Hi,

This one is kind of a doozy…so f**k it, let’s dive right in.

Let’s dive in ⬇️

So…I did a thing.

Well, I guess it’s actually kind of a big thing lol but a thing nonetheless.

In late May, I stepped away from my job after working there for 12 years without another job lined up.

Damn…I won’t lie, seeing that sentence typed out feels insane.

For context: I spent the last 12 years working in digital marketing + marketing at an independent record label/entertainment company that evolved into a content company.

I was incredibly blessed - I worked with some of the most talented artists & creators in the world, helped build artists from the ground up, worked with people I used to look up to, had incredible mentorship, worked with an amazing team that felt like family, and most importantly…provided value to artists and helped grow their careers.

Before landing that job in music (which to this day has been my only full-time job ever in the music industry), I actually worked in real estate. It was the first job I could find after college and allowed me the freedom and space to still pursue music after work hours. I remember working in real estate at a brokerage in New Jersey while interning at two record labels (United for Opportunity and Bar None Records), trying to find a way into the music industry. At that time, I was willing to do anything and everything to get a shot at working in music.

I even started writing for a hip-hop blog and doing phone interviews with artists to get my foot in the door. I’ll never forget interviewing Ty Dolla $ign super early on and being so nervous, I kept fumbling over my words. I ended the interview feeling embarrassed but also blown away that I had the chance to actually speak to someone whose music I listened to.

Fast forward, and I eventually got an opportunity in the form of an internship at Cinematic Music Group, which ultimately led to a paid position.

When I officially got hired, I couldn’t believe it.

In my mind…I made it.

You’re telling me I was getting paid to work in music and do something I love? To work with artists directly and help them? To get out of the corporate world and into a space I loved and cherished so much?

I was the luckiest guy in the world and to this day, owe everything to Jonnyshipes who took a chance on me back when he didn’t have to.

Fast forward and those 12 years flew by.

I legit feel like I blinked, looked up, and it was 2026. I grew a lot over those 12 years. I went from being a wide-eyed kid in his mid 20’s to an adult who built confidence, experience, and developed his own perspective on things. I went from being blown away at being in rooms with people I looked up to to it being normal (somewhat, though I still have to pinch myself sometimes).

If we continue fast-forwarding, while I felt very blessed and fortuanate to be in the position I was in, I felt like I needed a change.

After more than a decade doing marketing, I felt like I needed to switch things up but had no idea what that change was (or still is). I thought long and hard and realized I needed to take some time to step away, think, and really evaluate the next chapter as opposed to rushing into another job.

So…I left without anything else lined up.

Now, I know what you're thinking.

“It must be nice, Mike”.

To that I would say: you're right.

The only reason I can even do this is my parents who are letting me stay with them in Florida while I sort things out. If I had people depending on my income, I'd have looked for the next job in a heartbeat and this chapter wouldn’t exist. Shout out to my parents, because without them I'd be f'ed lol.

After leaving, I got to speak at the Music Ally conference in London in June, and since I was already in Europe, I tacked on Barcelona for a few days.

The "we need a plan" part of my brain could not handle it.

“Dude you're really gonna do all this shit without any new money coming in?”

Probably not the sharpest financial decision I've made but I felt like I had to do it.

The more I think about the whole thing, the crazier it feels…

It’s actually kind of funny in a way - the guy who lived his whole life trying to have a plan or a strategy for everything (sometimes down to the minute of every day lol), stepped away without any clue of what’s next.

I truthfully never imagined myself leaving a job without one lined up. But I figured I really needed time to think and explore what I’m still passionate about.

Since then…there’s this interesting thing I’m coming to terms with. And that is being comfortable living with uncertainty and not knowing what’s next. It’s funny, because to some degree, I hate not knowing. It’s uncomfortable for me.

I’ve lived my whole life trying to avoid it as much as possible. Now here I am living in uncertainty in one of the most extreme ways possible.

I’ve picked up some consulting (which I’m very grateful for) but even as I do that, I’m still unsure. If I’m being honest with myself…there is a part of me that isn’t even 100% sure if I still want to work in music long term. And if so, in what capacity.

Music is in a weird place right now (more on that in a future newsletter) and there are many days I wonder and question if I still love it the way I used to. I contemplate if I were to switch things up and leave music marketing, what would I do? Where would I go?

