Fall has always been the season I’m most conflicted about. It gets darker and colder, and in Colorado, things start to freeze. Especially in October. Since it’s October 22nd, I thought I’d pause to reflect on the past and look toward the future.
I’ve been assigned to think back on 2025 and look forward to 2026, and honestly, I’m a little stuck. It’s been a while since I’ve done real reflection and forward planning in a concrete way. Sure, I worry about things I’ve done or things to come, but that kind of worrying isn’t productive. Putting thoughts like these on the screen takes presence, and that’s something I’m learning to prioritize.
Personal Reflections on 2025
This year, I’ve continued to focus on taking care of myself, physically and mentally. I stopped drinking alcohol in 2020 and haven’t looked back. It’s simply not good for me, and I feel better without it. I still enjoy spending time with friends and family who do drink, but the biggest gift of quitting has been regaining my mornings. I wake up early now, feeling clear and creative. I’ve developed a morning writing habit that I plan to keep nurturing, as this very post demonstrates.
I’ve also been plant-based since 2012, and that lifestyle has become second nature. It keeps me healthy and helps me avoid overindulging in my favorite activity: eating. Lately, I’ve been using ChatGPT to plan meals and create recipes, which has expanded my culinary horizons and made learning generative AI feel tangible and practical.
Exercise and physical activity continue to be a work in progress. I use Apple Fitness+ most mornings. Their on-demand classes make it easy to stay consistent. Since I spend so much of my day at a desk (or couch), staying mobile is non-negotiable. I’ve gotten better about walking the dogs, taking breaks, and even getting out on my bike more often. I still haven’t conquered pull-ups yet, 2026 might be the year for that.
As I get older, my risk tolerance has shifted. I descend a bit slower on my mountain bike and snowboard. The thrill has evolved: it’s less about adrenaline now and more about being outdoors with friends. The joy is in the experience, not the edge.
Professional Reflections on 2025
Travel and Events
This year brought more work travel than any other in my career, and I’ve loved it. I’ve visited new cities and returned to familiar ones, but the highlight was Basel, Switzerland. It’s not everyone’s cup of tea, but I found it charming: kind people, beautiful old town, and a grounded energy. Presenting at WordCamp Europe there for the first time was a milestone. Altogether, I’ve attended 11 events so far in 2025, with three more to go. I’m genuinely enjoying the travel: meeting new people, reconnecting with colleagues, and deepening friendships.
Public Speaking
Public speaking has become one of the most rewarding shifts in my professional life. I went from just one talk in 2024 to seven so far this year, with one more in December, eight total. That’s a huge leap for someone who used to dread the stage. Joining my local Toastmasters club has helped immensely. It’s a space to refine my skills and encourage others to find their voice too.
Work Projects
Two big projects stand out: our open-source sponsorship program and our agency partner program relaunch.
The sponsorship project has distributed tens of thousands of dollars to contributors and projects worldwide. I still sometimes feel like an intermediary, but it’s deeply satisfying to see our company supporting something bigger than ourselves.
The agency partner program has been years in the making, and this year it finally relaunched. The goal is to help agencies grow their businesses using our infrastructure and services. It’s just the beginning. Now comes the real work of building relationships, understanding needs, and connecting partners with customers. WordPress may be free to download, but creating a consistent, professional experience takes collaboration. Helping agencies deliver that feels meaningful.
Generative AI
AI has found a permanent seat in my workflow. It saves time, helps me organize thoughts, and frees me to write more. Still, I sometimes question whether it’s making me sharper or lazier. Maybe both. The irony is that I’m writing more on my own now than I have since college.
The best part, though, is the conversations: hearing how others use AI and helping people integrate it into their work. It’s exciting to see curiosity turn into confidence.
Community
The Durango WordPress Meetup turned one year old this month since I relaunched it. It had gone dormant during COVID, and reviving it has been a rewarding challenge. Attendance fluctuates, you’d think free lunch would help, but I’m learning the importance of consistency and better outreach. The goal is simple: keep showing up and building community, one month at a time.
Personal Goals for 2026
I turn 50 at the end of next year, a milestone that somehow feels both heavy and light. My memory isn’t as sharp, my joints aren’t as forgiving, but overall, I feel strong and optimistic.
Goals for the year:
- Finally master the pull-up.
- Have a fun and injury-free snowboarding season.
- Plan an anniversary trip, location TBD.
- Deepen friendships, even if that means making more effort in a small town where few people work in tech.
- Decide how to use my upcoming month-long sabbatical. Last time, I took it in July, which opens up endless summer options. Or maybe I’ll chase snow to South America, learn Spanish, and keep winter going.
Professional Goals for 2026
Public Speaking
Toastmasters remains a cornerstone of my growth. I’m working through the Presentation Mastery pathway, starting with my Ice Breaker speech this year. More importantly, I’ve realized how much I need in-person connection. Remote work is efficient, but it can also be isolating. Toastmasters offers that rare combination of practice, feedback, and human contact.
Next year, I want to double my 2025 speaking engagements, aiming for 16 talks. That means applying to at least 32 events, knowing I’ll be accepted to some fraction of them. I’ll start that outreach soon. My focus areas include:
- The critical role of websites in an increasingly gated digital world.
- Automating plugin updates as the foundation of website security.
- Personal growth in a digital age: how to stay human amid constant change.
Agency Partnerships
My goal is to deepen relationships with agency partners and cut through the noise around AI. There’s still too much fear, confusion, and short-term thinking in digital marketing. Agencies that thrive will be the ones building fast, functional, mobile-friendly websites. Ones that make it easy for customers to take action. It’s surprising how many sites still make paying or contacting someone difficult.
I’ll keep focusing on co-marketing, lead sharing, and helping partners connect with clients who truly value quality.
Open Source and Community
Our open-source sponsorship program is off to a strong start, but I’d like to expand our impact, both as a company and as a community. Locally, I want to grow the Durango WordPress Meetup, build a simple website for it, and start publishing useful content for attendees. A little “dogfooding” wouldn’t hurt either.
Leadership and Mentorship
At this stage in my career, leadership feels less about titles and more about teaching. I want to help others see what’s possible on the web; to share what I’ve learned about creativity, communication, and connection. I might even reboot a blogging challenge like the one I ran years ago, this time with more focus and structure (and maybe some Toastmasters influence).
Do I want to move into management again? Maybe. There’s potential to grow our partnerships team in North America. The question is how to scale relationships while keeping them genuine.
AI Tools
AI continues to be the frontier. The tools are powerful, sometimes magical, but they still depend on thoughtful input and careful execution. I plan to take a few structured courses next year to deepen my understanding and consistency. The more I master these tools, the more effectively I can apply them to everything else I do.
Conclusion
That turned out longer than I expected, but worth it. Writing this helped me process a lot of what’s been swirling in my head. If you’ve made it this far, thanks for reading. I hope it inspires you to pause and take stock of your own year too.