Confessions Of A Workaholic

Failure only hurts when you know you could have tried harder

Nov 19, 2025

I do not work more because I love winning.
I work more because if I stop, I feel like I am losing.

My identity is tied to work. My ability to perform, to produce, to push... this is how I measure myself. When I am not working, I feel useless, and uselessness feels like failure. Not just for me, but for my family.

Work is not just what I do. It is how I soothe the insecurity that lives inside me.

What people often do not realize is that all of us carry anxiety about something in our lives.

The habits we form, the quirks we carry, the rituals we practice... they are all tied to soothing that insecurity. The danger comes when we cannot see it clearly. That is when addictive behaviors take root and pull us into destructive paths.

When you can see the insecurity for what it is, when you can name it and acknowledge it, and when you choose something constructive to manage it, you give yourself a fighting chance. You understand your baseline. You see the behaviors wrapped around it.

Also, none of us are free from insecurities.

Every one of us has them. The difference is whether we are aware of them. Most people already have a self-soothing mechanism, they just do not recognize it. For many, it becomes destructive. Binge eating. Gambling. Porn. Doom scrolling. Drinking. Partying to escape. Each one is only a mask over the red siren of insecurity blaring underneath.

For me, that mechanism is work.

Effort As Medicine

I do not crave the high of winning.
What I cannot stand is the feeling of losing.

I cannot stand the feeling of losing if I know I could have done more. If effort was the reason I did not achieve something I truly wanted, that is unbearable. If one more call, one more rep, one more memo could have made the difference, and I did not do it, that is torture.

That is why I keep pushing.

It is not workaholism for its own sake. It is the refusal to lose when the outcome is in my control.

So I raise the bar as a minimum standard mainly as a self-imposed mechanism for myself to perform. For most people, the bar is low. One call a day, one meeting, one rep. For me, the bar is unreasonable. Ten calls, a hundred, a thousand.
Honestly, whatever the hell it takes.

On the days I pour myself into that kind of effort, I go to bed tired but calm. On the days I fall short, I go to bed with anxiety and wake up feeling like a loser.

Working hard is my way of keeping a promise to myself. Because I just know that if I do not stop, I will not lose.

While this is clearly neurotic, I have poured this philosophy into everything I have built.

Over the last two decades, I’ve had five exits, including two billion-dollar companies, one that traded on Nasdaq and another acquired by a public company. None of those outcomes came from a single stroke of genius. They came from doing one more call, one more rep, one more memo… when most people would have stopped.

There is a great Aquaman quote that I repeat to myself when things get tough:
Not giving up is the most heroic thing you can do.

Where It Comes From

After years of reflection, I realized that I did not manufacture this attitude for myself.

I may have actually inherited it.

Some people might think, here we go again, Sharran blaming it on how he was raised.

That is not it.

I have the greatest parents, and they continue to be a profound influence in my life. They gave me something that I will never be able to repay. They instilled in me the tenacity to endure the hardships of life, and they showed me how to do that by example.

When I was growing up, my parents never rested. They never sat by a pool. They never wasted a weekend. Every waking hour was focused on squeezing the most out of life. They built everything from nothing.

They showed me that effort is the ultimate equalizer.
That gift, the ability to endure and to push, is quite possibly the greatest thing a parent can pass down. It has shaped every part of who I am, and it still guides me today.

I have carried that lesson through everything I have built and invested in, more than a hundred deals before I even stopped counting. I have never had the most money in the room, but I have always been willing to put in the work and do the boring reps. That willingness is the inheritance my parents gave me.

This is also how I think about legacy.

Legacy as a noun has never made sense to me. When we die, we are ashes, and we are gone. Maybe we are remembered by a tiny few, in a few fleeting moments, but even that fades. Legacy as a noun is not my focus, because I honestly do not understand it.

However, legacy as a verb is extremely approachable as a linguistic construct.

What if Legacy is something you can operationalize. Instead of it being an abstract memory, what if it was a set of lived behaviors. That is the way I choose to act today as a vehicle to share, to serve, and to leave an everlasting gift for my family. And that gift is not a generational trust or a multi-billion-dollar real estate portfolio, which they will probably receive anyway.

It is the gift of tenacity.

The ability to endure whatever life brings. If life is easy, they may never need it. If life is hard, it will be the only thing that saves them. That is the true inheritance. And now, as a parent, I think of my own legacy in the same way. My job is not only to provide for my children, but to show them the skeleton key to life. To live by example, to teach by example, to endure by example, and to pass that gift forward by example.

My Friends Are Not Dumb

People around me who care deeply sometimes worry about my intensity.

