The Entrepreneur and Mental Health (Part 2): My Advice to You

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This post is the second in a two-part blog post on leadership and mental health. Before proceeding forward, I suggest that you read Part 1 here.

In the now-famous Netflix Documentary “The Last Dance”, which documented Michael Jordan and the dominant Chicago Bulls of the mid-90s, Michael Jordan said something that entrepreneurs everywhere should never forget:

“Winning has a price. Leadership has a price.”

Indeed, everything that we do as entrepreneurs (late nights at the office, prioritizing the interests of others above our own, the constant stress levels, keeping our fears and anxieties to ourselves, etc.), does indeed have a price. You may not have to pay that price for days, months, or even years, but eventually, it always gets paid.

In my case, I felt impervious to this dynamic, always telling myself that I was a “grinder” who had persevered through literally every challenge that I had ever been presented with, personally or professionally. What I failed to realize was that my decisions and actions at the time were accumulating an ever-larger personal “debt” that I’d eventually have to pay back. In my case, I was completely unprepared when my debt came due, and I struggled enormously as a result.

I want to prevent the same from happening to you. Below is a list of lessons that I’ve learned over the years to prevent, as much as possible, the mental health toll that entrepreneurship (or leadership, or success) can take on you if you’re not careful about it. Of course, these lessons are only now clear to me with the benefit of hindsight, and with the benefit of the “distance” that I’m now privy to after having sold my company.

If nothing else, consider this a long list of the mistakes that I made that I hope you can now avoid for yourself.

1. Stop Prioritizing Everybody Else Over Yourself

The CEO is the only person in any given company that is inextricably linked to almost every stakeholder group both within and external to the business (employees, customers, investors, etc.). Each of these stakeholder groups have demands of your time, and has no regard for the demands of the other ones. Because I wasn’t thoughtful and deliberate about how I spent my own time, I spent almost a decade putting the interests of substantially everybody else over my own, even though I wasn’t necessarily consciously aware that I was doing it. I felt like I didn’t really have a choice. To satisfy the seemingly never-ending demands on my time, I would do things like miss workouts to make early morning meetings. I would stay at the office late and miss dinners with my wife & daughter. I would promise deliverables to key external stakeholders on timelines that I knew were highly aggressive.

What I came to learn is that this way of doing thing is highly unsustainable at best, and even dangerous at worst. If you’re the leader of a business, consider yourself the holder of a piece of debt. This piece of debt continues to accrue interest for each instance in which you put the needs of others before your own. For months or even years, you can continue to make interest-only payments, but eventually, that debt will come due. And unless you’ve made regular principal payments along the way (through acting on the 6 lessons I discuss here), then that debt will only get bigger over time as that interest continues to accrue.

I’ve never been one for tired and over-used analogies and metaphors in business, but at the risk of using one, this first lesson equates to what you’ve heard on every flight that you’ve ever been on: “Put your own oxygen mask on first”. After all, what good are you to your fellow passenger if you are oxygen deprived yourself? And if you’re not looking out for yourself, then who is? Putting your own interests above those of others will take a different shape for every CEO, but here are a few good examples that I’ve seen over the years:

• Don’t start a workday until you’ve finished your morning workout
• Take an hour lunch, away from your desk and outside of the office, every day
• Be home in time to have dinner with your spouse and/or kids
• Get 8 hours of sleep every night

I’d be remiss if I didn’t mention that you should not strive to do all of these things, all of the time. That’s impossible. In the real world, there are indeed tight deadlines and periods of higher-than-normal workloads. So as you work on putting your own oxygen mask on first, give yourself permission from now that you don’t have to be perfect. You don’t have to do everything on your list, and you certainly don’t need to do them every day. But, over time, you must ensure that you’re reducing the size of your debt, not accidentally watching it increase.

Before you tell me that you can’t afford to take the time to do these types of things, let me tell you this from personal experience: Over the long term, you can’t afford not to.

2. Don’t go it Alone

In my early years as a CEO, I figured that the very nature of my job was to personally bear the weight of the pressure, worry, and burden of expectation that comes with running a company. I didn’t want to share my company-specific worries with my employees, for fear of scaring them off. I didn’t want to share my uncertainties with my Board, because technically they could fire me at any point if they didn’t think I could handle the position and all that it entailed. I didn’t want to share the pressure that I felt with my friends or family, because I thought I’d just worry them, and I suspected that they wouldn’t understand anyways.

Of course, I was wrong. These were the musings of a rookie CEO.

With experience, you come to learn that you simply cannot do it alone. In fact, all of the best CEOs that I know are actually those who seek help in any place that they can find it. Once I finally did seek external help, I demonstrably became a much better CEO. Here are a few ideas of where good leaders should be going to seek help:

1. CEO Groups: Organizations like the Entrepreneurs Organization (“EO”) or Young Presidents Organization (“YPO”) literally exist to help CEOs deal with all of the problems and opportunities that come with the position. I have been a proud member of EO for 5+ years, and still consider it the best personal investment I’ve ever made. Every month, I meet with the same group of 7 CEOs from similarly sized companies across a variety of industries for us to help each other however we can. When I describe a problem or opportunity to my peers, there is nothing more comforting than seeing 3 – 5 other CEOs nodding their heads and saying something to the effect of “I felt the same thing when I went through something similar. Here’s what helped me get through it”.

