As part of my annual year-end review, I always take some time to write out my biggest lessons learned from the past year. 

I find that this helps them really sink in, fills me with a sense of gratitude and appreciation for everything I’ve experienced, and maybe even allows others to borrow some wisdom for themselves.

Here are my 12 biggest lessons from 2020.

More often than not, a problem is challenging only because of my unwillingness to feel the feeling it provokes

This was a big lesson for me from the first cohort of The Art of Accomplishment, a new group coaching program I helped launch and also participated in. 

Twice a week we’d get on calls specifically designed for getting in touch with and expressing our emotions, and I was often annoyed at having to stop what I was working on to attend. But I was surprised again and again how often I’d walk away from those calls with tremendous clarity about a problem I was facing in my work. 

It seems like the tension and uncertainty that often makes problems difficult to solve aren’t created by the problem – they come from the internal tension of not allowing a certain feeling to come to the surface and be felt. Once it does pass, almost like a bowel movement, everything seems much more calm and clear. This is very much in line with the biological basis of emotions I’ve written about before.

Attention is the most precious substance in the known universe; when applied, it will make any situation better

I’ve long been fascinated by the nature of attention. But having our son this year, in October, brought my studies in attention to a whole new level. You only really value something when it is in short supply. What I’ve noticed is that anything you apply attention to will automatically get better, regardless of any other action you take or don’t take. 

Pay enough attention to your weight, your fitness, your diet, your finances, or your relationships, and those things will invariably improve. The quality of a piece of writing is almost directly linked to how much attention I’ve invested in it. If I’m worried about an area of my life, it’s usually because I’m resisting paying enough attention to it. The pain and anxiety I feel in that area is a sign that it is demanding more of my attention.

People will usually show you how it’s going to go with them within the first 15 minutes of meeting them

This is something I learned from Joe Hudson, and have found it to be true. The way that someone does one thing is typically the way they do everything, which means that you only need to observe them for a short time to know how your relationship with them will go. 

This doesn’t mean you should judge a book by its cover. But by carefully watching my dynamic with someone in the first minutes and hours, I can always find valuable foreshadowing. If I feel annoyance or resentment initially, those are unlikely to decrease over time. I’ve learned to trust my instincts with people and more decisively bring such interactions to a close.

Once you know you’re going to succeed, the most important thing is to savor every minute spent getting there

Looking back on my 20s, I was consumed with the question of whether I would be “successful.” It seems silly in retrospect – I had so much going for me, so many ways that I could succeed. But I felt so at risk of “not making it,” though I would have had trouble telling you what it meant exactly to “make it.” 

I was struck by a line from I Am Michael Ovitz, the autobiography of the famed Hollywood agent and founder of Creative Artists Agency. He said that at the end of his career, after having made many billions and achieved his goal to reinvent the film industry, he thought his happiest moment was back at the very beginning. Sitting in their empty office space with his fellow partners, before there was even furniture, plotting world domination with dreamy eyes. That, he decided, was his peak. 

I’ve never forgotten that, and that story always reminds me that now, right now, is the time I will look back on fondly. These times are the good times. Once I have a goal I tend to go after it so aggressively that I forget to even notice the experience of getting there. But I’ve done enough of these reviews to notice that reaching a goal is mostly empty. As soon as it’s within reach, it stops being interesting. The impulse to immediately set yet another, even more ambitious goal is mostly an effort to get back to the feeling of wanting, striving, reaching. There’s nothing wrong with that, but it’s healthy to appreciate that it’s not the only feeling worth having.

An immense amount of meaning is condensed into the tiniest moments, mostly moments spent with family and friends

This observation came from my documentary film project. When you repeatedly watch the same footage again and again, you start to notice whole new layers of meaning. Micro-expressions, momentary glances, pregnant pauses – these are the subterranean geology of human communication. I noticed time and again that tremendous amounts of meaning were packed into the tiniest of moments. Meaning wasn’t distributed evenly through time. It came in stops and starts, peaks and valleys.

The same is true of normal waking life I’ve since realized. This is why awareness is important. It is only with awareness that I’ll be able to catch those moments. They don’t announce themselves and don’t happen on a schedule. They seem to happen more often with people I love, but it is often those very people that I have the least awareness with, thinking I already know everything they’re going to do or say.

People’s wants are generally a subset of their needs, which means there are a lot of things they need but don’t want

Conventional thinking is that people’s needs are a subset of their wants. In other words, people want A LOT of things, but only very few of those things do they actually need. I think this is actually reversed.

People’s needs are immense. Almost limitless. I was struck reading The Body Keeps the Score that the symptoms of trauma are practically universal. It is the people that don’t have trauma that are the extreme outliers. And that it is neglect that is most damaging to the human psyche, even more so than outright abuse. 

But who hasn’t experienced neglect in some shape or form? Who hasn’t had an unmet need? Who hasn’t been ignored when they were hurting? Who hasn’t been ignored when they cried out for help? This makes me wonder, how much love and attention does a human need to not feel neglect of any kind? And the answer seems to be, a whole helluva lot. 

If nearly all of us have experienced some form of neglect in some area of our lives, then how would we discover what those areas are? It isn’t by looking at our needs – we generally have worked our entire lives to not need the thing we didn’t have enough of. It is by looking at our wants, which are symptoms of unmet yet fundamental needs that have been repressed. I got this idea from adrienne maree brown’s writings – that our desires and cravings are something deep within us calling, against all odds, for a taste of something it has almost never had, whether that is love, caring, intimacy, or connection.

