It’s all about Joyful Structure. No, wait, I mean Structured Joy.

Structured Joy and Joyful Structure are two complementary approaches to having a successful and satisfying working (and marketing!) life.

It’s all about Joyful Structure. No, wait, I mean Structured Joy.


Structured Joy and Joyful Structure are two complementary approaches to having a successful and satisfying working (and marketing!) life.

Structured Joy emphasizes the importance of maintaining enthusiasm by actively encouraging enjoyment while Joyful Structure stresses the importance of planning and environment in creating a path of growth and success.

By making sure that you’re having fun and are surrounded by things that motivate and support you, you’ll make sure that your business is something you love and that you succeed in the long-term by loving the journey.

Leah and I had a wonderful moment this summer, as we walked through our neighbourhood to get some air after a tough working session.

As we crossed the street, one of our most beloved clients was commuting home on her ebike, and she made a gentle u-turn to catch up with us.

As we approached, her first words were, “We did what you said!”

“What do you mean?” Leah asked.

“Everything you told us to do first, it’s all done, so now we’re working on the next steps.”

“That’s amazing!” I said

But, because I can’t help myself, I quickly slipped into investigator mode.

“I know we weren’t the first people to give you some of those recommendations,” I said, “but it didn’t get done before. What was different about us or how we worked with you that helped you make that progress?”

She paused to think, and then a wry smile crossed her face: “It was your genius understanding of us,” she said.

“Not just you, and you,” she said, pointing from me to Leah, “but both of you, together. Your different perspectives about the same things that gave us a direction we could all agree on, and a process we could actually follow, step by step.”

“Because it came from us,” she said, “and what we wanted. You’re the only people who could get that from us.”

After we parted and the initial pride began to subside, Leah and I were simultaneously struck with a worrying thought: We don’t actually know what, exactly, our different perspectives are.

If that’s our critical difference, it feels important to have a good understanding of what it actually means.

For the next few months, we talked back and forth around the same point, and we kept running into the same argument: While we both agreed that our clients made so much progress because they enjoyed doing it, I would say our secret weapon is our “joyful structure” while Leah would frame it as “structured joy.”

I’ll admit I was a little annoyed that she was getting the phrasing wrong. Those are two completely different things, aren’t they? And surely we can’t recommend both.

In fact, aren’t they even opposites?

Joyful Structure implies that the most important thing is structure, so you do whatever it takes to maintain it—like making it joyful and at a more sustainable pace.

Structured Joy implies that the most important thing is the joy, and you’ll do whatever is necessary to maintain and protect it—including structuring and enforcing it.

And so we worked our way through each step of our process, and how we work with clients to identify what they truly want (as individuals and as a group), how they’re going to get what they want (step-by-step), and how they’re going to keep what they want (by making their efforts sustainable and adaptable).

The first thing we deliver to our clients is a summary of what they want, as an entrepreneur or as a team, and the direction they’ll need to commit to following to get it.

So, for an entrepreneur, the Joyful Structure approach would be to write down your intention to build and grow your business sustainably, over the long-term. Anyone can burn their life or future down to fuel something professionally in the short-term. It’s only impressive if you do great work while being a great person. If you’re committed to making your business work, and working at it until it does, write that down.

The Structured Joy approach would be to write down your intention to enjoy your working life. In many ways, how you feel about your business is how you feel about your life. Making your business something you love is a way to make your life something that brings you satisfaction. And passion from a place of purpose is way more motivating than desperation and fear of failure.

What about making progress and sticking to your commitment to build your business steadily and sustainably?

Well, I’d say that, under a Joyful Structure approach, you need to recognize that willpower is a myth, and relying on it is unsustainable. Instead, change your environment so that making slow, steady, and focused progress on what matters most is your default action. Is your office, phone, or computer set up and organized to avoid distractions and point you toward your highest-value, highest-satisfaction work? If not, change your default patterns by changing the work environment around you.

For Structured Joy, it would mean that if you’ve spent more time making your Zoom background look professional than you have making the background behind your computer screen look fun, motivating, and inspiring, you made the wrong bargain. The best things flourish in environments that support them. What is your day-to-day work environment supporting or reinforcing? If you’re staring into distracting chaos or boring blandness behind your screen, that’s what you’re filling your mind with.

But how do you stay motivated if it’s going to take a long time to get anywhere?

A Joyful Structure perspective would say that entrepreneurs have the privilege of doing what they love, which gives them the responsibility to try to enjoy it. Nobody’s impressed with someone who’s made their dream a living nightmare. Nobody’s impressed with the person who knew they were hiking a difficult path but still chose to wear uncomfortable shoes. You’re doing something that’s already difficult and saddled with poor odds—making it harder is actively betting against yourself.

A Structured Joy perspective would say that enjoying what you do is your competitive advantage, so you’ve got to structure your enjoyment. Celebrate your wins, pat yourself on the back, and remind yourself that what you’re doing is difficult and you’re amazing for getting it done. Let everyone else slog through the muck—discovering that there’s a dry path nearby isn’t cheating, it’s planning for a much longer hike.

Doesn’t that mean you’re just trying to make everything easier on yourself? Can you actually succeed if you’re having fun?

Joyful Structure: Trying to make your work more fun isn’t unprofessional, trivial, or childish. It’s actually harder. Because giving into the impulse to throw effort against thinking problems is easy, but ultimately unhelpful. The hard part is planning for the long road ahead, ditching everything that won’t help, and aiming for a path that’s completely impassable for everyone but someone with your unique mix of skills, experiences, interests, and goals. That’s playing on hard mode, and loving every minute of it.

Structured Joy: Growth feels bad. If things are easy, you’re not growing. If you’ve got a bad feeling in your tummy because you’re about to do something difficult, you’re growing. And, when you first attempt to structure joy into your work, it’s going to feel bad. You’re going to feel guilty. But when you can’t stop doing something because it feels too bad to give up, that’s a symptom of withdrawal from an addiction, not a work ethic to be proud of. Can you succeed if you’re having fun? I’d ask, how can you even consider it “success” if you’re not?

But what about if things go wrong? Isn’t a harder, tougher approach more defensible and effective if circumstances worsen?

Joyful Structure: The art of planning is not ensuring everything goes right so that you get what you want. It’s managing to get what you want, even if everything goes wrong—because you prepared for things to go wrong. Without enough slack in the system, any shock could break it, and you. Instead, buffer your time, your money, and your mind with the profit that comes from focus, and the joy that comes from structure.

Structured Joy: To make it to the long-term, we’ve got to do more than simply survive the short-term. We’ve got to enjoy it, and sometimes that takes actively encouraging ourselves and pushing ourselves to have more fun, more rest, and more time off. So that when it’s time to do our best work, we’re not tired or afraid, we’re bubbling with eagerness to solve another hard challenge that we’re best suited to take on.

Maybe, but taking your time is a luxury. Isn’t it more important to win big, quickly?

Joyful Structure: Pace is not a luxury, it’s the only thing that really matters. Because, sure, you might strike it big early. But if and when you don’t, you’re guaranteed to strike out. So if you’re a natural sprinter, pacing yourself is actually way more difficult than pushing harder and faster. But it’s vital. So make your structure fun. Make your hard work joyful. And make your marketing actually work, by working at it joyfully until it does.

Structured Joy: Let’s be clear, loving what you do is the only thing that matters, and the only way to keep loving it is to form a structure around your joy. It doesn’t take any brains, guts, or effort to hate your working life. Instead, focus on staying engaged, satisfied, and happy with your efforts, so that you never have to stop.

So is it Joyful Structure, or Structured Joy?

You tell me.