Lessons in Managing My Own Psychology


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Lessons in Managing my own Psychology In The Trenches

Ben Horowitz, the world-renowned Venture Capitalist and co-founder of Andreesen Horowitz, said it best when he said:

By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . .  very few people talk about it . . . In the end, this is the most personal and important battle that any CEO will face.

Indeed, my own experience taught me that unless you are deliberate about managing your own psychology, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time. And as the leader of a company, the circumstances that typically present themselves in your life at any given time are often challenging, uncertain, or worry-producing.

Against this backdrop, below I present the five most meaningful lessons that I’ve learned over the years related to better managing my own psychology as a leader. Though many of these lessons are easier said than done, I suspect that any degree of time and effort that you dedicate towards them will likely yield meaningful results. The goal isn’t necessarily to master each of these (indeed, few – if any – human beings have done so), but instead to be regularly aware of them, and to work on them in a deliberate way.

Lesson 1: Stop Comparing Yourself to Others

“Comparison is the thief of joy”
Theodore Roosevelt

I always seem to be more impressed with other people than I am with myself. Indeed, this is true of many, if not most people. I remember in my earlier years as a CEO, I would often leave conferences, seminars, and industry events with a certain level of self-consciousness and self-doubt: Everyone that I had seen on stage or interacted with personally seemed to know more than me, was moving faster than I was, or were more certain in their decisions. In short, it felt like everybody had it all figured out except for me. If you reflect back on your own experiences, perhaps you’ve felt something similar.

Over more recent history, I’ve come to appreciate the folly of comparing one’s self to others, despite how automatically our minds seem to make such comparisons. Indeed, with respect to every given aspect of your life, looked at in isolation, somebody in the world is doing better than you are. In fact, this is likely even true when contemplating only your first-degree connections, never mind the rest of the world.

This is just one of the reasons why selectively comparing ourselves to others tends to leave us feeling inferior in some way, particularly for driven and ambitious people who tend to be especially uncomfortable in second or third place. Not only does our propensity to compare ourselves to others rob us of joy and satisfaction, it can be argued that such comparisons almost never yield objectively accurate information, for three primary reasons:

i) Differences in Personal Values and Circumstances: What we often fail to realize is that each of us – either consciously or subconsciously – organizes our lives around our own unique sets of personal values and circumstances, and as a result, we each prioritize different things. When we compare ourselves to somebody with completely different sets of values and circumstances, we create an apples-to-oranges comparison that, by definition, cannot produce useful or accurate insights. Yet we tend to treat the results of such comparisons as objective truth.

The CEO who works 80 hours per week compares herself to the CEO who works 40 hours per week, and feels inferior about the relative lack of balance in her life, and wonders why she can’t be more efficient with her time. The CEO who works 40 hours per week compares herself to the CEO who works 80 hours per week and worries that she isn’t doing enough, and questions whether or not she’s really cut out to be an entrepreneur.

Yet neither of these people are aware of the unique values and personal circumstances that have shaped how her counterpart spends her time: Perhaps there is a difference between the two in the relative value of financial success versus ample free time. Perhaps one business necessitates a heavy workload on the CEO, whereas one doesn’t. Perhaps these two people are at different stages of their lives, with different personal or financial obligations. Perhaps one is more efficient with her time than the other. Perhaps one business has immediate-term cash flow concerns, whereas one does not.

Regardless of the reason(s), it is almost certainly true that there are values and circumstances unique to each entrepreneur that underlie the differences between them, and as a result, any comparison between the two will be of the apples-to-oranges variety.

ii) Nobody Has it All Figured Out: Human beings are notoriously bad when trying to objectively compare ourselves to others, especially in the face of incomplete information. Consider the fact that over 90% of people classify themselves as “better than average” drivers, which of course is statistically impossible (only 50% of drivers can be better than average). We all make similarly inaccurate assertions when we judge and compare ourselves relative to others.

