Welcome back to The Club List, a newsletter about making a business out of what you love.

I can hardly believe we’re less than a month away from SXSW! If you have something going on in Austin, let me know, and I’m going to be doing the same with you very soon. The first half of March, starting with The New Colossus in NYC, is going to be a real blitz of hangs and places to be.

Client spotlight: Kestrels’ incredible new album Better Wonder is finally out, and if you’re even a little into shoegaze, you owe it to yourself to listen! Removing myself from the equation as much as I can, this is a clear contender for my year-end albums of 2025 list. I will be on my way to Austin when they are playing in NYC on March 8 and March 9, but you should go anyway, and also check to see if they’re playing near you (hi Boston, hi Chicago, hi Paw Paw MI). This is their first-ever US headlining tour, and Bob Mould took them out a few years back for a reason.

Today, I’ll share a core principle that’s gotten me through countless tricky times and guides how I develop any creative business I work with. I often say I’m not a perfectionist. That’s true. But what I do, at all times, is give myself fewer chances to fail. Here’s what I mean.

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The Mantra

Give yourself fewer chances to fail.

I don’t mean that as in, try fewer things! In fact, quite the contrary.

Know your core intention, and develop around it.

The other day, I was catching up with a client who told me something that stopped me in my tracks.

We had been working together on professionalizing their painting and sketching work, using my Discovery Package framework. We’d put a pin in the strategy portion to come back to once other things in their life settled down, and I was revisiting that when they said this:

“I’m working on unlearning the mindset that says, ‘I should feel guilty because I wasted your time by not already having actualized everything we talked about.’”

Hold on, now. You mean to tell me that you couldn’t put every single point from an agency-grade business discovery project that includes a marketing audit - before we even start the strategy half - into practice, and you feel like you failed me?

Buddy.

The reason I love doing that specific thing for artist clients is because work that takes me hours can deliver several months of value if you keep coming back to it and putting it to use. What I told them was what I’ll tell you: no one can utilize everything I put forth in those sessions right away without help. They are meant to keep coming back to. 

And because we rarely look at ourselves with the same regard as we look upon others, this client couldn’t see what I see already. Since that initial work, they’d taken on private art students while still holding down their full-time day job, and they were becoming a leader in their community in the process. Now they have a weekly figure drawing night they host that’s open to the public, and when I see them around the city, there’s a high chance they’ll have a student or two with them painting or sketching. 

They’re still cleaning up the digital part of their marketing, and that’s fine. The physical part is being handled. That’s someone who’s well on their way.

I feel the difference. Everyone feels the difference. But they focus on how far they have to go.

And that’s why I say what I will say again: give yourself fewer chances to fail.

What I actually mean by “give yourself fewer chances to fail” is twofold:

First, check your benchmarking, and only keep what serves you. If you’re a startup with funding, you will have growth-focused KPIs that need to be hit, whether it’s you setting them or a funder setting them. But when you have a really meaningful business idea that resonates with people, you know good and well that KPIs don’t tell the whole story of what you’re building. So, consider: at what point do you have a new indicator to point to, such as one that points to sky-high customer satisfaction, or one that shows your ideal customer exists in an untapped category you’ll be poised to dominate?

That’s not the only kind of benchmarking you have to examine. In my past, I’ve driven myself nuts trying to make a set number of new connections in a month - whether for business development, or for creative work, or other purposes - and then falling short on that number even if the quality of connections I was making were stellar. Perhaps you’re the sort of musician who gets down on yourself if you haven’t written a new song yet this month. When you’re benchmarking on a quantity basis, you have to ask yourself why that’s the number you’re trying to hit. Because to a lot of people, the moment you don’t hit that benchmark in a set time frame is the moment you have failed - even if that’s an incredibly small part of your overall work. Yes, this is the moment where I stop most musicians and ask why they would micro-focus on streaming numbers when it’s well-established that they won’t pay your bills by themselves, including through industry influence.

If you have something scalable, and you can demonstrate this in other ways, then the benchmarks will catch up. Keep what serves you.

Secondly, give yourself more chances to succeed. Every creative person is well-served to acknowledge a weakness every human being has: You can’t see the future. Life doesn’t paint completely by numbers, and you shouldn’t either.

At the risk of sounding like one of those “rise and grind” chumps you see in the dustiest corners of LinkedIn, there is precisely one Jay-Z lyric that’s always stuck in my mind. And that’s the opening line from “On To The Next One:”

“I got a million ways to get it. Choose one.”

Peel all the braggadocio back, and there’s a genuinely amazing bit of insight to be had: Diversifying can be a superpower.

If you’re a musician, we’ve already established that streaming is unlikely to pay your bills. And increasingly, it’s difficult to turn a consistent profit from touring until you’re at a certain level. But what else can you do that’s right in front of your face, which doesn’t take an outsized spend of energy away from your core functions to get revenue? Maybe it’s selling merch, maybe it’s giving private lessons, or maybe it’s restructuring your non-music work in a way that allows you to take bigger risks with your art.

If you know you have multiple paths by which to get to your version of success, you can free yourself from a whole lot of extra anxieties.

And that also enables you to take some wild creative chances, while you’re at it. 

It’s important to get out of your comfort zone in a measured, deliberate way, with regularity. I’ll elaborate on that a little bit separately, because it’s a very critical short note of its own. But what it comes down to is, life changes very quickly. 

