2025 Year in Review: A CEO’s Honest Reflection on Growth, Hiring, and Hard Lessons

2025 Year in Review: This is a candid look back at what we built, what broke, and what this year taught us about growth, hiring, and leadership.

There’s always a point in December where the calendar finally stops asking questions.

No more meetings to prep for.

No more deadlines pretending they’re urgent.

Just a quiet stretch where you can actually look at the year instead of sprinting through it.

This is that pause.

2025 wasn’t a year of tidy growth or clean wins. It was a year of figuring things out while they were already in motion. Some things worked. Some things absolutely didn’t. And all of it shaped the business we’re heading into 2026 with.

This is the real reflection.

2025 Year in Review: The Numbers Behind the Work

Numbers don’t tell the whole story, but they do anchor it.

This year we logged:

• 16,000+ hours of work completed
• 64,000 Slack messages
• 650 hours of internal meetings
• 11 hires
• 4 team members remaining
• 4 new hires planned for January 2026
• 4 full-time Executive Assistants hired directly for clients
• 5 clients supported through Fractional Chief of Staff and COO work

We also worked across 12 stat holidays, and instead of treating that as a box to check, we made a conscious decision to offer more time off than the minimum.

On top of statutory days, we shut things down over the holidays with an extended, fully paid Christmas break. No one had to burn vacation days. No one had to “keep an eye on Slack.” Rest wasn’t something people had to justify… it was built in.

That choice mattered more than any policy we could have written.

Where We Got It Right

The work itself got better this year.

Not louder. Not faster. Better.

We placed four full-time Executive Assistants into roles where they were truly needed, not stretched thin across impossible expectations. And we stepped deeper into strategy, supporting five businesses at a Fractional CoS and COO level, helping owners think clearly about structure, decision-making, and what actually moves the needle.

Internally, we stretched ourselves too.

We learned AI tools that genuinely help, not the flashy kind that just creates more tabs.

We built Zapier automations that saved time instead of creating new problems.

We experimented carefully, broke a few things, and kept what worked.

Progress wasn’t perfect, but it was real.

Where It Hurt (And What It Taught Us)

Hiring was the hardest part of 2025.

We brought on 11 people, and only 4 remain.

That’s not a stat you gloss over.

We hired too fast. We assumed readiness. We pushed people forward before the foundation underneath them was solid enough to hold. While we did make the difficult calls to let people go once it was clear things weren’t working, that doesn’t undo the cost of getting there.

This year made one thing painfully clear: momentum will always tempt you to move faster than your systems can handle. And when you do, everyone pays for it.

That lesson is now baked into how we’re hiring going forward. Slower. Clearer. With far more runway.

Culture Isn’t What You Say, It’s What You Change

We also made some smaller decisions that ended up saying a lot.

Team happy hours didn’t survive 2025. Not because connection isn’t important, but because forcing it across four time zones just didn’t make sense. Someone was always in the middle of their day, someone else was half-asleep, and no one was fully present.

So we stopped pretending it worked.

That choice reinforced something I believe strongly now: culture isn’t about copying what other companies do. It’s about noticing when something doesn’t fit anymore and being willing to adjust without making it a big deal.

The Cost of Caring

There was a lot of overtime this year.

Late nights. Early mornings. The kind of weeks where you realize you’ve been carrying more than you should because it feels easier than slowing down.

Some of that effort was necessary. Some of it was avoidable. All of it was a reminder that caring deeply doesn’t mean sacrificing sustainability. That’s a balance we’re still learning how to protect… and one I take seriously as a leader.

Heading Into 2026

We’re entering the new year clearer than we’ve ever been.

We’re planning to bring on four new team members in January, but this time with better systems, more structure, and far more patience. Growth is still the goal, but not at the expense of stability.

2025 gave us data.

2026 gets the benefit of the lessons.

This year wasn’t perfect. But it was honest. And honesty builds stronger businesses than polished narratives ever will.

As this 2025 year in review comes to a close, the focus is onward and upward. Because what the fuck else is there?

Aspen

 

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