I mentioned above that at times I felt as if every CEO had it all figured out except for me. More recently however, after having worked with countless CEOs, I’ve come to appreciate that nobody has it all figured out, and that most people think that everybody else has it all figured out. For each virtue and success that you see, every other CEO (or, more broadly, every other person) has a worry, problem, or insecurity that you don’t see. In saying this, I’m not suggesting that you should derive some sense of joy or comfort in the struggles of others. I’m simply reminding you that everybody has something (in fact, everybody has lots of “things”).

As mentioned above, industry conferences, panels, and CEO roundtables used to be the primary breeding grounds for my own sense of inferiority, self-consciousness and self-doubt. However, knowing what I know now, I strongly suspect that if every conference, panel, or CEO roundtable forced all of their attendees to drink a truth serum immediately before the event started, the result is that most people would leave the event feeling comforted and supported, not inferior and worried.

iii) You Don’t Know What You Don’t Know: Put very simply, there’s a lot that you don’t know about other people and/or other companies. When speaking to others, people often put on their best and bravest faces and hide the anxieties, uncertainties, and worries that are simply part of the human condition. At times this is done consciously, but most of the time it’s done unconsciously. Though you probably dislike when people do this to you (I’ve privately accused more than my fair share of people of being fake or disingenuous to me), it’s humbling to notice that I myself have done this to others too (in fact, I regularly do this). I find it so interesting to note that vulnerability is often one of the traits that we most appreciate when its being demonstrated by others, yet it’s the trait that we least often demonstrate when we deal with others. Before you compare yourself to anybody else (or compare your business to somebody else’s), remind yourself of how little you truly know.

Lesson 2: Focus Only on What You Can Control

“Grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference”
Reinhold Niebuhr

The things that keep entrepreneurs and CEOs up at night can be broadly classified into one of three categories: (1) Things over which we have full control; (2) Things over which we have some influence but no control; and (3) Things over which we have no control whatsoever. 

Though the logical part of our brain tells us that we should naturally be expending our mental time and energy in category 1, the reality is that most of us actually spend most of our time in category 3. We worry about the economy, the state of our industry, the financial health of our customers, credit availability, how quickly our competitors are moving, and so on. Despite the fact that things like these can genuinely induce worry (and that being knowledgeable about them can be important), the practice of actually spending time worrying about them is a waste of time and mental energy.

Human beings are bestowed with a very finite amount of mental energy that we’re able to expend within any given 24-hour period. Thus, time spent worrying about the wrong things equates to time not spent worrying about the right things. As CEOs, our companies are only as good as the accumulated impact of the decisions that we make, and thus the quality and quantity of mental energy that we put into making those decisions. It is therefore our job to deliberately choose what to expend our mental energy on and what to ignore.

Has the economy ever improved because you worried about it? Has getting a bank loan ever been easier because you lost a night of sleep over whether or not you’d get one? Of course not. But there is almost certainly something that you can do within your business that would better protect you from an economic downturn should one occur. There is almost certainly something that you can do within your business that can make your company more creditworthy in the eyes of lenders. These latter considerations are productive to worry about. The former considerations are not.

Though this is all certainly much easier said than done, I’ve come to learn that it is by no means impossible (complete mastery may be impossible to attain, but improvement is likely easier than you may think). Some of the mental practices and routines that I’ll describe further in my next blog post (Tools in Managing My Own Psychology) now have me spending much less time worrying about the wrong things. Though I’m still prone to doing so (we all are), I’ve come to appreciate that what I spend time worrying about is not completely outside of my control.

Lesson 3: The Immense Payback of Better Understanding Yourself

“It is impossible for a person to begin to learn what he thinks he already knows”
Epictetus

One of the greatest gifts that I’ve received from my years in therapy is a much better understanding of who I am at the most fundamental level. In retrospect, it’s amazing to consider how little I knew about myself before I began employing deliberate practices to better understand what truly makes me tick. Based on my experience, I’d suggest that an investment in better understanding yourself is one of the most productive investments that you can make, both for yourself and for your business. After all, how can you optimize around what’s best for you (and minimize what’s worst for you) if you don’t have a genuine understanding of what those things are?

