Planning a Career is Insane — Here is a better approach

I graduated from business school in 2012.

The job I have now didn’t exist then and nor did the previous one. How do you plan landing your dream job if it might not exist yet?

Predicting the future is hard, so I’d like to offer a better approach:


When you are energized, you have energy throughout the day and even when you get home from work. People feed off this at work and come to you with interesting ideas, problems and opportunities. At home, you’ll have energy to read and explore other interests — not to mention having the energy to invest in relationships.

For me, I used this lens to slowly (really, it took years) figure out what excited me. I came to the realization that I didn’t like working for jerks or managers who did not invest in creating high-performing teams. Early in my career I took extra steps to avoid them and said to myself during business school that I would not compromise on this — life is too short.

So in one of my first jobs after business school, they replaced the President and installed a jerk. It was not a healthy atmosphere. Micromanagement, low team morale etc… This led me to quickly jump at an opportunity that was offered to me. Once I had some space from it — I realized I want to contribute to positive work environments.


Once I had figured this out, it really helped me channel my positive energy towards the workplace in and out. I started reading more about the workplace, organizational behavior etc… I realized I was really passionate about people, talent & culture.

At my next job, we were writing a report on organizational change. Part of that included content on leadership and talent. I threw myself at that area of research with my entire energy. I went out of my way to call the Senior Partner and share my passion (he was pumped to connect with a like-minded person despite my tenure). I volunteered to get involved in projects for several partners in the talent and culture space in addition to my own work. This helped me stand out and win some friends along the way.


One thing I’ve learned is that there really isn’t a dream job. There are 840 specific job categories in the BLS. What are the odds I am going to find the perfect “dream job”? Not likely at all.

I’ve learned to embrace the journey. One book that made me appreciate this was Mastery. I learned that Stephen King wrote every single day for NINE YEARS before selling a single book and that Leonardo da Vinci didn’t have his big break until he was 46. For me — the takeaway was that it was a little selfish to expect to land my dream job at 30 years old.


In business school, we had to write down a list of leadership principles. I tried to think about this a little more broadly. I came up with a list of nine principles that would help me guide how I thought about my career. #6 was this:

6. Don’t settle for a comfortable job, always be learning

For me, learning is core to who I am. If I am not learning — and learning fast, I am not optimizing my energy.

Because of this, I’ve always tried to push myself to constantly be moving — whether this means getting a new job, experimenting on the side or even just reading something completely outside my comfort zone.

This symbol above is pronounced shoshin and represents the concept of Beginner’s Mind. This was introduced to me in the The Art of Learning another great book. The magic of this is that putting yourself at the start allows you to put yourself in a humble position where you don’t know what you are doing, you don’t have full confidence and you need to rely on others.

Through making a number of moves in my career, it has actually made me more confident and more adaptable, not to mention emotionally calm when reacting to new situations


In some of the career coaching work I do, I often see people get overwhelmed by the idea of a “dream job.” If it does exist (I hope, one day?) it seems like a massive undertaking. If you define success by landing that dream job, you are setting yourself up for failure by essentially creating 734 failure points and one potential successful outcome (not good!).

For me, I actually realized I wanted to get my feet wet with career coaching. One way was for me to quit my job and do it 100% from the start. Thank god I didn’t because I learned so much about what aspects of it I liked and didn’t like (I mostly learned I would never want to do this 100% of my time).

The approach I did take was to experiment on my free time, take a minimum number of clients and then to adjust my approach and focus as I go. As I’ve done this, I’ve shifted away from career transitions towards helping startup founders and also shifted more towards writing and speaking to college student than spending a ton of time coaching.


Last of all, this picture sums up my thoughts:

I’ll let you cheat and steal my definition of success. No surprise that it has to do with energy.

This is pretty much what it looks like. Here are a couple scenarios:

My health goes downhill and everything else suffers:

My Career is struggling and everything else suffers:

You get the point. The takeaway here is to define success and then manager it.

To summarize:

  1. Manage your energy
  2. When you find what excites you, share it
  3. Embrace the journey
  4. Stay hungry, keep learning
  5. Experiment
  6. Define Success