It’s the last day of 2025, and I’m driving into work on a Wednesday morning. The sun’s barely up, and my mind is already racing through everything I need to get done today. But instead of mentally rehearsing my to-do list, I find myself thinking about something different: the things I’m still struggling with after all these years of running a business.
There’s something about the turn of the year that makes you reflective. You look back at what worked, what didn’t, and — if you’re being honest with yourself — what you’re still wrestling with despite your best efforts. I’ve had a lot of struggles throughout my career. Some I’ve conquered. Others keep showing up year after year like uninvited guests who don’t take hints.
So I thought I’d share three of my biggest ongoing struggles as a business owner and professional. Maybe getting them down in writing will help me come up with a plan for 2026. And honestly, I’m curious whether other people are dealing with the same things.
Struggle #1: Containing the Daily Whirlwind
Right now, we’ve got somewhere between 12 and 15 people at our survey company. We’re doing a lot of work for about half a dozen good clients across a variety of projects. By most measures, things are going well.
And yet, I have this fundamental struggle just trying to keep up with everything.
I’ve got a great team. I’m working hard to delegate. I try to be a fairly organized person. But I still find myself struggling to keep track of it all. There are just so many balls in the air at any given moment. And sometimes — not often, but sometimes — one of them drops.
Here’s what really gets me: I wake up almost every day knowing that I’m not going to accomplish everything I want to accomplish or need to accomplish that day. That’s just the baseline feeling now. Day after day after day. It’s become my normal, and I’m not sure that’s healthy.
I know some of this is self-imposed. I put too much on my plate. I’m involved in volunteer organizations and committees because there are causes I care about. Good organizations need help, and I want to contribute. But I’m starting to realize I need to restrain myself a bit more. Every “yes” to something outside the business is a “no” to something inside it — or a “no” to my own sanity.
The whirlwind doesn’t care about your good intentions. It doesn’t care that you have a great team or that you’re trying to be organized. It just keeps spinning, and your job is to keep up. Some days I do. Some days I don’t.
I don’t have a solution for this yet. But acknowledging it feels like a start.
Struggle #2: Spending Time on Tasks That Feel Unproductive
This one is related to the first, but it’s a different flavor of frustration.
I spend a lot of time on tasks that feel unproductive — even though I know they’re necessary. I’m not sure if I need to reframe how I view those tasks or if there’s something fundamentally broken about how I’m approaching them. Maybe they’re not actually unproductive. They just feel that way.
I think some of this comes with being a technical professional who now runs a business. Most of my day isn’t spent doing technical work anymore. And that creates this weird cognitive dissonance where I feel like I’m not being “productive” unless I’m doing the hands-on surveying and mapping work that I trained for and love.
The Email Problem
Let’s start with email. I spend at least a couple of hours a day on email. I’ve tried plug-ins. I’ve tried different systems. I haven’t found anything that genuinely makes email more efficient.
One thing we did right from the beginning — when we started the company during COVID — was implementing an internal messaging system. We’ve been using Microsoft Teams since day one (we might have started with Slack, I honestly can’t remember). That decision probably reduced my internal email volume by 75 percent. What used to be emails are now quick chat messages, which are way easier to process.
But I still get a ton of email from external parties. Some of that is newsletter subscriptions, and I’ve learned that every email newsletter comes with a processing cost. Even if I’m not reading them, I have to delete or file them. That takes mental energy.
And then there’s just the reality that in American business, we communicate by email now. Phone calls have become rare. So email is the channel, and I’m stuck managing it.
I’m using Outlook, and let me just say: Outlook is old and clunky. It’s not very scriptable. I just recently saw some decent integration with Microsoft Copilot, so I’m hoping that as large language models (LLMs) get better integrated into email clients, I’ll become more productive. But we’re not there yet on the technology curve.
What I really want is an easily scriptable email client with natural language processing built in. I want to be able to say, “Find all the emails from this client about that project, summarize them, and draft a response.” That tool doesn’t exist yet — at least not in a form I’ve found useful.
