Listen to This Blog Post

Tools in Managing my own Psychology – In The Trenches
In a previous blog post, Lessons in Managing My Own Psychology, I presented the five most meaningful lessons that I had learned during my tenure as a CEO related to better managing my own emotions. In today’s post I get much more tactical, and discuss the specific tools, routines, and practices that I have found to be particularly effective in doing the same.
I’m taking the time to write about this based on the following deeply held beliefs, all of which are based on my own experience as an Entrepreneur and CEO:
- A CEO’s ability to manage herself is at least as important as, if not more important than, her ability to manage her business (indeed, the two are inextricably linked). However, most business literature doesn’t seem to adequately recognize this reality
- 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 lack a clear path forward.
- Over time, the mood of the broader employee base often directly reflects that of the leader. When I was sluggish, tired, or worried, almost inevitably the broader employee base came to experience those same things. When I was excited, energetic, or optimistic, most others tended to feel the same way. This didn’t necessarily oscillate on a daily or weekly basis, but tended to be true in periods of time measured in months or quarters.
As a leader, investments in yourself indirectly become investments in others. Organizational health suffers unless the CEO has properly attended to her own personal health, both mentally and physically.
But First, Some Caveats
The list of routines and practices that I present below is not meant to capture every conceivable tool that one might choose to use in managing their own psychology. Instead, I’ve simply presented a list of tools that have worked for me, in hopes that at least some of them will work for you too.
Second, note that the effectiveness of many of these practices has been thoroughly documented in countless peer-reviewed studies. As a result, I will spend little to no time explaining why and how they work at an academic or intellectual level.
Lastly, the tools that I present below are so multifaceted that they have filled the pages of countless books all on their own. As a result, for the sake of brevity and practicality, I’m forced to limit my comments to only a paragraph or two for each topic, but know that there is much more depth to be explored for the curious reader.
Practice 1: Meditation
This may be surprising to some, but the number of world-class performers (regardless of their discipline) that are not yet regular meditators is already very small, and is indeed shrinking by the day. Contrary to popular belief, the goal of meditation is not to get rid of the thoughts that constantly occupy our racing minds (as any meditator will tell you, that is simply impossible), but is instead to be consciously and deliberately aware of our thoughts, and to view them as a sort of “interested third-party observer”, as opposed to personally identifying with them, as we all tend to do from time to time.
Though it takes time for meditation to yield its true benefits (indeed, impatience in realizing these benefits is one of the primary reasons why people give up meditation after first experimenting with it), my experience meditating has provided me with the following benefits:
- It’s amazing to simply sit and watch your mind operate for even 10-15 minutes per day, because once you do this frequently enough, you become more aware of and more comfortable with its constant and seemingly random machinations. This awareness and familiarity helps me when unpleasant thoughts arise during the course of my day-to-day life, as I’m now able to better attribute them to “the mind simply being the mind” (that is, a crazy, manic roommate living between our ears that is constantly throwing thoughts out to us in hopes that we’ll latch on to one of them)
- Increased ability to relax
- An increased ability to actually be present when spending time with friends and family (as opposed to just being physically present with my thoughts residing elsewhere)
- A shrinking tendency to get caught up in unpleasant thoughts, and/or to believe unpleasant narratives that solely reside within my mind that have no actual link to reality (Have you ever had an argument with somebody exclusively within your own head? Me too.)
If you aren’t yet a regular meditator, are skeptical of its benefits, or are just looking for an introductory overview, I might suggest watching this 60 Minutes segment from 2016 on mindfulness meditation. Note that mindfulness is just one of many forms of meditation, though it happens to be the one that I personally practice.
I’ve also found the following resources to be very helpful:
- Book: The Headspace Guide to Meditation and Mindfulness
- The headspace app: For an introduction to meditation, guided meditations, and helpful overviews of various techniques and tools
(Note that I am partial to Headspace, but many similar apps exist boasting similar tools and functionality)
Practice 2: Journaling
I’ll leave it to the academics and psychologists to explain why, but I’ve come to appreciate the awesome power of simply putting my thoughts on paper, even if I never do anything in particular with those thoughts. There is no right or wrong way to journal – you can write about anything, for any length of time, and for any reason. But in my experience, I’ve found journaling to yield the following benefits:
- Writing tends to add a layer of clarity to my thinking that would otherwise be very difficult to access if the thoughts resided only within my head. If you’ve ever used a whiteboard or a blank sheet of paper to help you think through a thorny problem or opportunity, then you’ve leveraged this same benefit whether you were consciously aware of it or not. The act of journaling has surfaced more than a few important realizations for me that I almost certainly would not have uncovered had I not taken the time to put my thoughts on paper
- My experience in therapy has taught me that there is incredible power in the simple act of consciously surfacing and explicitly talking about my problems, thoughts and emotions. For me, journaling does a very similar thing, except the dialogue takes place in the written form (as opposed to the spoken form). In this way, journaling can be viewed as a sort of “therapy without a therapist”
I find journaling to be particularly helpful when I find myself in times of challenge, worry or uncertainty, though its usefulness is certainly not limited to such periods. The next time you find yourself ruminating, worrying, or over-thinking something, try simply writing it all out (with no particular goal in mind), and pay attention to how you feel both before and after the exercise. If you’re anything like me, you’ll feel better afterwards, even if you didn’t come to any particular answers or realizations.
