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What I Wish I Understood When Starting Out In My Career

The best part of my job as host of the Masters in Business podcast is that I get to sit down with an incredibly talented and accomplished person each week to discuss their life and career. I save my favorite question for last: “What do you know today about your chosen field that you wish you knew when you were first starting out years ago?” Answers like “I wish I bought Apple shares when they were at $2” are not what I’m seeking.

I am aiming for something along the lines of what hard-won insight they gained over the course of their careers that would have been useful had they learned it earlier. It is not a “time machine” question, but rather one of process. This is probably why it is also a hit among listeners. I previously addressed why I ask the questions I do, but this one deserves a deeper look. So, I spent some time thinking about it and the result is 10 things I wish I understood when I first started out:

  1.  Build your skillstack: Just because you finished your formal education does not mean you are finished learning. Education truly begins when you start working in the real world. Continuing to learn new concepts and ideas that can help you succeed in professional situations is too important to be left to chance. This can be done by taking classes, reading non-fiction and learning. 1

  2. Addition by subtraction: Early on, I tried to learn by consuming everything I could. I eventually realized that not all content sources were equal. Basic information hygiene led me to remove the bad stuff, but it wasn’t until later in my career that I figured out that even the good stuff wasn’t good enough. To succeed, I needed to focus on excellence. That means eliminating all but the very best from my reading list, what assignments or jobs I took on, and even the clients I worked with. This may be counter-intuitive – we “systematically default to searching for additive transformations, and consequently overlook subtractive transformations” – but it’s a valuable skill.

  3.  Assemble a portfolio of people: There are a small group of talented people that I would pretty much do anything with or for: Hire them, work for them, invest in their start-ups, introduce them to my key contacts, etc. Just having them in your orbit makes your life better. This goes beyond simple networking. There are folks from early in my career I wish I had spent more time and effort nurturing relationships with.

  4. Trusted counsel: Having a person whose judgment you trust and who can provide unfiltered feedback is incredibly valuable. This is very different than an informal survey of friends and work pals. A solid counselor is worth his or her weight in gold. This was a big and obvious miss for me early in my career. Insistence on equity and/or control was the sort of advice that was a godsend later in my career, but would have been incredibly useful earlier.

  5. Failure is growth: Most of us fear failure, when we should embrace it. Without failure, there is no growth. If you are not failing, then you are not trying anything new or risky or out of your comfort zone. I became interested in the work of Ray Dalio, the founder of hedge fund Bridgewater Associates, because of how crucial the role of failure was to his career trajectory and success.

  6. What are the metrics of success? Every profession has a series of datapoints that are used to judge its practitioners: sales quotas, surgical outcomes, etc. You may not be explicitly told this is how you are being evaluated, but you are, and it’s critical to understand these metrics.

  7. Learn to time travel: It took me a while to learn how to “travel” a few decades into the future and then return to the present. Being able to conceptualize what the future looks like is one thing, but the real trick is recognizing that dynamism underlies everything. Nothing is static, and all things constantly change, adapt and move forward.

  8. Don’t worry about your first few jobs: So many Masters in Business guests gave this as their answer that it forced me to rethink the first decade of my career. If I had this advice, I may have been more productive, focused less on stuff that turned out to be meaningless and could have progressed faster.

  9. Collaboration: I spent the first half of my career working mostly by myself. I wish I had better understood what comes from working closely with others and being able to divide duties according to skillset. This allows you to focus on what you do best. The results of an ensemble show up in better productivity and higher quality work.

  10. Good habits: We are our habits. Some of mine are pretty good, like getting up at 4:30am each day to pound out 500 to 1,000 words of content for my blog. After 20 years of this, it has turned me into a better writer. Turning tasks into a routine that eventually becomes a habit is something I wish I learned decades ago.

Each of these are things I wish I knew decades ago. “Better late than never” applies to me, but those of you who are starting your career might find something worthwhile in this list.

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