Transitions - Puzzle in a World of Chess

Over a lifetime there are moments of clarity when the choice to change is obvious. The stars align and you feel, with certainty, “the time for change is now.”

Why this matters

Career transitions rarely unfold like a clean game of chess. They feel more like a puzzle you’re building without the picture on the box. This story is for leaders and professionals who’ve been “moved on the board” by others’ decisions and still chose to lead with self‑awareness, dignity, and faith that the next piece will reveal itself.

Chess Transitions

Some transitions feel like chess. You plan the move, line up the pieces, and wait for the right moment to capture the queen. I’ve watched peers make these “YES!!” transitions throughout my career. They calculate every move and political play to become champions of the game.

Puzzle Transitions

Then there are the other transitions – the puzzle kind. You’re building without the final picture, finding the edge pieces of your life but not yet seeing how it all fits together. It can be frustrating at first, then strangely exciting as the image slowly appears.

My knot art often begins this way. I start with a theme and a rough idea of how the yarn and colors will coil together. Then suddenly, a new idea or element appears and changes the original direction – and somehow strengthens the final piece.

Most of my life transitions have been puzzle‑like. No matter how much I believed in myself, the decision to leap was often scary as hell, even when logic said, “this is a must‑do‑now transition.” Puzzle transitions demand a huge leap of faith to begin something new.

In those moments, self‑awareness is the non‑negotiable: a belief in your fortitude, resilience, positive attitude, expertise, and willingness to learn.

My Biggest Puzzle

One of my biggest puzzle transitions was moving from Seattle to Orlando.

On paper, it was a career gift. A 2,300‑room resort and convention complex. Huge challenges, huge rewards. After ten years as a consultant and nine years in a corporate office, I hadn’t worked in a hotel for almost twenty years. This opportunity came out of the blue and was a godsend financially. It abruptly and positively changed the direction of my career.

But the personal cost was seismic. My parents had moved to Seattle to be close to my son, my brother, and me. I had deep friendships and never imagined leaving. The move meant leaving my son behind for four months while he finished middle school. It was a leap of faith for both me and the General Manager who hired me.

For over four years I felt like Alice in Wonderland. I respected the creativity and savvy of my peers and learned a great deal. I grew like Alice – stretching into a bigger version of myself – while some very political peers tried to shrink me. They were masters at chess.

My pride in our team’s accomplishments was tremendous. I will always be grateful for that “must‑do‑now” transition and for the leader who made it possible.

Then the board shifted.

Once the leader who hired me moved on, the game of chess began around my position. Over eighteen months – timed almost exactly with my son’s high school graduation in Orlando – a peer slowly “took the queen.” I found myself out‑played.

Another “must‑do‑now” transition arrived, this time not really my decision.

The owners and regional vice president decided to move me from the 44th largest hotel complex in the world, to a hotel 10% the size, not renovated in twelve years, with very “difficult” owners and a cloud of bankruptcy looming. No other options were presented.

I was told not to worry about the bankruptcy because it had been “looming for five years.” Not exactly comforting. It felt like a serious come‑down. It took every shred of self‑dignity to keep my attitude up during those last three weeks when people congratulated me on my “promotion.” Technically, I was being promoted to General Manager. It did not feel like a promotion.

Thirty days into the new role, I was informed the hotel would file for bankruptcy in sixty days. Yet another “must‑do‑now” transition, again not my decision.

As with all my transitions, I focused on what I could control: my self‑awareness – my belief in my fortitude, resilience, positive attitude, expertise, and willingness to learn.

My severance from that small, beat‑up, bankrupt hotel led me to one of the best hotel teams I ever worked with. Transition karma was at work, though I couldn’t see it at the time.

Still, I sometimes wonder: what might have happened if I’d been more of a chess player than a puzzle player?

My political skills were no match for my peer’s, so the outcome in Orlando probably wouldn’t have changed. But what if I had recognized the inevitable changes in Orlando ninety days earlier and maneuvered my own transition to a different hotel?

Like many paths not taken, I’ll never know.