I wrote about why I stepped down from a really exciting and successful stint as CEO of Hampton back in March, so I won’t rehash the whole thing here.

The short version: I was burnt out, wanted fewer stakeholders and dependencies, and felt a strong pull back toward the things I’d been neglecting, like my family, my health, and my time.

I joked with friends about “semi-retirement.” I made lists of new hobbies (pizza making). I brainstormed creative ways to get the six-pack that’s been evading me since my wedding day (it was barely a 4-pack, but still).

Now, almost nine months later, things are radically different, not just from running a high-flying startup, but from what I imagined this chapter would look like at all.

Financially, emotionally, and just day-to-day. 

Here’s what I learned, where I landed, and what surprised me most.

The first thing that happened when I stepped down was my calendar blew wide open.

It felt like someone pushed me off an insane treadmill and handed me spring water and an oxygen mask.

Holy shit. New energy, new life. LFG. 

That first month was great. Long walks with my wife. Planning ahead for a second dog (“I have so much free time now!”). Spring weather. Slow afternoons.

I speed-read through the Didion trilogy and then chased it with a side of SBF crypto-tragedy for dessert. Delightful.

Then, maybe a month in, I noticed something…

I kept checking my phone.

Not for book recommendations or new music, but for Slack.

Where were the daily pings from my EA? 

The constant stream of emergencies? 

The people who used to need me, my advice, my reassurance, my attention?

Slowly at first, then all at once, I realized the absence of the CEO title was starting to mess with my sense of self. No dopamine hits. No constant problem-solving.

Too fast had defined the last 20 years — I needed a break.

But too slow?

That felt like whiplash.

What I thought would feel like freedom started to feel like a low-grade melancholy. 

Nietzsche once said, “Idleness is the parent of psychology.” Translation: when you stop doing things, you start thinking too much.

I felt that in my bones.

I needed to find a way to be productive and creative.

Directed, but not boxed in. Moving forward, but without recreating the same grind.

The thing I’ve always loved most is writing.

So instead of overthinking it, I did what came naturally. I spun up a quick WordPress blog and started publishing whatever I was thinking about:

Panic selling.
Tariffapalooza.
Creatine.

Naturally, my mom, sister, and her three best friends wanted updates, so before long I moved everything over to Beehiiv and turned it into a newsletter. I picked a name, Signal // Noise, a small nod to Nate Silver — and kept moving.

No plan, really, just action.

Then a founder emailed me, asking if I’d consider doing advisory work.

I’d coached before and enjoyed it, so I said sure. I threw together a short contract, used the free tier of Notion to organize the basics, and suddenly had a new line of work.

What surprised me about this work out of the gate was just how clearly you could see certain things with an objective, third-party view. With distance, patterns jump out. Twenty years of experience and mistakes and reps suddenly became very useful.

Before June, I had four clients and more inbound than I could handle. That’s when I realized I needed to slow down to speed up.

I built a simple system: a Notion dashboard, intake forms, call tracking, progress notes.

By July, my inbox was really starting to explode.

It was old employees, old friends, agency owners, VPs looking to re-engage with startups.

One thing became clear fast: my network is one of my most valuable assets, and keeping it in my head was becoming a mess. 

So I built a quick-and-dirty Rolodex to track clients, prospects, colleagues, and contacts.

In roughly 90 days, this all happened:

Blog → Beehiiv → newsletter → coaching → internal infrastructure.

Once things felt more organized, I felt more comfortable leaning back in. 

I protected three creative days a week for reading and writing.

The other two days were for clients.

I wrote pieces I really liked (on luck, on leadership, on communication), partnered with my old crew at The Hustle to make The Community Playbook, went on a few podcasts, and started publishing work I was genuinely excited about.

Digging through my Google Drive felt like opening a time capsule: decks, templates, reports, notes. Thousands of potential content ideas.

So I organized them. Built a Knowledge Hub. Then started templatizing the most useful stuff for clients — vision, values, hiring, onboarding. 

