#27. Never Have I Ever... Played It Safe

Plus: The Daily Routine of Satya Nadella and more...

Hello and welcome to your weekly dose of actionable (and occasionally provocative) things.

As someone who believes aesthetics will save the world, I enjoy a weekly dose of eye candy from From Europe With Love.

One of their editions featured an image of a Fractal Vise.

With no reason or need, a thought struck me: I. Want. It!

So, without hesitation, I sent the link to my wife and asked for her blessing to buy it.

She, being the reasonable one, asked what it was and if it was meant for a project she wasnā€™t aware of.

Me: No.

Wife: Then why? What are you going to use it for?

Me: Itā€™s like a Tiffany ring for you - just a cool, shiny object I donā€™t really need. But unlike Tiffany, this one is actually functional and costs way less. Iā€™ll keep it on my desk, and itā€™ll please my eye every day.

She never responded to that one. I imagine she just set her phone aside, took off her glasses, closed her eyes, inhaled deeply, exhaled slowly, and started reminiscing about why she agreed to marry me in the first place.

Enjoy the edition.

ā€œLet it sinkā€¦ā€

ā

To avoid stupid mistakes, learn to be slightly silly

The eye-opening and jaw-dropping keyword for me here is ā€œslightlyā€ā€¦

Power moves

the author

It was my turn to start another round of "Never Have I Ever." About 12 folks I barely knew sat around a large table in a pub. Nobody else in the pub, just us. It was a Tuesday night.

We had just "graduated" from an English-speaking express course, and our teacher asked if we wanted to ā€œcelebrateā€.

I saw it as an extra opportunity to practice my English - so why not? A free class, just pay for your drinks. Sounded like a great deal.

Apparently, the whole group thought the same.

Despite spending 3 months together in class, we barely knew each other beyond the basics - names, occupations, and, in most cases, gender.

Classes took place in the evening, so I would commute straight from work and then rush home for 3 reasons:

  1. I had family (chances are my wife is still reading at this point),

  2. I was starving, and

  3. I was stupid enough not to take advantage of any further opportunities. Being an introvert can be inconvenient sometimes. But hey, the books wonā€™t read themselves.

Still, that night, I joined the group for an ā€œafterparty,ā€ and we ended up at the pub.

Instead of small talk, someone suggested we play "Never Have I Ever."

Great idea! Instantly accepted. The teacher took the lead, Googling some questions to get us started.

Who would have guessed that a silly drinking game would click something in my mind?

As the questions popped up, people took sips, shared their backstories - all in English, of course.

I sat there, still sober (ahhhā€¦ those glorious days when I enjoyed alcohol), and realized how genuinely cool these people were.

They had done some epic things - things they never expected, with outcomes they never regretted.

  • Never have I ever traveled soloā€¦

  • Never have I ever crashed a party I wasnā€™t invited toā€¦

  • Never have I ever had a lap danceā€¦

  • Never have I ever played strip pokerā€¦

  • Never have I ever shaved my headā€¦

  • Never have I ever gotten an unplanned tattooā€¦

And that was just the tip of the iceberg. My list of ā€œnever havesā€ was upsettingly long - no, a lap dance from my wife doesnā€™t count! (phewwā€¦ well played, that was a close oneā€¦).

Hearing their stories, I realized - I'd been playing it safe. Their ā€œnever have I everā€ list was wild. Mine was just - ā€œnever even considered itā€.

I had been living a corporate life where people spent most of their time trying to look intelligent. I was so busy keeping up appearances that I forgot to actually do things.

Hereā€™s an example:

I once mentioned to a friend that skydiving sounded like a cool thing to try, if the opportunity ever came up. For my next birthday, they gifted me a tandem skydiving certificate (I hate when people do that to me. Lesson learned: I now pay close attention to what my wife casually wishes for and makes it happen. Sometimes. No need for her to notice a pattern.)

Obvious outcome? I procrastinated, made excuses, convinced myself it wasnā€™t the right time - until the certificate expired.

I hated that mindset. Something had to change.

So, I started collecting a list of actionable "mind-honing" cues to push myself into the unknown. Inspiration came from articles, YouTube videos, and podcasts. Here are a few from my curated list:

  • Purposely embarrass yourself

  • Say YES now - figure it out later

  • Ask for forgiveness, not permission

  • Turn action into a competitive advantage

  • Always say ā€œIā€™ll go firstā€

Over time, this list migrated across different documents until it finally settled in Notion (not sponsored - I demanded a personal assistant as part of the deal. Still waiting).

I set a quarterly reminder to review and reflect on how Iā€™m doing.

As you can see, this wasnā€™t an overnight transformation.

So, what are the consequences?

  • I went on stage for a Mr. [Hotel Name] contest at a Turkish resort - took 1st place. Sober. (Yep, the winnerā€™s photo is in the title of this section.)

  • I started taking hip-hop classes in my 30s - everyone else in the class was a teenager.

  • I switched from full-contact karate to MMA - reset my proud black-belt status, got beaten like a newbie, tore my shoulder joint, endured surgery, and slept sitting up for five months.

  • I shaved my head for a one-time Halloween party - while still living my corporate, customer-facing life.

Most importantly, I stopped overthinking. And that had a positive impact on my career too.

In sales, I stopped assuming that ā€œno answer is the answerā€. Instead, I followed up relentlessly until I got an actual response. Anything. Yes or no. Zero regrets.

More often than not, it wasnā€™t a ā€œno.ā€ It was a ā€œno, butā€¦ā€ - a completely different kind of no - one that we could work with successfully.

Here's what I've learned:

We regret the things we donā€™t do more than the things we do.

Iā€™ve never regretted:

  • Taking a chance on an opportunity - even when it didnā€™t work out. (Proudly failed a few e-commerce projects)

  • Pushing through fear to do something. (Stepping onto a tatami mat to fight, knowing I could get injured, is not as easy as it seems)

  • Choosing authenticity over people-pleasing. (Although, I might regret this one - corporate life doesnā€™t always reward authenticity)

At the moment, I have no regrets about doing something - except for that time I didn't try skydiving. Maybe one day, I'll finally get the courage to jump... or maybe I'll just keep collecting "never haves".

Till next time.

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Tina Seelig's book is one of Stanford's best courses on personal development and creativity. Drawing from her own experiences, she shares unconventional approaches to solving business challenges, breakthrough thinking, and innovation.

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Satya Nadella isn't just Microsoft's CEO - he's the man who transformed it. When he took over in 2014, Microsoft was solid but stuck. He pushed cloud computing, AI, and innovation to new heights.

Interesting facts:

Learned Coding Late: Unlike many tech CEOs, Nadella didnā€™t start coding as a child. He learned programming in college, proving that itā€™s never too late to develop new skills.

Bought LinkedIn and GitHub: One of his biggest moves as CEO was acquiring LinkedIn for $26.2 billion in 2016 and GitHub for $7.5 billion in 2018, strengthening Microsoftā€™s presence in professional networking and software development.

NBA Team Owner: Nadella is a minority owner of the Seattle Sounders FC, showing his passion for sports beyond cricket.

Gaming Advocate: Nadella led Microsoftā€™s $68.7 billion Activision Blizzard deal, strengthening Xbox.

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