5 Lessons From 10 Years in Growth

On this day 10 years ago, I was flying to Anchorage to be a sea kayaking guide for the summer before getting my MBA from the Booth School of Business. Less than a week later, I deferred business school and flew to San Francisco to work for an early-stage startup.

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The following decade was a period of intense personal and professional growth. This post will cover five of the most fundamentally important lessons from that period.

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The original title for this post was “10 Reflections…” not “5 Lessons…” but after thinking about it more, I don’t think I have 10 things to say. Even 5 might be pushing it. And these are less reflective and more practical, if not tactical.

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Many of the following lessons overlap like a complex venn diagram. I will do my best to keep each reflection at least somewhat distinct from the others and let you put them together or wholly disregard them in a way that makes the most sense to you personally and professionally.

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Lesson 1: Optimize For Personal Growth

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In both work and life, it is often best to optimize for personal growth. Depending on your values, this can look infinite different ways, but one thing is certain: compromising your personal development is a direct path to discontent.

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For the version of me arriving in San Francisco, acutely aware and insecure about how little I understood the field I wanted to work in, personal growth theoretically sounded like learning as much as I could as quickly as possible. In practice, it looked like getting myself into as many situations as possible that I was dramatically unqualified and under-prepared for, and figuring things out.

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I don’t recommend this path for most people - in fact, in hindsight, I might not recommend it to my former self - but I can testify that, while often painful, it worked: I learned more in my first four years in San Francisco than many people learn in their first decade of working life.

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Personal growth depends entirely on the person, though, and should look different for each individual. For me, I was trying to solve an ignorance problem in a particular domain of knowledge. For some, they might be looking to grow their self-confidence, others their social skills or any number of other areas for personal growth.

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In the end, the “what” is less important than your commitment to identifying areas for growth that align with who you want to be and applying yourself to the difficult path of self-improvement.

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Lesson 2: Trust Yourself

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If you apply yourself to a path of personal growth, you will soon find yourself in need of the second lesson: the urgently necessary ability to trust oneself.

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Paul Graham describes the tension inherent in growth via the metaphor of learning how to ski: your initial instinct is to lean back, but you are actually better served by leaning forward. I will take the metaphor a step further: in skiing, as in life, you are not skiing hard enough if you aren’t falling (relatively safely) every now and then.

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Rather than focusing on the sick gnar shredded or epic wipeouts, however, you will want to focus on the minutiae that led to certain outcomes. By focusing on the inputs - nearly all of which you can control or influence - rather than outputs, you will learn what you are able to control versus what you are not, which will help you learn to trust your decisions in even the most difficult situations and without full information.

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Lesson 3: Learn Fast, Then Faster

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All growth is compounding. It is a common human error to forget this fact. When we review history, we often forget that the people and events of a certain time and place were also affected by those from totally different times and places. The impossibility of capturing the entire human experience thus leads us to narrow understandings of historical phenomena.

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Personal growth is no different. Inherently cross-disciplinary and building upon itself with time, we often over-attribute success to one thing, or in the case of this post, to “5 Lessons.” This is an inherent flaw within any understanding or explanation of any type of growth, but especially personal growth.

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This is why Steve Jobs’ advice to Stanford graduates actually works and makes sense. To many students, the idea of following your interests and trusting yourself to find a way to integrate them successfully into a satisfying life might seem insanely risky when there are so many more clear-cut career paths. But what Jobs was really getting at is that by pursuing what you are most interested in or passionate about, you are setting yourself up to learn/grow fastest. The integration necessary to combine your learnings into something that, with initiative, can be both economically and spiritually satisfying will largely happen naturally, in the same way that civilizations naturally affect one another through trade, conflict, etc. It is almost osmotic.

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So your goal is to learn how to learn fastest. Jobs gives you one hint: pursue your interests, however seemingly big-picture irrelevant they may seem. Graham (aided by Sir Francis Bacon) gives you another: analyze your inputs against your outputs. And we all tell you, most of all, to trust yourself while you are exploring. With any luck, you will feel totally lost at least once¹, and you will need to trust your ability to discover a path.

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Lesson 4: The Future Is Already Here

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Whether we are conscious of it or not, there is an inherent anxiety to learning.

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In most domains, the value of knowledge is derived from its predictive effect. We want to know things so that we can more accurately predict what will happen under a given set of circumstances in the future. For many of us, the pursuit of knowledge will be what drives the interests we explore, whether they are scientific, artistic, religious, etc, and so the anxious inner voice that asks, “How will this knowledge affect my existence?” will always be there, whether at the surface or just beneath it.

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Depending on your chemical makeup and upbringing, how you deal with this anxiety will be quite personal. But regardless of circumstance, while there is no escape from the doubt inherent to the study-integrate-apply-restart learning loop, we can at least learn to control it.

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In practical terms, this means awareness. Not only of the self, but of the self within its broader context and of the fact that any anxiousness you may feel is natural, understandable, and even (within reason) healthy. In career terms, it means observing your feelings of confusion, frustration, and fear as you explore your interests and struggle to integrate them in a way that allows you to reveal something new to the world.

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Few careers exist in a vacuum, and as such there will almost always be new ways to gain an edge and find success for the most observant members of a field. Deep or vast exploration combined with vigilant awareness will naturally integrate to novel application, which in turn will lead to success. In this way, when Ram Dass encourages us to “Be Here Now,” he is encouraging us to see being fully present in the moment as the path of least resistance to a future that, in many ways, is already here and just waiting to be discovered².

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Lesson 5: Stay On-Mission

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Finally, my last lesson from the past decade is to do your best to stay on-mission. On-mission here means on the path of personal growth that aligns with your values and who you want your future self to be.

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As the years slip by, you will find yourself tempted to explore many interests and curiosities that, when examined in depth, do not align with your personal development. Unfortunately, you won’t know what interests will resonate with you without exploring them, so there is no way to escape the temptation other than to veer off path, get far enough off that you realize you’re lost, and find your way back.

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In this way, finding meaningful contentment in the futility of staying on-mission is the ultimate synthesis of all the previous lessons. It is the “restart” in your personal study-integrate-apply-restart loop. Be kind to yourself when you find yourself back at the beginning: while it may be the beginning again, you are not who you were the last time you began again.

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These lessons have been hard-won for me, and I wish you way more than luck on your personal journey of self-knowledge.

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Notes

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¹Many people attempt to find the path of personal development in books, podcasts, or anywhere else but within themselves, and this is inherently impossible:

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How can you find your way when you were never lost? To find your way, you need to lose your way first.

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With that understanding, think back to when you were a child and found yourself lost with no parent or guardian. The feeling is terror. If you are pushing yourself to grow, you should feel terrified. It’s a good thing - keep going. And to keep going, you will need to trust yourself.

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²Trying to describe an idea as abstract as “the future” is an interesting exercise. Some people talk about trends, which are usually visualized as waves of interest. Others talk about seeds being planted and growing into great Sequoias. I would posit that the future is much more like this teen’s experience of God on LSD: it’s already here, in everything, and is just waiting for us to find it.

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