The Unexpected Identity Crisis After Financial Freedom

identity crisis after financial freedom

I didn’t expect this.

For 30 years, my life had structure — goals, promotions, deadlines, problems to solve, and a ladder to climb. Even when it was stressful, it was familiar. I knew who I was in that world. Then I stepped away.

Financially, we’re okay. We’ve been frugal. We’ve diversified. Even with market downturns, I’m not lying awake worried about money. And yet… I’m lying awake. At 5:00 a.m., grinding my teeth for the first time in ten years, my body burning like a furnace (thank you, perimenopause), covers on, covers off, sometimes moving to the leather couch just to cool down. ...  read more

Relationship Growth: Choosing Connection Over Being Right

Happy New Year.
I’m sorry I haven’t written for a while.

The last month caught me off guard when a relationship I value deeply became unexpectedly tense—not from anything dramatic, but from a handful of misunderstandings that slowly added up. It wasn’t the kind of conflict with a clear beginning or obvious fault. It was murkier than that, and harder to name. ...  read more

Why Acceptance Speeds Up Healing: A Personal Lesson in Patience

The last two weeks have been teaching me a lesson I’ve resisted for most of my life: acceptance can sometimes get you further—and faster—than force. I’m not a naturally patient person. When something slows me down, my instinct is to push harder, fix it quickly, or work around it. But this time? My body had other plans. ...  read more

How to Manage Overwhelm at Work When Everything Feels Mandatory

advice for the overwhelmed professional

A few weeks ago, my friend and colleague—let’s call him Andy—came to me completely overwhelmed. He’s been raising the same flag to his manager for the past six months: he and his team are under-resourced and overworked. His manager listens, nods, but nothing changes. No extra hands. No realistic reprioritization. Just more piling on. ...  read more

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

Embracing Change: Why Leaving My Job Feels Like a Blessing

A Surprising Calm in the Face of Change

After two weeks of traveling, attending conferences, and meeting with my boss in person for the last time, I received my year-end review—solid performance, full bonus payout, no surprises. But the bigger conversation was about what’s next.

Since I had turned down an offer to lead Risk & Control for digital, the writing was on the wall. My boss, Sam, even fought to keep me, but the decision was made. They needed my salary to fund that role, and my work was too far ahead of their priorities. Plus, as Sam put it, I was “too expensive” to be redirected elsewhere. (Guess I negotiated well five years ago!) ...  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