By Design — More Money Was the Wrong Goal

Hi Reader,

My side hustle was thriving way better than I'd dreamed it would in the first year. So, obviously, the next thing to do was to scale, right?

Nope. Absolutely wrong.

The online gurus, well-meaning family and friends, even total strangers, all drum in the same advice: hire hands so you don't have to be there all the time, reinvest your earnings in more equipment, take on as much new business as you can.

It was too tempting not to go for it. I invested in more equipment and more hands, and at first, it was great. It was more admin, but nothing I couldn't handle. There was real joy in the accomplishment. The euphoric feeling of doing the thing and it working.

There's a particular kind of excitement that comes from building something with your own hands and watching it succeed. It feels like proof. Proof that your instincts were right.

Then a friction hit me.

The things that used to bring joy started feeling like summits I had to brace myself for. Responding to clients, agreeing on approach, the networking, even the joy of doing the thing wasn't the same.

At first, I thought it was burnout from a packed wedding season followed by an equally busy holiday season. But then winter came: quiet time, space to rest, but I wasn't doing my usual strategizing and planning for the coming busy season; I was just uncomfortable. Something just felt off. I was producing and on track to produce even more, but I wasn't where I needed to be mentally.

That's when my design brain kicked in. Take stock. What have you done so far? Where are you now? Why isn't this place satisfying? Where are you supposed to be heading, and are you on track?

That's when I realized that I had completed the five-year design I had written for myself back in 2020. My career had evolved. My income had grown. My business existed and was successful. In many ways, I was standing inside the life I had only imagined.

The problem wasn't that I was failing. The problem was that I had arrived.

And without realizing it, I had continued optimizing a vehicle that had already reached its destination.

That's why scaling the business felt increasingly disconnected from what I actually wanted. The question wasn't whether the business could grow. It could. The question was whether that growth was taking me somewhere I genuinely wanted to go.

So I went back to the design table. This time, I wasn't designing five years out. I was designing ten.

At this stage of life, ten years felt like the more useful horizon. I wanted to understand what the middle and later years of my prime earning period were actually for. What kind of work did I want to be doing? What kind of impact did I want to have? What role did money play in the larger picture?

It became clear that scaling the photo booth business wasn't the right path at that time. The time, money, and energy it would take were better invested somewhere more aligned with where I actually wanted to go in the coming years.

Looking back, I can see how a simple product-thinking tool would have helped me get there faster.

The Five Whys:

• Why scale the business? To make more money.
• Why did making more money stop feeling like the answer? Because the work that once energized me was becoming increasingly heavy.
• Why wasn't that just burnout? Because even after I had time to rest, the feeling remained.
• Why did it remain? Because the discomfort wasn't coming from exhaustion. It was coming from misalignment.
• Why was I misaligned? Because I had already arrived at the destination I had designed five years earlier, yet I was still optimizing for it as though it were the next destination rather than the current one.

That was the real problem.

Not "How do I make more money?"

Not "How do I scale this business?"

Not even "How do I become more productive?"

The real problem was that I hadn't designed what came next, and that's the trap.

The first problem we notice is often real, but it isn't always the root problem. "Make more money" wasn't a bad goal. In many situations, it may be exactly the right goal. The mistake is assuming that the loudest problem in the room is automatically the most important one.

The Five Whys don't tell you what to do next. They help you make sure you're solving the right problem before you start.

If you're building something right now — a side hustle, a project, a business, a career — more money may genuinely be the next thing you need. Or it may simply be the most visible symptom of a deeper design problem.

The Five Whys won't tell you which one it is.

But they might help you discover whether you're building toward the right destination.

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P.S. If any of this resonates, hit reply — I'd love to hear your thoughts. And if someone in your world is building, scaling, or trying to figure out what to build next, feel free to forward this their way.

Intentionally,

Dami