The Pudding Factory

08/25/2026

You know when you order something from IKEA, you get a list of all the pieces, plus instructions on how to put them all together?

Why don’t we do that with people at work?

A user guide, complete with a person’s preferred ways of working. What’s their relationship with time? What environments give them energy and which ones suck the life out of them? What communication methods work best? What are their superpowers? What is their kryptonite?

You know who does this? Jeff Gibbard. Jeff is a speaker and coach with a mission to help leaders change the world. But we can’t do that if we don’t understand the folks we’re leading. Good thing one of Jeff’s superpowers is really seeing people. Jeff is neurodivergent, which has helped him recognize the value of each person’s unique way of showing up in the world.

When you create a user guide for everyone on the team, all of that comes into focus. Instead of saying, “why can’t they just…” we say, “oh, she’s different than me, cool.” Then we find ways to actually work better together.

Jeff wrote a book called “The Loveable Leader” where he goes into all of this and a lot more.

Love at work? What are you crazy? Maybe.

I think we’re all holding back some of our best craziness at work and it’s keeping us from doing great things.

So, what would your user guide say?

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Welcome to the DesuckifyWork® podcast. The show where we cut through the BS and find ways to make work more fun, more human and less ridiculous. All of which makes your business more profitable, by the way.

(Link to podcast in bio)

08/18/2026

Most agencies are in survival mode right now.
Hell, the entire world is in survival mode right now.
It’s a crappy place to be.
We’re defensive. On edge. Reactionary.
Nervous systems fully engaged all day long.

Good luck being creative when you’re crouched under your desk all day.

And yet, creativity is exactly what we need right now.
To build a new reality instead of being cowed by the current one.
To see something beyond mere survival.

It’s a leap of faith.
Faith in the one thing—creativity—that we’ve hung our hat on since folks actually wore hats to work.

Sam Littlefield took that leap in 2021,
when he told his agency, “it’s time to gather again.”
Mid-covid.
Barely a year into his role as agency president.
His peers thought he was nuts.
He didn’t care.
He saw what was on the other side,
locked arms with his team and said LFG.

They freakin’ went, and they’ve spent the last 5 years doing what many in our industry can barely remember doing. Growing. Building. Dreaming. They turned LFG into an agency rallying cry:

🐱 Littlefield Team First
🐱 Freaking Go to the Edge
🐱 Got to Adapt or Die

For Sam and the team, being back in the office was the necessary catalyst to make all of this happen. For your team, it may be something else. But whatever that thing is that you know in your gut is needed more than anything right now, do it.

The world needs more leaps of faith. Let’s freakin’ go.

—

Welcome to the DesuckifyWork® podcast. The show where we cut through the BS and find ways to make work more fun, more human and less ridiculous. All of which makes your business more profitable, by the way.

(Link to podcast in bio)

08/13/2026

Ad agencies are loaded with some of the best problem solvers in the world. Your clients benefit from this every day. What if you turned some of that talent inward and brought your creative energy to the biggest challenges facing your business? I spent over 25 years in the ad world, so I know you’ve got a bunch of stuff to work on.

It’s time to whip up a few briefs that put your agency name in the “client” slot and let your team have at it.

I can help, btw.

07/22/2026

The posters on the wall. The words on the website. The sizzle real that you share with every prospect.

Are they bu****it?

You know who knows? Your team. Take a look next time you reference your mission or your values. How far back into their heads do their eyes roll?

Slick messaging may help land a client or two, but I can guarantee you it’s turning more folks off if it doesn’t ring true. And if your team ain’t feeling it? Good luck delivering work that actually lives up to those lofty promises.

If you’re ready to lead like a grown up and live up to your words, it’s time to heed the words of Sandy Sullivan and ask better questions. Sandy is an executive coach and co-founder of The Alchemy Group with a low tolerance for BS and a high bar for leaders.

The quality of your questions will directly impact the way your teams perform. And the harsh truth? Most of our questions just kind of suck right now.

The best questions are what Sandy calls “Level 8 Questions.” And there are 4 simple ways to know if yours are hitting the mark:

1. Use “what” or “how” questions. Never “why.” Why not? Because “why” is loaded with judgment. “Why aren’t we winning more business?” Because you suck, presumably.
2. Add calibration & timeframe: Include qualifiers like “most,” “least,” “highest,” and a specific timeframe (e.g., “last quarter,” “next 30 days”).
3. Ask with Pure Curiosity: Listen without judgment or a pre-determined answer.
4. Generate New Thinking: The answer should create white space for reflection, not just recycle old thoughts.

Great questions show you care. And showing you care invites everyone else to do the same. That’s all most of us want, really—a reason to give a damn.

Less sizzle. More stake.

—

Welcome to the DesuckifyWork® podcast. The show where we cut through the BS and find ways to make work more fun, more human and less ridiculous. All of which makes your business more profitable, by the way.

(Link to podcast in bio)

07/04/2026

Grateful every day for the blessings this country provides. Happy 250th, America. 🎉

07/01/2026

I could run a marathon. I could write a book. I could be more accountable to my team.

Sounds lovely. So lovely that our brain actually thinks we did those things, just by thinking about them. There’s actual neuroscience to back this up.

And that’s how we get stuck. We want this thing. But there is something so comforting about thinking we “could” do it someday, and do it amazingly. How soothing to our identity to believe we are great at something we’ve yet to do.

Most of us spend a lot of time in this reality. I have pages of coulds written in my notes app. They feel like my friends.

But are they? They’re my bed rot buddies. My procrastination pals. But friends? Nope.

Friends want more for you.

The key to moving past “could,” in my experience, is realizing it’s okay not to be good at something. We’re all bad at things when we first try them. Or at least not as good as we’d like to be. That doesn’t mean we suck. That doesn’t mean we can’t get better. And it doesn’t mean we’re somehow less valuable as a human if we never get as great as we’d like at that one thing.

Keep playing, keep experimenting, keep growing. Be the friend to yourself that could, could never be.

06/26/2026

Where's the spicy thinking? The provocation? The POV? Think about how much better our feeds would be if this was the norm. Grateful to Rishad Tobaccowala for keeping it real during our recent podcast episode.

06/25/2026

You bust your butt to solve client problems every day. Let’s use that same energy, creativity and chutzpah to make your agency amazing.

It doesn’t have to be so hard.
Hard to think.
Hard to connect.
Hard to lead.
Hard to make sense of the constant noise that fights for our attention every second.
What if you could find the space to think, to explore, to play?
To focus on what truly matters?
You can. You have. You’re here.

Agency leaders, who’s ready to play?

06/11/2026