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On “life strategy” and making personal decisions

3 January 2019

Decision-making is difficult, and this is particularly true when decisions are most personal. Whether you’re choosing what to do after you finish your high school education or choosing your post-retirement ambitions, it can be extremely frightening – and also gratifying – to make such a big decision. Doing so with confidence and knowing that you’ve charted a path you feel good about, is critical.

This post is about sharing the essays that have helped me, as well as the team members I’ve worked with, understand how they make decisions, inform their decisions, and then execute on them. These are all short articles you can get through in an hour or two, because the real work should focus on the reflection and strategy around your decision. I’ve also tried to put them in the order I think is best to read them, which I will explain more at the end of this post.

  1. Why do Harvard kids go to Wall Street? While this essay focuses on those finishing post-secondary studies and choosing career options, I like to refer to this essay regularly as a reminder of how recruiting in well-known corporate brands works, and how we let our insecurities, peer pressure, or other external influences drive our personal decisions. In short: don’t fall into a trap of living up to other people’s expectations, and don’t use your current lifestyle as justification for avoiding change. A pithier version, particularly if you don’t relate to the above, is Seth Godin’s No reason to be surprised.
  2. How will you measure your life? A short read (though a book does exist), focusing on the importance of having a strategy for your life, and questioning the decisions and path you are on. In short, question your own goals, values, and intentions, and build a strategy for your life based on what you think a well-lived life means. Once you do this, you’ll be in a position to make big, difficult decisions that your older self can be proud of.
  3. Teaching smart people how to learn. I return to this article most often, as I find it useful on a weekly basis. Rather than focusing on strategy, it looks at how people learn from their mistakes and observations. I’ve met dozens of executives, consultants, and “rock star” employees who can easily explain away their failures by blaming an external event or force. This eventually leads them to plateau in their careers, as they stop learning from their mistakes. This article helps you take ownership over outcomes and provides a framework for understanding whether what you’re experiencing requires you to change your underlying assumptions about the world (or about yourself).
  4. Managing oneself. Continuing the theme of learning from your mistakes, this article helps you turn this process into a strategy. Understanding how you learn and how you communicate will help you make better decisions or generate a more thorough strategy. This article teaches you how to know yourself well enough to do this. Where Teaching smart people how to learn is tactical, Managing oneself helps lay down a strategy for personal development and decision-making that is unique to your strengths.
  5. Leadership that gets results. Now that you’ve dealt with your insecurities and built a strategy around how you learn and grow, it’s time to make some decisions! One of my biggest takeaways of the last few years has been that many people are overly democratic in their decision-making: they try to build consensus in every situation, even if they are a subject-matter expert or are working in a contentious hierarchy allergic to the thought of everyone agreeing about anything. Leadership that gets results lists different leadership and decision-making approaches, along with the pros and cons of each. If you’re making a decision about your life, you should also choose how best to communicate it and which stakeholders, if any, need to be involved. That’s not to say a democratic approach isn’t the right one, but there are other options as well.

I’m a big fan of these articles because the first two help you challenge your perceptions and insecurities, and encourage you to ask, “How did I get here?” The next two articles provide advice on building a new decision-making approach; one that actually takes your strengths and aspirations into account. The final article shows how you can make the decision to follow-through on your strategy and communicate it with those around you.

These five articles are relatively short reads because a large portion of the time you spend on making big decisions should be focused on reflection and analysis. While they provide great approaches to thinking about your decisions, where you’re coming from, and where you want to go, it is ultimately up to you to apply them to your unique and specific context. This is often very hard and there is rarely a clear answer. Have confidence in knowing that these decisions are difficult and that there is no “correct” answer, but that there are good answers. You’ll find them.


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