Some Days I Feel Like a Phony

A few days ago, I was working on the listing for our new vacation rental. The photos look great, the descriptions are written, and the unit is ready. And yet, running a short-term rental is new for me. I know there will be bumps in the road, and I find myself worrying that people will realize I don't fully know what I'm doing.

I’m not certain this is the correct term for how I feel, but I sometimes (often?) struggle with what’s called Imposter Syndrome. It’s when you feel unqualified to be doing something (a “phony”), and you fear that people are going to figure out you’re not qualified to be doing that thing.

Apparently, there are several forms of imposter syndrome (I just learned this while double-checking my definition was correct):

1. The Perfectionist: Sets crazy high goals and feels like a failure even if they meet 99% of them.

2. The Natural Genius: Feels like a fraud if they have to work to master a skill. It should come... naturally, right?

3. The Solist: Feels that asking for help is a sign of weakness. So, they must do everything themselves to prove their own worth.

4. The Expert: Constantly seeks more certifications/training, feeling they’ll never know “enough” to be truly qualified.

5. The Superhero: Pushes themselves to excel in every role (worker, parent, spouse) to cover up perceived insecurities.

Jessi (my wife) and I often fall into the first type: perfectionists. Actually, one of the things I appreciate about Jessi is that she sees the flaws. Not because she's negative, but because she genuinely wants things to be better. When I ask her for feedback, I know I’ll get her brutally honest thoughts and a clear map of where to improve. There’s a time and place for cheerleaders, but I’m finding them less helpful. Don't get me wrong, encouragement is nice, but I often want accurate feedback.

I appreciate the harsh truth from others, but it’s potentially destructive when done to myself because I see all the imperfections. Even if something turns out well, I can nitpick the process and my mindset. Yikes!

As a small business owner, I find myself regularly wading into the unknown and fighting perfectionist thoughts (and the natural genius... discounting years of practice to get to where I am today). For example, as my property management business grows, I keep wondering when people will realize I’ve never scaled a business before. It regularly feels like we’re just staying ahead… which is a classic imposter syndrome feeling! Of course it feels that way — growth, by definition, puts you into inexperienced territory.

Another example: I can no longer keep every unit and tenant in my head. Things fall through the cracks, and we’re building new processes (and ways to store/access info) while still maintaining daily operations. I keep thinking, “We just have to stay ahead for a bit longer… then it’ll be OK.” But, according to owners I respect, it’ll still be hard; it’ll be a different hard, but still hard.

The more experienced I get, the more I suspect most adults are just making it up as they go. Parents are raising kids they've never raised before. Managers are leading teams they've never led before. And business owners are solving problems they've never encountered before. The people I admire most aren't the ones who always know what to do, but the ones willing to move forward despite not knowing.

I suppose this is more of a note to myself to remember that, even though I sometimes feel like a phony. I still have things falling through the cracks, I still disappoint people occasionally, and I still find myself thinking that if I can just stay ahead a little longer, I'll eventually feel qualified. But perhaps that's how this works. Maybe competence isn't the absence of uncertainty (and mistakes). Perhaps a large component of competence is continuing to move forward despite the errors.

So, on the days I feel like a phony, I'm trying to remember: I may not be perfect, but I'm not starting from zero either.

The Baker Tower Penthouse Vacation Rental

Last year, we bought the Baker Tower and have been waiting for the top-floor tenants to move out so we could turn it into a vacation rental. Well... they moved out, and this last month we furnished the place — and it looks awesome!

I’m... shall we say... designed challenged. I care about functionality and have virtually no eye for what “looks good.” So, I hired an interior decorator to help. I gave her a video of the place, a budget, and let her loose on the IKEA website.


She picked out everything, and we had it delivered right before we showed up to assemble it. It was her and one of my investors (who gets credit for introducing me to her) who put it all together over a weekend. Then the following weekend, I returned with another friend (and real estate photographer) to do some finishing touches and get the photos below.

The Airbnb listing isn’t live yet because we still need to do a test run and identify missing items. But I’m too excited about it not to share it.

The view is amazing! It’s the tallest building in Oregon east of the Cascades. And on the 9th floor — the penthouse — the nearby Elkhorn Mountains look incredible. And now we have an interior to match.