Instead of treating people’s needs as “good” and their desires as “bad,” I’ve made a conscious effort to treat their desires as something inherently good and worthy. That doesn’t mean I have to give them what they want. It means that I treat the whole human as worthy of love and capable of meeting its own needs, even if that takes the form of compulsive cravings.

The more high end the product, the fewer features it needs

This is another lesson that it takes many, many tries to fully assimilate. I think it’s another symptom of my middle-class upbringing: to think that I have to get my money’s worth, and the best way to do that is to load up as many bells and whistles and features as I can possibly get my hands on. To treat overconsumption as a security blanket to ensure I don’t get taken advantage of. 

The most clear example in my own business was when I launched the Executive Edition of Building a Second Brain, to work directly with a small group of leaders, entrepreneurs, and executives. Charging more than 3 times the entry level course, I felt that I had to create almost an entirely new curriculum on top of the one I already had. More bells! Louder whistles! 

But the clear feedback I received was that the extra stuff was unnecessary, and actually a hindrance to their learning. They just needed more of my time, more of my attention (see lesson above). The more high-end a product or service or experience gets, the fewer (and better) features it needs. More features means more complexity and more to manage. When what people are really paying for is less to have to think about.

Fulfill the spirit of the project, if not necessarily the letter

As I’ve set more ambitious goals and taken on projects that I need help from others to complete, I’ve had to relax my definitions of success. It doesn’t make sense to rigidly insist that a project finish exactly the way I envisioned in my mind, way in the past when I had so much less information. 

It is instead the spirit of the project that matters. The intention, which is less precise but more meaningful and expansive than a desired outcome. Intentions have many ways of being fulfilled, many ways of coming true. I’ve learned that the further along a project gets, the more criteria I can relax without running the risk of it stalling. The closer to completion it is, the more those criteria represent the limitations of my imagination, not the endless possibilities of reality. 

It takes an entire village to support a single Very Productive Person

It’s become very clear to me that not only does it take a village to raise a child, it also takes a village to support just one Very Productive Person, or VPP. A VPP is someone who is able to make their own productivity their top priority. They are a rare and exotic kind of human, very unusual in the grand scheme of things.

In order to maximize their own productivity, a VPP has to outsource or eliminate all sorts of responsibilities: cooking, cleaning, and caring for others above all. They require large amounts of unstructured time to throw at any problem that might arise. They have to be able to spend time lavishly to improve the quality of their output only slightly. They have to spare no expense.

I can clearly see that I am such a rare and exotic VPP. I’m not ashamed of it, but I do recognize more than ever all the people needed to enable that: the gardener looking after our lawn and plants, the house cleaners maintaining our home, our families to take care of our son when we need to work, my personal assistant managing my emails, and all sorts of other service providers I call upon when I need something to happen. 

Everything, EVERYTHING has maintenance overhead

It’s so tempting working online to not account for overhead costs. You put up a website and it feels like it doesn’t cost you anything to maintain. You publish a course and it feels like it should just live there on its own indefinitely. But of course that couldn’t be further from the truth. Everything takes maintenance. There is no such thing as “passive income,” only more or less active income. 

I’ve tried to remind myself of this throughout the year as I’ve been faced with decisions about which opportunities and projects to pursue. I have a strong bias to pursue projects that can be run at a distance, in parallel, with light touches, by others, or only occasionally as desired. But as our business grows it becomes more and more important to protect our reputation, which means that anything we do must be done well. It must meet a certain standard of ongoing quality, which means it requires a certain amount of ongoing investment, which means something else will receive less. 

Most of the time I’m seeking achievement what I really want is connection

I’ve noticed many times over the years that almost the moment I reach an important milestone, such as signing a book deal or finishing a course launch, I’m off to the next one. In the AOA course I realized that much of the time I’m relentlessly seeking a new achievement, what I really am after is connection. 

Achievement gives me a semblance of connection – I feel connected to the needs of my customers, to the problem I’m solving, to the success of the team. But instead of going after the next white rabbit, I know that I can also just seek connection by itself. Knowing this is half the battle. It takes the form of a conversation with Lauren on the couch, taking a walk with my son, or calling up a friend. 

Ask: Do I have enough joy in my life?

I’ve been trying to kick several bad habits recently, like consuming sugar. I’m learning a lot about why I turn to sugar. It’s usually to avoid feeling boredom or loneliness, or to have more excitement or contentment in a day that feels devoid of it. It’s an unthinking habit and continues because it is effective at its purpose: allowing me to avoid checking in with what I’m feeling.

I’ve started asking myself a question every time I have a sugar craving: asking myself “Do I have enough joy in my life?” The question prompts an internal search for joy, which provokes a “zooming out” in my perspective from that one moment to my broader view of life. Once I have that wider perspective, even just a little bit, the answer is obvious: of course I do. Of course there is more than enough joy in my life, more joy in each and every moment than I can possibly contain. Then what am I seeking by eating this cookie, or cupcake, or doughnut? 

It’s the internal dialogue that is crucial. An internal dialogue that is about asking questions, looking for sources of joy, and being curious about the answer. I am learning to use my internal dialogue to be kind to myself, instead of to beat myself up.


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