Top 10 Career and Life Lessons (to date)

(Thanks to Brian Balfour and Lenny Rachistksy for inspiring this. Listen to their conversation here.)

I offer these thoughts to inspire you to create your own list, and then ideally update it each year. If you are willing to share, I would love to see your thoughts.

Two Caveats

  • This list is a work in progress. 
  • No single lesson is applicable in all situations. There are always exceptions and nuances.


My Lessons

  1. Increase optionality.
  2. Think like an outsider.
  3. Distrust certainty; remain open-minded.
  4. Take risks, in a thoughtful manner.
  5. Be contrarian, to offer balance.
  6. There is no free lunch.
  7. Work to align incentives.
  8. Be kind and forgive.
  9. Think long term.
  10. Problems are a feature of life, not a bug.


Diving a Bit Deeper into Each Lesson

  1. Increase optionality, once you have made some important life choices. Meet new people, take an interest in new topics, and help others just because. These activities take time and also increase the chances of satisfaction and success.
  2. Think like an outsider. Be curious. Ask questions. Spend time outside of your function and industry. Understand how others think and approach problems.
  3. Distrust certainty and remain open minded. When you feel certain or think you know the answer, think again before acting or speaking. Ask yourself what the other side of the argument might be. There is no one answer, specific set of instructions, or ideal path. In careers, in life, in our spiritual journeys, and even in scientific progress. 
  4. Take risks, in a thoughtful manner. Nothing ventured, nothing gained. The key is knowing that you are taking a risk. Failure is totally normal and even acceptable when the risk has been identified. Differentiate between big bets and experiments. Undertakes lots of experiments. Take big risks selectively.
  5. Be contrarian, to offer balance. Think and act in a somewhat contrarian manner to what is common in your environment. For example, in early-stage, high growth businesses focus more on efficiency. While in mature, cash-flowing businesses, focus more on growth.
  6. There is no free lunch. Benefits are accompanied by costs. Weaknesses are partners to strengths. If anything looks too good to be true, you simply have not identified the cost.
  7. Work to align incentives. Be aware of the power of incentives and spend time aligning them across your organization and life. Ensure everyone really has some skin in the game tied to shared objectives. It’s surprising how often incentives are different between people who are meant to be on the same team or pursuing the same long-term goal.
  8. Be kind and forgive. Kindness is the best way to make the world a better place for everyone. When you haven’t acted as your best self, swallow your pride, acknowledge the missteps, and apologize. If you feel wronged by others, forgive them. Anger and resentment hurts you more than anyone else.
  9. Think long term. Slow and steady tends to win the race. The benefits of small good habits accrue and compound over time. Celebrate short term wins, but never get too attached to them. Be aware that quick wins often have downsides or hidden 2nd order problems.
  10. Problems are a feature of life not a bug. There will always be problems. Just different ones. If you are able to solve problems, it is likely you will be given more of them to address.

I am a big believer in pursuing excellence and giving our best effort to jobs and careers. In my work, I do want to be surrounded by people who think and act similarly.  

In addition, I am aware that much of what we do in our careers will not matter that much in the grand scheme of life. The feelings we get from the successes at work — from accolades, recognition and compensation — are short-lived.

Our hearts and souls are more deeply impacted by awe inspiring moments which happen with loved ones (friends, family, pets) and in nature. When you have reached a certain level of life comfort, seek out more awe in life rather than incremental compensation or career rewards.

Aditya Dehejia

Adi’s experiences as a CFO and HR leader in start-up companies inspired him to start the CxO Leadership Accelerator. He saw firsthand the challenges in building a satisfying career, the importance of leaders in developing people, and the difficulty in building broad business acumen while excelling in your functional role. Prior to his operating career in start-ups, Adi held roles in a growth capital investment firm and in the corporate development and strategy department at a Fortune 500 company. Adi is an active volunteer mentor in the FirstRound Capital and TechStars networks as well as within his University alumni communities. Adi was born in India and immigrated to the US at age ten. He attended Princeton University (graduated with a degree in Politics) and the Stanford Graduate School of Business. He lives in the suburbs of New York City and has two adult sons and two lovable, crazy dogs.

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