Thanks to everyone who helped make this happen. Check it out:

I Built An AI Agent. It was Both Amazing And Underwhelming

Good news, kind of. I think it’ll be a while before AI starts taking over swaths of jobs and displacing people, or at least I think it’s true at the small-business level.

I've been playing around with different AI tools recently, trying to figure out ways to incorporate them into my business, and it's been an interesting adventure. On the one hand, there are things AI can do that are helpful, and I think most of us have experience with: drafting messages, summarizing large documents, and creating cool images (like above). It's genuinely useful but not transformational.

So I've started experimenting with more agentic types of processes, specifically using lindy.ai, and the experience has been interesting. The basic idea is that you can create a workflow that's based on a trigger. It could be off a timer, an incoming message, a webhook, or whatever. If you’ve ever used Apple Shortcuts, it’s the same idea. Here’s a simple example:

Every morning, my team discusses ongoing maintenance and tenant issues, and then we create a plan for the day. We record those meetings, transcribe them, and save them in a Google Drive folder.

Now, every Monday morning at 9am, it grabs all the new transcripts from the past week (that’s the purple loop) and compares them against our existing knowledge base (KB) articles. In the final blue-circled-magical-AI step, it looks for gaps and missing information and sends me an email with suggested article topics.

At this step, it's not fully written-out articles; it's just internal and external topic ideas. Eventually, Lindy will write full articles on approved topics, let me edit them, and save them to our KB. The KB, by the way, is what we use to automate message replies (therefore, in the long-run, saving time while keeping a consistent communication style).

But here’s the deal: this “simple” flow took me an hour to build. And really, it started with a prompt to Lindy’s Agent Builder, which took a first (second, third, fourth,...) pass. I had to enter some manual data (like my KB’s API Token), but most of the time I copied/pasted errors from a test run and the Agent Builder to try to fix them.

At one point, the Agent Builder told me:

“I need to stop and be honest with you. We've been going in circles for a while, and the core issue is clear... [reasons why it’s not working] .... The real fix is a different architecture. Instead of a separate LLM node, the analysis should happen inside an AI State node — which DOES have context accrual and can see all upstream data naturally.”

You see, that magical blue box used to be four separate steps that didn’t work. Which, for the record, the Agent Builder created! This current version works, but it was a process to get there, and it’s still not what I fully want...

AI Agents Are Both Amazing And Underwhelming

On the one hand, creating this was amazing because I just typed in a prompt for what I wanted, and it made it (eventually). Without the Agent Builder, I would have struggled to even get started.

On the other hand, it's a strange combination of doing something fairly simple, but in an overly complex way. It reminds me of Adobe’s Dreamweaver in the early 2000’s. Sure, it was a drag-and-drop website builder (easier to make vs coding), but in an effort to match your design exactly, it fixed everything in place with a ridiculous number of nested elements. It easily doubled or tripled the file size of a “human-made” version while being less responsive (yikes!).

I get it — there’s a balance. Dreamweaver enabled more people to build websites, but those websites were fragile. Lindy feels the same way (and Make, and n8n). It enables normal people — like me — to automate workflows, but it’s not as robust or flexible as writing code in my own server environment.

And to be clear: this is just an automation; I wouldn’t call this an “AI agent” (I mean... I will, because it sounds cooler, but strictly speaking, I don’t think it is). There’s no feedback, learning, or figuring out its own path. It’s funny, the Agent Builder feels like AI, but this output doesn’t.

I’m fairly certain it’s worth my time to create these automations, but it’s not an obvious win. It’ll partly depend on the maintenance requirements, but it’ll mostly depend on how close it gets to my quality requirements. Is it worth the eventual productivity gains if it’s only 80% as good? What about 95%? It probably depends on the process.

That’s Why AI Isn’t Taking Your Job Anytime Soon

For these reasons — it’s hard to implement/upkeep and fragile — I don’t see AI taking thousands of jobs this year. Instead, I think it’ll continue to be a solid multiplier on existing efforts. And let’s be honest, no healthy company is going to say, “let’s just do the same with less.” Instead, they’ll use the efficiencies to tackle new opportunities (because if they don’t, their competitors will). That’s what happened with calculators, personal computers, and smartphones.

