I wrote most of this on the plane, flying back from NYC. Feeling inspired.

I normally write something either on my birthday or at the start of the year. 2017, 23, 2018. I skipped my birthday post and I’ll be in Italy for the start of 2020. Publishing something now feels like a good in-between.

And I also know these moments of inspiration can be fleeting. If I don’t publish now, it might never see the light of day.

I’m 24 — it has been about 1.5 years since finishing college. I think I’ve generally kicked a** in life…

Disclaimer: I do not express the thoughts, views, etc. of my employer. All opinions are my own.

It’s been just over a year since I joined Thumbtack, a major local services marketplace. Since then I’ve learned a lot about the space. As a result, I thought it would be fun to synthesize my learnings and speculate wildly on where I think we’re going.

Why There Is Still No Clear Winner

Arguably the 1st local services marketplace was craigslist, which popped up in 1995. Now, almost 25 years later — there is still no clear winner.

Here are the major players:

Of the major players in this space…

For the bast 6 weeks, I’ve been going to therapy for 1 hour every Monday.

I’ve told almost no one (until now 😊). For whatever reason, I’m at least slightly embarrassed.


  • I have problems, like all humans
  • I have always hated the idea of therapy without being able to articulate why. Whenever this happens, I take it as a signal that I should try the thing I’m questioning
  • I get 6 weeks of free therapy through my job!

At the moment, I have no plans to continue with therapy, but it was a valuable experience.

Regulating your nervous system

The most import skill…

We talk about flywheels in the context of companies all the time. It’s the idea that if you can get the wheel moving — it will keep moving. And if you feed any part of the flywheel its movement will accelerate.

In the context of Amazon it looks something like this:

Some companies have come to design their whole business around creating a flywheel.

Yet no one does this with their life.

The Daily Flywheel (Micro)

The first 15–45 minutes of my day typically dictate how the rest of my day will go.

My day tends to go radically different ways depending on whether…

Today I turned 23. In Thailand. Over the past few months, I’ve been lucky enough to travel to Cambodia, Malaysia, Myanmar, and Thailand. I’ve made friends from all over the world.

The trip was not without its risks …

By the time this post is published, I’ll be back home. Back to a routine, back to having more than 3 t-shirts, back to sleeping in my own room, back to good coffee, and back to family dinners.

So before I forget, I want to document a few lessons I learned away from these things. These might not apply to everyone, they probably don’t. …

Photo by Joshua Earle on Unsplash

Like most 17 year-olds, when I graduated from high school, I had no idea what the hell I wanted to do with my life. So I decided to take a gap year.

Since then I’ve come to realize the enormous amount of value of taking off after high school to explore interests without the pressure of school pushing us towards a career path.

I’ll try not to rant on too long, but to read more of my thoughts checkout Why Taking a Gap Year Needs to be the New Normal.

I’ve seen far too many of my peers go through…

Over winter break I was lucky enough to spend a few days in Cape Cod with a few of my friends. We had no real plans or goals. Just fun.

The first morning we woke up, it turned out to be a gorgeous day. 60s in the middle of January. My friend and I quickly dressed, laced up our running shoes, and ventured into the outdoors.

“Should I bring my phone?” my friend asked. “Nah, I think we’re good”.

Although we didn’t know the area at all, I’d looked at google maps beforehand and had I rough plan for our…

The San Francisco intern fam

Just forty-five minutes into my first day at Braintree, I hopped onto a conference call with two of the engineerings on my team and one of Braintree’s clients.

It’s safe to say I had no idea what was going on.

This would set the tone for my summer at Braintree, a tone of diving straight into the unknown.

Flash forward to now, nearly ten weeks later. There’s still a seemingly infinite amount I don’t know, but I’ve made hundreds of commits, many of which are now running on Braintree’s production codebase.

It’s been a fun journey with lots of experiences…

Obligatory first day of work selfie

It’s crazy to think that my first week here has already come and gone.

Quick Update: I’m loving it.

I won’t lie, I was a little skeptical of San Francisco before coming here. It’s dominated by the tech industry, doesn’t get warm in the summer, and rent is crazy expensive.

I’d heard people love it here…but why?

After my first week here, I think I’m starting to get it. The food is amazing, it’s easy to get around, and there are beautiful parks everywhere.

Sunset over Ocean Beach on my first night

For the next 10 weeks I’ll be living in San Francisco while I intern at Braintree.

In the days leading up to my departure I began to feel the rush of anxiety and excitement that comes with moving across the country to start a new job.

This summer marks two important firsts for me: living in a city, and my first job working as a (kinda) professional software developer.

Naturally, I spent the last few days prior to my departure frantically searching for blog posts from past interns trying to figure out what the heck I’ve gotten myself into.

Taylor Milliman

Software engineer @Thumbtack. Writer @CodeWithMosh

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