They call me a workaholic, sometimes to my face, and I am pretty sure they do it lovingly behind my back. They often tell me that I have no balance. They point to the health breakdowns I have had as proof. And they are not wrong.

In fact, I want to honor them here. The fact that they notice, the fact that they care enough to say something, means the world to me. It takes love to call someone out. It takes courage to speak the truth when you see someone pushing too hard. I am grateful for that, and I love them for it.

At the same time, I am a little different. Work is my yoga. It is my self-care. It is my meditation. It is my late-night bowl of ice cream. It is my run, my weightlifting session, my game of pickleball.

Work is my working out.
Because work is how I show that I care. It is how I prove, to myself and to others, that I am committed to the highest standards, most of which I clearly manufactured for myself.

Yeah, but what about balance?

I have seen time and time again that balance does not create excellence, or even happiness. Balance is the biggest myth fed to you by society. Balance is not the input to a great life of happiness, contentment, or accomplishment. Intensity will get you to your goals faster than balance ever will. In fact, you will reach a balanced life sooner if you live with extreme intensity first.

People who worry about my intensity sometimes forget that intensity is also what keeps my life integrated. I have been married nearly two decades. I have two kids. I have made nearly every recital, driven them to practice, cheered at weekend soccer games, helped with homework, gone on date nights and also take out the trash.

I have learned that intensity is actually the secret ingredient of all my relationships.
I go hard. All the time.

Being Honest With Yourself

This is simply who I am.

Sometimes, my intensity irritates people. Ask any friend and they will say I am intense AF, but they will also say I am (generally) kind. Both are true.

I am not asking anyone to give up their family or friends. I have a better relationship with mine than most people who claim balance. My life is built with intensity, and I bring that same intensity to relationships, health, business, and everything else.

You do not need to be like me.
You need to be like you.

Naval Ravikant once said, “Intelligence is just getting what you want out of life.” That begins with self-awareness. This is not about sitting with your thoughts and being a fugging monk. This is about being honest with yourself.

If you love sitting by the pool, then design your life to sit by the pool. If you choose the pool and then complain about money, you got what you wanted.

Awareness gives you choice. If you want a Lambo, then want it without apology. Build the effort, the skill, and the plan to get it. If you want family time, then design for it. Whatever it is, own it fully. Do not let society, influencers, or balance gurus sway you to wanting what they may have.

I don’t just say this from theory. I run the 5AM Club, the longest-running daily call for entrepreneurs, fourteen years straight, 365 days a year, without a break. I own more than 3,500 units of real estate. I’ve seen every stage of the entrepreneurial journey up close, and the same truth repeats itself: balance is a myth, intensity is what creates excellence.

The Future I Want

Over the years I learned to be okay with the boring work. The grind. The mundane. That was the training ground.
Now I want to work more, not less.

But I want to spend a greater percentage of my time on what fascinates and motivates me. On what lights me up. On what sits in my zone of genius.

Joy for me is not a beach. While I love my family more than anything else in this world, joy is not spending every waking hour with my wife or my kids. In fact, my true joy is letting them live their lives fully while I live mine fully. When our lives overlap, those moments are richer because they are chosen, not forced by some unqualified social construct of “spending more time with my family”.

Normal people chase balance. I never understood normalcy. It is vague, overrated, and a self-issued pass to laziness. I am sorry, that is why normal people just don’t win.

The Point of This Confession

This took a lot of courage for me to write this, mainly because I know I will be judged.
But being judged for who you truly are is also being seen for who you truly are, and I am okay with that. Who cares if I embody the ideals of “work hard and be kind.” Maybe for me it is “work super hard and be super kind.”
You do not need to be like me.
You need to be like you.

I am being vulnerable enough here that I would be comfortable for my therapist to read this and feel, for a brief moment, like she failed me. But I know she would quickly realize that this piece is exactly why she is in my life. She succeeded years ago. She helped me not just make peace with who I am, but find insane strength in it.

So it is okay for me to say it clearly: I do not work just to win.
Of course I enjoy winning, but I work because stopping feels like losing, especially when I know the effort I could put in could create a bigger and better future for me, for our team, for our company, and for the people I care about.

And if that effort causes parts of my life to break down, I will understand them, rebuild them, and learn from them. Each breakdown only teaches me more about who I am and how I am built. That process of rebuilding is part of the deal, and it is what makes me the intense, reliable, and deeply caring person that the people in my life know they can count on.

And maybe that is the part that matters for you too.

This is not an excuse for my choices, and it is definitely not an invitation to be like me. It is a reminder to find the promise inside yourself that you cannot afford to break, because the purest form of integrity is keeping the promises you make to yourself.

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