Over time, automation tools will get easier and more robust, just as Squarespace does today with drag-and-drop responsive websites. But it’ll take a while to get there, and chances are good that healthy companies will adapt along the way.

My Trip To Uganda Taught Me About Active Patience

I recently returned from a trip to Uganda to visit some missionary friends. It was my first time in Africa, and while I loved the sights and people, what stayed with me most wasn’t the experience itself  — it was what I learned about patience.

I expected to be inspired by my friends’ big vision of a new retreat center. What surprised me instead was their attitude toward failure.

One person we visited moved to Uganda 32 years ago, and she’s a legend! She brought peace between warring tribes through her veterinary work. It’s incredible! (There’s even an Adventures in Odyssey episode about her.)

Her vehicle, which helps people know it's her.

During the trip, we visited three places that told the story of her life’s work:

• the location of her first assignment, where she regularly washed her hair in a waterfall,
• her (and her husband’s) current home and ministry,
• and the site of their future retreat center.

The retreat center is just getting started. A few small buildings stand now, but their vision includes a massive A-frame space that’ll serve as a training ground for mission training, veterinary education, and farming instruction.

The retreat center at night.

But working in Uganda is hard.

For example, the land they purchased is being contested by the seller’s son, and title protections aren’t the same as in the US. They also have to deal with antics like neighbors trying to plow their land to claim it as their own. At one point, they built a fence, but raiders stole the fence materials. So they hired a guard, bought all new materials, and built another fence.

It’s regularly two steps forward, one step back.

What struck me most wasn’t their vision, but their patience. Yes, they have enormous goals, yet their daily focus remains simple: take steps each day, even if it’s a repeat of yesterday’s steps. Again and again, they spoke about trusting God’s timing and finding God’s purpose in setbacks.

How many dudes does it take to fix a broken tractor?

Be Patient

Reflecting on their work reminded me of something I had read many times but never fully felt: the steady faithfulness described in the book of James.

Unlike some early followers, James stayed in Jerusalem through decades of hardship. His letter was written to believers scattered by persecution: people facing loss, poverty, and uncertainty, wondering how long their suffering would last.

In response, James points to a farmer:

'Be patient, therefore, brothers, until the coming of the Lord. See how the farmer waits for the precious fruit of the earth, being patient about it, until it receives the early and the late rains. You also, be patient. Establish your hearts, for the coming of the Lord is at hand.'

James 5:7-8

The image would have resonated immediately. Most were from agrarian communities in Palestine and knew there were two rainy seasons: planting and harvest. The farmer couldn’t control the rain, but he could prepare the soil, sow the seed, and wait in trust.

The farmer’s patience wasn’t passive. It was active.

He worked while he waited.

Digging up a root to make medicine for a sick goat.

James, like my friends, knew this firsthand. He led the struggling Jerusalem church with limited resources and many trials, including political tension, famine, and persecution. When he writes:

' Count it all joy, my brothers, when you meet trials of various kinds, for you know that the testing of your faith produces steadfastness. And let steadfastness have its full effect, that you may be perfect and complete, lacking in nothing. '

James 1:2-4

He isn’t offering theory. He’s describing a life shaped by endurance.

Growth takes time. But waiting isn’t inactivity. The farmer tills, plants, and prays. In the same way, James calls us to active patience: a quiet trust combined with faithful action. Delays aren’t signs that God has forgotten, but signs that He is ripening something precious in time.

Burn dry grass to make way for new grass when rain comes.

Count It All Joy

Just as the early church learned to persevere through hardship, and just as my friends continue building despite constant setbacks, we are invited into the same kind of patience.

Most of us aren’t building retreat centers in Uganda. But we’re all waiting for rain somewhere.

Maybe it’s a business that’s growing slower than expected. A relationship that feels stuck. A calling that hasn’t produced visible results yet. A season where faithfulness feels repetitive and progress feels invisible.

Active patience means doing today’s work well while trusting God with tomorrow’s outcome.

We prepare the soil.

We plant the seed.

We keep showing up.

And in time — often longer than we’d prefer — the rain comes, and the harvest arrives in ways only God could produce.

I can't believe she washed her hair in this waterfall...

