Let’s Get Personal — Success Can Be Boring and Failure is an Option

In fact, it’s something worth chasing, celebrating, and definitely worthy of forgiveness

David Drake
9 min readJun 28, 2021
Photo by: — My face thinking about all of my failures, of which there are many.

Today’s morning meditation was about failure; something I’ve experienced quite a few times in my life in various ways. I’ve failed to get a startup off the ground (but I’m working on it), failed at marriage, had my face broken trying to rescue somebody, wasn’t able to hack it living in paradise, and more. However, if there’s one thing I’ve learned in 38 years on this planet so far, it’s that failure is inevitable.

My failures are my stories, and they’re probably yours too.

The Anna Karenina principle is one I like to bring up a lot when talking to folks going through problems in their lives.

“All happy families are alike; each unhappy family is unhappy in its own way.”

— Leo Tolstoy (1877). Anna Karenina.

There’s a lot of different ways to take that quote and it’s been applied to a bunch of different disciplines from science, to philosophy, to ecology, and everywhere in between. The gist that I take from it is that it’s not our successes that make us what we are, at all. In fact: those are pretty boring to talk about and don’t define who we are in any way. If anything, they simply show how similar we are to others, not how we’re exceptional.

We can look at any social media, be it Facebook, Instagram, LinkedIn, or anywhere else, and see that there are mounds of people expounding upon their successes.

Success Porn is Totally a Thing (But Maybe Don’t Search for it on Google)

Success after success after success. We can find it everywhere and people love to write about it, post about it, share about it, and read about it. Hell, Medium is no exception to this rule. My feed is currently full of article after article about how to “make it” as a writer. Or how some person’s side hustle made them $10,000 in one month.

It’s exhausting. How can one possibly live up to these standards that are being shown to us on a daily basis? The answer is: we can’t, and we don’t. There’s a term for this, that’s a risky search on Google, and it’s called “success porn.” We love the dopamine that’s produced when we identify with other folks being successful. We love to see smiles, read stories of folks “making it” and think: gosh, I could “make it,” too.

But the thing is: none of this is a reflection of real life. Real life is tough. There are plenty of people making hundreds of thousands of dollars a year, millions of dollars a year, or even more, and they’re miserable. They quit their jobs. They work so hard that they end up missing their children grow up. They burn out. Even the great Wolfgang Puck said that he regretted working so hard and that he wished he wouldn’t have missed out on his kids growing up in the latest documentary about him on Disney+.

“Shaq is rich. The white man who signs his check… is wealthy. ‘Ah, here you go, Shaq. Go buy yourself a bouncing car. Bling, bling!’”

— Chris Rock (2004). “Chris Rock: Never Scared.”

When I lived in the Virgin Islands for a few years, I had the opportunity to drink, play cards, and hang out with some of the wealthiest people on the whole planet.

Literal princes. People who owned megayachts; not the people who lease them or use them most of the time, but the folks who own them. CEOs, retirees, celebrities, hedge fund managers, and more. And y’know what? They were just as happy and just as miserable as anyone else. Get them drinking and, almost inevitably, all they’d do is complain or even cry.

There are plenty of successful people, but their successes aren’t extraordinary. How they failed on the way there? Those are some interesting stories.

The Only Thing Constant in Life is Change… and Failure

Photos by: — One of my favorite quotes that I’ve been saying for years. — Art by @zuhg_art

Last night I felt like I failed, right before I felt like a million bucks. It was about 9:15pm or so and I was lying in my bed with my iPad open about to do some writing to keep up with my 60 days of creating a writing habit. During the day I had only written a single haiku and it was not a good one. I was tired from a long day single parenting and hanging out with my daughter in 115º weather in an inflatable pool. Just as I started to type out the title of my writing for the evening, I heard the door open.

There stood my daughter, stuffy in hand.

“I miss my mommy,” she said.

My heart sank. My parents divorced when I was about her age and every time she says something like that it brings back my own childhood traumas and pains. I empathize so much with those words and there’s very little I can do to help when I hear them.

“I’m sorry, sweetheart. I know that’s hard. It’s okay to miss people. I understand. What would you like to do?”

“I want to sleep in your bed.”

“Honey, you’re five and a half and about to start kindergarten in a couple of months. We need to start being a big girl and I’m sorry but you can’t come sleep in my bed. Would you like me to snuggle with you in your bed?”

“Uh huh.”