Working with a therapist is certainly one way to do this, and I’d highly recommend it. The insights are deep, though they can take time to extract. That said, I’ve been able to extract similar insights into myself from two other practices. Though the insights may not be as profound relative to therapy, they’re still incredibly useful:

1. Personality Tests: One of the best things that I did with my own senior management team was have everybody (including me) take a personality test. The benefits to the team were incredible: In one instance, we were able to uncover why two managers tended to work so well with each other, while in another, we discovered why two managers had a propensity to have regular conflict with each other. Evaluating the results of my own test also provided me with a lot of actionable insights. It turned out that my dominant personality trait was that of an “Achiever”, meaning that in order for me to feel fulfilled, my mind needed to feel a sense of accomplishment every single day, whether that sense of achievement was big or small. Based on this insight, I’ve adopted some new routines, including:

  • Working out in the morning instead of the evening
  • Tackling one thing on my “nagging to do list” daily
  • Tracking progress against various personal goals daily, using my smartphone
  • Employing the “One Minute Rule”: If any task can be completed in one minute or less, simply do it without hesitation 

Though these small “achievements” may sound insignificant, each of them provides me with an almost subconscious sense of accomplishment, usually at the beginning of each day, which almost inevitably sets me up to have a more productive and enjoyable rest of the day. What small practices might you build into your own routine once you have a deeper understanding of what your mind needs on a daily basis to feel content?  

2. Track (and Understand) Your Good Days and Bad Days: Jim Collins, the famous author of Good to Great, Great by Choice, and many other seminal business books, employs a daily practice that has drastically improved his life: He utilizes a simple spreadsheet in which he rates each day on a subjective scale between -2 to +2. (-2 is a terrible day, -1 is a bad day, 0 is a neutral day, 1 is a good day, 2 is a great day). He simply enters the number before he goes to bed each night, and adds a few sentences explaining what he did on that day that led to the day’s rating. After he engaged in this practice for a month or two, he looked back on his results and gained a more nuanced understanding of what drove his +2 days, and what drove his -2 days. Armed with this knowledge, he began to organize his life around doing more of his “+2 activities”, and minimizing, delegating or eliminating all of his “-2 activities”. Though you may think you already know what these activities are for you, I would challenge you to try this practice for at least one month. I suspect you will learn something new, and may even find yourself surprised by the results.

Lesson 4: Ambition is Essential, but be Mindful of its Price

“Treat what you don’t have as nonexistent. Look at what you have, the things you value most, and think of how much you’d crave them if you didn’t have them”
Marcus Aurelius

Having a relentless sense of ambition has certainly served me well from a career perspective, and I suspect that the same is true for you. However, an untethered sense of ambition comes with a price. Though inexhaustible ambition tends to be an almost necessary ingredient of the entrepreneurial success formula, without the appropriate context and understanding it can have unintended consequences on one’s sense of fulfillment, happiness and well-being. Simply being aware of these common pitfalls is the first step to ensuring that you don’t fall victim to them. Namely:

