How to Work with a New Boss When Your Manager is on Leave

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Leadership transitions are tricky — even more so when your trusted manager goes on temporary leave, and you suddenly find yourself reporting to a skip-level boss. The dynamics shift, the expectations aren’t always clear, and even well-intentioned communication can be misunderstood.

In a recent coaching conversation, we explored Chelsea’s situation: a smart, capable team member grappling with this very challenge. If you’ve ever felt frustrated, confused, or unrecognized during a leadership transition, her story — and the lessons from it — may resonate with you. ...  read more

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

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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

Farewell and See You Out There

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rollercoaster ride

After 4+ unforgettable (and occasionally truly unhinged) years, it’s time to say farewell.

When I joined, I thought I was signing up for one job… but 4 months in, surprise! A merger turned all of our jobs upside down and gave us a front-row seat to a masterclass in change management (and “how to bond with strangers over shared chaos”).  From there, it only got more interesting—company collapse, another acquisition, new teammates, new systems, new acronyms. ...  read more

A Birthday Letter to My Mom — And a New Tradition

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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

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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

Embracing Change: Why Leaving My Job Feels Like a Blessing

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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

Finding Connection Through Letters: A Gift for Dad’s 81st Birthday

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My dad loves me in his way. He just doesn’t always know how to show it, so instead, he teaches me lessons every time we talk—even when I was little. As I’ve grown older, and as he has aged into his 80s, I’ve come to appreciate him more for who he is. I know he won’t change, but that doesn’t mean I can’t find new ways to connect with him. This letter idea seems like a good try. ...  read more