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

I’m at Austin Psych Fest in Texas through this weekend! If you happen to be down this way, we should chat. New Yorkers, I’ll see you again at the end of this. For everyone else, I think it’s safe to say that this and SXSW won’t be my only times on the road this year.

For those of you looking for a great show to see in May in NYC, mark your calendars: Palehound is headlining a benefit for the Immigrant Defense Project at Baby’s All Right on May 27. Good intentions and good performances? That’s a win. I’ll see you there.

Today, I realized it’s been a full year since going out on my own professionally. This is a look at that, which I hope informs creative endeavors of your own that may require much more bravery.

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Start From This Question

Let me ask you a very simple question.

If you could do anything at all, what would you do?

There are levels to this question, which you can add in next:

If you could do any kind of work, what would it be?

If you could put any kind of idea into the world, what would you want to make?

And then, the most brutal of layers:

What is in the way of you doing this?

Unlike whatever buzzy self-help guru this may have reminded you of, I’m not going to sit here and say that just because you have an idea to do something means you can do it right this second. That’s logistically untrue for many people. But what you do need to do is define what you want to do, and then sort out how you might do it.

Sometimes, history and current science won’t be on your side. I don’t have the power of flight, for example, and I probably will not in my lifetime unless I learn to fly planes. But I’m awfully glad that passenger jets exist, and I find myself amazed at the people and discoveries I would have missed out on if I weren’t born in an era where catching a flight is possible. So I’m okay with not having my own jetpack yet. (Emphasis on yet.)

Sometimes, you don’t have enough money, or enough time. It’s one thing to have limited resources, but when you’re behind on rent or working 70+ hours a week to stay afloat, that takes priority. Dreaming any kind of dream is hard in those situations.

But one of the great parts of the original question is that the answer can include what you already do, if you enjoy it enough.

And when I went solo under the Me In The Club banner a year ago, it was a question I had to ask myself.

Think about it. Now picture me considering it.

If you could do anything at all, what would you do?

Anything at all.

Anything.

I’ve talked before about some of my formative experiences that led to working in music, and I would find it redundant to do so again. (Hell, I did it last issue!) 

But asking yourself a question about what wild things you might want to do with your life at 24 is one thing. Asking yourself about what you might want to do with your life at 37 - which I was, at this time last year - can be quite another thing. So in writing about it here, I’m hoping to distill the process a bit for you and myself both, for moments when we might wish to ask it again at 49, or at 63, or at 80.

Here’s how I answered it.

Firstly, I thought about what I loved about the life I had at that moment. I had an exceptional support network, loads of goodwill built up from the work I’d done to grow artists and businesses over many years, and I had the kind of occupation that allowed me to travel and do good things for others while on the road. 

And importantly, I enjoyed the marketing work I did. In a world where defense contractors and hate groups and unscrupulous mega-CEOs all have brand narratives that work for them, I have a core need to help good things, challenging art, useful ideas, and compelling stories find their audiences. I’d built a career on that, and to this day, I feel it is my method of subverting a world that’s not always invested in promoting meaningful, positive stuff.

But I had gotten to where I no longer felt I was working with creativity itself directly enough. I didn’t just want to support a growing company with a good idea; I wanted to be caught up in the idea next to them, while still having time for my own ideas and my own art too. I wanted to feel as invested in an artist’s success - and in whatever they believed success was - as they were themselves.

So that answered the question, and addressed some of those middle layers.

If you could do anything at all, what would you do?

“I would handle marketing and business development for the best clients I could find in a way that leaves a concrete impact on them, make more art for myself whether it was commercially successful or not, and travel more for work and for life. And I would do it on my terms, while accepting it would require lots of work.”

Great, there’s the main answer.

But then comes the bigger question:

What is in the way of you doing this?

And the answer to that was, I didn’t quite trust myself to do it alone because I never had, though intellectually, I knew I could. So, I needed to rip it all up and start from scratch, and prove it to myself first. The curse of expert-level knowledge in a trade category is also knowing what you don’t know, at any given time - and so, I badly needed to become a student of the game again. (Some people have egos that help insulate them from this worry. I am not one of those, though I sometimes suspect it would be nice.)