It’s all moving so fast and sometimes can feel super confusing.

Part of me wants to on a daily basis “have it figured it out already” and land on the answer of what’s next.

Here's the interesting part I didn't see coming and part of the reason I'm writing this.

I thought I'd take a few weeks, sit with my thoughts, and arrive at somewhat of an answer. Clarity would eventually show up and I'd know what the next chapter looked like.

Two months in and I’m realizing that is not how it works haha. Not even close.

I’m realizing that clarity doesn't always arrive as an answer from thinking - it can arrive with subtraction.

Each week I’m aiming to try something: a consulting project, building a tool, having a conversation…

And using that to learn what I like and don’t like. The picture doesn't necessarily get built, it gets carved around what I’m trying and testing. I’m learning to rule things out until what's left is the shape of whatever the next chapter might be.

Which means the only way to get clarity is to keep moving while I’m still confused. Sitting still and thinking harder produces nothing. I have tested this extensively lol.

Most people reading this aren't going to quit with no plan, and plenty of people who are in transition chapters didn't get a choice about leaving at all.

What I’m also learning is that you can't eliminate options you don't have which means before subtraction, there's a step not many people talk about: you need things showing up to rule out. This doesn't happen from applying into the void.

For me it's been posting content - simply publishing what I'm actually working on and what I find interesting. I’ve been fortunate that other people find it interesting too.

I know what you're thinking…yeah, the guy with the newsletter says post more content, shocking lol. Fair! But hear me out…I can point to specific things it produced.

The Music Ally talk in London came from LinkedIn. From posting consistently, most of which landed on nobody, until one post I didn't think much of must’ve got in front of the right person. I’m learning that's actually how it goes…dozens of posts into silence with one that landed.

Same with the tools. I built Spotify and YouTube tools mostly for myself, wrote how I did it, and some of the conversations that came from those were more useful than anything I got recently.

Now…the honest truth is that most of what I put out has returned nothing.

I've built tools that maybe five people ever saw. I've posted things I was certain would land that went absolutely nowhere. To this day, Anthropic has not called to say they’ve seen my content and ask if I'd like to run their music division LOL.

That said, I'm still doing it. Partly because I'd be doing most of it anyways because building the thing is the fun part, especially in the current AI age we’re in. If it never turned into anything, I'd still be in there messing with it.

But mostly because I stopped keeping score post by post. You can't tell in advance which one gets in front of whom, so scoring individual pieces is a fast way to talk yourself out of it pretty fast. What you're actually doing by posting is widening the surface area, and surface area truly pays on a long timeline. 6 months. 12 months. It's not a single bet, it's a compounding effect.

The post that led to Music Ally post wasn't necessarily the good one. It was just the one that got seen.

Someone told me this quote years ago that has always stayed with me:

“People can't pay you if they can't see you.”

I used to hear that as marketing advice but it’s deeper than that.

Nobody can offer you an opportunity for a thing they don't know you can do and a résumé only says where you've been. Building in public shows what you're becoming, which is what people actually hire for when they're not just filling a slot (at least I think).

So if you're in the in-between right now, voluntary or not: I’d encourage you to publish something this week. The tool you made. The thing you figured out that took three years to learn. The breakdown of why that campaign worked. It could be written or video.

It likely won’t feel like it's doing anything. It didn't for me either, for a while. Then it did, all at once, from what felt like out of nowhere.

Where I've landed so far: I'm not sure I want to keep doing marketing the exact way I've done it for 12 years. Music is where I'm useful and where the interesting problems are so I'm questioning the shape of the role and the industry.

The actual state of things is in-progress with no dramatic ending. I'm still confused most days and I'm getting more okay with that than I expected to be.

I'll keep sharing the journey as it goes.

Hopefully this was helpful on your journey.

Thanks for reading, until next time.

P.S. I've been taking on a small number of consulting projects while I figure things out. Mostly artist marketing strategy, digital and social builds, and helping teams work out where AI actually fits into their workflow (and where it doesn't). If that's useful for you or someone on your team, just hit reply, since it comes straight to me.

1) Claude Design - Claude’s new Design functionality that rolled out last week. The design capabilities are not only some of the highest I’ve ever seen but you can export directly to Canva which makes it super interesting. An interesting option for creatives looking for more resources to create with. More info HERE