The boring but essential work that a lot of startup founders skip.

It was fun, but man was it starting to take up a lot of time. 

Even as a one-man operation, I found myself buried in admin:

So I did what ambitious people do: I hired help.

We were becoming a team. Surely, this would make things easier, simpler, faster. 

But within 60-days my relationship with the EA had fallen apart; there was a breach of trust, it was more work than it was worth. 

The content person wasn’t working out, and it wasn’t fun.  

Endless pings across time zones. Stress. People who needed things from me.

I had accidentally recreated the exact life I’d tried to leave.

The main difference this time? I noticed faster.

I cut what wasn’t working and then made a new rule: I only work with people I genuinely enjoy and trust — and only when it’s truly necessary.

By November, things felt right again. My team size arc: 18 → 0 → 4 → 2.

Outside of writing and advisory work, I tried a few new things.

I went on a podcast or two. 

I helped copy chief some senior copywriters at my old company.

I agreed to be a growth coach for Codie Sanchez’s biz owner community.

I also dipped into some public speaking; a local Morgan Stanley Entrepreneur Summit. No travel, so it was an easy yes. I spoke about the power of your network and moderated a CEO panel.

None of this was about chasing a new identity or becoming a circuit speaker.

It was about pressure-testing what actually gives me energy, and trying to pay attention to the signal.

My financial goal this year was simple: find my footing.

I’d saved well. I’d done the math. Nine months of burn was survivable. 

What I didn’t anticipate was a tariff-driven market drop that messed with my head more than I expected. A month after quitting, the market had plunged 10%+.

Despite being a very seasoned investor, it still played games with my mind, and that fear pushed me to replace my CEO-level comp faster than planned.

Fortunately, I’ve been able to. The transparent version is: I’ve largely replaced my base salary through advisory work. I have six CEO clients and I charge $4,250/month. I’m very grateful for that.

Elsewhere, I’m not making much - the newsletter isn’t being monetized. When it gets a bit larger, I’ll think about it; but it won’t be generic ads, it’ll need to feel additive and exciting for the reader. 

Some days I really miss building. So I let myself scratch that itch by writing reports, exploring products, experimenting, but without forcing it.

One of my biggest goals this year -- besides family time -- was health and fitness.

In my head, this was going to be the year I finally optimized everything. Better labs. Higher HDL, lower LDL. Best shape of my life. Body fat down to 14%. With all this newfound time, how hard could it be?

Turns out: pretty hard.

A big part of that is the medical context I don’t talk about often. I don’t have a thyroid. In 2019, I had two surgeries due to follicular thyroid cancer, and since then, my body has been dependent on synthetic hormone replacement. If you’ve ever gone down this road -- or know someone who has -- you know it’s not as simple as “take a pill and move on.”

This year, getting my hormone levels dialed in has been brutal. My TSH has been a rollercoaster. I’ll feel hot, then freezing cold. Wired, then exhausted. Anxious for no obvious reason. Completely flat the next day. It’s incredibly frustrating, and it messes with everything: energy, mood, motivation, and body composition. I suspect a lot of my inability to get into the shape I want, and to stabilize other labs, ties back to this.

So while I didn’t “crush” my health the way I hoped, I’m also just trying to not be so hard on myself in this area. Practicing a little patience, I guess. 

This year, I’m on track to read 30 books (prior record: 22), per my Goodreads Annual Challenge. What surprised me wasn’t just the volume, but also the shift from reading less non-fiction to reading more novels.

I think something about 2025 made me want fewer inspirational business books and more great stories.

The increasingly lonely feeling of being a laptop junky, alone behind a screen, sitting at a desk by yourself; it really crept up on me.

By November, it was undeniable that working from home full-time was less engaging, less healthy for me, and honestly, less healthy for my relationship with my wife.

Sitting at home all day does sneaky things to your brain.