Over the years, I’ve worked with plenty of artists who wanted to change their names. Companies, too. They’d felt as if they had stagnated, for unclear reasons they couldn’t always articulate, and they felt it was time to rebrand.

Nearly every time I’ve worked with someone who had an engaged audience but wanted a name change, I fought it. For artists, it’s a great way to take a growing career and hit “restart” on it, while rarely making other material changes. For companies, it can sow more distrust than if you proceeded with the existing brand, plus it reboots any emotional loyalty people feel to what you’re doing.

But after last year, it will be rare that I push back against a rebrand like this ever again. Because I now know an intrinsic truth:

Sometimes in life, doing a difficult new thing to present yourself to different experiences is more important than doing what you are comfortable with.

Cut to me considering my old agency’s business model - a still-successful one! - and deciding that building a new model for myself around my executive-for-hire motivations was necessary to fully engage with all parts of my life the way I wanted to again. I needed to challenge myself for greater independence and greater inspiration both. If I could do that while also helping creative people learn how to be better entrepreneurs - in a climate that barely teaches artists to do this, yet callously demands it of them - then I’d be doing what I wanted to do with my life. 

Did I have the full support of my network in this, including my old business partners? You bet. They’re all still here, and I am too.

Was it scary? Yes. The day I walked out of our office in Times Square and down to my informal goodbye party, I did have a moment where I wondered if I’d lost my mind.

Would I do it again? A thousand times.

And the funny thing is, since going solo, I can’t say I’ve done anything alone. My people were there, and I was there for others in my way, and the communal aspects I find so important (and often-neglected) about creative work showed themselves to me in spades. I love the teams I work with among my corporate clients, and I learn as much from the artists I work with as they do from me, if not more. I think I answered the main question in the way I should have.

Now it’s your turn. Ask yourself, if you have a moment. Don’t be shy.

If you could do anything at all, what would you do?

And as you answer it:

What is in the way of you doing this?

One Thing You Can Use Today

Your sleep quality means a lot more than you think.

If you’re trying to build a creative business, you are likely working more than one full-time job’s worth of hours weekly, and you’re likely out meeting people with similar interests at night (especially if you’re based in a major city). This tends to erode your sleep quality. Over time, this erodes other cognitive functioning and makes it harder to be creative.

If you’re the sort of nerd that uses a wearable device for work or fitness (me!), this device can track your sleep habits for you so long as you leave it attached at night. If you have access to this kind of thing, it’s immensely valuable.

But if you don’t have anything like that, you can still keep a sleep journal.

Keep it by your bedside at night, then note the time you started getting ready for bed. By “started getting ready,” I mean to note the precise time after you finished brushing your teeth, but before turning the lights off. (Or, before you brushed your teeth. The time itself is not that serious.)

Do this for a week.

Did you notice a positive change in how you feel? If you didn’t, add an hour of sleep to whatever you have scheduled, then do it again next week. If you did, great - sometimes, the effort to fix a sleep schedule is enough by itself.

Do this for as many weeks as it takes to feel yourself feel better.

Over time, you’ll be surprised at how much this assists with executive dysfunction. It’s amazing how much easier it is to make a choice when your morning coffee is more of a choice and less of a requirement. More dreams in sleeping hours will tend to equal better vision in the daytime, too.

And if you’re noticing that adding time isn’t changing anything, changing what you do when going to bed can help with making the most of the hours you have.

Track of the Week

dirty marmalade - “XIX:XI”

Do I know the story behind the song title or that voicemail intro? Nope. Is that the nastiest bassline I’ve heard in a couple of years? Absolutely. There are lots of bands doing this sort of laddish post-punk thing in the Irish scene, but very few of them can play like dirty marmalade, and it’s a delight to hear them bounce licks off of each other while that filthy bass parades around your speakers.

Spotify | Apple Music | Bandcamp

List of Clubs

Back next issue, as I’m at Austin Psych Fest this week. Scope that lineup HERE!

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.