Practice 3: Sleep and Exercise
I’m grouping these two together as so much has already been said about the importance of each of them, and you’re likely already aware of their benefits (at least, I hope you are). Because so much literature already exists about the effectiveness of both sleep and exercise, I will limit my comments to the following:
Sleep: If you adopt only a single practice from this entire post, I would encourage you to rearrange your life (yes, if drastic measures are required, then you should take them) to ensure that you’re getting at least 8 hours of sleep each night. If you don’t, then few of the tools and practices contained within this post are likely to work for you (or, at least, not to their full extent). Skeptics are encouraged to read Matthew Walker’s book, Why We Sleep, to learn more about the foundational benefits of getting adequate sleep.
Exercise: A simple google search will likely overwhelm you with peer-reviewed research about the proven psychological benefits of exercise (to say nothing of its physical benefits). Several studies have shown that regular vigorous exercise is at least as effective as, if not more effective than, most physician-prescribed anti-depressants. Not only does exercise provide us with a small “accomplishment” each day (which is psychologically important for type-A overachievers like me, and possibly you too), but it also provides us with a set of goals to pursue outside of work, which is more important than you may realize: Countless studies on happiness have pointed to growth, progress & learning as foundational components to achieving enduring levels of happiness. In my experience, it’s been beneficial to pursue growth, progress & learning outside of my role as an entrepreneur and CEO. This is important because, inevitably, there will be periods in your professional life where you won’t experience growth, progress or learning (sometimes, it will feel like you’re experiencing the complete opposite), so it’s helpful to still have pursuits in other contexts that provide you with these important psychological benefits.
Practice 4: Doing Nice Things for Other People and Expecting Nothing in Return
One of the apparent paradoxes within the study of enduring human happiness is the following: One of the best ways to increase your own happiness is to focus on increasing the happiness of others.
I don’t say this to suggest that being altruistic is something that you should do for self-serving purposes. Instead, I’m saying that an increase in your own happiness is a sort of pleasant (if unintended) consequence of focusing your efforts on helping others. A genuine “win-win” in every sense of the phrase.
Helping others can take any form, but in my opinion would ideally:
- Leverage the things that you’re already personally interested in doing; &
- Leverage what you are uniquely suited to help people with
If you already enjoy cooking, perhaps volunteer at a community kitchen that cooks and distributes meals for the less fortunate. If you’re passionate about helping others with their mental health, perhaps volunteer as a hotline operator. If you love baseball, perhaps volunteer as a coach for a youth baseball team.
Practice 5: Gratitude
Tony Robbins has said that one can’t be simultaneously angry and grateful. Though I’m sure many readers think of themselves as being inherently grateful for their circumstances, similar to journaling, there is great power in surfacing that gratitude and making it explicit, ideally on a daily basis. This could take a very simple form (like writing down one thing that you’re grateful for each morning or evening), or could take a more structured form, like that which is proposed within The Five Minute Journal , a tool that I used a number of years ago to add more structure and guidance to my own journaling practice.
Regardless of how you choose to do this, being regular and explicit with your gratitude helps to focus the mind on what you already have, and consequently decreases the amount of time that you spend thinking about the things that you wish were somehow different.
Practice 6: Therapy
In a previous blog post, The Entrepreneur and Mental Health (Part 2), I discussed the benefits of therapy, and specifically discussed why some people’s view of the use of therapists is misguided at best, and antiquated at worst: You don’t need to have a “problem” to see a therapist. You don’t have to be battling any issue in particular, nor do you have to be “unhappy”. I’ve always thought of my therapist as my personal trainer for my mind. If I pay trainers at the gym to help my body be at its best, why wouldn’t I hire a personal trainer to help my mind be at its best?
If you’re an Entrepreneur or CEO and you aren’t yet seeing a therapist, I’d suggest that you’re leaving a large opportunity on the table.