I should probably look more seriously at setting up automated rules in Outlook. That’s not something I’ve invested time in. And I work really hard not to use my email inbox as a task manager. But it’s tough. I don’t want to file or delete an email because I’m afraid I’ll forget to do the task associated with it. Even when things make it onto my actual task manager, they sometimes slip through the cracks.
The Timesheet Problem
Then there’s my timesheet. I do a daily log, which I use to populate my timesheet at the end of each pay period.
If I could just remember to do it every day, it would be easy. Five minutes, tops. But inevitably I go a week without touching it, and then it takes me two hours to reconstruct what I did. It’s a pain.
I’ve started using AI to help with this. I record a daily journal as an audio recording on my commute. I try to take a couple of minutes to talk about what I accomplished at work that day. That helps with the timesheet and daily log — a little. But it’s still a struggle.
All the Other “Stuff”
And it’s not just email and timesheets. So much of my day goes to things like:
- Helping technical team members or business support staff with questions they have
- Coordinating field crew logistics
- Trying to get contracts executed
- Keeping an eye on the weather (because it affects when we can work)
- Looking at our cash flow
- Checking the mailbox and depositing checks
There’s just stuff that comes with running a business. None of it is technical work. All of it is necessary.
Here’s the honest truth: sometimes the guilt gets so bad that I’ll work late just to carve out a couple of hours for technical work. That’s probably not healthy. But it’s where I am.
Struggle #3: The Firehose of Technology
My third big struggle is how much there is to learn from a technology perspective.
In the last two or three years, this has really accelerated for me. With machine learning and large language models becoming mainstream, there’s just so much powerful technology now available at your fingertips. It’s genuinely exciting. And it’s genuinely overwhelming.
One thing I’ve realized — just in the last couple of months, really — is that I’ve got to pull back and focus on a few tools. I’m not going to have time to learn all the tools I want to learn. Not even close.
This is true from a surveying and geospatial perspective, but also from a general technology perspective. My business partner and I are both curious about tech. We geek out on this stuff. But I’ve been spreading myself too thin, and I’d probably be better off mastering a few tools rather than having mediocre exposure to a bunch of them.
So I’m trying to tighten up. I’ve got two or three LLMs that I use for specific tasks now. I’ve got a couple of web applications that I use for specific workflows. I’m starting to get the kinks ironed out of some critical processes that involve natural language processing.
But I get sidetracked. A lot. A curious mind is both a gift and a curse when you’re staring at an endless buffet of shiny new tools.
Here’s what I’ve noticed: probably 80 percent of the tools I come across are nifty or cool, but they don’t significantly move the needle for me. They’re interesting diversions, not game-changers. The other 20 percent? Those really move the needle.
For me right now, the heavy lifters are things like Google Gemini as a research tool, Google NotebookLM for organizing and synthesizing information, and Google Recorder for capturing ideas on the go. These tools move a lot of weight for me. They’re worth the investment of time to learn deeply.
The challenge is having the discipline to say “no” to the 80 percent and “yes” to going deeper on the 20 percent that actually matters.
So What’s the Plan?
I’ll be honest: I don’t have a fully baked plan for how to address these struggles in 2026. Not yet.
I know I need to be more careful about volunteer commitments. I know I need to get better at email management and staying on top of my daily log. I know I need to focus on fewer tools and master them rather than dabbling in everything.
There are other things I need to work on too — being a little more organized, a little less cluttered. But these three struggles are the big ones. They’re the ones that keep me up at night and make me feel like I’m always running behind.
Maybe the first step is just naming them. Getting them out of my head and onto paper (or screen). That’s what this is — a brain dump at the end of the year, an attempt to be honest with myself about where I’m falling short.
What About You?
I’m curious: what are your big struggles heading into 2026?
Are you drowning in the daily whirlwind? Feeling guilty about not doing enough “real” work? Overwhelmed by the pace of technological change?
I’d love to hear about it. Not because misery loves company — though it kind of does — but because I think there’s value in knowing we’re not alone in these struggles. And maybe, just maybe, someone out there has figured out something I haven’t.
Drop me a note. Share your big three. Let’s compare notes and see if we can help each other figure this out.
Here’s to a better, more focused 2026.
— Landon