This summer, between his second and third years of college, my son, Jeremy, taught seventh grade math in a program called Breakthrough.

Breakthrough is designed to help bright kids from underserved urban areas to reach their potential. In addition to helping these kids to “break through,” Jeremy had a breakthrough of his own.

I asked if he wanted to write a post about any aspect of the experience and he sent me the following, which he says is the first in a series of possibly as many as six (one for each of the “Six Simple Rules.”) While I can be accused of bias, Jeremy is a super bright kid and there is a lot of wisdom in his words. The post might be especially useful for younger people, but it’s got many ideas for all ages. Enjoy!


I believe that my career—which will occupy a large chunk of the rest of my life—will have a major impact on my happiness. Only half-way finished with my time as an undergraduate university student, however, notions about my career have been wavering and unreliable. One of the points in the first chapter of my dad’s book, Six Simple Rules for a Better Life—that happiness stems from doing what you love, and loving what you do—has resonated with me deeply as I’ve tossed around different career path options.

There are many reasons why “doing what you love” sounds more complicated than it is. Chiefly, what if “doing what you love” is not financially sustainable? What if you just don’t have the resources to pursue what you love? As someone who hasn’t reached financial independence, I see another complication; a complication that is perhaps fundamental to this issue; a complication that, if overcome early on, can put you on a fast, simple track to happiness. The ultimate question for me is this: How can you do what you love, if you don’t know what you love?

This summer, I worked as an intern, teaching for the New York site of an incredible organization called Breakthrough Collaborative. Through my experience with Breakthrough, I fully realized my love for teaching. I’m fortunate to have discovered that I love teaching with time left to adjust my undergraduate plans. But whether you’re still in high school, or you’ve been working on the same career path for decades, I believe the following advice about discovering what you love (so that you can do it, and be happy!) still applies:

1) Don’t rationalize, and don’t rule anything out just yet.

I can date my interest in teaching back to when I was in sixth grade (I was extremely unimpressed with my math teacher, so much so that I thought I should go into teaching because I felt I could be a better teacher than her). Other signs of my interest in teaching: As far back as 10th grade I thought that after college I would want to apply for Teach for America; when asked during my first year of college, I told my peers that I wanted to be a school administrator; and the teaching internship opportunities I had bookmarked in my Web browser for over a year.

A reason that I initially ignored my calling towards teaching was because of the reputation that teaching has as an underpaid profession. As a business school student, coming from a comfortable upbringing, I could not fathom how teaching would suit the adult lifestyle that I imagined for myself. This was a huge mistake, and it could have prevented me from ever realizing my love for teaching.

The most important thing is to identify what you love. Like I asked before, how can you do what you love, if you don’t know what you love? Once you’ve figured out what you want to do, you can start to figure out how to make it work. So don’t rule anything out just yet!

2) Try everything!

Now that you have an unrefined list of things you think you’ll love to do, you can start trying them out! Just like picking up a new hobby or breaking a bad habit, refining your understanding of what you love to do requires time and effort, but can be done without completely disrupting your life.

The best way to do this is to find free time in your schedule. Do you have free time after school days, or on weekends? Are there any major breaks in your schedule, during which you could partake in a part-time opportunity?

To test out the waters for teaching, I looked at the freest time in my schedule—the summer. I had plans to travel in May, and needed to be back at school in August, so I found a program that ran from June through the beginning of August.

Another way is to think about how trying out a new career might still support other career options. A goal of mine for the summer was to gain relevant professional experience, so I sought out a program that would not just teach me about teaching, but would also support my growth with feedback, and would help to build my professional skills, such as clear communication and resourcefulness.

3) Break it down: What did you like about this? What did you hate about this?

Does my example of a summer internship to try out teaching sound too convenient? I agree—I was lucky with my timing. But a lesson I learned, through conversations with other teachers, is that trying things out is never a waste of time.

If it turns out that you didn’t enjoy the thing that you tried, that’s unfortunate. But wait! Before you cross it off your list and set it out of mind, take an hour or two to wholly reflect on the experience. What did you like about the experience? Why did you ultimately dislike it? Get specific! This will help you more fully understand what it is that you love to do.

A great example from my life is a PR internship that I had during the spring of my senior year of high school. My school offered an internship or community service program for students who passed certain criteria, and I thought it would be a great chance to beef up my resume and gain some insight into my future.

At the time, I was interested in marketing and PR, yet uninformed about what either of those really were. The month I spent at the small PR firm was not something that I enjoyed, and I knew I wouldn’t be a PR person after only a few days with them. But at the end of the internship, I reflected:

– I liked working closely with the small staff.
– I liked preparing proposals for clients.
– I did not like writing press releases for clients like dog-walking companies, Martha Stewart-esque baking supply stores, and sports sunglasses manufacturers.
– I did not like researching potential clients, such as those mentioned above.

These understandings about my own likes and dislikes helped to guide my university course selection the next year and to make my search for what I love to do more effective.

4) Research, research, research.

This is where you should start to introduce some of that rationale that I suggested you ignore at first. After you’ve tried a bunch of things, refined your list of options, and fully reflected on what you liked and didn’t like about each experience, you’ve got to figure out how you’ll make it all work for your life.

This does not mean just going on the internet and searching average work-week hours and yearly salaries. The research should be specifically tailored to the likes and dislikes that you’ve identified, as well as your current situation and your future plans.

What job do you have right now? How stable are you financially? Are there opportunities to merge your current work with what you would love to do?

Then, turn to the internet, look for books and other sources of information, and (maybe most importantly) ask your friends and family for introductions to people they know in your field of interest so that you can learn more about what careers in that field are really like.

Near the end of my summer at Breakthrough, all of the intern teachers sat down for a big conversation with our instructional coaches (all full-time teachers) about what life as a teacher is really like. I walked away from the conversation with much more insight into the life of a teacher, and felt more confident that I could do what I love, love what I do, and live the lifestyle I’ve always pictured for myself.

(I’ve always desired the opportunity to travel regularly in my future. After speaking with some people in the field, I realized that there are plenty of opportunities to spend time abroad as a teacher. Teaching English or volunteering in other countries during summer vacation, for example, provides me with a realistic opportunity to go to other countries and support myself financially! I hope to continue finding opportunities that meet my lifestyle desires and my love for teach. I’m confident that you can find similar opportunities in your own search!)

5) Try everything, again!

If you’re still not positive that you’ve landed on something you love to do, take another trial run! Luckily in the field of education, Teach for America, teacher fellowships, teacher residency corps, and other programs provide opportunities for people to try teaching for a few years (and support for the organizations when their members decide to pursue another career path.)

Another great example is my dad. He has always wanted to write and support the personal development of others. He learned about that passion over many years of life experience. He was able to test his love for the field first by working with urban youth. He also had a lab in his own house with parenting serving as an opportunity for personal development. Eventually he wrote Six Simple Rules for a Better Life and started this blog.

Now that he’s fully realized how much he loves it, he’s committing more time to conducting seminars, blogging, and promoting his work. And he did all of this without sacrificing his dedication to his family or his career.

It’s never too late!

I realize that as a 20-year old, it sounds funny for me to say this, but, really, it’s never too late! Life is long, and you can make positive changes at any point. So, why not start to figure out what you love to do, and start doing it, so that you can be happy? It’s that simple.

What do you think? What are your ideas to help discover what you love to do, and to pursue it? Join the conversation with your comments…