The loneliness of a tech CEO

No one really understands the loneliness — the deafening isolation. This year, you’ve come to understand it.

They say solitude is deadly. It warps the brain, wrecks your health. They say man needs company and compassion or he will die. Those who are socially isolated die years before their peers.

You thought you were the exception. Maybe you were wrong.

You feel like the world around you is crumbling and there’s no one to talk to about it. You feel like the sole architect of your fate. You feel like the Roman bridge builders who were summoned to stand below their works when the scaffolding was removed.

Your cofounder flies across the country, back to his wife and you stay alone, late at night in the office. Your employees go to dinner with friends and family, and you stay glued to your laptop, responding to emails with a false sense of urgency tied to each one.

You feel like you’re giving up the prime of your life for this thing… what is “this thing”? You can’t even tangibly describe it any more. Let alone judge if it will be worth it.

Your best friends have gotten engaged, and then married, and you’re wondering where it all went wrong — god, you had a woman who gave everything up for you, and you threw it all away. You admitted to yourself — and to anyone who would listen — she was the only woman in the world who could put up with your shit… that statement seems to prove itself more true every day.

You got overconfident and swore those couple of women in your past would always be there for you if you needed them. And then you look them up and they’ve moved on… they’ve found new men, men who will treat them better and love them more. They don’t even write back anymore… They swore you left an indelible mark on their lives, told you they would never forget, promised you were the one… it’s all gone. These lines suddenly come to mind as you write to yourself:

I had a woman down with me

But to me it seemed like she was down to get me

She helped me out in this shit

But to me she was just another bitch

Now she’s back with her mother

Now I’m realizing that I love her

Now I’m feelin’ lonely

My mind is playin’ tricks on me

You went from being the most confident guy on the block to feeling like just another anonymous nobody on a train… where you’re writing this screed to yourself and lamenting the shots at love you squandered.

There’s this one girl you still talk to but you feel nothing when you’re with her. It’s just someone to pass the time. You string her along because there’s no one else left… and you wonder if she’s the best you’ll ever be able to get. You’ll settle.

“Settle”… those words a decade ago were anathema.

You were so scared of that word. You were always about the best, now what? Fuck man, you had a whole plan laid out.

The girls your age have all moved on, you were the reason they learned their lesson… The girls you date today are too young, no one takes you seriously — you remember how old your age sounded when you were 21, many years ago… Is that how these girls think about you?

Your whole life you felt like your whole life was in front of you, now it feels like it’s all over.

Look how it turned out.

This is your life. The unique byproduct of all the decisions you’ve made. It’s the combination of what you chose to do, and — just as importantly — what you chose not to do. And now it’s ending, one day at a time.