Almost two years ago, on my first day back from paternity leave, a calendar invite from HR titled “quick sync” landed in my inbox.

You know the rest.

Shortly after that, I decided to try consulting (i.e., working for myself) full-time. Two years feels like just enough time to give an honest evaluation on how it’s all going.

What I actually do

Here are my clients and what I do for work:

• Clay: A business sales software company that uses AI to help other businesses grow. I’m on their education team. I build their self-serve, DIY education courses. So I learn the different tools and strategies, then record videos and documentation showing others how to do it too.

• OpenAI: They own and created ChatGPT. I’m also on their education team. I build their self-serve, DIY courses and certifications. The goal is to upskill millions of workers on how to use AI at their work.

• Remote Life OS: I help people with their careers through my newsletter, coaching, and services.

• Good Morning Philly: This is a hyperlocal weekly newsletter I launched in February! Currently, this covers Fishtown, NoLibs, Kensington, and Port Richmond, but will probably expand. I’m having more fun with it than I expected.

As much as possible, I try to dedicate whole days to one client, e.g., Monday and Tuesday on Clay, Wednesday on OpenAI, etc. That keeps me from bouncing between contexts, and mostly it works, but sometimes the calendar has other plans.

I work as much as possible between 4:30 – 7:00 am, before the kids wake up. Then when the kids are at school, I’m pretty locked in. I’m working with AI a lot, which has really changed how I work. A lot. That deserves its own post; for now, the way I describe it is work feels like a full-contact sport.

You can get a lot done, but you can only sprint for short periods of time, and then you’re drained.

I try to be “done” with work around 5:00 pm, when I leave to pick up the kids for activities. Usually, I’ll log in after dinner to check a few things.

Most weekends, I work in the mornings.

The fancy term for all this is “soloproneurship.” I hate that term for some reason. I prefer “portfolio career.”

The money

Let’s start with how my income mix has changed.

What this hints at: I didn’t just get laid off and decide I’d do consulting, and then I magically landed my clients.

I found my first client while I was working at Reforge. That gave me my first taste of consulting in a low-stakes way. If I hated it or couldn’t juggle the two, it was easy to drop.

I paused everything for a couple of years while I was living in Ireland (I was busy enough and didn’t want to deal with the tax implications).

Then, when I moved back to the States, I picked this back up.

In 2025 (and 2026), 95% of what I earn comes from consulting. The rest comes from the career coaching and a resume review service.

The plan is to slowly flip that ratio between 2026-2030: earn more from selling products and services, less from selling time.

What’s good about a portfolio career?

I choose who I work with. Every client is someone I opted into, a company whose work I find interesting, with people I enjoy talking to and learning from.

With consulting, a hidden benefit is that optionality cuts both ways. Yes they can let you go faster. But that’s true for you, too. If something’s not working out, you can just leave.

Getting paid well is great. But it’s not just the money. It’s knowing you can get the money. You prove to yourself that someone will pay you for your expertise. And if one person will pay you that means other will, too.

The variety keeps me sharp. This past Monday, I worked on a new course on AI agents. Then, on Wednesday, I wrote about what opened on Frankford Ave. Yesterday, I coached someone on how to change their job titles so they were a better fit for the roles companies are hiring for in this market. It’s pretty neat.

I get to walk my kids to school every day. Beforehand, we’re playing wiffle ball or kickball in the street with the neighborhood kids. When I pick them up, I can focus on asking them about their day. I don’t need to be on a call or feel guilty about not minding Slack.

After years of juggling weird time zones and logging back on at 8:30 to work until 11:30 pm, I finally have more consistent hours. I’m sleeping better.

Then I wake up excited to work. There’s so much I love about a portfolio career.

What’s hard about a portfolio career?

I want to be honest about the other side, too.

There are no benefits. No PTO. If your partner does not work, or you’re not covered by their insurance, this alone can make a reasonable person reconsider their life choices.

It’s a lot of time by yourself. You have to get really comfortable with that, and if you’re a social person, it takes a lot of ownership to build that into your life. It’s not just going to “happen” for you. Serendipity is not on your side.

You can be your best friend or your worst enemy. You have to choose every single day. It’s so easy to get up inside your own head (about the work, about what people think, about whether they’ll keep you on for next week) and not be able to find a way out.

There’s a lot of FOMO. At fast-growing companies, especially AI companies, there’s a lot of excitement about what’s coming next. And you’re kinda part of it, but not really. That can be a weird thing to navigate.

The hardest part is the uncertainty. You don’t know how long a client will stick with you… or how long you should stick with a client. You take it week by week, which leads to nights where I ask myself:

Because the option is there. I’ve been asked if I wanted to go full-time, and for now, I’ve deferred. Is that being irresponsible, with four kids, a mortgage, and no benefits?

Even when things are going well, the doubt doesn’t go away. It gets quieter, but it’s always there.

Why a “real job” isn’t the answer

I talked to Brian Balfour about this. I told him I got offers and asked what he thought. He reminded me:

There’s the perception that there’s more security with a full-time, w2 role, because there used to be. That’s the way it worked. Then it stopped working that way.

We’ve all watched that transition play out.

I’m in a group chat with six other people, and all of us were laid off in 2024.

One got cut two days before the company’s seven-figure annual offsite, the one that was supposed to celebrate their growth. Another found out via a Slack message. A third was a week away from his one-year cliff and lost nearly a million in equity because someone pulled the trigger seven days early.

A full-time role is no longer secure.

Instead, optionality is the actual security. The ability to dip in and out of companies and find new work fast, and charge appropriately for your services. Basically, everything I’m learning is with my portfolio career journey.