Practice 7: Reading About (and Attempting to Practice) Stoicism
Though my wife playfully (and regularly!) pokes fun at me for reading philosophy books at night, I couldn’t write this post without mentioning the benefits that have accrued to me as a result of my study of stoic philosophy. Make no mistake, I don’t exactly sit by candlelight and study ancient scrolls long into the night – instead my “study” has been largely characterized by reading a small collection of books, and then attempting to put into practice what I have read.
Unfortunately, when the word “stoic” comes to mind, most people tend to think of a person who is seemingly devoid of any emotions, and seems almost robotic at times. Interestingly, this description couldn’t be further from the actual philosophy from which the word “stoic” derives its name. It’s difficult to encapsulate an entire philosophy of life in a few soundbites, but at the risk of attempting to do so, stoic philosophy largely revolves around the following tenets:
- There are things that are within our control, and things outside of our control. Focus your attention on the former, and ignore the latter
- It is not external circumstances that dictate our happiness (outside of our control), but is instead our reaction to those external circumstances (within our control) that does
- Deeply appreciate what you already have, and ignore what you do not yet have. When you visualize and contemplate losing the things that you already have, you’ll develop a greater appreciation for them
- When you contemplate your own mortality, you realize that your time is a gift, and you tend to use it more wisely
- Time spent thinking about the past and the future is time wasted. It is only time spent in the present moment that matters
- In the context of human history, everything that is currently happening to you has happened a thousand times before, and will happen a thousand times again
If any of these resonate with you, you might be interested in checking out the following resources to learn more:
- Though stoicism is a philosophy that is thousands of years old, Ryan Holiday deserves much of the credit in reintroducing this philosophy into the modern day. His blog, emails, and books should be considered required reading in your study of “Stoicism 101”. This is probably where I’d start
- Book: A Guide to the Good Life: The Ancient Art of Stoic Joy, by William B Irvine : A logical second step after reading some of Ryan Holiday’s materials. This is another good introductory resource, written in a very accessible way, that applies modern day interpretations to the ancient texts on which stoic philosophy is based
(For more introductory resources, check out my “Books” page , under the headline “Managing Yourself”)
Practice 8: Maintaining Strong Personal Relationships
In a now famous longitudinal Harvard study on human happiness, it was found that our relationships have a formative influence on both our physical and mental health, and are also one of the best predictors of overall happiness.
I mention this because as an entrepreneur or CEO, you’re likely maniacally focused on your professional pursuits, and if you’re anything like I was, some of your personal relationships with friends and family might have suffered as a result. While it is understandable if this happens in short-term spurts, in the long run allowing your relationships to deteriorate is likely to negatively impact both your physical and mental health (and, as a result, will almost certainly negatively impact those professional pursuits on which you’re so maniacally focused).
To combat this, it’s important to continue to foster and strengthen those relationships that are important to you, and simple practices can help you do this. It could be as simple as a regular date night scheduled with your spouse, or a goal to spend time with a friend or family member at least once every 2-4 weeks. It’s especially important to spend time with people who don’t particularly care about your standing as an entrepreneur or CEO (not that they aren’t interested, just that they’d like you just the same if you were an artist, athlete, or insurance broker).
In Sum
As a leader, investments in yourself become investments in others. Organizational health suffers unless the CEO has properly attended to her own personal health, both mentally and physically.
I wish I was better at these things when I was a CEO. To tell you the truth, I was pretty lousy in putting these tools into practice, and indeed might be a case study on the detrimental effects of not being more deliberate about managing one’s psychology when in a position of leadership. I’m writing this now in hopes that you’ll pursue a more sustainable path than I did.
Even today, I have an infinite amount of room for improvement on all of these items. Please don’t think that I have it all figured out, because I certainly do not: I don’t meditate daily, I wish I journaled more often, I regularly fail to express my gratitude, I’ve skipped many therapy sessions, and there are more than a few relationships in my life that are not nearly as strong as I want them to be.
But, as I’ve come to learn, it’s not about being perfect. It’s just about being a little better (or more deliberate, or more regular) than you were previously. Over time, through taking small incremental steps, I hope and suspect that the accumulated impact of this better psychological hygiene routine will have notable impacts on both your personal and professional lives.
This post is brought to you by Cayne Crossing. Over the past 12 months alone, Cayne Crossing has completed 61 QofE projects on behalf of prospective buyers, with a combined transaction value of $1B+. Their median transaction value is ~$10M (with a range of $350,000 to $115M+), putting them right in the range of most SMB buyers.
Unlike any other QofE provider that I’m aware of, Cayne Crossing often co-invests alongside their buyers in the acquisition in question, which aligns their interests in a way that I simply haven’t seen anywhere else.
Cayne Crossing is offering a special discount to readers & listeners of In The Trenches: Just click the button below, and scroll down to the “Contact” form on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.