I couldn’t help but feel like a failure at that moment for three reasons:

  1. I felt like I didn’t give her enough love, affection, and attention during the day to supplant the emotion of yearning a kid of divorced parents experiences. I felt responsible for her sadness; a totally horrible feeling to have.
  2. I knew I probably wasn’t going to end up publishing anything online for day 6 of 60 for creating a writing habit.
  3. I knew I was going to be tired in the morning and therefore not be able to finish up some writing for work I wanted to get done before the day started.

And so, I snuggled with her in her bed after putting some ocean sounds on the HomePod mini. I laid there stroking her hair, telling her everything was going to be okay, and that she was an amazing little girl. Expounding upon how smart she was, how proud of her I was, and talking about how I really enjoyed our day together.

She fell asleep. Then I fell asleep.

I woke up at 11:30pm; the sound of her faintly breathing in and out, deep in slumber, accompanying the drone of the fan and the sounds of the ocean. I couldn’t help but smile as I slowly and carefully extracted my arm from underneath her head, tucked her in, and walked into my own room.

I breathed a heavy sigh.

I forgave all of my three failures:

  1. I don’t have any control over her feelings. It’s normal for a child to miss a parent when they’re gone. It’s not my fault, at all, that she feels sad. I’m a very good father and I’m getting better at it every day.
  2. I did write something. It wasn’t great, but I did write something. And I also never promised myself I’d actually publish something online every day for 60 days, just that I’d write.
  3. There’s always work to do. My child is my priority in my life. I will get my stuff done for work tomorrow, and getting it done a few hours later than I wanted to is not going to make or break the success of it.

And I slept like a baby.

Learning to Forgive Myself is One of My Favorite Parts About Self-Love

Public Domain — Frontispiece for “An Essay on Criticism”

And while self-love each jealous writer rules,
Contending wits become the sport of fools:
But still the worst with most regret commend,
For each ill author is as bad a friend.
To what base ends, and by what abject ways,
Are mortals urg’d through sacred lust of praise!
Ah ne’er so dire a thirst of glory boast,
Nor in the critic let the man be lost!
Good nature and good sense must ever join;
To err is human; to forgive, divine.

— Alexander Pope (1707). “An Essay on Criticism: Part 2.”

This is one of the more personal pieces of writing I’ve shared in a long time. It feels dangerous to be so vulnerable in such a public way. To share my feelings to people I don’t know; to be available to be criticized or judged. But it’s okay, because I’ve already forgiven myself for the failures that make up some of the more vulnerable parts of this piece.

I only recently learned to forgive my failures and my past mistakes and I’m the happiest I’ve ever been in my whole life. It only took me 38 years, but I can finally say:

  • I don’t really have many regrets; just failures I’m always working to forgive myself for.
  • I’m proud of who I am and what I’ve accomplished.
  • I’m excited about where my life is taking me, and always eager to see what tomorrow brings.

Without my failures, I wouldn’t be who I am today. I have learned so much from messing up, and have gained so much experience, knowledge, and perhaps most importantly, perspective, from my failures. They are, literally, what have made me who I am today.

I’ve done lots of things that could be defined as successes as well. I went to college and studied abroad, acted professionally, had steady 6-figure jobs, raised millions for a startup, lived in the Caribbean and drank rum punches on white sandy beaches for years. But so have many people. You can read hundreds of stories about that, or find photos on feeds of influencers doing all kinds of activities like that all day, every day.

To Wrap it All Up? Life is Still Very Hard.

Today? I struggle every day. I’m not rich. I don’t own a home; in fact, I’m in the 24th place I’ve called home. I’m working hard to revitalize the startup that I had to leave behind when my marriage failed and I found myself the sole caretaker of a 9-month-old little girl. I have to constantly negotiate and communicate with an ex-wife who doesn’t particularly care for me. I’ve got plenty of credit card debt like most Americans. I’m attempting to figure out how to date and find love with a partner again. I’m in constant pain from my own negligence and overconfidence with a herniated and desiccated L4-L5 disc.

But y’know what? I’m thankful for the opportunity and the challenges that face me every single day.

These are the things that I deal with or think about every day that make up who I am.

I reflect upon my failures.

I try to be better today than yesterday because of my failures.

I am my failures, and so are you.

Day 6, I mean, 7 of 60 for developing a writing habit.

Day 5 of 60 for developing a writing habit:

Day 9 of 60 for developing a writing habit:



David Drake

Accomplished Father, Leader, Engineer, Writer, and Wannabe Chef. @randomdrake