2026 Annual Letter: Exciting Growth!

If 2024’s theme was survival (with Jessi’s brain tumor and saying goodbye to our dog). 2025’s theme was new growth! I grew a new business, learned new skills, grew our rental portfolio, watched our new dog grow, and visited new places. Lots of new, exciting growth areas!

Property Management

At the tail end of 2024, I started a property management company, but didn’t get my first owner/client until January 2025. Since then, I’ve been on what feels like a steep growth curve with 87 units under management (in addition to managing 105 of my units). I spent considerable time building out my systems and team to keep up with growth (while occasionally going to fix something). It’s been fun solving new types of problems (like setting up payroll), but finding the balance between working in my business versus working on my business is challenging.

All of my growth has come through word of mouth, and this year I’d like to be more intentional about generating leads. One idea is to provide valuable rental tools/insights for real estate agents, since they’re often the ones making recommendations to investors. The goal is to build a liking/trust with them so they recommend my company.

I’m excited to keep growing here!

Drone Pilot License

I like flying, but it isn’t the best use of my time or money to learn to pilot airplanes. So, a second choice was to get my Part 107 license so I could fly my drone. I took the class through the Pilot Institute, and it was fantastic. I enjoyed learning about the different airspaces, how to read aerial maps, and so much more. And now I can legally take photos for my business.

 CCB License

It turns out that in Oregon, if you build a house with the intent to sell it, you’re required to have your contractor’s license. So, I got my general contractor’s licence from the Construction Contractors Board (well... almost, I’m still waiting for final approval from the CCB). Beyond letting me do development projects, it might also be useful for my management company.

Baker Tower

I syndicated my first deal, and it’s awesome. At 10 stories, the Baker Tower is the tallest building in Oregon east of the Cascade Mountains. It’s a historic mixed-use building (built in 1929) with residential, commercial, and a ballroom. It’s just cool. The only downside is that it’s a six-hour drive from my house.

I syndicated the purchase to five investors, each of whom owns an equity stake, and the plan is to hold it for a while. We visited in November and plan to visit regularly as a family. My not-so-secret hope is that this becomes a place with many family memories.

Raising the funds and structuring the deal is significantly more complicated than offering private money loans on short-term flips, but the upside and impact are worth it.

Chuck!

As I wrote in June, we got a new dog this year. Chuck has been a genuine joy... despite his fondness for chewing our clothes. We all love having him around the house, going on walks, and playing fetch. It’s so fun having a dog who actually listens and does what you want (85% of the time).

One funny thing: when I’m on the couch, he’ll lie down beside me... Then he’ll put his head on my lap... Then his front paws... until he’s slowly wiggled his entire self on top of me! I think it’s hilarious and reward him with plenty of pets.

Travel

We traveled a bunch, which I love. Here are some pictures of places we visited.

Spain

As part of Jessi’s sabbatical, we visited Barcelona and Málaga. It was so wonderful speaking Spanish and enjoying some sun.

Alaska

A friend from college wanted to visit, so we went for it!

Camping In The Redwoods

We spent time with my side of the family during an extended camping weekend. So much fun. We had Chuck for about a week at this point.

Backpacking Part of the Corvallis To The Sea Trail

The kids did amazing! We hiked 5 miles each day for 2 days. I’d like to keep exploring parts of the 60-mile trail.

Tucson, Arizona

We finished the year with my family in a vacation rental. My favorite part (besides being with family) was swimming in the heated pool each day. We also got some nice family photos.

Looking Ahead

2025 was a great year, and I’m looking forward to 2026. The kids keep growing and becoming more independent (like staying home alone). We also have more travel planned (like Uganda, Mexico, and Boston) which all of us enjoy.

I'm also having a blast growing my property management company and have a great team helping me. Growing it is major focus this year because I believe we can help lots more owners and renters.

Finally, I’m listening to books that collectively span American history to celebrate the US’s 250th birthday. Right now I'm listening to George Washington's biography and next will be about Lewis and Clark. I have to listen to 40 minutes a day on average to hit my goal, and so far it's been fun.

I'm excited!

Pictures From 2025

Samson likes to dress up. This time as Harry Potter

A sign for a new storage facility

The boys having fun together

Chuck doesn't love to have his nails trimmed. So we got this...

We took a tour of the USS Blueback submarine at OMSI.

Elinor's piano recital

The kids served parents books that they read aloud