A Letter to Myself: Lessons in Leadership, Loss, and Letting Go
Each year, as I haul out my (somewhat excessive) Christmas display, think airport-runway levels of lighting, I also unpack something smaller, quieter, and far more personal: a letter to myself.
It’s a simple tradition I started years ago. Every December, after the lights are up and the house looks like Clark Griswold’s West Coast cousin moved in, I sit down to write a letter. It’s part reflection, part prediction, a look back at the year that was and a hopeful guess at what the next one might bring. Then I tuck it into one of the decoration boxes and forget about it for 12 months.
When I open it again the following year, it’s like finding a time capsule from a slightly more naïve version of myself.
The Year My Letter Got It Wrong
The letter I wrote at the end of 2023 was optimistic, realistic, but optimistic. I talked about our plans to grow TurningPoint Executive Search by 10–12% in 2024, strengthening our team culture, and continuing to build on our momentum.
Then reality hit.
By November 2024, our revenues were down by 45%, I had laid off half our team and paid myself a fraction of my usual salary. I even considered walking away from recruiting altogether. It was one of the hardest stretches of my 27+ years in recruiting.
In hindsight, that 2023 letter also carried a message I didn’t fully appreciate at the time — a reminder to stay curious, stay open, and stay aligned with my north star.
Because when everything you’ve built suddenly changes – or craters - that north star is what helps you decide whether to fight, pivot, or start fresh.
When the Unexpected Becomes the Opportunity
By the time I sat down to write my 2024 letter, the tone had changed. It still included a few predictions — but they looked different. This time, I talked about the harsh reality facing the recruiting industry. I ended the letter by saying, “While I don’t know where the business will be this time next year, 1 of 3 scenarios will play out…
I will have closed the business and will be working in another industry,
I will be running the business myself, back to how I started in 2007,
Something that hasn’t presented itself yet will drive the next chapter in my life.”
I’m not sure where that flicker of optimism came from, but it was my resilient self trying to break through a bad situation.
Sure enough, in the midst of all that uncertainty came two completely unexpected possibilities: selling the firm or merging with Seann Richardson and the Collabrie team.
Neither was part of my “plan” for 2025. But both forced me to step back and ask, What does success look like now?
After a lot of reflection and discussions with friends, family, and colleagues (and more than a few sleepless nights), I decided to merge. It wasn’t the easiest choice, but it was the one most aligned with my long-term vision—my north star!
The Top 5 Reasons I Decided to Merge
Shared values. In Seann, I found a partner who shares my belief in the high-touch, relationship-first approach to recruiting, one that prioritizes people and purpose over transactions. I also found someone with a great sense of humor, which is another one of my core values.
Complementary strengths. Seann’s former firm, Collabrie, brought deep expertise in Accounting, Operations, HR, and Finance, perfectly complementing TurningPoint’s focus on Executive, Sales, Operations, and Marketing leadership — blending Seann’s analytical approach with my creative, big-picture mindset.
Stability & Opportunity in a shifting market. The merger gave us an opportunity to offer a wider suite of solutions to our clients, while also giving our team room to breathe and to grow.
A broader platform for our people. Our recruiters and leaders now have more opportunity to do what they love - partnering with our clients and candidates - at scale.
A redefined definition of growth. It’s no longer just about headcount or revenue — it’s about alignment, purpose, and impact.
What started as one of the most difficult professional years of my life became the catalyst for one of the best decisions I’ve ever made.
The Leadership Lesson
Every leader faces moments when the plan falls apart. You can cling to what you thought the year would be, holding on so tightly that you end up going down with the ship...or you can look for what it could become, opening yourself up to a completely new direction.
Being open to change isn’t a weakness. It’s wisdom. It’s what allows you to see opportunity in the unexpected, to pivot without losing your core identity, and to lead from a place of grounded optimism instead of fear.
As you head into this holiday season, I encourage you to try a version of my tradition. Write yourself a letter. Capture where you are, what you’ve learned, and what you hope for the year ahead. Then pack it away.
When you read it next Thanksgiving, don’t just measure how much you achieved — measure how much you grew. Because sometimes, the best gifts are the ones you didn’t see coming.