The scary part of this is that the path is a whole lot less clear. Elena Verna had a great post on what the potential trajectory could look like. The short version:

The “risk” isn’t being a consultant with four kids and a mortgage. It’s putting 100% of your earning power inside one company that can fire you on a Tuesday morning because it’s looking after shareholder value, and you have zero leverage to do anything about it.

That’s not to say I won’t ever go back. Never say never, and as I said, there are awesome things about working with a great company. The gravitational pull of working on a hard problem with smart people and feeling like you’re onto something is amazing.

But I think when I went all in on this, I saw a portfolio career as a bridge for the moment, a way to bide my time before going back to a real job.

Two years later, it’s setting in that a portfolio career is what gets me out of needing one.

That a portfolio career is the whole game.

In January, I ran into a parked Tesla outside of a store that sold overpriced cookies in Fishtown. Not a big deal (it was just a fender bender), but I felt terrible.

I called the owner to tell her.

She picked up the phone:

You’re telling me.

By any objective measure, it was a rough start to 2026. There was The Tesla Incident. Our fridge broke. We found water leaking through the stucco on the back of our house, which means we need to replace the entire exterior. We lost Deefer, our dog, in January.

So yeah. Rough quarter.

Underneath all of that, a lot happened.

What happened in Q1

Good Morning Philly newsletter

The biggest thing I built was Good Morning Philly, a free weekly newsletter covering the River Wards (Fishtown, Northern Liberties, Kensington, Port Richmond) that ships every Monday at 6 AM.

Deefer passed away on January 19th, 2026. This is my goodbye letter.

I write and publish birthday letters for the kids. Yes, this includes Deefer Dog. You can read Deefer’s 10th birthday letter here. And here are Oliver’s, Annabel’s, Theodore’s, and Madeline’s recent letters.

Eight months ago, we asked the vet when we’d know it was time. She didn’t hesitate:

I wanted specifics. A date. Confidence levels. Standard deviations. But that was all she gave us.

So I did what any reasonable person would do. I started feeding ChatGPT his entire medical history.

Stage 4 heart murmur. A mass on his adrenal gland invading his vena cava. Seven different pills every day. I logged it all. If the vet couldn’t give me a formula, I’d build one myself.

For eight months, it worked. More good days than bad.

—-

Friday. Amy ran upstairs to get ready. I was trying to get the kids to play Mario Kart. Deefer threw up three times. Then he started throwing up his water. And he kept throwing it up.

This is my friends & family newsletter. You probably signed up after reading one of my articles, a LinkedIn post, or after we met. You’ll get a new letter 1-2x per month.

Madeline Mei Jing Lee was born on November 26th, 2025.

I write and publish birthday letters for the kids. You can read Oliver’s, Annabel’s, Theodore’s, and Deefer’s recent letters.

We went to visit our family friends, Ali and Tommy, with your Mima. They’d just finished remodeling their house.

Ali opened her walk-in closet.

“Tada,” she said. Shoes lined the room floor to ceiling—Manolo Blahnik pumps and Jimmy Choo and Louboutin heels, all on perfect display. I wear Hokas for every occasion, but somewhere The Corrs were playing. It left me breathless.

Later, Tommy took us to the basement, showed us his tool collection. Everything perfectly hung, tools stenciled to the pegboard so you’d know exactly where each one belonged. Everything in its place.

My dream house.

When we left, I asked your Mima: “Did they want kids?”

“Ali did,” she said. “Tommy didn’t. They nearly divorced over it, years ago.”

“Then what?”

She shrugged.

—

Your grandad suggested a few names for you.

We didn’t hesitate. We’ll take the calm one.

Your parents are optimists, Madeline. We wanted to conjure some stillness into your personality. This house runs on chaos—usually after dinner, before bed, the volume rising until someone cries. We were hoping you’d bring some balance.

So far, you’ve held up your end of the bargain. Like you knew we needed it.

You’re also the last one. Which means there’s this tension: we know the most about parenting, but have the least time to do anything about it.

I can’t promise Louboutins or an orderly life. With four of you, I’m not even promising college. You all might flip for it—the winner goes.

But I promise you this: you are born into a family that will show up for you. Everyone is cheering you on. There’s so much love here, Madeline.

It’ll leave you breathless.

This is my friends & family newsletter. You probably signed up after reading one of my articles, a LinkedIn post, or after we met. You’ll get a monthly email.

It was only after Chris died last November that I finally got a reply from an old friend. I’ll call him “Alex”.

Eight years of emailing Alex, with no response. Birthday messages. Life updates. The occasional “thinking of you, man.” I never got anything back.

It took a message about the motorcycle accident to break the radio silence.

It keeps me up sometimes. Because there were times I wasn’t a great friend. There were times (cringey, crawl-into-ball-and-die moments) where I chose convenience over loyalty, where I let him down. And I think maybe I earned the eight-year silent treatment.

But there were good moments too. Times I showed up when it mattered. I want to believe it balances out. I’m not sure it does.

The only move left: look at where you failed, and try to fail less. Look at where you succeeded, and do more of that.

That’s what these reflections are for. Once a year, once a month, every day… the frequency is a detail. But you have to look. Reflection is how you steer instead of drift.

This is a review of my 2025 and a public sharing of my 2026 goals.

At the end, I share why I do this and how I review the year.

To summarize: This helps me look back at what worked, what didn’t, and what I want to focus on in 2026.

My friend Chris passed on November 9, 2024, in a motorcycle accident. He was riding slowly out of a parking lot in Los Angeles. They think he hit something. He fell and died. Last week, I went back to New York for his memorial service.