So I Left My Job and Now I Can’t Sleep: The Challenges with Financial Freedom Nobody Talks About

financial freedom challenges

It’s been two weeks since I officially said farewell to full-time work. You would think I’d be living the dream right now — waking up whenever I want, traveling the world, feeling nothing but freedom. After all, I worked 28 years for this. And yet, reality looks a little different.

The weirdest part? I’m actually having trouble sleeping.  I use to sleep soundly for at least 7-8 hours.  Now I find myself waking up at 5 or 6 am, thinking.  It’s like my brain is floating around, searching for a new anchor now that the old one — work — is gone.  Yes, financial freedom means I can have vocational freedom now – work with who I want, how I want, and on what I want.    But what is that?    I have some ideas but nothing concrete.  Freedom sounds amazing in theory, but in practice? It’s a lot. ...  read more

A Birthday Letter to My Mom — And a New Tradition

Last month, I started something new — something simple but meaningful. I wrote a letter to my dad for his 81st birthday.  That letter wasn’t about making peace or fixing the past. It was about connection — sharing small but cherished memories that shaped how I see him, and showing him, in writing, how much he means to me. ...  read more

I’m Happy, Excited, Lost, and Anxious – All at the Same Time

What it feels like to leave traditional work and walk into the unknown

On April 11, I’ll officially leave my corporate job—and with it, close the chapter on 30 years of traditional work. But this isn’t just about quitting a job. It’s about stepping away from the structure that has defined most of my adult life and stepping into a space I’ve never fully explored: freedom...  read more

How Making a Career Limiting Move can Lead to Greater Opportunities

A lot happened last week, leaving me with a tough decision. I received an unexpected invite from my big boss (let’s call him Richard) for a one-on-one meeting at 8:30 AM on Tuesday. The invite simply stated that he wanted to discuss “upcoming opportunities.”

Unsure of what it meant, I reached out to my immediate manager (let’s call him Sam) to see if he had any insights. Sam speculated that it was likely about me helping out with some risk-related work we had discussed plus some Chief of Staff responsibilities. ...  read more

How to Recover Quickly After a Work Mistake – 5 Tips

We’ve all been there—staring at our screen, replaying a mistake we made at work, feeling that pit in our stomach. It happens to the best of us. Just recently, I found myself in this exact situation.

My Work Mistake

I had an important meeting with my big boss, and I knew I needed to be concise. My leader had even advised me to focus on just one row of a particular slide, but for some reason—maybe pride in my work, maybe just being half-asleep on a Monday morning—I explained all six rows in detail. ...  read more

How to Crush Your New Year Resolutions & Become Your Best Self

crush your new year resolution with identity based goals

Every January, millions of people commit to New Year resolutions. “I want to lose 10 pounds,” “I’ll join a pickleball league,” or “I’ll be kinder to myself.” These resolutions often feel like they have a binary outcome: success or failure. For years, I avoided setting these types of goals because they felt rigid and defeating. Instead, I began focusing on who I wanted to become in the new year, rather than what I wanted to achieve. It was a subtle but transformative shift. ...  read more

Start 2025 Right: Must-Read Books on Money, Fitness, Life, and Family

Happy New Year!  I hope you had a wonderful holiday season filled with joy, laughter, and meaningful moments. Here’s to a 2025 full of adventure, growth, and plenty of fun!

I know it’s been a while since my last post—I’ve missed connecting with you. Life had its own plans for me recently, involving unexpected work travel, my daughter’s knee surgery, and a health scare with excessive bleeding. But I’m back, and I’ll share more details in future posts. ...  read more