You start noticing everything you don’t love about your house. You get irrationally annoyed when the dogs bark during a meeting. You drink way more coffee than you need. You find yourself staring longingly at the couch in the middle of the afternoon. And most importantly, it dramatically increases distractions -- which increases the switching costs of everything you do.

Work bleeds into home, home bleeds into work, and neither feels great.

So I made a change. I started working from coffee shops more, going to a coworking space a few days a week, and it’s been a huge improvement. I’m more focused, I’m happier, too. 

Over the next few months, I plan to find a more permanent office, somewhere I can go to work, and then leave.

A little separation of church and state. 

A huge reason I wanted to leave my last job was to be more present for the people I love. Not in some vague, aspirational way, but in the very real, day-to-day sense of actually showing up again.

Getting back to relationship-building with the people already in my life.

More often than not, I succeeded in this regard. And that alone made the entire year feel worth it.

I wanted to be a more present father, and that one has been a big accomplishment.

I’m in the weekend activities. I’m around in the mornings before school. I’m here after dinner. I’m not mentally trapped in Slack or half-paying attention to a screen while pretending I’m “around.”

That shift alone has been massive.

I was also able to be there for my sister during a big transition -- her son leaving for college. I threw my nephew a big graduation party, which was important to him, and important to her, and awesome for us. She’s one of the most important people in my life, and it felt relieving to be available for moments like that again.

One of the biggest gaps I needed to confront this year was my Philly boys -- the guys I grew up with and that I’ve known forever. These were relationships I cared deeply about, but had slowly neglected. Texts unanswered. No proactivity. Always meaning to reconnect “soon.”

I wrote about this in No New Friends (Just the Real Ones), but this year I finally did something about it. I organized a poker night with seven or eight guys, and it’s been awesome. 

Even more than the night itself, I’m back in the text threads, the inside jokes, shit-talking, Eagles drama, the daily nonsense. 

And it feels good to be back in the mix.

I also made meaningful progress on my 2025 goals. I do a formal goal-setting exercise every year, and this year I knocked out a lot of what I set out to do.

We did our family fun day and finally made it on a camping trip. 

I’d wanted to do Jesse Itzler’s Big Ass Calendar for a while, and I finally did that, too, and I’m already planning for it again next year.

I never scheduled the intensive pizza-making course I kept romanticizing.

I wanted to find a meaningful way to give back locally — something that really lit me up.

I volunteered at a food pantry for a couple of months, but they honestly didn’t need me much. I enjoyed it, but it didn’t spark the “this is it” feeling I was hoping for. I’m a little disappointed I didn’t find my volunteering groove this year, but I’m also trying not to be overly hard on myself about it.

I also wanted to find something special that was just for my son and I, something we could really connect on together. We have different interests, and that turned out to be harder than I expected. That one’s still unresolved, and I’ve gotta be honest about that, too. 

Last but not least, I learned something uncomfortable but clarifying: when you quit being a CEO -- a role that comes with a lot of implied utility -- it becomes very clear who’s in your life for you, and who was there for the version of you that could immediately help them.

Some people in my professional life really disappointed me this year. That sucked. 

But it also simplified things. I’m not interested in carrying resentment or keeping score. I keep the real people close. I let go of the rest. And I don’t lose sleep over relationships that were more transactional than I wanted to believe at the time.

I can’t pretend to have this all figured out. Life’s balance will probably be forever evolving, in one way or another. 

But, I learned I still love writing. I’ll continue doing it, as it’s the best creative outlet I’ve found.

Personally, therapy came back into my life after a long hiatus, and it’s been invaluable.

I learned a few traps to avoid:

Next year I want to find a way to get back to my normal health regiment and set some more realistic goals. 

I want to launch a podcast -- a way to tell stories, learn from others, and explore voices outside my normal tech/media circle.

I’m still ambitious. I still want to build. I just want to do it in a way that I’m proud of, that reflects my own personal brand, my own values, and not those of someone else. 

More writing. More creativity. 

Fewer self-inflicted traps. 

And work that really feels worth showing up for. 

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