If you have a business of your own and went through the arrival of COVID-19, for example, you know exactly what I’m talking about. I was right there with you. Revenue streams halted, new methods had to be calculated, and strategies were blown up overnight. Some figured out ways to pivot, some figured out ways to ride it out, some changed career paths by choice or necessity. (I would say I did a little of all of that!) A lot of pain and challenge came from that extreme situation, across the board. But smaller-scale events play out constantly to throw a wrench in the gears of whatever you’re currently doing, and you have to be ready for doors to close as you are opening others.

A lot of what marketing, and business development, ultimately comes down to is maximizing the opportunities you have. Sometimes, this looks like higher-probability moves to support lower-probability gambles. Sometimes you just need more opportunities, period; other times, you need to figure out what else you could do with them that isn’t already being done.

When you give yourself more chances to succeed, you give yourself fewer chances to fail.

If you’re implementing a thing that will help your business, but doing it in an imperfect way, then that’s still a fresh chance to succeed. And when you figure out how to do it in a better way from that, that’s a whole extra chance to succeed. Your best shot at drawing the card you want is to draw more than one.

And believe it or not, having two chances to succeed at something because you approached it from two new directions pushes you towards a positive economy of scale. You’re dividing the same time spent on a problem across two new ways to do it, which - from a “time is money” perspective - means your per-unit fixed cost just dropped, and you’re now closer to the upswing of a long-run average costs curve. (If your investors did MBA coursework, they’ll love you for pointing this out.)

All of this adds up. And all of this pays off.

If you do something that would benefit from my services or want to talk about anything from this newsletter, my door is open! Say hello at [email protected].

One Thing You Can Use Today

Be exploratory.

You never know where it will take you, but it will almost certainly lead you to a better place than you’re currently imagining.

I’m the sort of person that likes to try new-to-me places constantly. It took me years to find comfort in routines, because I liked to have my day always unfold in a slightly different manner. And I’m unlikely to enjoy going to the same restaurant or bar in a large city more than a few times, unless I’ve made a significant bond with the regulars and establish it as a “home base” from when my other exploring is done. Museums and galleries are a happy place for me.

But the moment that my professional life really took off came when I started applying that to how I did things at my job.

As my radio promo years drew to a close, I had taken on a middle-management promotion that counted sales as a significant component. At the time, I knew that coloring in the lines wasn’t going to be how I made things work, because the agency I was at back then had a huge number of its own well-established relationships.

So, I baked in a very specific (and very achievable) benchmark for myself.

Every week, I attempted to book at least one meeting that was fully outside of my comfort zone. 

It could be with a brand I didn’t know, a different music company that I didn’t see a clear way to work with up front, or in a totally unassociated industry where ways to collaborate may or may not exist.

What happened?

Well, it didn’t result in a significant amount of extra sales for me…at first. But what it did do was give me an understanding of pain points across different kinds of businesses, and because I was ambitious enough to try to work with these people, they started to come to me first when something they were doing might make sense to market to that agency’s network. 

That caused a significant domino effect over time.

I’ve written in this space about the power of compounding. This was that, but because it was cross-industry, it was exponential. I ended up sketching out business models and partnership agreements that were simply outside of my skillset a few months prior to starting that effort, to the point that I later saw a podcast ad network launch elsewhere using a framework I’d drafted back then (a whole separate story!).

And it was all because I would show up accepting I only knew a little, and aim to know more from there. There was so much knowledge coming into my head that I was suddenly struggling to keep a price on what was coming out of my head. What an awesome problem. It led to me becoming a business owner, and it would later lead to me becoming the fractional executive you see now.

Being exploratory challenges your self-concept, in small ways, and adds to your intellectual elasticity.

Curiosity is a muscle to exercise. You’ll be amazed at how much lifting it can do.

Track of the Week

Scratch Massive - “Inner Symphony”

They’ve been a known quantity in the French electronic scene for quite a while now, but one quick listen to Scratch Massive’s new album Nox Anima would easily have you thinking they’re a new act on Dais, Italians Do It Better, or any number of labels that like it dark and synth-y half as much as I do. Scratch Massive tends to skew very pop or very club depending on the song, in a way that can be jarring at first; clubgoers, start right here. “Inner Symphony” is a maximalist, downtempo, atmosphere-laden track that doesn’t seem to ever want itself or the night to end, and that’s exactly what I’m looking for in music like this.

Spotify | Apple Music

List of Clubs

These are the kinds of clubs I’d like to be in around NYC! Wherever you might find music, art, or a compelling experience under one roof, that’s a club to me. I only list clubs I’d enjoy going to. If I list a client, you’ll know.

Friday, February 21 - UGLY MAGIC @ 14BC Gallery
I have one of Aaron Zimmerman’s paintings in my office (scroll down), and it’s not too common to see him do an art opening but always worth taking part in. You’ll find few painters who can combine puerile and powerful so effectively. 5-9pm, free, 626 E 14th St.

Friday, February 21 - Mirari Presents @ PUBLIC Hotel Artspace
A full night of top-tier house, not too far from the gallery show above. Will you see me in the club? Possibly.

Saturday, February 22 - 95 Bulls @ Alphaville (late show)
A really affordable post-11pm show at Alphaville, with the always-explosive local heroes 95 Bulls headlining. Minor spoiler: you will see me in this club.

Thanks for reading! And now, an image of me in the club…

The Club List is a newsletter from MeInTheClub.com. All issues are available at TheClubList.net. To inquire about marketing services for your work, contact [email protected] and include "Services” in the subject line.