The Art of Questing

People have been engaging in grand challenges or “quests” since antiquity, in some cases defining their lives around these quests, such as pilgrims on a spiritual journey or explorers seeking new trade routes. With the digital age, you can easily discover more examples of various quests that people pursue, which vary radically in style and scope. Modern examples include Alastair Humphreys who bicycled around the world or Scott Young who completed the entire online MIT Computer Science curriculum for a four-year bachelor’s degree in a year.

Grand quests appeal to me; my first was the pursuit of my doctorate, which took six years to complete. Committing myself to getting a PhD provided direction amid a flood of potential life options; I was able to judge opportunities to pursue based on whether they helped me make progress in my quest. Though perhaps “provided direction” is an inaccurate description. Getting a PhD is akin to bicycling across the United States in the dark with a compass that only intermittently functions. It involves a lot of sustained effort and you end up going down false paths that require you to backtrack and recalibrate your direction while occasionally having to deal with a friendly thunderstorm.

While completing my doctorate I experienced tremendous personal and professional growth. I became more proficient and confident in software development, design, teaching, and the research process, among other things. The experience also left me with many work opportunities, such as designing future software products at Apple, continuing on as an educational researcher, and various entrepreneurial paths.

However, this new flood of opportunities was both a blessing and a curse. After finishing my quest I felt directionless, akin to someone is trying to decide where to go for a vacation but considering every place in the world as a potential destination. After having a clear goal for so long, the range of possibilities of what to do next was overwhelming.

Since completing my PhD, I have been in an exploratory mode with my newfound freedom, continuing to work as a researcher while exploring side projects and experiencing life in various cities. However, recently I have returned to the idea of pursuing another quest. I was pleased to discover that Chris Guillebeau, an author and entrepreneur I admire for his novel The $100 Startup, recently wrote a book about questing called The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life. Chris completed a quest to visit every country before he was 35 and in this book he analyzes himself and several others as case studies for embarking on a quest. Throughout the book he breaks down how to find and structure a quest and offers advice on how to handle the process during and after you finish.

Chris defined a quest as “A journey towards something specific, with a number of challenges throughout”. In the book he noted that quests take a number of different forms:

With any major decision, such as undertaking a grand quest, there are a number of advantages and disadvantages:


  1. Provides direction: your goal helps you orient yourself and can bring a sense of purpose to your life. This can reduce the time and emotional turmoil you may feel in trying to decide your next steps and help you to avoid wasting time on tasks that distract from your goal.
  2. Rallying force: you are able to craft a clear way to describe what you care about and what you are doing. If your quest benefits from community involvement, this makes it easier to attract like-minded individuals who can support your cause or learn from you. Having a clear message increases the positive impact that your quest has on the world, whether through inspiring others to follow in your footsteps or directly helping others.
  3. Accelerated growth: these grand challenges are tasks that will push you outside of your comfort zone repeatedly, leaving you no choice but to grow. Depending on the type of quest, you can increase your self-confidence, hone a new set of skills, and increase your ability to impact the world.


  1. Huge opportunity cost: pursuing a grand challenge requires you to choose against many other tasks. For example, you could pursue your career at home, be part of a recreational sports team, and take music lessons all at the same time. However, you could not continue doing all these things if you decided to bicycle across the world.
  2. Reduced flexibility: this follows on the upfront opportunity cost. Having a grand quest that you are pursuing can reduce your ability to pursue alternative paths that could be very rewarding. Of course you can always give up your current quest, but this leads to:
  3. Potential for misery: in the midst of pursuing your quest, you may find yourself hating the day to day life and desire to quit, but continue on because you feel the stakes are too high or you feel too committed to your goal. While there are always rough period in any task, being overly committed can lead to months or even years of misery. I have witnessed friends who are miserable for years while pursuing their doctorate yet they feel unable to quit for a multitude of reasons. While some claim it was all worth it in the end, others are quite adamant that it was a waste of time and they should have left earlier.

So while embarking on a quest can change your life, it is important to acknowledge the sacrifices it requires. Chris’s Guillebeau’s book, The Happiness of Pursuit, is a great overview of the topic and a wonderful read to learn more about questing. If you are considering pursuing your own quest, it would be helpful to find other questers who are further along a similar path and get a sense of their daily life and the challenges they have to face.