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Unpacking Your Life
Unpacking Your Life

Exploring the crossroads of life, security, and self.

  • About Brian
  • Undermined
Unpacking Your Life

Exploring the crossroads of life, security, and self.

Category: General

It’s Time to Come Clean to My Microsoft Family

Posted on July 6, 2026July 2, 2026 By UPL Admin

It is finally time to come clean to my Microsoft family. For the last five years, I have been living in two very different worlds. By day, I was a Senior Escalation Engineer at Microsoft, working in the support world, helping solve complex problems, jumping into the hard cases, and…

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Reading the Writing on the Wall, Then Choosing the Exit

Posted on July 2, 2026July 1, 2026 By UPL Admin

In May of 2025, Brandi and I were in Fiji celebrating our 25th wedding anniversary. Twenty five years will make you think differently. It has a way of turning down the noise and turning up the truth. You start thinking less about titles and more about peace. Less about what…

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Being Good at Everything (and Great at Nothing)

Posted on January 15, 2026January 15, 2026 By UPL Admin

There’s a certain kind of professional who doesn’t fit cleanly into a job title or headline. These are the people whose specialists expertise makes them broadly skilled, and who truly embody the concept of specialists expertise broadly skilled individuals in the workplace. They can step into almost any situation, understand…

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The Quiet Reset

Posted on January 1, 2026December 29, 2025 By UPL Admin

Delete. Accept. Forget. Restart. There comes a moment when survival quietly shifts into something else. Not relief, not celebration—just a subtle realization that continuing the same way is no longer sustainable. You begin to understand that carrying everything, everyone, and every version of yourself forward isn’t strength. It’s weight. And…

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Riding Into 50: The Year of the Motorcycle Journey

Posted on October 20, 2025October 19, 2025 By UPL Admin

Turning 50 isn’t something I want to mark with a single party or a single moment. Half a century deserves more than cake and candles — it deserves a journey. That’s why I’ve decided to embark on a 50 year adventure.The real question is: Is 50 a one-day event… or…

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Breaking Others Down Doesn’t Build You Up

Posted on September 21, 2025September 21, 2025 By UPL Admin

In any community-driven organization, mental health plays a crucial role as people come together to share their time, talents, and lived experiences. That is a gift. Whether someone gives an hour, a skill, or a perspective shaped by their personal journey, it deserves to be received with gratitude. Yet too…

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When Leadership Blocks the Conversation

Posted on August 30, 2025August 30, 2025 By UPL Admin

Leadership isn’t about titles. It isn’t about seniority. And it certainly isn’t about being the loudest voice in the room. Leadership is about listening—seeking out perspectives from all levels, weighing them with humility, and using that knowledge to guide decisions. But too often, organizations face a frustrating reality: the higher…

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The Mechanic’s Car Is Always Broken

Posted on August 4, 2025August 4, 2025 By UPL Admin

I was sitting with a good friend the other day, having one of those conversations that meanders through life, work, and all the messy pieces in between. At some point, he asked about the latest crypto theft—if I’d heard anything new from the forensics team. I sighed. “No. And honestly,…

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People. Process. Product. And… Getting Blocked

Posted on July 28, 2025July 30, 2025 By UPL Admin

Over a few months, I had been reaching out to someone I already knew—someone I genuinely respected and thought could be an amazing addition to something I was working on. This wasn’t some random cold outreach. We had a small relationship. We’d crossed paths before. My plan?✅ Grab some lunch…

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Two Writers, One Story: Dinner with Carrie Nyman

Posted on July 12, 2025July 13, 2025 By UPL Admin

Last night was one of those rare and unforgettable evenings that reminds you just how powerful human connection can be. After months of working together to bring Undermined into the world, I finally had the opportunity to meet Carrie Nyman—my ghostwriter, editor, and the emotional compass who helped shape my…

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I’m a work in progress, constantly learning from the path behind me while keeping an open heart for what’s ahead. Life rarely goes as planned—but that’s where the best parts happen.
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ex-Microsoft. There is life on the other side...

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Open post by chopperbriano with ID 18073166726716123
ex-Microsoft. There is life on the other side...

Live your best life every day 😎

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Open post by chopperbriano with ID 18182432713415658
Live your best life every day 😎

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Open post by chopperbriano with ID 18108655963915624
Instagram post 18108655963915624

This weekend was a quick trip to our place in Arkansas. I needed to replace some shingles on the roof. I burned my butt through the jeans. Brandi arranged it so I had enough time to replace the exhaust on my 996 on Monday night.

For some reason this trip she took lots of pictures of me. Weird.

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Open post by chopperbriano with ID 18088695899208348
This weekend was a quick trip to our place in Arkansas. I needed to replace some shingles on the roof. I burned my butt through the jeans. Brandi arranged it so I had enough time to replace the exhaust on my 996 on Monday night. 

For some reason this trip she took lots of pictures of me. Weird.

To end our trip last Saturday we had drinks at the Golden Gai, then dinner at The Mayfair Supper Club. A fitting end to a very special weekend with my very special lady. Happy Birthday Brandi.

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Open post by chopperbriano with ID 18136830487621879
To end our trip last Saturday we had drinks at the Golden Gai, then dinner at The Mayfair Supper Club. A fitting end to a very special weekend with my very special lady. Happy Birthday Brandi.

Happy Birthday to my lovely wife @brandioakes. Fun fact we have been married for 26 years and together for 30. Thanks for being my person, and thank you for always being supportive regardless of how crazy the idea ends up being. Love you 😎

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Open post by chopperbriano with ID 18463151887188424
Happy Birthday to my lovely wife @brandioakes. Fun fact we have been married for 26 years and together for 30. Thanks for being my person, and thank you for always being supportive regardless of how crazy the idea ends up being. Love you 😎

Saturday morning at the track. New personal best. Arte Mesuem. Spending time with @brandioakes priceless.

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Open post by chopperbriano with ID 18408128446083648
Saturday morning at the track. New personal best. Arte Mesuem. Spending time with @brandioakes priceless.

Friday evening dinner at Giada... Excellent food and service. White people in a driving shopping cart. Absinthe. Great show. Not for everyone.

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Open post by chopperbriano with ID 18082167467312747
Friday evening dinner at Giada... Excellent food and service. White people in a driving shopping cart. Absinthe. Great show. Not for everyone.
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— Brian Oakes (@chopperbrian) September 21, 2024
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