The Year in Delegation: My Biggest Wins and Lessons for 2026

Clockwise from top-left: Grand Anse Beach in Grenada; Monument Valley in Arizona; Grand Prismatic Spring in Yellowstone National Park (Wyoming); My altar in my new flat (Minneapolis, Minnesota); Tal-Mixta Cave on Gozo Island, Malta; Antelope Canyon in Page, Arizona

As this year comes to a close, I’ve been reflecting on what delegation has taught me — not just about running businesses, but about trust, expertise, freedom, and what it really takes to build something sustainable while living a full life.

2025 was a year of building, experimenting, listening closely, and sometimes learning the hard way. I led teams in very different contexts, delegated in situations where I was the expert and others where I very much was not, and continued the ongoing work of designing a life that allows me to work from anywhere in the world.

Here are the biggest lessons I’m carrying with me into 2026.

1. There’s no substitute for doing the work yourself — at least once

This year, I working on building out a brand-new customer support function at Index. I've been doing the work myself — answering tickets, building relationships with clients, understanding how they actually use our product, and seeing where friction shows up in real life.

It was eye-opening.

I learned how our clients think, what questions come up repeatedly, and where our documentation or processes could be improved. More importantly, I built trust — with customers and internally.

What I didn’t fully expect was how much this role would deepen my respect for our engineering team. Supporting customers meant standing at the intersection between what users experience as “magic” and the very real technical constraints engineers navigate every day.

I saw firsthand how much invisible labor, trade-off analysis, and precision goes into making complex systems feel simple — and how rarely that effort is understood from the outside.

Being able to see through the eyes of our customers and our technical guardians gave me a new appreciation for the productive tension where they have to meet. That space — where expectations, constraints, and creativity collide — turned out to be some of the most fertile ground for growth.

In 2026, I plan to transition some of the data stewards I've worked with for six years now into customer support roles. And because I spent this year doing the work firsthand, I know I'll be able to train them thoroughly and confidently.

This reminded me of something I’ve seen before: When leaders have real expertise in the work their reports are doing, trust comes faster.

When I stepped into leadership at Sourceress, I already had deep credibility with the writing team because I had been the company's writer #1. I understood their challenges because I had lived them.

That foundation made delegation smoother, feedback clearer, and collaboration stronger.

Lesson: Delegation (on the giving and receiving ends) works best when it’s grounded in lived understanding — even if only for a season.

2. Delegating work you don’t understand can be even more powerful

At the same time, founding Astrolabe Assistants taught me the opposite lesson: sometimes the best thing you can do for your business is delegate work you aren’t an expert in.

While I was learning how to set up an LLC this year (and how to move it from Washington to Minnesota), I had incredible help from people whose skills far exceed my own in certain areas.

Anaam, based in Chennai, helped me set up payments and key backend systems for the business website. She’s also working on her neuroscience PhD — in Spain, in a language she doesn’t speak fluently — and her focus and discipline genuinely inspire me.

Tyrell, based in Burgos in the Philippines, brought infectious enthusiasm and sharp execution to new lead generation systems. Watching him work reminded me how energizing it can be to lead people who are genuinely excited about what they’re building.

Managing people who are experts in areas you’re not requires something different:

• humility

• deep listening

• extra clarity in communication

• and a real willingness to defer to your team’s expertise

But when you do that well, your business benefits enormously.

Lesson: Great delegation isn’t about control — it’s about partnership.

3. Groundedness makes freedom sustainable

In my personal life, I made a meaningful shift this year: I signed a lease on a place of my own for the first time in ten years.

I don’t plan to be there often. But I've reached a place of needing my own space to recharge and recalibrate between adventures—one that I can set up exactly the way I need it for maximum soul-nourishment.

It's giving me a new sense of groundedness that actually makes continuing my travels more sustainable, not less.

This year took me to five countries — including two mainstays countries I can't live without, two new ones, and one I haven't been to since 2019.

There were long, restorative days communing with the ocean in Grenada. There were adventurous days exploring sea caves and Michelin-starred restaurants in Malta. I had the gift of deeply slowing down in both places.

I also traveled across six regions of the U.S., from the dramatic cliff-scapes of Monument Valley to the towering forests of the Rocky Mountains. One of the highlights was a month-long stay in a waterfront home on a tiny island across Puget Sound from Seattle — one of the most restorative periods of my entire year.

Throughout all of it, I worked fully remotely.

That freedom wasn’t accidental.

Lesson: Freedom isn’t about absence of structure — it’s about the right structure.

4. Systems and delegation make the remote life possible

Every place I traveled, every project I led, every transition I navigated this year was supported by systems — and by people I trusted to help run them.

Without clear delegation, documented processes, and thoughtful communication, none of this would have been possible. Travel would have meant constant stress. Leadership would have meant burnout. Growth would have stalled.

Instead, delegation became a stabilizing force — not something that added risk, but something that reduced it.

That belief is at the heart of Astrolabe Assistants.

In 2026, we’re focused on helping founders:

• design systems that match their work style

• delegate in ways that build trust, not friction

• and create businesses that support real freedom — not just flexibility on paper

Looking Ahead to 2026

This year reminded me that delegation is not a single skill — it’s a practice. One that evolves as your business, your team, and your life change.

Sometimes the best move is to do the work yourself. Sometimes it’s to step back and let someone else lead. And often, it’s knowing the difference.

If you’re entering 2026 wanting more space, more focus, and a business that actually supports the life you want to live, you don’t have to figure it out alone.

Astrolabe Assistants exists to help you build exactly that.

Here’s to clearer systems, deeper trust, and a year of delegation done well.