no one else doing?
This is straightforward, but also a cerebral way of thinking of things. What is a need in the world, that no one is currently addressing? What is your blue ocean strategy that could turn into something amazing if pursued?
15. What gets you excited?
Pursuing what excites you is always a great idea because it comes with an innate drive to do that thing. Motivation comes from external or internal factors. External motivators are things like hype, financial gain, and fame. These are powerful but fleeting. Internal motivators are things like curiosity, purpose, and value, things that get you going and excite you. These have true staying power. Chase what excites you and you’ll be on a good path.
16. What is your legacy? What is your infinite game?
Consider the bigger picture, what do you want your legacy to be? What is the meaning of your life? Asked another way – what is your infinite game (as defined by James P. Carse)? That thing that will last well after you are gone?
A few final thoughts.
Pick the questions that resonate with you. There are a lot of questions here and not all of them may suit your needs.
Questions may result in conflicting ideas and answers – that’s a good thing. Understanding your situation from many perspectives and positions will force you to confront what you want.
There is no wrong answer. The purpose of the questions is simply to gain some insight into yourself and where you may want to go next.
In the end, I hope these questions will help you better understand yourself and give you a hint towards where you want to go next, as much as they have for me over the years.