• CEO Coaches: The CEO coaching industry is undergoing rapid growth, and for good reason. CEOs are starting to realize the enormous value that coaching can bring to both them and their companies. Before you tell me that a coach can’t help you because they couldn’t possibly understand your business nearly as well as you do, let me remind you that Tiger Woods has a swing coach. Roger Federer has a tennis coach. Tiger Woods’ swing coach isn’t a better golfer than Tiger is, nor does he have a more perfect swing – he’s there to identify blind spots that Tiger may have, share perspectives and lessons from other golfers with whom he has worked, and to ask Tiger important questions that he may not think to ask of himself. (You can listen to my podcast on CEO Coaches here)

• Therapists: 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. After all, 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?

3. Share Your Problems With the People Most Able to Help you

As I’ve mentioned, good CEOs don’t try to do everything on their own. They share their problems with others, and specifically with the people in their lives who are most able to help them solve those problems. Of course, I didn’t do this as a rookie CEO, and I suffered as a result. The lightbulb moment came for me when I got my management team together in 2020 to let them know that I had decided to step down as CEO to focus on the declining state of my mental health. This was a very frightening conversation for me, as I was scared that they’d think that I was quitting on them. I was scared that they’d think that my decision was a reflection of my views of the future prospects of the business. I was scared that they’d say “Well if Steve is out, then I’m out”, which might have put the business at risk.

Of course, none of these things happened.

Instead, what they said to me should serve as a lesson to you. They said “I wish you had told us sooner”. They told me that if I were more open with them about the anxieties, worries, and personal burdens that I had been feeling over the years, they happily would have worked with me to address them in any way that they could have. After all, as my senior management team, these were the 6 people in my life most able (and, as I came to learn, most willing) to help me solve any number of the problems that I thought had to reside solely with me.

After I left the company, I discussed this same idea with another CEO, who shared a great analogy with me. He said “If you’re jumping out of a plane, there’s a right time to pull the chute. It isn’t 10 feet from the plane, and it isn’t when you’re 10 feet from the ground”. In my case, I had waited until I was 10 feet from the ground to pull the chute (i.e. seek help), and by that point, it was too late.

Lastly, I came to learn that my management team genuinely appreciated me finally being vulnerable with them and talking about the things that were bugging me. I’m a bit embarrassed to say that up until that point, my management team sometimes described me as a bit “robotic”, in that I never really shared my emotions or burdens with them. This not only “humanized” me in a way that was long overdue, but ultimately led to a closer relationship between myself and each member of my management team.

4. Force Yourself to Take Stock of Your Accomplishments

As natural “achievers”, most CEOs aren’t interested in hearing what they’re doing well – they’re often more interested in how else they might be able to improve. While the spirit behind this sentiment is understandable, at extreme ends of the spectrum it can become dangerous over time. In my case, having never stopped to genuinely take stock of my accomplishments (or ascribing all of my accomplishments to good luck or good timing), I focused solely on the things that I wasn’t doing well enough, and over-time, almost subconsciously, I ended up convincing myself that I wasn’t doing my job well despite significant evidence of the contrary, both within and outside of the company.

One way that I learned to combat this was to keep a simple journal of my accomplishments that I filled out daily, weekly, or monthly. The accomplishments that you keep track of can be “major” (hired a new CFO, released a new product), or “minor” (hired a recruiter to begin the search for a CFO, narrowed down list of new product candidates to three). Not only does the act of writing these things down serve as positive reinforcement that works at both a conscious and unconscious level, but over time you’ll easily be able to look back at all of the things that you’ve done well, which will help you during the difficult periods that will inevitably arise.

5. Treat Yourself as You’d Treat Others

It’s amazing how much more critical we are of ourselves than we would be of somebody else in the exact same situation, and under the exact same circumstances. While you may think that your self-criticism has been a key ingredient to your success, know that it may grow to become an increasingly heavy burden on you, even if you’re not consciously aware of it. Next time you find yourself chastising yourself, for, say, making some sort of mistake, ask yourself: How would I advise my best friend/brother/sister/etc. if they found themselves in an identical situation under an identical set of circumstances? Chances are, instead of calling them short-sighted, accusing them of moving too slowly or too quickly, or telling them that they should know better, you would almost certainly advise them to recognize the difficulty of the situation that they had found themselves in, acknowledge the extenuating circumstances surrounding the decision, and tell them mistakes are to be expected and act as key lessons that must be learned along the way. If it’s intuitive and logical to advise others in this way, why isn’t it equally as intuitive and logical to advise ourselves in this same way?

6. Actually Live Your Values.

My guess is that if you ran a poll of 100 randomly selected CEOs and asked them what their values were, on average you’d probably see something like this as the most frequent answer: (1) Family; (2) Health; (3) Work/Money.

I’d also guess that if you actually observed each of these same 100 entrepreneurs every day for one month, you’d observe that the values that they actually lived might look something like this: (1) Work/Money; (2) Family; (3) Health.

Some of us have codified personal values, but most of us don’t actually live them. One of the best ways to ensure that you’re on a sustainable path as a CEO is to first codify your values, but at regular intervals (say, monthly) critically and objectively evaluate the extent to which you’re actually living those values. Even better, ask those around you (spouses, friends, parents, etc.) to evaluate you. Chances are they’ll approach this question with a greater degree of objectivity than you would. By being deliberate about the extent to which you’re living your values, you won’t allow life to simply happen to you. You’ll be in better control of how and where you spend your time & energy.