  • The Fleeting Nature of Achievement: Human beings have an unfortunate tendency to over-focus on what we don’t have, and under-focus on what we do have. Even when we achieve our goals, we tend miss out on satisfaction and fulfillment because the first thing that we do when we arrive at a destination is move the goal line further away (likely in the direction of a new or larger goal). This is particularly true for highly ambitious people: Like addicts, we’re always seeking our next high, though in this case our vice isn’t drugs or alcohol, but instead the feeling of achievement. While this tendency can be helpful (and perhaps even healthy) in our pursuit of ever more challenging goals, it can also rob us of the happiness and fulfilment that we should feel once we actually achieve the goals that we had set out for ourselves. When we relentlessly pursue the next customer, the next funding round, or the next million dollars of revenue, what we’re often actually saying is “I’ll be happy/satisfied when…”. Almost inevitably however, that happiness or satisfaction never comes (or if it does come, it’s fleeting) because of our tendency to immediately move the goal line forward.
  • Focusing on Processes vs. Outcomes: We also tend to over-focus on outcomes, and under-focus on the processes through which we attempt to arrive at those outcomes. The former likely includes elements that are completely outside of our control, yet the latter likely resides entirely within our control. What’s more, the former tends to produce a more fleeting sense of fulfillment, and the latter tends to produce a more sustainable one. Hitting or missing a goal in and of itself should not the be yardstick against which you measure your sense of accomplishment and fulfillment, because chances are that luck and circumstance played an outsized role in whatever the outcome was. If however you measure your satisfaction by the progress against the goals that you set for yourself (namely things that are within your control like effort, focus, execution, and so on), you’re much more likely to achieve a more enduring sense of happiness, that importantly is completely untethered from whatever outcome the world happened to produce.

Lesson 5: “First World Problems” Are Still Problems

“Not everything that is faced can be changed. But nothing can be changed until it is faced.”
– James Baldwin

I mentioned above that no matter how well you’re doing, there is somebody else who is doing better than you are. But the opposite is true as well: No matter what your problems are, there are countless others who are facing problems that are either more numerous or more severe than yours are. This latter fact often creates an unfortunate tendency for us to brush off our own problems as being of the “first world” or “champagne” variety, which in turn can create situations where we either don’t deal with our problems, or we feel decadent or guilty when we attempt to do so. Though it’s certainly healthy and appropriate to situate your fortune (either good or bad) into an appropriately wide context, know that this context risks becoming unhealthy when it minimizes the problem to such an extent that you don’t adequately address it.

During the early few weeks of the COVID-19 pandemic, I was speaking to my therapist about the extreme stress levels that my wife and I were facing as a two-income household working from home while simultaneously trying to take care of our 2-year-old daughter without any external help. After expressing the problem, I immediately couched this issue as a “first world problem”, as we were all healthy and my wife and I were still employed, something that not everybody could say at the time. Though this broader sense of context was an important data point to have, my therapist noticed that I was using it to attempt to minimize the stress that I should have been feeling at the time. Subconsciously, the more stressed I became, the more guilty I felt, because I kept telling myself that – relatively speaking – I still had it pretty good.

The fact that others may have more serious or more numerous problems than you does not mean your problems aren’t worthy of empathy or efforts to address them. I encourage you to still be grateful for your circumstances and to maintain a healthy perspective around whatever problems you may be facing at any given time. But don’t use that context to minimize or ignore those problems, else you will not be able to adequately deal with them.

In Sum

Though many of these concepts are easier said than done, you owe it to yourself and others to start being thoughtful about deliberately managing your own psychology, which turns out to be one of the most important skills that a CEO can develop. Though awareness of these things is indeed a productive first step on that journey, there are also specific tools and practices that can help get you a little further along. These tools will be the focus of my next blog post, “Tools in Managing My Own Psychology” (note hyperlink will not work until the post is published).


If you’re interested in learning more:

Meditations, written by the Roman Emperor Marcus Aurelius, is one of the founding books of the philosophy of Stoicism. Reading about stoic philosophy has been one of the most useful tools in my own toolkit as it relates to managing my own psychology, and it may prove to be equally useful for you too. Among other things, stoicism celebrates the virtues of controlling your perceptions and reactions to external events, avoiding thoughts of the past and future in favor of the present moment, being part of a broader inter-connected whole, and valuing your own opinion over those of others. Given that the book was written in roughly 161 to 180 AD, it requires some translation: Be sure to pick up the translation by Gregory Hayes (pictured here), as it’s by far the most digestible. I’ve found other translations to be difficult to get through.

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